Propan-1-ol
Encyclopedia
1-Propanol is a primary alcohol
with the molecular formula of C3H8O, and a structural formula of CH3CH2CH2OH. It is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, n-propanol, or simply propanol. It is an isomer
of isopropanol (2-propanol). It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.
. Thus it can be converted to alkyl halides
; for example red phosphorus
and iodine
produce n-propyl iodide
in 80% yield, while PCl3
with catalytic ZnCl2
gives 1-chloropropane. Reaction with acetic acid
in the presence of an H2SO4
catalyst under Fischer esterification
conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7
and H2SO4 gives only a 36% yield of propionaldehyde
, and therefore for this type of reaction higher yielding methods using PCC
or the Swern oxidation
are recommended. Oxidation with chromic acid
yields propionic acid
.
s when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of propanol.
1-Propanol is manufactured by catalytic hydrogenation
of propionaldehyde
. The propionaldehyde is itself produced via the oxo process, by hydroformylation
of ethylene
using carbon monoxide
and hydrogen
in the presence of a catalyst such as cobalt octacarbonyl
or a rhodium
complex.
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide
with moist Ag2O
.
of fusel oil.
in its effects on human body, but 2-4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid
. Effects include alcoholic intoxication and high anion gap metabolic acidosis
. As of 2011, only one case of lethal 1-propanol poisoning was reported.
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
with the molecular formula of C3H8O, and a structural formula of CH3CH2CH2OH. It is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, n-propanol, or simply propanol. It is an 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 isopropanol (2-propanol). It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.
Chemical properties
1-Propanol shows the normal reactions of a primary alcoholPrimary alcohol
A primary alcohol is an alcohol which has the hydroxyl radical connected to a primary carbon. It can also be defined as a molecule containing a “–CH2OH” group.Examples include ethanol and butanol....
. Thus it can be converted to alkyl halides
Haloalkane
The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and...
; for example red phosphorus
Phosphorus
Phosphorus is the chemical element that has the symbol P and atomic number 15. A multivalent nonmetal of the nitrogen group, phosphorus as a mineral is almost always present in its maximally oxidized state, as inorganic phosphate rocks...
and iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
produce n-propyl iodide
N-Propyl iodide
n-Propyl iodide is a colorless, flammable chemical compound. It has the chemical formula C3H7I and is prepared by heating n-propyl alcohol with iodine and phosphorus....
in 80% yield, while PCl3
Phosphorus trichloride
Phosphorus trichloride is a chemical compound of phosphorus and chlorine, having chemical formula PCl3. Its shape is trigonal pyramidal. It is the most important of the three phosphorus chlorides. It is an important industrial chemical, being used for the manufacture of organophosphorus compounds...
with catalytic ZnCl2
Zinc chloride
Zinc chloride is the name of chemical compound with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. ZnCl2 itself is hygroscopic and even deliquescent. Samples should therefore be protected from...
gives 1-chloropropane. Reaction with acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...
in the presence of an H2SO4
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
catalyst under Fischer esterification
Fischer esterification
Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer and Arthur Speier in 1895. Most carboxylic acids are suitable for the...
conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7
Sodium dichromate
Sodium dichromate is the chemical compound with the formula Na2Cr2O7. Usually, however, the salt is handled as its dihydrate Na2Cr2O7·2H2O. Virtually all chromium ore is processed via conversion to sodium dichromate. In this way, many millions of kilograms of sodium dichromate are produced...
and H2SO4 gives only a 36% yield of propionaldehyde
Propionaldehyde
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturated 3-carbon aldehyde and is a structural isomer of acetone...
, and therefore for this type of reaction higher yielding methods using PCC
Pyridinium chlorochromate
Pyridinium chlorochromate is a reddish orange solid reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Pyridinium chlorochromate, or PCC, will not fully oxidize a primary alcohol to the carboxylic acid as does the Jones reagent. A disadvantage to using PCC is...
or the Swern oxidation
Swern oxidation
The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine...
are recommended. Oxidation with chromic acid
Chromic acid
The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixture for glass. Chromic acid may also refer to the...
yields propionic acid
Propionic acid
Propanoic acid is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent odor...
.
Preparation
1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acidAmino acid
Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...
s when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of propanol.
1-Propanol is manufactured by catalytic hydrogenation
Hydrogenation
Hydrogenation, 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...
of propionaldehyde
Propionaldehyde
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturated 3-carbon aldehyde and is a structural isomer of acetone...
. The propionaldehyde is itself produced via the oxo process, by hydroformylation
Hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond...
of ethylene
Ethylene
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...
using carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
and 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...
in the presence of a catalyst such as cobalt octacarbonyl
Dicobalt octacarbonyl
Dicobalt octacarbonyl is the inorganic compound Co28. This metal carbonyl is a reagent and catalyst in organometallic chemistry and organic synthesis. It is used as a catalyst for hydroformylation, the conversion of alkenes to aldehydes....
or a rhodium
Rhodium
Rhodium is a chemical element that is a rare, silvery-white, hard and chemically inert transition metal and a member of the platinum group. It has the chemical symbol Rh and atomic number 45. It is composed of only one isotope, 103Rh. Naturally occurring rhodium is found as the free metal, alloyed...
complex.
- H2C=CH2 + CO + H2 → CH3CH2CH=O
- CH3CH2CH=O + H2 → CH3CH2CH2OH
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide
N-Propyl iodide
n-Propyl iodide is a colorless, flammable chemical compound. It has the chemical formula C3H7I and is prepared by heating n-propyl alcohol with iodine and phosphorus....
with moist Ag2O
Silver(I) oxide
Silver oxide is the chemical compound with the formula Ag2O. It is a fine black or dark brown powder that is used to prepare other silver compounds.-Preparation:...
.
History
1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillationFractional distillation
Fractional distillation is the separation of a mixture into its component parts, or fractions, such as in separating chemical compounds by their boiling point by heating them to a temperature at which several fractions of the compound will evaporate. It is a special type of distillation...
of fusel oil.
Safety
1-Propanol is thought to be similar to ethanolEthanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
in its effects on human body, but 2-4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid
Propionic acid
Propanoic acid is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent odor...
. Effects include alcoholic intoxication and high anion gap metabolic acidosis
High anion gap metabolic acidosis
High anion gap metabolic acidosis is a form of metabolic acidosis characterized by a high anion gap.The list of agents that cause high anion gap metabolic acidosis is similar to but broader than the list of agents that cause a serum osmolal gap.-"Mudpiles":...
. As of 2011, only one case of lethal 1-propanol poisoning was reported.