NationMaster - Encyclopedia: Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, very poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C (78.8 °F). HCN has a faint, bitter, almond-like odor that some people are unable to detect due to a genetic trait.^[1] Hydrogen cyanide is weakly acidic and partly ionizes in solution to give the cyanide anion, CN^–. The salts of hydrogen cyanide are known as cyanides. HCN is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... Cyanogen is a chemical compound (CN)2. ... Cyanogen chloride, also known as CK, is a highly toxic blood agent first proposed for use in warfare by the French. ... One common use of this reagent is to convert pyridine-N-oxides into 2-cyanopyridine. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Making a saline water solution by dissolving table salt (NaCl) in water This article is about chemical solutions. ... H2O and HOH redirect here. ... Color is an important part of the visual arts. ... The skull and crossbones symbol (Jolly Roger) traditionally used to label a poisonous substance. ... The ability of a liquid to evaporate quickly and at relatively low temperatures. ... Boiling, a type of phase transition, is the rapid vaporization of a liquid, which typically 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 atmospheric pressure. ... For other uses, see Room temperature (disambiguation). ... Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... For other uses, see Fahrenheit (disambiguation). ... Binomial name (Mill. ... â€œAromaâ€ redirects here. ... The olfactory system is the sensory system used for olfaction. ... For other uses, see Gene (disambiguation). ... In biology, a trait or character is a genetically inherited feature of an organism. ... For other uses, see Acid (disambiguation). ... Ionization is the physical process of converting an atom or molecule into an ion by changing the difference between the number of protons and electrons. ... The cyanide ion, CNâˆ’. From the top: 1. ... For other uses, see Salt (disambiguation). ... The cyanide ion, CNâˆ’. From the top: 1. ...

Production and synthesis

Currently hydrogen cyanide is produced in large quantities by three processes. In the year 2000, 1.615 billion pounds (732,552 tons) were produced in the US.[2] The most important process for the production of hydrogen cyanide is the Andrussov oxidation invented by Leonid Andrussow in which methane and ammonia react in the presence of oxygen at about 1200 °C over a platinum catalyst:^[2] The Andrussov Oxidation is an organic reaction describing the oxidation of methane in the presence of oxygen, ammonia, and a platinum catalyst to produce hydrogen cyanide. ... Leonid Andrussow in 1933 Leonid Andrussow (*28. ... Methane is a chemical compound with the molecular formula CH4. ... For other uses, see Ammonia (disambiguation). ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number platinum, Pt, 78 Chemical series transition metals Group, Period, Block 10, 6, d Appearance grayish white Standard atomic weight 195. ...

The energy needed for the reaction is provided by the part 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:^[3] Degussa Logo Degussa AG is a multinational chemistry corporation based in DÃ¼sseldorf, Germany. ...

This reaction is akin to steam reforming, the reaction of methane and water. In another process, practiced at BASF, formamide is heated and split into hydrogen cyanide and water: Steam reforming, hydrogen reforming or catalytic oxidation, is a method of producing hydrogen from hydrocarbons. ... Methane is a chemical compound with the molecular formula CH4. ... This article is about the German chemical company. ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ...

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.

Reactions

HCN adds to ketones and aldehydes to give cyanohydrins. Amino acids are prepared by this reaction; the essential amino acid methionine is manufactured by this route.The cyanohydrin of acetone is a precursor to methyl methacrylate.^{[citation needed]} Ketone group A ketone (pronounced as key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... An aldehyde. ... Cyanohydrin is any of several compounds that contain both the CN and OH radicals. ... Phenylalanine is one of the standard amino acids. ... Methionine is an Î±-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and Î²-ketopropane) is the simplest representative of the ketones. ... Methyl methacrylate is a chemical compound mostly known as monomer for the production of the transparent plastic polymethyl methacrylate (PMMA). ...

In hydrocyanation, HCN adds to alkenes to give nitriles. This reaction is employed to manufacture adiponitrile, the precursor to Nylon 66. Hydrocyanation is, most fundamentally, the process whereby H+ and –CN ions are added to a molecular substrate. ... The chemical structure of ethylene, the simplest alkene. ... R-phrases , , , S-phrases , , Flash point 93 Â°C (decomposition) Autoignition temperature 460 Â°C Explosive limits 1. ... For other uses of this word, see nylon (disambiguation). ...

Occurrence and applications

Cyanide is used in tempering steel, dyeing, explosives, engraving, the production of acrylic resin plastic, and other organic chemical products (eg: historically: formic acid). The less toxic ethyl acetate (C₄H₈O₂) has now largly replaced the use of cyanide in insect killing jars. Cyanide is also being used for capital punishment. Tempering is a heat treatment technique for metals and alloys. ... For other uses, see Steel (disambiguation). ... Look up dye in Wiktionary, the free dictionary. ... This article is concerned solely with chemical explosives. ... Engraving is the practice of incising a design onto a hard, flat surface, by cutting grooves into it. ... Structure of methyl methacrylate, the monomer that makes up PMMA Polymethyl methacrylate (PMMA) or poly(methyl 2-methylpropenoate) is the synthetic polymer of methyl methacrylate. ... Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... R-phrases , , , S-phrases , , Flash point âˆ’4 Â°C Related Compounds Related carboxylate esters Methyl acetate, Butyl acetate Related compounds Acetic acid, ethanol Supplementary data page Structure and properties n, Îµr, etc. ... Orders Subclass Apterygota Archaeognatha (bristletails) Thysanura (silverfish) Subclass Pterygota Infraclass Paleoptera (Probably paraphyletic) Ephemeroptera (mayflies) Odonata (dragonflies and damselflies) Infraclass Neoptera Superorder Exopterygota Grylloblattodea (ice-crawlers) Mantophasmatodea (gladiators) Plecoptera (stoneflies) Embioptera (webspinners) Zoraptera (angel insects) Dermaptera (earwigs) Orthoptera (grasshoppers, etc) Phasmatodea (stick insects) Blattodea (cockroaches) Isoptera (termites) Mantodea (mantids) Psocoptera... A killing jar is a device used by entomologists to kill captured insects quickly, humanely and with minimal damage. ... Capital punishment, or the death penalty, is the execution of a convicted criminal by the state as punishment for crimes known as capital crimes or capital offences. ...

Fruits that have a pip, such as cherries and apricots, bitter almonds and apples, from which almond oil and flavoring are made, contain small amounts of cyanohydrins such as mandelonitrile (CAS#532-28-5). Such molecules slowly release hydrogen cyanide.^[4]^[5] Some millipedes release hydrogen cyanide as a defense mechanism,^[6] as do certain insects such as some burnet moths. Hydrogen cyanide is contained in the exhaust of vehicles, in tobacco and wood smoke, and in smoke from burning nitrogen-containing plastics. For other uses, see Fruit (disambiguation). ... For other uses, see Cherry (disambiguation). ... Binomial name Prunus armeniaca L. For other uses, see Apricot (disambiguation). ... Binomial name (Mill. ... For other uses, see Apple (disambiguation). ... Cyanohydrin is any of several compounds that contain both the CN and OH radicals. ... For other uses, see Millipede (disambiguation). ... Type species Zygaena filipendulae (Six-Spot Burnet moth) Subfamilies Callizygaeninae Chalcosiinae Phaudinae Procridinae Zygaeninae The Zygaenidae are a family of Lepidoptera (moths) typically day-flying with a slow fluttering flight, and with rather clubbed antennae. ... Shredded tobacco leaf for pipe smoking Tobacco can also be pressed into plugs and sliced into flakes Tobacco is an agricultural product processed from the fresh leaves of plants in genus Nicotiana. ... The term plastics covers a range of synthetic or semi-synthetic organic condensation or polymerization products that can be molded or extruded into objects or films or fibers. ...

100g of crushed apple seeds can yield 217mg of Amygdalin which can generate ~10mg of HCN.^{[citation needed]}

HCN and the origin of life

Hydrogen cyanide has been discussed as a precursor to amino acids and nucleic acids. It is possible, for example, that HCN played a part in the origin of life. Leslie Orgel, among many researchers, has written extensively on the condensation of HCN.^[7] Although the relationship of these chemical reactions to the origin of life remains speculative, studies in this area have led to discoveries of new pathways to organic compounds derived from condensation of HCN.^[8] This article does not adequately cite its references or sources. ... Leslie Eleazer Orgel (born Jan 12, 1927 in London) is a chemist. ...

Hydrogen cyanide as a chemical weapon

An HCN concentration of 300 parts per million in air will kill a human within a few minutes.^[9] The toxicity is caused by the cyanide ion, which prevents cellular respiration. Hydrogen cyanide (under the brand name Zyklon B) was perhaps most infamously employed by the Nazi regime in mid-20th century as a method of mass murder. More recent examples include the usage of this gas in gas chambers. Homo sapiens (Latin: wise man) is the scientific name for the human species. ... The cyanide ion, CNâˆ’. From the top: 1. ... Cellular respiration was discovered by mad scientist Mr. ... Zyklon B label — Note that “Gift” translates as “poison” Zyklon B was the tradename of a pesticide ultimately used by Nazi Germany in some Holocaust gas chambers. ... Nazi Germany, or the Third Reich, commonly refers to Germany in the years 1933–1945, when it was under the firm control of the totalitarian and fascist ideology of the Nazi Party, with the Führer Adolf Hitler as dictator. ... For other uses, see Gas chamber (disambiguation). ...

Hydrogen cyanide is commonly listed amongst chemical warfare agents which cause general poisoning.^[10] 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 OPCW. Early detection of chemical agents Sociopolitical climate of chemical warfare While the study of chemicals and their military uses was widespread in China, the use of toxic materials has historically been viewed with mixed emotions and some disdain in the West (especially when the enemy were doing it). ... Schedule 3 substances, in the sense of the Chemical Weapons Convention, are either toxic enough to be used as chemical weapons, or precursors of other listed substances. ... Chemical Weapons Convention Opened for signature January 13, 1993 in Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preparatory Commission Parties 181 (as of Oct. ... The Organisation for the Prohibition of Chemical Weapons (OPCW) is an agency of the United Nations. ...

Although there have been no verified instances of this compound being used as a weapon, it has been reported that hydrogen cyanide may have been employed by Iraq in the war against Iran and against the Kurds in northern Iraq during the 1980s^[11]. Kurds are one of the Iranian peoples and speak Kurdish, a north-Western Iranian language related to Persian. ... The 1980s refers to the years from 1980 to 1989. ...

In 1995 a device was discovered in a restroom in the Kayabacho Tokyo subway station consisting of bags of sodium cyanide and sulfuric acid with a remote controlled motor to rupture them in what was believed to be an attempt to produce toxic amounts of hydrogen cyanide gas by the Aum Shinrikyo cult^[12] . In 2003, Al Qaeda reportedly planned to attack the New York City Subway using hydrogen cyanide gas but aborted the attack for unknown reasons.^[13] For other uses, see Tokyo (disambiguation). ... Sodium cyanide is a highly toxic chemical compound, also known as sodium salt of hydrocyanic acid and cyanogran. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, Îµr, etc. ... This article does not cite any references or sources. ... This article does not discuss cult in its original meaning. ... Map of major attacks attributed to al-Qaeda Al-Qaeda (also al-Qaida or al-Qaida or al-Qaidah) (Arabic: â€Ž , translation: The Base) is an international alliance of terrorist organizations. ... Times Squareâ€“42nd Street station entrance The New York City Subway is a rapid transit system owned by the City of New York and leased to the New York City Transit Authority , an affiliate of the Metropolitan Transportation Authority and also known as MTA New York City Transit. ...

Hydrogen cyanide gas in air is explosive at concentrations over 56,000 ppm^[14]. Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ...

Footnotes

^ Online Mendelian Inheritance in Man, Cyanide, inability to smell
^ L. Andrussow (1935). "The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide.". Angewandte Chemie 48: 593-595.
^ F. Endter (1958). "Die technische Synthese von Cyanwasserstoff aus Methan und Ammoniak ohne Zusatz von Sauerstoff". Chemie Ingenieur Technik 30 (5): 281-376. DOI:10.1002/cite.330300506.
^ J. Vetter (2000). "Plant cyanogenic glycosides". Toxicon. 38: 11-36. DOI:10.1016/S0041-0101(99)00128-2.
^ D. A. Jones (1998). "Why are so many food plants cyanogenic?". Phytochemistry 47: 155-162. DOI:10.1016/S0031-9422(97)00425-1.
^ M. S. Blum, J. P. Woodring (1962). "Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood)". Science 138: 512 - 513. DOI:10.1126/science.138.3539.512.
^ Matthews, C. N. "The HCN World: Establishing Protein-Nucleic Acid Life via Hydrogen Cyanide Polymers" Cellular Origin and Life in Extreme Habitats and Astrobiology (2004), 6 (Origins : Genesis, Evoluation and Diversity of Life), 121-135.
^ Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. "The Chemistry of Diaminomaleonitrile and its Utility in Heterocyclic Synthesis" Tetrahedron (2003), 59, 2749-2763. CODEN: TETRAB ISSN:0040-4020
^ http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html
^ Hydrogen Cyanide. Organization for the Prohibition of Chemical Weapons. Retrieved on 2006-10-07.
^ http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp
^ Chronology of Aum Shinrikyo's CBW Activities (pdf).
^ http://www.time.com/time/magazine/article/0,9171,1205478,00.html
^ [1]

The Mendelian Inheritance in Man project is a database that catalogues all the known diseases with a genetic component, and - when possible - links them to the relevant genes in the human genome. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Part of a scientific laboratory at the University of Cologne. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 280th day of the year (281st in leap years) in the Gregorian calendar. ...

References

See also

The cyanide ion, CNâˆ’. From the top: 1. ... Hydrogen isocyanide is a chemical with molecular formula HNC (c. ...

External links

Categories: All articles with unsourced statements | Articles with unsourced statements since February 2007 | Inorganic compounds | Cyanides | Hydrogen compounds | Chemical weapons | Fumigants Concise International Chemical Assessment Documents (also known as CICADs) are published by the World Health Organization within the framework of the Inter-Organization Programme for the Sound Management of Chemicals (IOMC). ... Image File history File links WMD-chemical. ... Chemical warfare is warfare (and associated military operations) using the toxic properties of chemical substances to kill, injure or incapacitate an enemy. ... A blood agent (also called a cyanogen agent) is a compound that prevents the normal transfer of oxygen from the blood to the body tissues, resulting in chemical asphyxiation. ... Cyanogen chloride, also known as CK, is a highly toxic blood agent first proposed for use in warfare by the French. ... Blister agents are named for their ability to cause large, painful water blisters on the bodies of those affected. ... Lewisite is a chemical compound from a chemical family called arsines. ... The sulfur mustards, of which mustard gas is a member, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin. ... The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. ... Nerve agents (also known as nerve gases, though these chemicals are liquid at room temperature) are a class of phosphorus-containing organic chemicals (organophosphates) that disrupt the mechanism by which nerves transfer messages to organs. ... Tabun or GA (Ethyl N,N-dimethylphosphoramidocyanidate) is an extremely toxic substance that is one of the worlds most dangerous military weapons. ... For other uses, see Sarin (disambiguation). ... Boiling point 198 Â°C (388 Â°F) Freezing/melting point âˆ’42 Â°C (âˆ’44 Â°F) Vapor pressure 0. ... Cyclosarin or GF (Cyclohexyl methylphosphonofluoridate) is an extremely toxic substance that is one of the worlds most dangerous weapons of war. ... Skeletal formula of GV Ball-and-stick model of GV GV (P-[2-(dimethylamino)ethyl]-N,N-dimethylphosphonamidic fluoride) is an organophosphate nerve agent. ... VE (S-(Diethylamino)ethyl O-ethyl ethylphosphonothioate) is a V-series nerve agent closely related to the better-known VX nerve gas. ... VG (also called Amiton or Tetram) is a V-series nerve agent closely related to the better-known VX nerve agent. ... VM (Phosphonothioic acid, methyl-, S-(2-(diethylamino)ethyl) O-ethyl ester) is a V-series nerve agent closely related to the better-known VX nerve agent. ... This article does not cite any references or sources. ... Novichok (Russian Ð½Ð¾Ð²Ð¸Ñ‡Ð¾Ðº: Newcomer) is a series of nerve agents that were developed by the Soviet Union in the 1980s and 1990s and allegedly the most deadly nerve agents ever made. ... Categories: Chemical weapons | Stub ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Chloropicrin is a slightly oily, colorless or faintly yellow liquid of the formula CCl3NO2. ... Phosgene is a highly toxic chemical compound with the formula COCl2. ... Diphosgene (ClCO2CCl3) Diphosgene (Trichloromethyl chloroformate, ClCO2CCl3) is a chemical originally developed for chemical warfare, a few months after the first use of phosgene. ... The term incapacitating agent is defined by the U.S. Department of Defense as An agent that produces temporary physiological or mental effects, or both, which will render individuals incapable of concerted effort in the performance of their assigned duties. ... Diagram of a BZ molecule 3-quinuclidinyl benzilate (QNB), empirical formula C21H23NO3, full chemical name 1-azabicyclo[2. ... KOLOKOL-1 is an opiate-derived incapacitating agent. ... This article does not cite any references or sources. ... Pepper spray (also known as OC spray (from Oleoresin Capsicum), OC gas, capsicum spray, or oleoresin capsicum) is a lachrymatory agent (a chemical compound that irritates the eyes to cause tears, pain, and even temporary blindness) that is used in riot control, crowd control and personal self-defense, including defense... Related Compounds Related compounds SDBS Supplementary data page Structure and properties n, Îµr, etc. ... Not to be confused with hydrogen cyanide, HCN. CN, or chloroacetophenone, is a gas used as a riot control agent. ... CR gas or dibenzoxazepine, chemically dibenz[b,f][1,4]oxazepine, is an incapacitating agent and a lachrymatory agent. ...

Contents

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