Hydrogen cyanide
Encyclopedia
Hydrogen cyanide is a chemical compound
with chemical formula
HCN. It is a color
less, extremely poison
ous liquid that boils
slightly above room temperature
at 26 °C (78.8 °F). Hydrogen cyanide is a linear molecule, with a triple bond
between carbon and nitrogen. A minor tautomer
of HCN is HNC, hydrogen isocyanide
.
Hydrogen cyanide is weakly acid
ic with a pKa
of 9.2. It partly ionizes
in water solution to give the cyanide
anion, CN–. A solution
of hydrogen cyanide
in water is called hydrocyanic acid. The salts of hydrogen cyanide are known as cyanides.
HCN has a faint, bitter, burnt almond
-like odor
that only some people are able to detect
owing to a gene
tic trait. The volatile
compound has been used as inhalation rodenticide and human poison. Cyanide ions interfere with iron-containing respiratory enzymes.
HCN is produced on an industrial scale and is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.
) which had been known from 1704 but whose structure was unknown. It is now known to be a coordination polymer with a complex structure and an empirical formula of hydrated ferric ferrocyanide. In 1752, the French chemist Pierre Macquer
made the important step of showing that Prussian blue could be converted to iron oxide
plus a volatile component and that these could be used to reconstitute the dye. The new component was what we now know as hydrogen cyanide. Following Macquer's lead, it was first isolated from Prussian blue in pure form and characterized about 1783 by the Swedish chemist Carl Wilhelm Scheele
, and was eventually given the German name Blausäure (literally "Blue acid") because of its acidic nature in water and its derivation from Prussian blue. In English it became known popularly as Prussic acid.
In 1787 the French chemist Claude Louis Berthollet
showed that Prussic acid did not contain oxygen, an important contribution to acid theory, which had hitherto postulated that acids must contain oxygen (hence the name of oxygen
itself, which is derived from Greek elements that mean "acid-former" and are likewise calque
d into German as Sauerstoff). In 1815 Joseph Louis Gay-Lussac
deduced Prussic acid's chemical formula. The radical cyanide in hydrogen cyanide was given its name from the Greek word for blue, again owing to its derivation from Prussian blue.
. In the year 2000, 732,552 tons were produced in the US.
The most important process is the Andrussow oxidation
invented by Leonid Andrussow
at IG Farben
in which methane
and ammonia
react in the presence of oxygen
at about 1200 °C over a platinum
catalyst:
The energy needed for the reaction is provided by the partial oxidation of methane and ammonia.
Of lesser importance is the Degussa process (BMA process
) in which no oxygen is added and the energy must be transferred indirectly through the reactor wall:
This reaction is akin to steam reforming
, the reaction of methane
and water to give carbon monoxide and hydrogen.
In the Shawinigan Process, hydrocarbons, e.g. propane
, are reacted with ammonia:
When heated strongly, formamide
decomposes to hydrogen cyanide and water vapor:
In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of alkali metals:
This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN.
, who patented a method to produce hydrogen cyanide by passing ammonia
over glowing coal
in 1892. This method was used until Hamilton Castner
in 1894 developed a synthesis starting from coal, ammonia, and sodium
yielding sodium cyanide, which reacts with acid to form gaseous HCN.
and potassium cyanide
, which are used mainly in mining. Via the intermediacy of cyanohydrin
s, a variety of useful organic compounds are prepared from HCN including the monomer
methyl methacrylate
, from acetone
, the amino acid
methionine
, via the Strecker synthesis, and the chelating agents EDTA
and NTA
. Via the hydrocyanation
process, HCN is added to butadiene to give adiponitrile
, a precursor to Nylon 66
.
s that have a pit, such as cherries
, apricot
s, apple
s, and bitter almonds, from which almond oil and flavoring are made. Many of these pits contain small amounts of cyanohydrin
s such as mandelonitrile
and amygdalin
, which slowly release hydrogen cyanide. One hundred grams of crushed apple seeds can yield about 10 mg of HCN. Some millipede
s release hydrogen cyanide as a defense mechanism, as do certain insects, such as some burnet moth
s. Hydrogen cyanide is contained in the exhaust of vehicles, in tobacco
and wood smoke, and in smoke from burning nitrogen-containing plastic
s. So-called "bitter" roots of the cassava
plant may contain up to 1 gram of HCN per kilogram.
. Although the relationship of these chemical reactions to the origin of life theory remains speculative, studies in this area have led to discoveries of new pathways to organic compounds derived from condensation of HCN.
. Since then, extensive studies have probed formation and destruction pathways of HCN in various environments and examined its use as a tracer for a variety of astronomical species and processes. HCN can be observed
from ground-based telescope
s through a number of atmospheric
windows. The J=1→0, J=3→2, J= 4→3, and J=10→9 pure rotational transition
s have all been observed.
HCN is formed in interstellar
clouds through one of two major pathways: via a neutral-neutral reaction (CH2 + N → HCN + H) and via dissociative recombination (HCNH+ + e- → HCN + H). The dissociative recombination pathway is dominant by 30%; however, the HCNH+
must be in its linear form. Dissociative recombination with its structural isomer, H2NC+ produces hydrogen isocyanide
(HNC), exclusively.
HCN is destroyed in interstellar clouds through a number of mechanisms depending on the location in the cloud. In photon-dominated regions (PDRs), photodissociation dominates, producing CN
(HCN + ν → CN + H). At further depths, photodissociation by cosmic rays dominate, producing CN (HCN + cr → CN + H). In the dark core, two competing mechanisms destroy it, forming HCN+ and HCNH+ (HCN + H+ → HCN+ + H; HCN + HCO+ → HCNH+ + CO). The reaction with HCO+ dominates by a factor of ~3.5. HCN has been used to analyze a variety of species and processes in the interstellar medium. It has been suggested as a tracer for dense molecular gas and as a tracer of stellar inflow in high-mass star-forming regions. Further, the HNC/HCN ratio has been shown to be an excellent method for distinguishing between PDRs and X-ray-dominated regions (XDRs).
by inhibiting an enzyme in mitochondria called cytochrome c oxidase
.
Hydrogen cyanide absorbed into a carrier for use as a pesticide (under IG Farben's brand name Cyclone B, or in German Zyklon B
, with the B standing for Blausäure) was employed by Nazi Germany
in the mid-20th century in extermination camps. The same product is currently made in the Czech Republic
under the trademark "Uragan D2." Hydrogen cyanide is also the agent used in gas chamber
s employed in judicial execution in some U.S. states, where it is produced during the execution by the action of sulfuric acid
on an egg-sized mass of potassium cyanide
.
Hydrogen cyanide is commonly listed amongst chemical warfare
agents known as blood agents. As a substance listed under Schedule 3 of the Chemical Weapons Convention
as a potential weapon which has large-scale industrial uses, manufacturing plants in signatory countries which produce more than 30 tonnes per year must be declared to, and can be inspected by, the Organisation for the Prohibition of Chemical Weapons
.
Under the name prussic acid, HCN has been used as a killing agent in whaling
harpoons.
Hydrogen cyanide gas in air is explosive at concentrations over 5.6%, equivalent to 56000 ppm.
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...
with chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
HCN. It 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, extremely poison
Poison
In the context of biology, poisons are substances that can cause disturbances to organisms, usually by chemical reaction or other activity on the molecular scale, when a sufficient quantity is absorbed by an organism....
ous liquid that boils
Boiling
Boiling is the rapid vaporization of a liquid, which occurs when a liquid is heated to its boiling point, the temperature at which the vapor pressure of the liquid is equal to the pressure exerted on the liquid by the surrounding environmental pressure. While below the boiling point a liquid...
slightly above room temperature
Room temperature
-Comfort levels:The American Society of Heating, Refrigerating and Air-Conditioning Engineers has listings for suggested temperatures and air flow rates in different types of buildings and different environmental circumstances. For example, a single office in a building has an occupancy ratio per...
at 26 °C (78.8 °F). Hydrogen cyanide is a linear molecule, with a triple bond
Triple bond
A triple bond in chemistry is a chemical bond between two chemical elements involving six bonding electrons instead of the usual two in a covalent single bond. The most common triple bond, that between two carbon atoms, can be found in alkynes. Other functional groups containing a triple bond are...
between carbon and nitrogen. A minor tautomer
Tautomer
Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...
of HCN is HNC, hydrogen isocyanide
Hydrogen isocyanide
Hydrogen isocyanide is a chemical with the molecular formula HNC. It is a minor tautomer of hydrogen cyanide, HCN). Its importance in the field of astrochemistry is linked to its ubiquity in the interstellar medium.- Nomenclature :...
.
Hydrogen cyanide is weakly acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
ic with a pKa
Acid dissociation constant
An acid dissociation constant, Ka, is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction known as dissociation in the context of acid-base reactions...
of 9.2. It partly ionizes
Ionization
Ionization is the process of converting an atom or molecule into an ion by adding or removing charged particles such as electrons or other ions. This is often confused with dissociation. A substance may dissociate without necessarily producing ions. As an example, the molecules of table sugar...
in water solution to give the cyanide
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....
anion, CN–. A solution
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...
of hydrogen cyanide
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....
in water is called hydrocyanic acid. The salts of hydrogen cyanide are known as cyanides.
HCN has a faint, bitter, burnt almond
Almond
The almond , is a species of tree native to the Middle East and South Asia. Almond is also the name of the edible and widely cultivated seed of this tree...
-like odor
Odor
An odor or odour is caused by one or more volatilized chemical compounds, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction. Odors are also commonly called scents, which can refer to both pleasant and unpleasant odors...
that only some people are able to detect
Olfactory system
The olfactory system is the sensory system used for olfaction, or the sense of smell. Most mammals and reptiles have two distinct parts to their olfactory system: a main olfactory system and an accessory olfactory system. The main olfactory system detects volatile, airborne substances, while the...
owing to a gene
Gene
A gene is a molecular unit of heredity of a living organism. It is a name given to some stretches of DNA and RNA that code for a type of protein or for an RNA chain that has a function in the organism. Living beings depend on genes, as they specify all proteins and functional RNA chains...
tic trait. The volatile
Volatility (chemistry)
In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...
compound has been used as inhalation rodenticide and human poison. Cyanide ions interfere with iron-containing respiratory enzymes.
HCN is produced on an industrial scale and is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.
History of discovery
Hydrogen cyanide was first isolated from a blue dye (Prussian bluePrussian blue
Prussian blue is a dark blue pigment with the idealized formula Fe718. Another name for the color Prussian blue is Berlin blue or, in painting, Parisian blue. Turnbull's blue is the same substance but is made from different reagents....
) which had been known from 1704 but whose structure was unknown. It is now known to be a coordination polymer with a complex structure and an empirical formula of hydrated ferric ferrocyanide. In 1752, the French chemist Pierre Macquer
Pierre Macquer
Pierre-Joseph Macquer was an influential French chemist.He is known for his Dictionnaire de chymie . He was also involved in practical applications, to medicine and industry, such as the French development of porcelain. He was an opponent of Lavoisier's theories...
made the important step of showing that Prussian blue could be converted to iron oxide
Iron oxide
Iron oxides are chemical compounds composed of iron and oxygen. All together, there are sixteen known iron oxides and oxyhydroxides.Iron oxides and oxide-hydroxides are widespread in nature, play an important role in many geological and biological processes, and are widely utilized by humans, e.g.,...
plus a volatile component and that these could be used to reconstitute the dye. The new component was what we now know as hydrogen cyanide. Following Macquer's lead, it was first isolated from Prussian blue in pure form and characterized about 1783 by the Swedish chemist Carl Wilhelm Scheele
Carl Wilhelm Scheele
Carl Wilhelm Scheele was a German-Swedish pharmaceutical chemist. Isaac Asimov called him "hard-luck Scheele" because he made a number of chemical discoveries before others who are generally given the credit...
, and was eventually given the German name Blausäure (literally "Blue acid") because of its acidic nature in water and its derivation from Prussian blue. In English it became known popularly as Prussic acid.
In 1787 the French chemist Claude Louis Berthollet
Claude Louis Berthollet
Claude Louis Berthollet was a Savoyard-French chemist who became vice president of the French Senate in 1804.-Biography:...
showed that Prussic acid did not contain oxygen, an important contribution to acid theory, which had hitherto postulated that acids must contain oxygen (hence the name of 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...
itself, which is derived from Greek elements that mean "acid-former" and are likewise calque
Calque
In linguistics, a calque or loan translation is a word or phrase borrowed from another language by literal, word-for-word or root-for-root translation.-Calque:...
d into German as Sauerstoff). In 1815 Joseph Louis Gay-Lussac
Joseph Louis Gay-Lussac
- External links :* from the American Chemical Society* from the Encyclopædia Britannica, 10th Edition * , Paris...
deduced Prussic acid's chemical formula. The radical cyanide in hydrogen cyanide was given its name from the Greek word for blue, again owing to its derivation from Prussian blue.
Production and synthesis
Hydrogen cyanide forms in at least limited amounts from many combinations of hydrogen, carbon, and ammonia. Hydrogen cyanide is currently produced in great quantities by several processes, as well as being a recovered waste product from the manufacture of acrylonitrileAcrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...
. In the year 2000, 732,552 tons were produced in the US.
The most important process is the Andrussow oxidation
Andrussow oxidation
The Andrussow process is an industrial process for the production of hydrogen cyanide from methane and ammonia in the presence of oxygen and a platinum catalyst....
invented by Leonid Andrussow
Leonid Andrussow
Leonid Andrussow was a German chemical engineer. He developed the process for the production of hydrogen cyanide based on the oxidation of ammonia and methane, which is named after him Andrussow oxidation.-Biography:Leonid Andrussow was born in Riga, Russian Empire...
at IG Farben
IG Farben
I.G. Farbenindustrie AG was a German chemical industry conglomerate. Its name is taken from Interessen-Gemeinschaft Farbenindustrie AG . The company was formed in 1925 from a number of major companies that had been working together closely since World War I...
in which 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...
and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
react in the presence of 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...
at about 1200 °C over a 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...
catalyst:
- 2 CH4 + 2 NH3 + 3 O2 → 2 HCN + 6 H2O
The energy needed for the reaction is provided by the partial oxidation of methane and ammonia.
Of lesser importance is the Degussa process (BMA process
BMA process
The BMA process or Degussa process is a chemical process developed by the German chemical company Degussa for the production of hydrogen cyanide from methane and ammonia in presence of a platinum catalyst...
) in which no oxygen is added and the energy must be transferred indirectly through the reactor wall:
- CH4 + NH3 → HCN + 3H2
This reaction is akin to steam reforming
Steam reforming
Fossil fuel reforming is a method of producing hydrogen or other useful products from fossil fuels such as natural gas. This is achieved in a processing device called a reformer which reacts steam at high temperature with the fossil fuel. The steam methane reformer is widely used in industry to...
, the reaction of 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...
and water to give carbon monoxide and hydrogen.
In the Shawinigan Process, hydrocarbons, e.g. propane
Propane
Propane is a three-carbon alkane with the molecular formula , normally a gas, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used as a fuel for engines, oxy-gas torches, barbecues, portable stoves, and residential central...
, are reacted with ammonia:
- C3H8 + 3 NH3 → 3 HCN + 7 H2
When heated strongly, formamide
Formamide
Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is used primarily for manufacturing sulfa drugs and synthesizing vitamins and as a softener for paper and fiber...
decomposes to hydrogen cyanide and water vapor:
- CH(O)NH2 → HCN + H2O
In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of alkali metals:
- H+ + NaCN → HCN + Na+
This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN.
Historical methods of production
The demand for cyanides for mining operations in the 1890s was met by George Thomas BeilbyGeorge Thomas Beilby
Sir George Thomas Beilby was a British chemist.He was born in Edinburgh, the son of a doctor and educated at Edinburgh Academy and Edinburgh University...
, who patented a method to produce hydrogen cyanide by passing ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
over glowing coal
Coal
Coal is a combustible black or brownish-black sedimentary rock usually occurring in rock strata in layers or veins called coal beds or coal seams. The harder forms, such as anthracite coal, can be regarded as metamorphic rock because of later exposure to elevated temperature and pressure...
in 1892. This method was used until Hamilton Castner
Hamilton Castner
Hamilton Young Castner was an American industrial chemist.-Biography:He was born in Brooklyn, New York and educated at the Brooklyn Polytechnic Institute, then at the Columbia University School of Mines. He left without a degree and in 1879 joined his brother, E. B. Castner, as a consulting chemist...
in 1894 developed a synthesis starting from coal, ammonia, and sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...
yielding sodium cyanide, which reacts with acid to form gaseous HCN.
Applications
HCN is the precursor to sodium cyanideSodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...
and potassium cyanide
Potassium cyanide
Potassium cyanide is an inorganic compound with the formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include jewelry for chemical gilding and...
, which are used mainly in mining. Via the intermediacy of cyanohydrin
Cyanohydrin
A cyanohydrin is a functional group found in organic compounds. Cyanohydrins have the formula R2CCN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids...
s, a variety of useful organic compounds are prepared from HCN including the monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...
methyl methacrylate
Methyl methacrylate
Methyl methacrylate is an organic compound with the formula CH2=CCOOCH3. This colourless liquid, the methyl ester of methacrylic acid is a monomer produced on a large scale for the production of poly .-Production:...
, from 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...
, the amino acid
Amino 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...
methionine
Methionine
Methionine is an α-amino acid with the chemical formula HO2CCHCH2CH2SCH3. This essential amino acid is classified as nonpolar. This amino-acid is coded by the codon AUG, also known as the initiation codon, since it indicates mRNA's coding region where translation into protein...
, via the Strecker synthesis, and the chelating agents EDTA
EDTA
Ethylenediaminetetraacetic acid, widely abbreviated as EDTA , is a polyamino carboxylic acid and a colourless, water-soluble solid. Its conjugate base is named ethylenediaminetetraacetate. It is widely used to dissolve limescale. Its usefulness arises because of its role as a hexadentate ligand...
and NTA
Nitrilotriacetic acid
Nitrilotriacetic acid , C6H9NO6, is a polyamino carboxylic acid and is used as a chelating agent which forms coordination compounds with metal ions such as Ca2+, Cu2+ or Fe3+.The uses of NTA are similar to that of EDTA...
. Via the hydrocyanation
Hydrocyanation
Hydrocyanation is, most fundamentally, the process whereby H+ and –CN ions are added to a molecular substrate. Usually the substrate is an alkene and the product is a nitrile. When –CN is a ligand in a transition metal complex, its basicity makes it difficult to dislodge, so, in this...
process, HCN is added to butadiene to give adiponitrile
Adiponitrile
Adiponitrile is the organic compound with the formula 42. This dinitrile, a viscous, colourless liquid, is an important precursor to the polymer nylon 66. In 2005, about one billion kilograms were produced annually.-Early routes:...
, a precursor to Nylon 66
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...
.
Occurrence
HCN is obtainable from fruitFruit
In broad terms, a fruit is a structure of a plant that contains its seeds.The term has different meanings dependent on context. In non-technical usage, such as food preparation, fruit normally means the fleshy seed-associated structures of certain plants that are sweet and edible in the raw state,...
s that have a pit, such as cherries
Cherry
The cherry is the fruit of many plants of the genus Prunus, and is a fleshy stone fruit. The cherry fruits of commerce are usually obtained from a limited number of species, including especially cultivars of the wild cherry, Prunus avium....
, apricot
Apricot
The apricot, Prunus armeniaca, is a species of Prunus, classified with the plum in the subgenus Prunus. The native range is somewhat uncertain due to its extensive prehistoric cultivation.- Description :...
s, apple
Apple
The apple is the pomaceous fruit of the apple tree, species Malus domestica in the rose family . It is one of the most widely cultivated tree fruits, and the most widely known of the many members of genus Malus that are used by humans. Apple grow on small, deciduous trees that blossom in the spring...
s, and bitter almonds, from which almond oil and flavoring are made. Many of these pits contain small amounts of cyanohydrin
Cyanohydrin
A cyanohydrin is a functional group found in organic compounds. Cyanohydrins have the formula R2CCN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids...
s such as mandelonitrile
Mandelonitrile
Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.-Occurrence:...
and amygdalin
Amygdalin
Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet...
, which slowly release hydrogen cyanide. One hundred grams of crushed apple seeds can yield about 10 mg of HCN. Some millipede
Millipede
Millipedes are arthropods that have two pairs of legs per segment . Each segment that has two pairs of legs is a result of two single segments fused together as one...
s release hydrogen cyanide as a defense mechanism, as do certain insects, such as some burnet moth
Zygaenidae
The Zygaenidae moths are a family of Lepidoptera. The majority of zygaenids are tropical, but they are nevertheless quite well represented in temperate regions. There are about 1000 species. Various species are commonly known as Burnet or Forester moths, often qualified by the number of spots,...
s. Hydrogen cyanide is contained in the exhaust of vehicles, in tobacco
Tobacco
Tobacco is an agricultural product processed from the leaves of plants in the genus Nicotiana. It can be consumed, used as a pesticide and, in the form of nicotine tartrate, used in some medicines...
and wood smoke, and in smoke from burning nitrogen-containing plastic
Plastic
A plastic material is any of a wide range of synthetic or semi-synthetic organic solids used in the manufacture of industrial products. Plastics are typically polymers of high molecular mass, and may contain other substances to improve performance and/or reduce production costs...
s. So-called "bitter" roots of the cassava
Cassava
Cassava , also called yuca or manioc, a woody shrub of the Euphorbiaceae native to South America, is extensively cultivated as an annual crop in tropical and subtropical regions for its edible starchy tuberous root, a major source of carbohydrates...
plant may contain up to 1 gram of HCN per kilogram.
HCN and the origin of life
Hydrogen cyanide has been discussed as a precursor to amino acids and nucleic acids. For example, HCN is proposed to have played a part in the origin of lifeAbiogenesis
Abiogenesis or biopoesis is the study of how biological life arises from inorganic matter through natural processes, and the method by which life on Earth arose...
. Although the relationship of these chemical reactions to the origin of life theory remains speculative, studies in this area have led to discoveries of new pathways to organic compounds derived from condensation of HCN.
HCN in space
HCN has been detected in the interstellar mediumInterstellar medium
In astronomy, the interstellar medium is the matter that exists in the space between the star systems in a galaxy. This matter includes gas in ionic, atomic, and molecular form, dust, and cosmic rays. It fills interstellar space and blends smoothly into the surrounding intergalactic space...
. Since then, extensive studies have probed formation and destruction pathways of HCN in various environments and examined its use as a tracer for a variety of astronomical species and processes. HCN can be observed
Observation
Observation is either an activity of a living being, such as a human, consisting of receiving knowledge of the outside world through the senses, or the recording of data using scientific instruments. The term may also refer to any data collected during this activity...
from ground-based telescope
Telescope
A telescope is an instrument that aids in the observation of remote objects by collecting electromagnetic radiation . The first known practical telescopes were invented in the Netherlands at the beginning of the 1600s , using glass lenses...
s through a number of atmospheric
Atmosphere
An atmosphere is a layer of gases that may surround a material body of sufficient mass, and that is held in place by the gravity of the body. An atmosphere may be retained for a longer duration, if the gravity is high and the atmosphere's temperature is low...
windows. The J=1→0, J=3→2, J= 4→3, and J=10→9 pure rotational transition
Rotational transition
A rotational transition is an abrupt change in angular momentum in quantum physics. Like all other properties of a quantum particle, angular momentum is quantized, meaning it can only equal certain discrete values, which correspond to different rotational energy states. When a particle loses...
s have all been observed.
HCN is formed in interstellar
Interstellar medium
In astronomy, the interstellar medium is the matter that exists in the space between the star systems in a galaxy. This matter includes gas in ionic, atomic, and molecular form, dust, and cosmic rays. It fills interstellar space and blends smoothly into the surrounding intergalactic space...
clouds through one of two major pathways: via a neutral-neutral reaction (CH2 + N → HCN + H) and via dissociative recombination (HCNH+ + e- → HCN + H). The dissociative recombination pathway is dominant by 30%; however, the HCNH+
HCNH+
HCNH+, also known as protonated hydrogen cyanide, is a molecular ion of astrophysical interest.- Structure :The ground state structure of HCNH+ is a simple linear molecule...
must be in its linear form. Dissociative recombination with its structural isomer, H2NC+ produces hydrogen isocyanide
Hydrogen isocyanide
Hydrogen isocyanide is a chemical with the molecular formula HNC. It is a minor tautomer of hydrogen cyanide, HCN). Its importance in the field of astrochemistry is linked to its ubiquity in the interstellar medium.- Nomenclature :...
(HNC), exclusively.
HCN is destroyed in interstellar clouds through a number of mechanisms depending on the location in the cloud. In photon-dominated regions (PDRs), photodissociation dominates, producing CN
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....
(HCN + ν → CN + H). At further depths, photodissociation by cosmic rays dominate, producing CN (HCN + cr → CN + H). In the dark core, two competing mechanisms destroy it, forming HCN+ and HCNH+ (HCN + H+ → HCN+ + H; HCN + HCO+ → HCNH+ + CO). The reaction with HCO+ dominates by a factor of ~3.5. HCN has been used to analyze a variety of species and processes in the interstellar medium. It has been suggested as a tracer for dense molecular gas and as a tracer of stellar inflow in high-mass star-forming regions. Further, the HNC/HCN ratio has been shown to be an excellent method for distinguishing between PDRs and X-ray-dominated regions (XDRs).
Hydrogen cyanide as a poison and chemical weapon
A hydrogen cyanide concentration of 300 mg/m3 in air will kill a human within about 10 minutes.A hydrogen cyanide concentration of 3500 ppm (about 3200 mg/m3) will kill a human in about 1 minute. The toxicity is caused by the cyanide ion, which halts cellular respirationCellular respiration
Cellular respiration is the set of the metabolic reactions and processes that take place in the cells of organisms to convert biochemical energy from nutrients into adenosine triphosphate , and then release waste products. The reactions involved in respiration are catabolic reactions that involve...
by inhibiting an enzyme in mitochondria called cytochrome c oxidase
Cytochrome c oxidase
The enzyme cytochrome c oxidase or Complex IV is a large transmembrane protein complex found in bacteria and the mitochondrion.It is the last enzyme in the respiratory electron transport chain of mitochondria located in the mitochondrial membrane...
.
Hydrogen cyanide absorbed into a carrier for use as a pesticide (under IG Farben's brand name Cyclone B, or in German Zyklon B
Zyklon B
Zyklon B was the trade name of a cyanide-based pesticide infamous for its use by Nazi Germany to kill human beings in gas chambers of extermination camps during the Holocaust. The "B" designation indicates one of two types of Zyklon...
, with the B standing for Blausäure) was employed by Nazi Germany
Nazi Germany
Nazi Germany , also known as the Third Reich , but officially called German Reich from 1933 to 1943 and Greater German Reich from 26 June 1943 onward, is the name commonly used to refer to the state of Germany from 1933 to 1945, when it was a totalitarian dictatorship ruled by...
in the mid-20th century in extermination camps. The same product is currently made in the Czech Republic
Czech Republic
The Czech Republic is a landlocked country in Central Europe. The country is bordered by Poland to the northeast, Slovakia to the east, Austria to the south, and Germany to the west and northwest....
under the trademark "Uragan D2." Hydrogen cyanide is also the agent used in gas chamber
Gas chamber
A gas chamber is an apparatus for killing humans or animals with gas, consisting of a sealed chamber into which a poisonous or asphyxiant gas is introduced. The most commonly used poisonous agent is hydrogen cyanide; carbon dioxide and carbon monoxide have also been used...
s employed in judicial execution in some U.S. states, where it is produced during the execution by the action of sulfuric acid
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...
on an egg-sized mass of potassium cyanide
Potassium cyanide
Potassium cyanide is an inorganic compound with the formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include jewelry for chemical gilding and...
.
Hydrogen cyanide is commonly listed amongst chemical warfare
Chemical warfare
Chemical warfare involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from Nuclear warfare and Biological warfare, which together make up NBC, the military acronym for Nuclear, Biological, and Chemical...
agents known as blood agents. As a substance listed under Schedule 3 of the Chemical Weapons Convention
Chemical Weapons Convention
The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and use of chemical weapons. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction...
as a potential weapon which has large-scale industrial uses, manufacturing plants in signatory countries which produce more than 30 tonnes per year must be declared to, and can be inspected by, the Organisation for the Prohibition of Chemical Weapons
Organisation for the Prohibition of Chemical Weapons
The Organisation for the Prohibition of Chemical Weapons is an intergovernmental organization, located in The Hague, Netherlands. The organization promotes and verifies the adherence to the Chemical Weapons Convention which prohibits of the use of chemical weapons and requires their destruction...
.
Under the name prussic acid, HCN has been used as a killing agent in whaling
Whaling
Whaling is the hunting of whales mainly for meat and oil. Its earliest forms date to at least 3000 BC. Various coastal communities have long histories of sustenance whaling and harvesting beached whales...
harpoons.
Hydrogen cyanide gas in air is explosive at concentrations over 5.6%, equivalent to 56000 ppm.
External links
- Institut national de recherche et de sécurité (1997). "Cyanure d'hydrogène et solutions aqueuses". Fiche toxicologique n° 4, Paris:INRS, 5pp. (PDF file, in French)
- International Chemical Safety Card 0492
- Hydrogen cyanide and cyanides (CICAD 61)
- National Pollutant Inventory: Cyanide compounds fact sheet
- NIOSH Pocket Guide to Chemical Hazards
- European Chemicals Bureau
- Department of health review
- OSHA: HCN Health Guidelines