Benzene
Encyclopedia
Benzene is an organic
chemical compound
. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C
6H
6.
Benzene is a natural constituent of crude oil
, and is one of the most basic petrochemical
s. Benzene is an aromatic hydrocarbon
and the second [n]-annulene
([6]-annulene), a cyclic hydrocarbon with a continuous pi bond
. It is sometimes abbreviated Ph–H. Benzene is a color
less and highly flammable liquid with a sweet smell. Because it is a known carcinogen
, its use as an additive in gasoline
is now limited, but it is an important industrial solvent
and precursor
to basic industrial chemicals including drugs, plastics, synthetic rubber, and dyes.
), an aromatic resin known to European pharmacists and perfumers since the 15th century as a product of southeast Asia. "Benzoin" is itself a corruption of the Arabic expression "luban jawi", or "frankincense
of Java
". An acidic material was derived from benzoin by sublimation, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.
Michael Faraday
first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen.
In 1833, Eilhard Mitscherlich
produced it via the distillation
of benzoic acid
(from gum benzoin) and lime
. He gave the compound the name benzin.
In 1836, the French chemist Auguste Laurent
named the substance "phène"; this is the root of the word phenol
, which is hydroxylated benzene, and phenyl, which is the radical formed by abstraction of a hydrogen atom (free radical H*) from benzene.
In 1845, Charles Mansfield, working under August Wilhelm von Hofmann
, isolated benzene from coal tar
. Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method. Gradually the sense developed among chemists that substances related to benzene represent a diverse chemical family. In 1855 August Wilhelm Hofmann used the word "aromatic" to designate this family relationship, after a characteristic property of many of its members.
structure, with just one hydrogen
atom for each carbon
atom, was challenging to determine. Archibald Scott Couper
in 1858 and Joseph Loschmidt in 1861 suggested possible structures that contained multiple double bonds or multiple rings, but too little evidence was then available to help chemists decide on any particular structure.
In 1865, the German chemist Friedrich August Kekulé
published a paper in French (for he was then teaching in Francophone Belgium) suggesting that the structure contained a six-membered ring of carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject. Kekulé used evidence that had accumulated in the intervening years—namely, that there always appeared to be only one isomer
of any monoderivative
of benzene, and that there always appeared to be exactly three isomers of every diderivative—now understood to correspond to the ortho, meta, and para patterns of arene substitution
—to argue in support of his proposed structure. Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio.
The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the German Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail (this is a common symbol in many ancient cultures known as the Ouroboros
or Endless knot
). This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was 7 years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. It is curious that a similar, humorous depiction of benzene had appeared in 1886 in the Berichte der Durstigen Chemischen Gesellschaft (Journal of the Thirsty Chemical Society), a parody of the Berichte der Deutschen Chemischen Gesellschaft, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote. Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well-known through oral transmission even if it had not yet appeared in print. Others have speculated that Kekulé's story in 1890 was a re-parody of the monkey spoof, and was a mere invention rather than a recollection of an event in his life. Kekulé's 1890 speech in which these anecdotes appeared has been translated into English. If one takes the anecdote as the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.
The cyclic nature of benzene was finally confirmed by the crystallographer Kathleen Lonsdale
in 1929.
carbon bonds:
X-ray diffraction shows that all of six carbon-carbon bonds in benzene are of the same length of 140 picometre
s (pm). The C–C bond length
s are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is consistent with electron delocalization
: the electrons for C–C bonding are distributed equally between each of the six carbon atoms. The molecule is planar. One representation is that the structure exists as a superposition of so-called resonance structures, rather than either form individually. The delocalization of electrons is one explanation for the thermodynamic stability of benzene and related aromatic compounds
. It is likely that this stability contributes to the peculiar molecular and chemical properties known as aromaticity
. To indicate the delocalized nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms:
The delocalized picture of benzene has been contested by Cooper, Gerratt and Raimondi in their article published in 1986 in the journal Nature
. They showed that the electrons in benzene are almost certainly localized, and the aromatic properties of benzene originate from spin coupling rather than electron delocalization. This view has been supported in the next-year Nature issue, but it has been slow to permeate the general chemistry community.
As is common in organic chemistry, the carbon atoms in the diagram above have been left unlabeled. Realizing each carbon has 2p electrons, each carbon donates an electron into the delocalized ring above and below the benzene ring. It is the side-on overlap of p-orbitals that produces the pi clouds.
Derivatives of benzene occur sufficiently often as a component of organic molecules that there is a Unicode
symbol in the Miscellaneous Technical
block with the code U+232C (⌬) to represent it with three double bonds, and U+23E3 (⏣) for a delocalized version.
. Examples of simple benzene derivatives are phenol
, toluene
, and aniline
, abbreviated PhOH, PhMe, and PhNH2, respectively. Linking benzene rings gives biphenyl
, C6H5–C6H5. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as naphthalene
and anthracene
. The limit of the fusion process is the hydrogen-free allotrope of carbon, graphite
.
In heterocycles, carbon atoms in the benzene ring are replaced with other elements. The most important derivatives are the rings containing nitrogen
. Replacing one CH with N gives the compound pyridine
, C5H5N. Although benzene and pyridine are structurally related, benzene cannot be converted into pyridine. Replacement of a second CH bond with N gives, depending on the location of the second N, pyridazine
, pyrimidine
, and pyrazine
.
, toluene
hydrodealkylation, toluene disproportionation, and steam cracking. According to the ATSDR Toxicological Profile for benzene, between 1978 and 1981, catalytic reformats accounted for approximately 44–50% of the total U.S benzene production.
Until World War II
, most benzene was produced as a by-product of coke
production (or "coke-oven light oil") in the steel
industry. However, in the 1950s, increased demand for benzene, especially from the growing polymer
s industry, necessitated the production of benzene from petroleum. Today, most benzene comes from the petrochemical
industry, with only a small fraction being produced from coal.
s with boiling points between 60–200 °C is blended with hydrogen
gas and then exposed to a bifunctional
platinum
chloride or rhenium
chloride catalyst at 500–525 °C and pressures ranging from 8–50 atm. Under these conditions, aliphatic hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by extraction
with any one of a number of solvent
s, including diethylene glycol
or sulfolane
, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. So-called BTX (benzene-toluene-xylene) process consists of such extraction and distillation steps. One such widely used process from UOP
was licensed to producers and called the Udex process.
In similar fashion to this catalytic reforming, UOP
and BP
commercialized a method from LPG (mainly propane and butane) to aromatics.
converts toluene
to benzene. In this hydrogen-intensive process, toluene is mixed with hydrogen, then passed over a chromium
, molybdenum
, or platinum
oxide
catalyst at 500–600 °C and 40–60 atm pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to benzene and methane
:
This irreversible reaction is accompanied by an equilibrium side reaction that produces
biphenyl
(aka diphenyl) at higher temperature:
If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen.
A typical reaction yield exceeds 95%. Sometimes, xylene
s and heavier aromatics are used in place of toluene, with similar efficiency.
This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) processes.
, then toluene disproportionation
(TDP) may be an attractive alternative to the toluene hydrodealkylation. In the broad sense, 2 toluene molecules are reacted and the methyl groups rearranged from one toluene molecule to the other, yielding one benzene molecule and one xylene molecule.
Given that demand for para-xylene (p-xylene
) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called Selective TDP (STDP) may be used. In this process, the xylene stream exiting the TDP unit is approximately 90% paraxylene. In some current catalytic systems, even the benzene-to-xylenes ratio is decreased (more xylenes) when the demand of xylenes is higher.
and other alkene
s from aliphatic hydrocarbons
. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called pyrolysis gasoline
. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or distilled (in BTX process) to separate it into its components, including benzene.
-rich materials undergo incomplete combustion
. It is produced in volcano
es and forest fires, and is also a component of cigarette
smoke. Benzene is a principal product from the combustion of PVC (polyvinyl chloride).
(methyl benzene), which has similar physical properties but is not as carcinogenic.
In 1903, Ludwig Roselius
popularized the use of benzene to decaffeinate
coffee
. This discovery led to the production of Sanka
(the letters "ka" in the brand name stand for kaffein). This process was later discontinued. Benzene was historically used as a significant component in many consumer products such as Liquid Wrench, several paint strippers, rubber cements, spot removers and other hydrocarbon-containing products. Some ceased manufacture of their benzene-containing formulations in about 1950, while others continued to use benzene as a component or significant contaminant until the late 1970s when leukemia deaths were found associated with Goodyear's Pliofilm production operations in Ohio. Until the late 1970s, many hardware stores, paint stores, and other retail outlets sold benzene in small cans, such as quart size, for general-purpose use. Many students were exposed to benzene in school and university courses while performing laboratory experiments with little or no ventilation in many cases. This very dangerous practice has been almost totally eliminated.
As a gasoline
(petrol) additive, benzene increases the octane rating
and reduces knocking
. As a consequence, gasoline often contained several percent benzene before the 1950s, when tetraethyl lead replaced it as the most widely-used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as a gasoline additive in some nations. In the United States
, concern over its negative health effects and the possibility of benzene's entering the groundwater
have led to stringent regulation of gasoline's benzene content, with limits typically around 1%. European petrol specifications now contain the same 1% limit on benzene content. The United States Environmental Protection Agency has new regulations that will lower the benzene content in gasoline to 0.62% in 2011.
for resins and adhesives (via cumene
), and cyclohexane
, which is used in the manufacture of Nylon. Smaller amounts of benzene are used to make some types of rubber
s, lubricant
s, dye
s, detergent
s, drug
s, explosives, napalm
, and pesticide
s.
In both the US and Europe, 50% of benzene is used in the production of ethylbenzene
/styrene, 20% is used in the production of cumene
, and about 15% of benzene is used in the production of cyclohexane
(eventually to nylon
).
Currently, the production of and demand for benzene in the Middle East register the greatest increases worldwide. It will probably see its share of the global supply and demand expand by 3.7 and 3.3 percentage points, respectively, until 2018. However, the Asia-Pacific region will continue to dominate the market and account for almost half of the global demand.
In laboratory research, toluene
is now often used as a substitute for benzene. The solvent-properties of the two are similar, but toluene is less toxic and has a wider liquid range.
Benzene has been used as a basic research tool in a variety of experiments including analysis of a two-dimensional gas
.
File:Benzene_uses.png|center|Major commodity chemicals and polymers derived from benzene. Clicking on the image loads the appropriate article|600px|thumb
rect 39 660 435 807 Benzene
rect 665 60 1062 207 Ethylbenzene
rect 665 426 1062 579 Cumene
rect 665 795 1062 942 Cyclohexane
rect 665 1161 1062 1317 Aniline
rect 665 1533 1062 1686 Chlorobenzene
rect 1215 345 1614 495 Acetone
rect 1215 636 1614 783 Phenol
rect 1764 57 2163 210 Styrene
rect 1764 432 2163 585 Bisphenol A
rect 1764 1083 2163 1233 Adipic acid
rect 1764 1332 2163 1482 Caprolactam
rect 2313 57 2712 207 Polystyrene
rect 2313 315 2712 462 Polycarbonate
rect 2313 570 2712 717 Epoxy resin
rect 2313 822 2712 975 Phenolic resin
rect 2313 1083 2712 1233 Nylon 6-6
rect 2313 1335 2712 1485 Nylon 6
desc bottom-left
and eukaryote
s.
In bacteria, dioxygenase
enzyme can add an oxygen
molecule to the ring, and the unstable product is immediately reduced (by NADH) to a cyclic diol
with two double bonds, breaking the aromaticity.
Next, the diol is newly reduced by NADH to catechol.
The catechol is then metabolized to acetyl CoA and succinyl CoA, used by organisms mainly in the Krebs Cycle for energy production.
The American Petroleum Institute
(API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero." The US Department of Health and Human Services (DHHS) classifies benzene as a human carcinogen
. Long-term exposure to excessive levels of benzene in the air causes leukemia
, a potentially fatal cancer
of the blood-forming organs, in susceptible individuals. In particular, Acute myeloid leukemia
or acute non-lymphocytic leukaemia (AML & ANLL) is not disputed to be caused by benzene. IARC rated benzene as "known to be carcinogenic to humans" (Group 1).
Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions. About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from exposure to tobacco smoke.
Vapors from products that contain benzene, such as glues, paints, furniture wax, and detergents, can also be a source of exposure, although many of these have been modified or reformulated since the late 1970s to eliminate or reduce the benzene content. Air around hazardous waste sites or gas stations may contain higher levels of benzene. Because petroleum hydrocarbon products are complex mixtures of chemicals, risk assessments for these products, in general, focus on specific toxic constituents. The petroleum constituents of primary interest to human health have been the aromatic hydrocarbons (i.e., benzene, ethylbenzene, toluene, and xylenes). OSHA requires that a mixture "shall be assumed to present a carcinogenic hazard if it contains a component in concentrations of 0.1% or greater, which is considered to be a carcinogen.
The short-term breathing of high levels of benzene can result in death
; low levels can cause drowsiness, dizziness, rapid heart rate, headache
s, tremors, confusion, and unconsciousness. Eating or drinking foods containing high levels of benzene can cause vomiting, irritation of the stomach
, dizziness, sleepiness, convulsions, and death.
The major effects of benzene are manifested via chronic
(long-term) exposure through the blood
. Benzene damages the bone marrow
and can cause a decrease in red blood cells, leading to anemia
. It can also cause excessive bleeding and depress the immune system
, increasing the chance of infection
. Benzene causes leukemia and is associated with other blood cancers and pre-cancers of the blood.
Human exposure to benzene is a global health problem. Benzene targets liver, kidney, lung, heart and the brain and can cause DNA
strand breaks, chromosomal damage, etc. Benzene causes cancer
in both animals and humans. Benzene was first reported to induce cancer in humans in the 1920s. The chemical industry claims it was not until 1979 that the cancer-inducing properties were determined "conclusively" in humans, despite many references to this fact in the medical literature. Industry exploited this "discrepancy" and tried to discredit animal studies that showed that benzene causes cancer, saying that they are not relevant to humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.
Some women having breathed high levels of benzene for many months had irregular menstrual
periods and a decrease in the size of their ovaries. Benzene exposure has been linked directly to the neural birth defects spina bifida and anencephaly
. Men exposed to high levels of benzene are more likely to have an abnormal amount of chromosomes in their sperm, which impacts fertility and fetal development.
Animal studies have shown low birth weights, delayed bone formation, and bone marrow damage when pregnant animals breathed benzene.
Benzene has been connected to a rare form of kidney cancer in two separate studies, one involving tank truck drivers, and the other involving seamen on tanker vessels, both carrying benzene-laden chemicals.
industry, oil refineries, coke and chemical plants, shoe manufacturers, and gasoline
-related industries. Downstream petroleum industry operations include the following categories: refinery, pipeline, marine, rail, bulk terminals and trucks, service stations, underground storage tanks, tank cleaning, and site characterization and remediation.
Exposure of the general population to benzene mainly occurs through breathing, the major sources of benzene being tobacco smoke (about 50%) as well as automobile service stations, exhaust from motor vehicles and industrial emissions (about 20% altogether). Vapors (or gases) from products that contain benzene, such as glues, paints, furniture wax, and detergents, can also be a source of exposure. The average smoker (32 cigarettes per day) takes in about 1.8 milligrams (mg) of benzene per day. This amount is about 10 times the average daily intake of benzene by nonsmokers.
In 1987, OSHA
estimated that about 237,000 workers in the United States were potentially exposed to benzene, but it is not known if this number has substantially changed since then.
Water and soil contamination
are important pathways of concern for transmission of benzene contact. In the US alone, there are approximately 100,000 different sites that have benzene soil or groundwater contamination. In 2005, the water supply to the city of Harbin
in China with a population of almost nine million people, was cut off because of a major benzene exposure. Benzene leaked into the Songhua River
, which supplies drinking water to the city, after an explosion at a China National Petroleum Corporation (CNPC) factory in the city of Jilin on 13 November.
In March 2006, the official Food Standards Agency
in Britain
conducted a survey of 150 brands of soft drinks. It found that four contained benzene levels above World Health Organization
limits. The affected batches were removed from sale. (See also benzene in soft drinks
).
has set a maximum contaminant level
(MCL) for benzene in drinking water at 0.005 mg/L (5 ppb), as promulgated via the National Primary Drinking Water Regulations. This regulation is based on preventing benzene leukemogenesis. The maximum contaminant level goal (MCLG), a nonenforceable health goal that would allow an adequate margin of safety for the prevention of adverse effects, is zero benzene concentration in drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported to the EPA.
The US Occupational Safety and Health Administration
(OSHA) has set a permissible exposure limit of 1 part of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The short term exposure limit for airborne benzene is 5 ppm for 15 minutes. These legal limits were based on studies demonstrating compelling evidence of health risk to workers exposed to benzene. The risk from exposure to 1 ppm for a working lifetime has been estimated as 5 excess leukemia deaths per 1,000 employees exposed. (This estimate assumes no threshold for benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.
The National Institute for Occupational Safety and Health
(NIOSH) revised the Immediately Dangerous to Life or Health (IDLH) concentration for benzene to 500 ppm. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment [NIOSH 2004]. The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable breathing apparatus providing maximum worker protection is permitted [NIOSH 2004]. In September 1995, NIOSH issued a new policy for developing recommended exposure limits (RELs) for substances, including carcinogens. Because benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm. The NIOSH STEL (15 min) is 1 ppm.
American Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.
Under New Jersey's Right-to-Know law, respiratory protection for benzene is discussed. As stated, improper use of respirators is dangerous. Respirators should only be used when there is a written respiratory program in place as described in the OSHA Respiratory Protection Standard (29 CFR 1910.134). The employer is to develop and implement a written respiratory protection program with required worksite-specific procedures and elements for required respirator use. This program must be administered by a suitably trained program administrator. Employers must use the assigned protection factors (APF) listed in Table 1 of 29 CFR 1910.134 to select a respirator that meets or exceeds the required level of employee protection. For benzene:
Each employer with a place of employment where occupational exposures to benzene occur shall monitor each of these workplaces and work operations to determine accurately the airborne concentrations of benzene to which employees may be exposed. Representative 8-hour TWA employee exposures need to be determined on the basis of one sample or samples representing the full shift exposure for each job classification in each work area. Unless air samples are taken frequently, the employer does not know the concentration and would not know how much of a protection factor is needed.
In providing consultation on work safety during oil clean-up operations following the Deepwater Horizon accident, OSHA has worked with a number of other government agencies to protect Gulf cleanup workers. OSHA partnered with the NIOSH to issue "Interim Guidance for Protecting Deepwater Horizon Response Workers and Volunteers" and recommend measures that should be taken to protect workers from a variety of different health hazards that these workers face. OSHA conceded that it recognizes that most of its PELs are outdated and inadequate measures of worker safety. In characterizing worker exposure, OSHA instead relies on more up-to-date recommended protective limits set by organizations such as NIOSH, the ACGIH, and the American Industrial Hygiene Association (AIHA), and not on the older, less protective PELS. Results of air monitoring are compared to the lowest known Occupational Exposure Limit for the listed contaminant for purposes of risk assessment and protective equipment recommendations.
, phenylmercapturic acid, phenol
, catechol, hydroquinone
and 1,2,4-trihydroxybenzene
. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they may still be present for some days after exposure has ceased. The current ACGIH biological exposure limits for occupational exposure are 500 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.
seems to play an important role by protecting against benzene-induced DNA breaks and it is being identified as a new biomarker for exposure and effect. Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple myeloma caused by chronic exposure. These aberrations can be monitored using fluorescent in situ hybridization
(FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity. Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects of benzene exposure. Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase (EPHX) and deletion of the glutathione S-transferase T1 (GSTT1) showed a greater frequency of DNA single-stranded breaks.
(ATSDR) (2007), benzene is both an anthropogenically produced and naturally occurring chemical from processes that include: volcanic eruptions, wild fires, synthesis of chemicals such as phenol, production of synthetic fibers, and fabrication of rubbers, lubricants, pesticides, medications, and dyes. The major sources of benzene exposure are tobacco smoke, automobile service stations, exhaust from motor vehicles, and industrial emissions; however, ingestion and dermal absorption of benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the urine. Measurement of air and water levels of benzene is accomplished through collection via activated charcoal tubes, which are then analyzed with a gas chromatograph. The measurement of benzene in humans can be accomplished via urine, blood, and breath tests; however, all of these have their limitations because benzene is rapidly metabolized in the human body into by-products called metabolites.
OSHA regulates levels of benzene in the workplace. The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. Because benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit of 0.1 ppm.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
6H
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
6.
Benzene is a natural constituent of crude oil
Petroleum
Petroleum or crude oil is a naturally occurring, flammable liquid consisting of a complex mixture of hydrocarbons of various molecular weights and other liquid organic compounds, that are found in geologic formations beneath the Earth's surface. Petroleum is recovered mostly through oil drilling...
, and is one of the most basic petrochemical
Petrochemical
Petrochemicals are chemical products derived from petroleum. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as corn or sugar cane....
s. Benzene is an aromatic hydrocarbon
Aromatic hydrocarbon
An aromatic hydrocarbon or arene is a hydrocarbon with alternating double and single bonds between carbon atoms. The term 'aromatic' was assigned before the physical mechanism determining aromaticity was discovered, and was derived from the fact that many of the compounds have a sweet scent...
and the second [n]-annulene
Annulene
Annulenes are completely conjugated monocyclic hydrocarbons. They have the general formula CnHn or CnHn+1...
([6]-annulene), a cyclic hydrocarbon with a continuous pi bond
Pi bond
In chemistry, pi bonds are covalent chemical bonds where two lobes of one involved atomic orbital overlap two lobes of the other involved atomic orbital...
. It is sometimes abbreviated Ph–H. Benzene is a color
Color
Color or colour is the visual perceptual property corresponding in humans to the categories called red, green, blue and others. Color derives from the spectrum of light interacting in the eye with the spectral sensitivities of the light receptors...
less and highly flammable liquid with a sweet smell. Because it is a known carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
, its use as an additive in gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...
is now limited, but it is an important industrial solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
and precursor
Precursor (chemistry)
In chemistry, a precursor is a compound that participates in the chemical reaction that produces another compound. In biochemistry, the term "precursor" is used more specifically to refer to a chemical compound preceding another in a metabolic pathway....
to basic industrial chemicals including drugs, plastics, synthetic rubber, and dyes.
Discovery
The word "benzene" derives historically from "gum benzoin", sometimes called "benjamin" (i.e., benzoin resinBenzoin resin
Benzoin resin or styrax resin is a balsamic resin obtained from the bark of several species of trees in the genus Styrax. It is used in perfumes, some kinds of incense, as a flavoring, and medicine . Its principal component is benzoic acid...
), an aromatic resin known to European pharmacists and perfumers since the 15th century as a product of southeast Asia. "Benzoin" is itself a corruption of the Arabic expression "luban jawi", or "frankincense
Frankincense
Frankincense, also called olibanum , is an aromatic resin obtained from trees of the genus Boswellia, particularly Boswellia sacra, B. carteri, B. thurifera, B. frereana, and B. bhaw-dajiana...
of Java
Java
Java is an island of Indonesia. With a population of 135 million , it is the world's most populous island, and one of the most densely populated regions in the world. It is home to 60% of Indonesia's population. The Indonesian capital city, Jakarta, is in west Java...
". An acidic material was derived from benzoin by sublimation, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.
Michael Faraday
Michael Faraday
Michael Faraday, FRS was an English chemist and physicist who contributed to the fields of electromagnetism and electrochemistry....
first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen.
In 1833, Eilhard Mitscherlich
Eilhard Mitscherlich
Eilhard Mitscherlich was a German chemist, who is perhaps best remembered today for his law of isomorphism , which states that compounds crystallizing together probably have similar structures and compositions...
produced it via the distillation
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
of benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...
(from gum benzoin) and lime
Calcium oxide
Calcium oxide , commonly known as quicklime or burnt lime, is a widely used chemical compound. It is a white, caustic, alkaline crystalline solid at room temperature....
. He gave the compound the name benzin.
In 1836, the French chemist Auguste Laurent
Auguste Laurent
Auguste Laurent was a French chemist who discovered anthracene, phthalic acid, and identified carbolic acid....
named the substance "phène"; this is the root of the word phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
, which is hydroxylated benzene, and phenyl, which is the radical formed by abstraction of a hydrogen atom (free radical H*) from benzene.
In 1845, Charles Mansfield, working under August Wilhelm von Hofmann
August Wilhelm von Hofmann
August Wilhelm von Hofmann was a German chemist.-Biography:Hofmann was born at Gießen, Grand Duchy of Hesse. Not intending originally to devote himself to physical science, he first took up the study of law and philology at Göttingen. But he then turned to chemistry, and studied under Justus von...
, isolated benzene from coal tar
Coal tar
Coal tar is a brown or black liquid of extremely high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal iscarbonized to make coke or gasified to make coal gas...
. Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method. Gradually the sense developed among chemists that substances related to benzene represent a diverse chemical family. In 1855 August Wilhelm Hofmann used the word "aromatic" to designate this family relationship, after a characteristic property of many of its members.
Ring formula
The empirical formula for benzene was long known, but its highly polyunsaturatedSaturation (chemistry)
In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...
structure, with just one hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atom for each carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
atom, was challenging to determine. Archibald Scott Couper
Archibald Scott Couper
Archibald Scott Couper was a Scottish chemist who proposed an early theory of chemical structure and bonding...
in 1858 and Joseph Loschmidt in 1861 suggested possible structures that contained multiple double bonds or multiple rings, but too little evidence was then available to help chemists decide on any particular structure.
In 1865, the German chemist Friedrich August Kekulé
Friedrich August Kekulé von Stradonitz
Friedrich August Kekule von Stradonitz was a German organic chemist. From the 1850s until his death, Kekule was one of the most prominent chemists in Europe, especially in theoretical chemistry...
published a paper in French (for he was then teaching in Francophone Belgium) suggesting that the structure contained a six-membered ring of carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject. Kekulé used evidence that had accumulated in the intervening years—namely, that there always appeared to be only one isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
of any monoderivative
Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by some chemical or physical process. In the past it was also used to mean a compound that can be imagined to arise from another compound, if one atom is replaced with another atom or group of atoms, but modern...
of benzene, and that there always appeared to be exactly three isomers of every diderivative—now understood to correspond to the ortho, meta, and para patterns of arene substitution
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...
—to argue in support of his proposed structure. Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio.
The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the German Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail (this is a common symbol in many ancient cultures known as the Ouroboros
Ouroboros
The Ouroboros is an ancient symbol depicting a serpent or dragon eating its own tail. The name originates from within Greek language; οὐρά meaning "tail" and βόρος meaning "eating", thus "he who eats the tail"....
or Endless knot
Endless knot
The endless knot or eternal knot is a symbolic knot and one of the Eight Auspicious Symbols. It is an important cultural marker in places significantly influenced by Tibetan Buddhism such as Tibet, Mongolia, Tuva, Kalmykia, and Buryatia...
). This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was 7 years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. It is curious that a similar, humorous depiction of benzene had appeared in 1886 in the Berichte der Durstigen Chemischen Gesellschaft (Journal of the Thirsty Chemical Society), a parody of the Berichte der Deutschen Chemischen Gesellschaft, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote. Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well-known through oral transmission even if it had not yet appeared in print. Others have speculated that Kekulé's story in 1890 was a re-parody of the monkey spoof, and was a mere invention rather than a recollection of an event in his life. Kekulé's 1890 speech in which these anecdotes appeared has been translated into English. If one takes the anecdote as the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.
The cyclic nature of benzene was finally confirmed by the crystallographer Kathleen Lonsdale
Kathleen Lonsdale
Dame Kathleen Lonsdale, DBE FRS was a crystallographer, who established the structure of benzene by X-ray diffraction methods in 1929, and hexachlorobenzene by Fourier spectral methods in 1931...
in 1929.
Structure
Benzene represents a special problem in that, to account for all the bonds, there must be alternating doubleDouble bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...
carbon bonds:
X-ray diffraction shows that all of six carbon-carbon bonds in benzene are of the same length of 140 picometre
Picometre
A picometre is a unit of length in the metric system, equal to one trillionth, i.e. of a metre, which is the current SI base unit of length...
s (pm). The C–C bond length
Bond length
- Explanation :Bond length is related to bond order, when more electrons participate in bond formation the bond will get shorter. Bond length is also inversely related to bond strength and the bond dissociation energy, as a stronger bond will be shorter...
s are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is consistent with electron delocalization
Delocalized electron
In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or one covalent bond....
: the electrons for C–C bonding are distributed equally between each of the six carbon atoms. The molecule is planar. One representation is that the structure exists as a superposition of so-called resonance structures, rather than either form individually. The delocalization of electrons is one explanation for the thermodynamic stability of benzene and related aromatic compounds
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
. It is likely that this stability contributes to the peculiar molecular and chemical properties known as aromaticity
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
. To indicate the delocalized nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms:
The delocalized picture of benzene has been contested by Cooper, Gerratt and Raimondi in their article published in 1986 in the journal Nature
Nature (journal)
Nature, first published on 4 November 1869, is ranked the world's most cited interdisciplinary scientific journal by the Science Edition of the 2010 Journal Citation Reports...
. They showed that the electrons in benzene are almost certainly localized, and the aromatic properties of benzene originate from spin coupling rather than electron delocalization. This view has been supported in the next-year Nature issue, but it has been slow to permeate the general chemistry community.
As is common in organic chemistry, the carbon atoms in the diagram above have been left unlabeled. Realizing each carbon has 2p electrons, each carbon donates an electron into the delocalized ring above and below the benzene ring. It is the side-on overlap of p-orbitals that produces the pi clouds.
Derivatives of benzene occur sufficiently often as a component of organic molecules that there is a Unicode
Unicode
Unicode is a computing industry standard for the consistent encoding, representation and handling of text expressed in most of the world's writing systems...
symbol in the Miscellaneous Technical
Miscellaneous Technical (Unicode)
Miscellaneous Technical is the name of a a Unicode block ranging from U+2300 to U+23FF, which contains various common symbols which are related to and used in the various technical, programming language and academic professions....
block with the code U+232C (⌬) to represent it with three double bonds, and U+23E3 (⏣) for a delocalized version.
Substituted benzene derivatives
Many important chemical compounds are derived from benzene by replacing one or more of its hydrogen atoms with another functional groupFunctional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
. Examples of simple benzene derivatives are phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
, toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
, and aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
, abbreviated PhOH, PhMe, and PhNH2, respectively. Linking benzene rings gives biphenyl
Biphenyl
Biphenyl is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula 2...
, C6H5–C6H5. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
and anthracene
Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings. It is a component of coal-tar. Anthracene is used in the production of the red dye alizarin and other dyes...
. The limit of the fusion process is the hydrogen-free allotrope of carbon, graphite
Graphite
The mineral graphite is one of the allotropes of carbon. It was named by Abraham Gottlob Werner in 1789 from the Ancient Greek γράφω , "to draw/write", for its use in pencils, where it is commonly called lead . Unlike diamond , graphite is an electrical conductor, a semimetal...
.
In heterocycles, carbon atoms in the benzene ring are replaced with other elements. The most important derivatives are the rings containing nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
. Replacing one CH with N gives the compound pyridine
Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...
, C5H5N. Although benzene and pyridine are structurally related, benzene cannot be converted into pyridine. Replacement of a second CH bond with N gives, depending on the location of the second N, pyridazine
Pyridazine
Pyridazine is a heteroaromatic organic compound with the molecular formula C4H4N2, sometimes called 1,2-diazine. It contains a six-membered ring with two adjacent nitrogen atoms. It is a colorless liquid with a boiling point of 208 °C....
, pyrimidine
Pyrimidine
Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring...
, and pyrazine
Pyrazine
Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2.Pyrazine is a symmetrical molecule with point group D2h. Derivatives like phenazine are well known for their antitumor, antibiotic and diuretic activity. Pyrazine is less basic in nature than pyridine, pyridazine...
.
Production
Four chemical processes contribute to industrial benzene production: catalytic reformingCatalytic reforming
Catalytic reforming is a chemical process used to convert petroleum refinery naphthas, typically having low octane ratings, into high-octane liquid products called reformates which are components of high-octane gasoline...
, toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
hydrodealkylation, toluene disproportionation, and steam cracking. According to the ATSDR Toxicological Profile for benzene, between 1978 and 1981, catalytic reformats accounted for approximately 44–50% of the total U.S benzene production.
Until World War II
World War II
World War II, or the Second World War , was a global conflict lasting from 1939 to 1945, involving most of the world's nations—including all of the great powers—eventually forming two opposing military alliances: the Allies and the Axis...
, most benzene was produced as a by-product of coke
Coke (fuel)
Coke is the solid carbonaceous material derived from destructive distillation of low-ash, low-sulfur bituminous coal. Cokes from coal are grey, hard, and porous. While coke can be formed naturally, the commonly used form is man-made.- History :...
production (or "coke-oven light oil") in the steel
Steel
Steel is an alloy that consists mostly of iron and has a carbon content between 0.2% and 2.1% by weight, depending on the grade. Carbon is the most common alloying material for iron, but various other alloying elements are used, such as manganese, chromium, vanadium, and tungsten...
industry. However, in the 1950s, increased demand for benzene, especially from the growing polymer
Polymer
A polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...
s industry, necessitated the production of benzene from petroleum. Today, most benzene comes from the petrochemical
Petrochemical
Petrochemicals are chemical products derived from petroleum. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as corn or sugar cane....
industry, with only a small fraction being produced from coal.
Catalytic reforming
In catalytic reforming, a mixture of hydrocarbonHydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
s with boiling points between 60–200 °C is blended with hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
gas and then exposed to a bifunctional
Bifunctional
In organic molecules, functional groups are atom or atoms which are responsible for the characteristic properties of that molecule with the exceptions of double and triple bonds which are also functional groups....
platinum
Platinum
Platinum is a chemical element with the chemical symbol Pt and an atomic number of 78. Its name is derived from the Spanish term platina del Pinto, which is literally translated into "little silver of the Pinto River." It is a dense, malleable, ductile, precious, gray-white transition metal...
chloride or rhenium
Rhenium
Rhenium is a chemical element with the symbol Re and atomic number 75. It is a silvery-white, heavy, third-row transition metal in group 7 of the periodic table. With an average concentration of 1 part per billion , rhenium is one of the rarest elements in the Earth's crust. The free element has...
chloride catalyst at 500–525 °C and pressures ranging from 8–50 atm. Under these conditions, aliphatic hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by extraction
Liquid-liquid extraction
Liquid–liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubilities in two different immiscible liquids, usually water and an organic solvent. It is an extraction of a substance from one liquid phase into another liquid...
with any one of a number of solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
s, including diethylene glycol
Diethylene glycol
Diethylene glycol is an organic compound with the formula 2O. It is a colorless, practically odorless, poisonous, and hygroscopic liquid with a sweetish taste. It is miscible in water, alcohol, ether, acetone, and ethylene glycol. DEG is a widely used solvent...
or sulfolane
Sulfolane
Sulfolane is a clear, colorless liquid commonly used in the chemical industry as an extractive distillation solvent or reaction solvent. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene...
, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. So-called BTX (benzene-toluene-xylene) process consists of such extraction and distillation steps. One such widely used process from UOP
UOP LLC
UOP LLC, formerly known as Universal Oil Products, is a multi-national company developing and delivering technology to the petroleum refining, gas processing, petrochemical production, and major manufacturing industries....
was licensed to producers and called the Udex process.
In similar fashion to this catalytic reforming, UOP
UOP LLC
UOP LLC, formerly known as Universal Oil Products, is a multi-national company developing and delivering technology to the petroleum refining, gas processing, petrochemical production, and major manufacturing industries....
and BP
BP
BP p.l.c. is a global oil and gas company headquartered in London, United Kingdom. It is the third-largest energy company and fourth-largest company in the world measured by revenues and one of the six oil and gas "supermajors"...
commercialized a method from LPG (mainly propane and butane) to aromatics.
Toluene hydrodealkylation
Toluene hydrodealkylationHydrodealkylation
Hydrodealkylation is a chemical reaction that often involves reacting an aromatic hydrocarbon, such as toluene, in the presence of hydrogen gas to form a simpler aromatic hydrocarbon devoid of functional groups. An example is the conversion of 1,2,4-trimethylbenzene to xylene. This chemical process...
converts toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
to benzene. In this hydrogen-intensive process, toluene is mixed with hydrogen, then passed over a chromium
Chromium
Chromium is a chemical element which has the symbol Cr and atomic number 24. It is the first element in Group 6. It is a steely-gray, lustrous, hard metal that takes a high polish and has a high melting point. It is also odorless, tasteless, and malleable...
, molybdenum
Molybdenum
Molybdenum , is a Group 6 chemical element with the symbol Mo and atomic number 42. The name is from Neo-Latin Molybdaenum, from Ancient Greek , meaning lead, itself proposed as a loanword from Anatolian Luvian and Lydian languages, since its ores were confused with lead ores...
, or platinum
Platinum
Platinum is a chemical element with the chemical symbol Pt and an atomic number of 78. Its name is derived from the Spanish term platina del Pinto, which is literally translated into "little silver of the Pinto River." It is a dense, malleable, ductile, precious, gray-white transition metal...
oxide
Oxide
An oxide is a chemical compound that contains at least one oxygen atom in its chemical formula. Metal oxides typically contain an anion of oxygen in the oxidation state of −2....
catalyst at 500–600 °C and 40–60 atm pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to benzene and methane
Methane
Methane is a chemical compound with the chemical formula . It is the simplest alkane, the principal component of natural gas, and probably the most abundant organic compound on earth. The relative abundance of methane makes it an attractive fuel...
:
- C6H5CH3 + H2 → C6H6 + CH4
This irreversible reaction is accompanied by an equilibrium side reaction that produces
biphenyl
Biphenyl
Biphenyl is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula 2...
(aka diphenyl) at higher temperature:
- 2 +
If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen.
A typical reaction yield exceeds 95%. Sometimes, xylene
Xylene
Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...
s and heavier aromatics are used in place of toluene, with similar efficiency.
This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) processes.
Toluene disproportionation
Where a chemical complex has similar demands for both benzene and xyleneXylene
Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...
, then toluene disproportionation
Disproportionation
Disproportionation, also known as dismutation is used to describe a specific type of redox reaction in which a species is simultaneously reduced and oxidized so as to form two different products....
(TDP) may be an attractive alternative to the toluene hydrodealkylation. In the broad sense, 2 toluene molecules are reacted and the methyl groups rearranged from one toluene molecule to the other, yielding one benzene molecule and one xylene molecule.
Given that demand for para-xylene (p-xylene
P-Xylene
p-Xylene is an aromatic hydrocarbon, based on benzene with two methyl substituents. The “p” stands for para, identifying the location of the methyl groups as across from one another....
) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called Selective TDP (STDP) may be used. In this process, the xylene stream exiting the TDP unit is approximately 90% paraxylene. In some current catalytic systems, even the benzene-to-xylenes ratio is decreased (more xylenes) when the demand of xylenes is higher.
Steam cracking
Steam cracking is the process for producing ethyleneEthylene
Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...
and other alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
s from aliphatic hydrocarbons
Aliphatic compound
In organic chemistry, aliphatic compounds are acyclic or cyclic, non-aromatic carbon compounds.Thus, aliphatic compounds are opposite to aromatic compounds.- Structure :...
. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called pyrolysis gasoline
Pyrolysis gasoline
Pyrolysis gasoline or Pygas is a naphtha-range product with a high aromatics content. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called pyrolysis gasoline...
. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or distilled (in BTX process) to separate it into its components, including benzene.
Other sources
Trace amounts of benzene may result whenever carbonCarbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
-rich materials undergo incomplete combustion
Combustion
Combustion or burning is the sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat and conversion of chemical species. The release of heat can result in the production of light in the form of either glowing or a flame...
. It is produced in volcano
Volcano
2. Bedrock3. Conduit 4. Base5. Sill6. Dike7. Layers of ash emitted by the volcano8. Flank| 9. Layers of lava emitted by the volcano10. Throat11. Parasitic cone12. Lava flow13. Vent14. Crater15...
es and forest fires, and is also a component of cigarette
Cigarette
A cigarette is a small roll of finely cut tobacco leaves wrapped in a cylinder of thin paper for smoking. The cigarette is ignited at one end and allowed to smoulder; its smoke is inhaled from the other end, which is held in or to the mouth and in some cases a cigarette holder may be used as well...
smoke. Benzene is a principal product from the combustion of PVC (polyvinyl chloride).
Early uses
In the 19th and early-20th centuries, benzene was used as an after-shave lotion because of its pleasant smell. Prior to the 1920s, benzene was frequently used as an industrial solvent, especially for degreasing metal. As its toxicity became obvious, benzene was supplanted by other solvents, especially tolueneToluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
(methyl benzene), which has similar physical properties but is not as carcinogenic.
In 1903, Ludwig Roselius
Ludwig Roselius
Ludwig Roselius was a German coffee merchant and founder of the company KAFFEE HAG. He was born in Bremen and is credited with the development of commercial decaffeination of coffee...
popularized the use of benzene to decaffeinate
Caffeine
Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants...
coffee
Coffee
Coffee is a brewed beverage with a dark,init brooo acidic flavor prepared from the roasted seeds of the coffee plant, colloquially called coffee beans. The beans are found in coffee cherries, which grow on trees cultivated in over 70 countries, primarily in equatorial Latin America, Southeast Asia,...
. This discovery led to the production of Sanka
Sanka
Sanka is a brand of instant decaffeinated coffee, sold around the world, and was one of the earliest decaffeinated varieties. Sanka is distributed in the United States by Kraft Foods.-History:...
(the letters "ka" in the brand name stand for kaffein). This process was later discontinued. Benzene was historically used as a significant component in many consumer products such as Liquid Wrench, several paint strippers, rubber cements, spot removers and other hydrocarbon-containing products. Some ceased manufacture of their benzene-containing formulations in about 1950, while others continued to use benzene as a component or significant contaminant until the late 1970s when leukemia deaths were found associated with Goodyear's Pliofilm production operations in Ohio. Until the late 1970s, many hardware stores, paint stores, and other retail outlets sold benzene in small cans, such as quart size, for general-purpose use. Many students were exposed to benzene in school and university courses while performing laboratory experiments with little or no ventilation in many cases. This very dangerous practice has been almost totally eliminated.
As a gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...
(petrol) additive, benzene increases the octane rating
Octane rating
Octane rating or octane number is a standard measure of the anti-knock properties of a motor or aviation fuel. The higher the octane number, the more compression the fuel can withstand before detonating...
and reduces knocking
Engine knocking
Knocking in spark-ignition internal combustion engines occurs when combustion of the air/fuel mixture in the cylinder starts off correctly in response to ignition by the spark plug, but one or more pockets of air/fuel mixture explode outside the envelope of the normal combustion front.The...
. As a consequence, gasoline often contained several percent benzene before the 1950s, when tetraethyl lead replaced it as the most widely-used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as a gasoline additive in some nations. In the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
, concern over its negative health effects and the possibility of benzene's entering the groundwater
Groundwater
Groundwater is water located beneath the ground surface in soil pore spaces and in the fractures of rock formations. A unit of rock or an unconsolidated deposit is called an aquifer when it can yield a usable quantity of water. The depth at which soil pore spaces or fractures and voids in rock...
have led to stringent regulation of gasoline's benzene content, with limits typically around 1%. European petrol specifications now contain the same 1% limit on benzene content. The United States Environmental Protection Agency has new regulations that will lower the benzene content in gasoline to 0.62% in 2011.
Current uses
Today, benzene is used mainly as an intermediate to make other chemicals. Its most widely-produced derivatives include styrene, which is used to make polymers and plastics, phenolPhenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
for resins and adhesives (via cumene
Cumene
Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C...
), and cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
, which is used in the manufacture of Nylon. Smaller amounts of benzene are used to make some types of rubber
Rubber
Natural rubber, also called India rubber or caoutchouc, is an elastomer that was originally derived from latex, a milky colloid produced by some plants. The plants would be ‘tapped’, that is, an incision made into the bark of the tree and the sticky, milk colored latex sap collected and refined...
s, lubricant
Lubricant
A lubricant is a substance introduced to reduce friction between moving surfaces. It may also have the function of transporting foreign particles and of distributing heat...
s, dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....
s, detergent
Detergent
A detergent is a surfactant or a mixture of surfactants with "cleaning properties in dilute solutions." In common usage, "detergent" refers to alkylbenzenesulfonates, a family of compounds that are similar to soap but are less affected by hard water...
s, drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
s, explosives, napalm
Napalm
Napalm is a thickening/gelling agent generally mixed with gasoline or a similar fuel for use in an incendiary device, primarily as an anti-personnel weapon...
, and pesticide
Pesticide
Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...
s.
In both the US and Europe, 50% of benzene is used in the production of ethylbenzene
Ethylbenzene
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. This aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a common plastic material....
/styrene, 20% is used in the production of cumene
Cumene
Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C...
, and about 15% of benzene is used in the production of cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
(eventually to nylon
Nylon
Nylon is a generic designation for a family of synthetic polymers known generically as polyamides, first produced on February 28, 1935, by Wallace Carothers at DuPont's research facility at the DuPont Experimental Station...
).
Currently, the production of and demand for benzene in the Middle East register the greatest increases worldwide. It will probably see its share of the global supply and demand expand by 3.7 and 3.3 percentage points, respectively, until 2018. However, the Asia-Pacific region will continue to dominate the market and account for almost half of the global demand.
In laboratory research, toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
is now often used as a substitute for benzene. The solvent-properties of the two are similar, but toluene is less toxic and has a wider liquid range.
Benzene has been used as a basic research tool in a variety of experiments including analysis of a two-dimensional gas
Two-dimensional gas
A two-dimensional gas is a collection of N objects which are constrained to move in a planar or other two-dimensional space in a gaseous state. The objects can be: ideal gas elements such as rigid disks undergoing elastic collisions; elementary particles, or any object in physics which obeys laws...
.
File:Benzene_uses.png|center|Major commodity chemicals and polymers derived from benzene. Clicking on the image loads the appropriate article|600px|thumb
rect 39 660 435 807 Benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
rect 665 60 1062 207 Ethylbenzene
Ethylbenzene
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. This aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a common plastic material....
rect 665 426 1062 579 Cumene
Cumene
Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C...
rect 665 795 1062 942 Cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
rect 665 1161 1062 1317 Aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
rect 665 1533 1062 1686 Chlorobenzene
Chlorobenzene
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.-Uses:...
rect 1215 345 1614 495 Acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
rect 1215 636 1614 783 Phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
rect 1764 57 2163 210 Styrene
rect 1764 432 2163 585 Bisphenol A
Bisphenol A
Bisphenol A is an organic compound with two phenol functional groups. It is used to make polycarbonate plastic and epoxy resins, along with other applications....
rect 1764 1083 2163 1233 Adipic acid
Adipic acid
Adipic acid is the organic compound with the formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon...
rect 1764 1332 2163 1482 Caprolactam
Caprolactam
Caprolactam is an organic compound with the formula 5CNH. This colourless solid is a lactam or a cyclic amide of caproic acid. Approximately 2 billion kilograms are produced annually...
rect 2313 57 2712 207 Polystyrene
Polystyrene
Polystyrene ) also known as Thermocole, abbreviated following ISO Standard PS, is an aromatic polymer made from the monomer styrene, a liquid hydrocarbon that is manufactured from petroleum by the chemical industry...
rect 2313 315 2712 462 Polycarbonate
Polycarbonate
PolycarbonatePhysical PropertiesDensity 1.20–1.22 g/cm3Abbe number 34.0Refractive index 1.584–1.586FlammabilityV0-V2Limiting oxygen index25–27%Water absorption – Equilibrium0.16–0.35%Water absorption – over 24 hours0.1%...
rect 2313 570 2712 717 Epoxy resin
rect 2313 822 2712 975 Phenolic resin
rect 2313 1083 2712 1233 Nylon 6-6
Nylon 6-6
Nylon 6-6, also referred to as nylon 6,6, is a type of nylon. Nylon comes in many types, the two most common for textile and plastics industries are: nylon 6 and nylon 6,6.- Composition :...
rect 2313 1335 2712 1485 Nylon 6
Nylon 6
Nylon 6 or polycaprolactam is a polymer developed by Paul Schlack at IG Farben to reproduce the properties of nylon 6,6 without violating the patent on its production. Unlike most other nylons, nylon 6 is not a condensation polymer, but instead is formed by ring-opening polymerization. This makes...
desc bottom-left
Reactions
The most common reactions that benzene undergoes are substitution reactions.- Electrophilic aromatic substitutionElectrophilic aromatic substitutionElectrophilic aromatic substitution EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile...
is a general method of derivatizing benzene. Benzene is sufficiently nucleophilicNucleophileA nucleophile is a species that donates an electron-pair to an electrophile to form a chemical bond in a reaction. All molecules or ions with a free pair of electrons can act as nucleophiles. Because nucleophiles donate electrons, they are by definition Lewis bases.Nucleophilic describes the...
that it undergoes substitution by acylium ions or alkyl carbocationCarbocationA carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer valence shell instead of the eight valence electrons that ensures maximum stability . Therefore carbocations are often reactive,...
s to give substituted derivatives.
- The Friedel-Crafts alkylation involves the alkylationAlkylationAlkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...
of benzene (and many other aromatic rings) using an alkyl halide in the presence of a strong Lewis acid catalyst.
- The Friedel-Crafts acylation is a specific example of electrophilic aromatic substitutionElectrophilic aromatic substitutionElectrophilic aromatic substitution EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile...
. The reaction involves the acylationAcylationIn chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
of benzene (or many other aromatic rings) with an acyl chlorideAcyl chlorideIn organic chemistry, an acyl chloride is an organic compound with the functional group -CO-Cl. Their formula is usually written RCOCl, where R is a side chain. They are usually considered to be reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride,...
using a strong Lewis acidLewis acid]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...
catalyst such as aluminium chlorideAluminium chlorideAluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...
or Iron(III) chlorideIron(III) chlorideIron chloride, also called ferric chloride, is an industrial scale commodity chemical compound, with the formula FeCl3. The colour of iron chloride crystals depends on the viewing angle: by reflected light the crystals appear dark green, but by transmitted light they appear purple-red...
, which act as a halogen carrier.
- SulfonationAromatic sulfonationAromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution.-Mechanism:...
. The most common method involves mixing sulfuric acid with Sulfur trioxideSulfur trioxideSulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain. It is prepared on massive scales as a precursor to sulfuric acid.-Structure and bonding:Gaseous SO3 is a trigonal planar molecule of...
, a mixture called fuming sulfuric acid. The sulfuric acid protonates either itself or Sulfur trioxideSulfur trioxideSulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain. It is prepared on massive scales as a precursor to sulfuric acid.-Structure and bonding:Gaseous SO3 is a trigonal planar molecule of...
, giving the sulfur atom a permanent, rather than resonance stabilized positive formal charge. This molecule is electrophilic enough to be attacked by the aromatic ring, the electrophilic aromatic substitution occurs. - NitrationNitrationNitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
: Benzene undergoes nitration with nitronium ions (NO2+) as the electrophile. Thus, warming benzene at 50–55 °C, with a combination of concentrated sulfuric and nitric acid to produce the electrophile, gives nitrobenzene. - HydrogenationHydrogenationHydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
(reduction): Benzene and derivatives convert to cyclohexane and derivatives when treated with hydrogen at 450 K and 10 atm of pressure with a finely divided nickelNickelNickel is a chemical element with the chemical symbol Ni and atomic number 28. It is a silvery-white lustrous metal with a slight golden tinge. Nickel belongs to the transition metals and is hard and ductile...
catalyst. - Benzene is an excellent ligandLigandIn coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...
in the organometallicComplex (chemistry)In chemistry, a coordination complex or metal complex, is an atom or ion , bonded to a surrounding array of molecules or anions, that are in turn known as ligands or complexing agents...
chemistry of low-valent metals. Important examples include the sandwich and half-sandwich complexes, respectively, Cr(C6H6)2Bis(benzene)chromiumBischromium is the organometallic compound with the formula Cr2. It is sometimes called dibenzenechromium. The compound played an important role in the development of sandwich compounds in organometallic chemistry and is the prototypical complex containg two arene ligands.-Preparation:The...
and [RuCl2(C6H6)]2.
Environmental transformation
Even if it is not a common substrate for the metabolism of organisms, benzene could be oxidized by both bacteriaBacteria
Bacteria are a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals...
and eukaryote
Eukaryote
A eukaryote is an organism whose cells contain complex structures enclosed within membranes. Eukaryotes may more formally be referred to as the taxon Eukarya or Eukaryota. The defining membrane-bound structure that sets eukaryotic cells apart from prokaryotic cells is the nucleus, or nuclear...
s.
In bacteria, dioxygenase
Dioxygenase
In molecular biology, a dioxygenase is an enzyme which catalyses the incorporation of both atoms of molecular oxygen into substrates using a variety of reaction mechanisms. Cleavage of aromatic rings is one of the most important functions of dioxygenases, which play key roles in the degradation of...
enzyme can add an oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
molecule to the ring, and the unstable product is immediately reduced (by NADH) to a cyclic diol
Diol
A diol or glycol is a chemical compound containing two hydroxyl groups A geminal diol has two hydroxyl groups bonded to the same atom...
with two double bonds, breaking the aromaticity.
Next, the diol is newly reduced by NADH to catechol.
The catechol is then metabolized to acetyl CoA and succinyl CoA, used by organisms mainly in the Krebs Cycle for energy production.
Health effects
Benzene causes cancer and other illnesses. Benzene is a "notorious cause" of bone marrow failure. "Vast quantities of epidemiologic, clinical, and laboratory data" link benzene to aplastic anemia, acute leukemia, and bone marrow abnormalities.The American Petroleum Institute
American Petroleum Institute
The American Petroleum Institute, commonly referred to as API, is the largest U.S trade association for the oil and natural gas industry...
(API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero." The US Department of Health and Human Services (DHHS) classifies benzene as a human carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
. Long-term exposure to excessive levels of benzene in the air causes leukemia
Leukemia
Leukemia or leukaemia is a type of cancer of the blood or bone marrow characterized by an abnormal increase of immature white blood cells called "blasts". Leukemia is a broad term covering a spectrum of diseases...
, a potentially fatal cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
of the blood-forming organs, in susceptible individuals. In particular, Acute myeloid leukemia
Acute myeloid leukemia
Acute myeloid leukemia , also known as acute myelogenous leukemia, is a cancer of the myeloid line of blood cells, characterized by the rapid growth of abnormal white blood cells that accumulate in the bone marrow and interfere with the production of normal blood cells. AML is the most common acute...
or acute non-lymphocytic leukaemia (AML & ANLL) is not disputed to be caused by benzene. IARC rated benzene as "known to be carcinogenic to humans" (Group 1).
Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions. About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from exposure to tobacco smoke.
Vapors from products that contain benzene, such as glues, paints, furniture wax, and detergents, can also be a source of exposure, although many of these have been modified or reformulated since the late 1970s to eliminate or reduce the benzene content. Air around hazardous waste sites or gas stations may contain higher levels of benzene. Because petroleum hydrocarbon products are complex mixtures of chemicals, risk assessments for these products, in general, focus on specific toxic constituents. The petroleum constituents of primary interest to human health have been the aromatic hydrocarbons (i.e., benzene, ethylbenzene, toluene, and xylenes). OSHA requires that a mixture "shall be assumed to present a carcinogenic hazard if it contains a component in concentrations of 0.1% or greater, which is considered to be a carcinogen.
The short-term breathing of high levels of benzene can result in death
Death
Death is the permanent termination of the biological functions that sustain a living organism. Phenomena which commonly bring about death include old age, predation, malnutrition, disease, and accidents or trauma resulting in terminal injury....
; low levels can cause drowsiness, dizziness, rapid heart rate, headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...
s, tremors, confusion, and unconsciousness. Eating or drinking foods containing high levels of benzene can cause vomiting, irritation of the stomach
Stomach
The stomach is a muscular, hollow, dilated part of the alimentary canal which functions as an important organ of the digestive tract in some animals, including vertebrates, echinoderms, insects , and molluscs. It is involved in the second phase of digestion, following mastication .The stomach is...
, dizziness, sleepiness, convulsions, and death.
The major effects of benzene are manifested via chronic
Chronic (medicine)
A chronic disease is a disease or other human health condition that is persistent or long-lasting in nature. The term chronic is usually applied when the course of the disease lasts for more than three months. Common chronic diseases include asthma, cancer, diabetes and HIV/AIDS.In medicine, the...
(long-term) exposure through the blood
Blood
Blood is a specialized bodily fluid in animals that delivers necessary substances such as nutrients and oxygen to the cells and transports metabolic waste products away from those same cells....
. Benzene damages the bone marrow
Bone marrow
Bone marrow is the flexible tissue found in the interior of bones. In humans, bone marrow in large bones produces new blood cells. On average, bone marrow constitutes 4% of the total body mass of humans; in adults weighing 65 kg , bone marrow accounts for approximately 2.6 kg...
and can cause a decrease in red blood cells, leading to anemia
Anemia
Anemia is a decrease in number of red blood cells or less than the normal quantity of hemoglobin in the blood. However, it can include decreased oxygen-binding ability of each hemoglobin molecule due to deformity or lack in numerical development as in some other types of hemoglobin...
. It can also cause excessive bleeding and depress the immune system
Immune system
An immune system is a system of biological structures and processes within an organism that protects against disease by identifying and killing pathogens and tumor cells. It detects a wide variety of agents, from viruses to parasitic worms, and needs to distinguish them from the organism's own...
, increasing the chance of infection
Infection
An infection is the colonization of a host organism by parasite species. Infecting parasites seek to use the host's resources to reproduce, often resulting in disease...
. Benzene causes leukemia and is associated with other blood cancers and pre-cancers of the blood.
Human exposure to benzene is a global health problem. Benzene targets liver, kidney, lung, heart and the brain and can cause DNA
DNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
strand breaks, chromosomal damage, etc. Benzene causes cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
in both animals and humans. Benzene was first reported to induce cancer in humans in the 1920s. The chemical industry claims it was not until 1979 that the cancer-inducing properties were determined "conclusively" in humans, despite many references to this fact in the medical literature. Industry exploited this "discrepancy" and tried to discredit animal studies that showed that benzene causes cancer, saying that they are not relevant to humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.
Some women having breathed high levels of benzene for many months had irregular menstrual
Menstruation
Menstruation is the shedding of the uterine lining . It occurs on a regular basis in sexually reproductive-age females of certain mammal species. This article focuses on human menstruation.-Overview:...
periods and a decrease in the size of their ovaries. Benzene exposure has been linked directly to the neural birth defects spina bifida and anencephaly
Anencephaly
Anencephaly is a cephalic disorder that results from a neural tube defect that occurs when the cephalic end of the neural tube fails to close, usually between the 23rd and 26th day of pregnancy, resulting in the absence of a major portion of the brain, skull, and scalp...
. Men exposed to high levels of benzene are more likely to have an abnormal amount of chromosomes in their sperm, which impacts fertility and fetal development.
Animal studies have shown low birth weights, delayed bone formation, and bone marrow damage when pregnant animals breathed benzene.
Benzene has been connected to a rare form of kidney cancer in two separate studies, one involving tank truck drivers, and the other involving seamen on tanker vessels, both carrying benzene-laden chemicals.
Exposure to benzene
Workers in various industries that make or use benzene may be at risk for being exposed to high levels of this carcinogenic chemical. Industries that involve the use of benzene include the rubberRubber
Natural rubber, also called India rubber or caoutchouc, is an elastomer that was originally derived from latex, a milky colloid produced by some plants. The plants would be ‘tapped’, that is, an incision made into the bark of the tree and the sticky, milk colored latex sap collected and refined...
industry, oil refineries, coke and chemical plants, shoe manufacturers, and gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...
-related industries. Downstream petroleum industry operations include the following categories: refinery, pipeline, marine, rail, bulk terminals and trucks, service stations, underground storage tanks, tank cleaning, and site characterization and remediation.
Exposure of the general population to benzene mainly occurs through breathing, the major sources of benzene being tobacco smoke (about 50%) as well as automobile service stations, exhaust from motor vehicles and industrial emissions (about 20% altogether). Vapors (or gases) from products that contain benzene, such as glues, paints, furniture wax, and detergents, can also be a source of exposure. The average smoker (32 cigarettes per day) takes in about 1.8 milligrams (mg) of benzene per day. This amount is about 10 times the average daily intake of benzene by nonsmokers.
In 1987, OSHA
Occupational Safety and Health Administration
The United States Occupational Safety and Health Administration is an agency of the United States Department of Labor. It was created by Congress of the United States under the Occupational Safety and Health Act, signed by President Richard M. Nixon, on December 29, 1970...
estimated that about 237,000 workers in the United States were potentially exposed to benzene, but it is not known if this number has substantially changed since then.
Water and soil contamination
Soil contamination
Soil contamination or soil pollution is caused by the presence of xenobiotic chemicals or other alteration in the natural soil environment....
are important pathways of concern for transmission of benzene contact. In the US alone, there are approximately 100,000 different sites that have benzene soil or groundwater contamination. In 2005, the water supply to the city of Harbin
Harbin
Harbin ; Manchu language: , Harbin; Russian: Харби́н Kharbin ), is the capital and largest city of Heilongjiang Province in Northeast China, lying on the southern bank of the Songhua River...
in China with a population of almost nine million people, was cut off because of a major benzene exposure. Benzene leaked into the Songhua River
Songhua River
The Songhua or Sunggari River is a river in Northeast China, and is the largest tributary of the Heilong River , flowing about from Changbai Mountains through Jilin and Heilongjiang provinces. The river drains of land, and has an annual discharge of .As the Second Songhua River, it joins the...
, which supplies drinking water to the city, after an explosion at a China National Petroleum Corporation (CNPC) factory in the city of Jilin on 13 November.
In March 2006, the official Food Standards Agency
Food Standards Agency
The Food Standards Agency is a non-ministerial government department of the Government of the United Kingdom. It is responsible for protecting public health in relation to food throughout the United Kingdom and is led by a board appointed to act in the public interest...
in Britain
United Kingdom
The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...
conducted a survey of 150 brands of soft drinks. It found that four contained benzene levels above World Health Organization
World Health Organization
The World Health Organization is a specialized agency of the United Nations that acts as a coordinating authority on international public health. Established on 7 April 1948, with headquarters in Geneva, Switzerland, the agency inherited the mandate and resources of its predecessor, the Health...
limits. The affected batches were removed from sale. (See also benzene in soft drinks
Benzene in soft drinks
Benzene in soft drinks is of some concern due to the carcinogenic nature of the benzene molecule. This contamination is a public health concern and has caused significant outcry among environmental and health advocates. Benzene levels are regulated in drinking water nationally and internationally,...
).
Benzene exposure limits
The United States Environmental Protection AgencyUnited States Environmental Protection Agency
The U.S. Environmental Protection Agency is an agency of the federal government of the United States charged with protecting human health and the environment, by writing and enforcing regulations based on laws passed by Congress...
has set a maximum contaminant level
Maximum Contaminant Level
Maximum Contaminant Levels are standards that are set by the United States Environmental Protection Agency for drinking water quality. An MCL is the legal threshold limit on the amount of a substance that is allowed in public water systems under the Safe Drinking Water Act...
(MCL) for benzene in drinking water at 0.005 mg/L (5 ppb), as promulgated via the National Primary Drinking Water Regulations. This regulation is based on preventing benzene leukemogenesis. The maximum contaminant level goal (MCLG), a nonenforceable health goal that would allow an adequate margin of safety for the prevention of adverse effects, is zero benzene concentration in drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported to the EPA.
The US Occupational Safety and Health Administration
Occupational Safety and Health Administration
The United States Occupational Safety and Health Administration is an agency of the United States Department of Labor. It was created by Congress of the United States under the Occupational Safety and Health Act, signed by President Richard M. Nixon, on December 29, 1970...
(OSHA) has set a permissible exposure limit of 1 part of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The short term exposure limit for airborne benzene is 5 ppm for 15 minutes. These legal limits were based on studies demonstrating compelling evidence of health risk to workers exposed to benzene. The risk from exposure to 1 ppm for a working lifetime has been estimated as 5 excess leukemia deaths per 1,000 employees exposed. (This estimate assumes no threshold for benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.
The National Institute for Occupational Safety and Health
National Institute for Occupational Safety and Health
The National Institute for Occupational Safety and Health is the United States’ federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the Centers for Disease Control and Prevention within the U.S...
(NIOSH) revised the Immediately Dangerous to Life or Health (IDLH) concentration for benzene to 500 ppm. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment [NIOSH 2004]. The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable breathing apparatus providing maximum worker protection is permitted [NIOSH 2004]. In September 1995, NIOSH issued a new policy for developing recommended exposure limits (RELs) for substances, including carcinogens. Because benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm. The NIOSH STEL (15 min) is 1 ppm.
American Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.
Under New Jersey's Right-to-Know law, respiratory protection for benzene is discussed. As stated, improper use of respirators is dangerous. Respirators should only be used when there is a written respiratory program in place as described in the OSHA Respiratory Protection Standard (29 CFR 1910.134). The employer is to develop and implement a written respiratory protection program with required worksite-specific procedures and elements for required respirator use. This program must be administered by a suitably trained program administrator. Employers must use the assigned protection factors (APF) listed in Table 1 of 29 CFR 1910.134 to select a respirator that meets or exceeds the required level of employee protection. For benzene:
- If there is a potential for exposure to 0.1 ppm, a NIOSH-approved half face respirator must be worn with an organic vapor cartridge (APF 10).
- If there is a potential for exposure to 0.5 ppm, a NIOSH-approved full face respirator must be worn with an organic vapor cartridge (APF 50).
- Where the potential exists for exposure to over 5 ppm, a NIOSH-approved air-supplied respirator with a full facepiece operated under pressure-demand or other positive-pressure mode must be used (APF 1,000).
Exposure monitoring
Airborne exposure monitoring for benzene must be conducted in order to properly assess personal exposures and effectiveness of engineering controls. Initial exposure monitoring should be conducted by an industrial hygienist or person specifically trained and experienced in sampling techniques. Contact an AIHA Accredited Laboratory for advice on sampling methods.Each employer with a place of employment where occupational exposures to benzene occur shall monitor each of these workplaces and work operations to determine accurately the airborne concentrations of benzene to which employees may be exposed. Representative 8-hour TWA employee exposures need to be determined on the basis of one sample or samples representing the full shift exposure for each job classification in each work area. Unless air samples are taken frequently, the employer does not know the concentration and would not know how much of a protection factor is needed.
In providing consultation on work safety during oil clean-up operations following the Deepwater Horizon accident, OSHA has worked with a number of other government agencies to protect Gulf cleanup workers. OSHA partnered with the NIOSH to issue "Interim Guidance for Protecting Deepwater Horizon Response Workers and Volunteers" and recommend measures that should be taken to protect workers from a variety of different health hazards that these workers face. OSHA conceded that it recognizes that most of its PELs are outdated and inadequate measures of worker safety. In characterizing worker exposure, OSHA instead relies on more up-to-date recommended protective limits set by organizations such as NIOSH, the ACGIH, and the American Industrial Hygiene Association (AIHA), and not on the older, less protective PELS. Results of air monitoring are compared to the lowest known Occupational Exposure Limit for the listed contaminant for purposes of risk assessment and protective equipment recommendations.
Biomarkers of exposure
Several tests can determine exposure to benzene. Benzene itself can be measured in breath, blood or urine, but such testing is usually limited to the first 24 hours post-exposure due to the relatively rapid removal of the chemical by exhalation or biotransformation. Most persons in developed countries have measureable baseline levels of benzene and other aromatic petroleum hydrocarbons in their blood. In the body, benzene is enzymatically converted to a series of oxidation products including muconic acidMuconic acid
Muconic acid is a dicarboxylic acid. There are three isomeric forms designated trans,trans-muconic acid, cis,trans-muconic acid, and cis,cis-muconic acid which differ by the geometry around the double bonds....
, phenylmercapturic acid, phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
, catechol, hydroquinone
Hydroquinone
Hydroquinone, also benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, having the chemical formula C6H42. Its chemical structure, shown in the table at right, has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid...
and 1,2,4-trihydroxybenzene
Hydroxyquinol
Hydroxyquinol is a benzenetriol.It is a catechin biodegradation product formed by Bradyrhizobium japonicum.Hydroxyquinol 1,2-dioxygenase is an enzyme that uses hydroxyquinol and O2 to produce 3-hydroxy-cis,cis-muconate....
. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they may still be present for some days after exposure has ceased. The current ACGIH biological exposure limits for occupational exposure are 500 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.
Methods of excretion
Most inhaled benzene is not metabolized. Inhaled benzene is primarily expelled unchanged through exhalation. In a human study 16.4 to 41.6% of retained benzene was eliminated through the lungs within five to seven hours after a two- to three-hour exposure to 47 to 110 ppm and only 0.07 to 0.2% of the remaining benzene was excreted unchanged in the urine. After exposure to 63 to 405 mg/m3 of benzene for 1 to 5 hours, 51 to 87% was excreted in the urine as phenol over a period of 23 to 50 hours. In another human study, 30% of absorbed dermally applied benzene, which is primarily metabolized in the liver, was excreted as phenol in the urine.Molecular toxicology
The paradigm of toxicological assessment of benzene is slowly shifting towards the domain of molecular toxicology as it allows understanding of fundamental biological mechanisms in a better way. GlutathioneGlutathione
Glutathione is a tripeptide that contains an unusual peptide linkage between the amine group of cysteine and the carboxyl group of the glutamate side-chain...
seems to play an important role by protecting against benzene-induced DNA breaks and it is being identified as a new biomarker for exposure and effect. Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple myeloma caused by chronic exposure. These aberrations can be monitored using fluorescent in situ hybridization
Fluorescent in situ hybridization
FISH is a cytogenetic technique developed by biomedical researchers in the early 1980s that is used to detect and localize the presence or absence of specific DNA sequences on chromosomes. FISH uses fluorescent probes that bind to only those parts of the chromosome with which they show a high...
(FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity. Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects of benzene exposure. Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase (EPHX) and deletion of the glutathione S-transferase T1 (GSTT1) showed a greater frequency of DNA single-stranded breaks.
Biological oxidation and carcinogenic activity
One way of understanding the carcinogenic effects of benzene is by examining the products of biological oxidation. Pure benzene, for example, oxidizes in the body to produce an epoxide, benzene oxide, which is not excreted readily and can interact with DNA to produce harmful mutations.Summary
According to the Agency for Toxic Substances and Disease RegistryAgency for Toxic Substances and Disease Registry
The Agency for Toxic Substances and Disease Registry is a federal public health agency within the United States Department of Health and Human Services. The agency focuses on minimizing human health risks associated with exposure to hazardous substances...
(ATSDR) (2007), benzene is both an anthropogenically produced and naturally occurring chemical from processes that include: volcanic eruptions, wild fires, synthesis of chemicals such as phenol, production of synthetic fibers, and fabrication of rubbers, lubricants, pesticides, medications, and dyes. The major sources of benzene exposure are tobacco smoke, automobile service stations, exhaust from motor vehicles, and industrial emissions; however, ingestion and dermal absorption of benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the urine. Measurement of air and water levels of benzene is accomplished through collection via activated charcoal tubes, which are then analyzed with a gas chromatograph. The measurement of benzene in humans can be accomplished via urine, blood, and breath tests; however, all of these have their limitations because benzene is rapidly metabolized in the human body into by-products called metabolites.
OSHA regulates levels of benzene in the workplace. The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. Because benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit of 0.1 ppm.
See also
- Industrial Union Department v. American Petroleum InstituteIndustrial Union Department v. American Petroleum InstituteIndustrial Union Department v. American Petroleum Institute , , was a case heard before the United States Supreme Court. This case represented a challenge to the OSHA practice of regulating carcinogens by setting the exposure limit "at the lowest technologically feasible level that will not impair...
- Benzene in soft drinksBenzene in soft drinksBenzene in soft drinks is of some concern due to the carcinogenic nature of the benzene molecule. This contamination is a public health concern and has caused significant outcry among environmental and health advocates. Benzene levels are regulated in drinking water nationally and internationally,...
- BTEXBTEXBTEX is an acronym that stands for benzene, toluene, ethylbenzene, and xylenes. These compounds are some of the volatile organic compounds found in petroleum derivatives such as petrol . Toluene, ethylbenzene, and xylenes have harmful effects on the central nervous system.BTEX compounds are...
External links
- Benzene (www.eco-usa.net)
- International Chemical Safety Card 0015
- USEPA Summary of Benzene Toxicity
- NIOSH Pocket Guide to Chemical Hazards
- Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene
- Video Podcast of Sir John Cadogan giving a lecture on Benzene since Faraday, in 1991
- Substance profile
- U.S. National Library of Medicine: ChemIDplus – Benzene
- NLM Hazardous Substances Databank – Benzene