| Hydrogen cyanide | |
|---|---|
 |  |
| IUPAC name | hydrogen cyanide methanenitrile hydridonitridocarbon |
| Other names | Hydrocyanic acid prussic acid formonitrile formic anammonide carbon hydride nitride cyanane cyclon |
| Identifiers | |
| CAS number | [74-90-8] |
| RTECS number | MW6825000 |
| SMILES | C#N |
| Properties | |
| Molecular formula | HCN |
| Molar mass | 27. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 03 g/mol |
| Appearance | Colorless gas or pale blue highly volatile liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 687 g/cm³, liquid. |
| Melting point | -13. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 4°C (259. 75 K, 7. 88°F) |
| Boiling point | 26°C (299. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 15 K, 78. 8°F) |
| Solubility in water | Completely miscible. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. |
| Acidity (pKa) | 9. 2 - 9. 3 |
| Hazards | |
| Main hazards | Highly toxic, highly flammable. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in |
| NFPA 704 |  4 4 2 |
| R-phrases | R12, R26, R27, R28, R32. Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous |
| S-phrases | (S1), (S2), S7, S9, S13, S16, S28, S29, S45. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. |
| Flash point | −17. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air 78 °C |
| Related compounds | |
| Related compounds | Cyanogen Cyanogen chloride trimethylsilyl cyanide |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Hydrogen cyanide is a chemical compound with chemical formula HCN. Cyanogen is the Chemical compound with the formula ( C[[nitrogen N]]2 Cyanogen chloride is a Chemical compound with the formula CNCl Trimethylsilyl cyanide is the Chemical compound with the formula (CH33SiCN In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes A solution of hydrogen cyanide in water is called hydrocyanic acid. In Chemistry, a solution is a Homogeneous Mixture composed of two or more substances Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Hydrogen cyanide is a colorless, very poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C (78. In the context of Biology, poisons are substances that can cause damage, Illness, or Death to Organisms usually by Volatility in the context of Chemistry, Physics and Thermodynamics is a measure of the tendency of a substance to Vaporize. Boiling (also called ebullition) a type of Phase transition, is the rapid vaporization of a Liquid, which typically occurs when a liquid Room temperature (also referred to as ambient temperature) is a common term to denote a certain Temperature within enclosed space at which humans are accustomed The Celsius Temperature scale was previously known as the centigrade scale. 8 °F). Fahrenheit is a temperature scale named after Daniel Gabriel Fahrenheit (1686–1736 a German Physicist who proposed it in 1724 HCN has a faint, bitter, almond-like odor that some people are unable to detect due to a genetic trait. The Almond ( Prunus dulcis, syn Prunus amygdalus Batsch Amygdalus communis L The Olfactory helps and relates sense of smell. The olfactory system is the Sensory system used for Olfaction. History See also History of genetics The existence of genes was first suggested by Gregor Mendel (1822-1884 who in the 1860s studied inheritance A trait is a distinct phenotypic character of an organism that may be inherited environmentally determined or somewhere in between [1] Hydrogen cyanide is weakly acidic and partly ionizes in solution to give the cyanide anion, CN–. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Ionization is the physical process of converting an Atom or Molecule into an Ion by adding or removing charged particles such as Electrons A cyanide is any Chemical compound that contains the cyano group (C≡N which consists of a Carbon Atom triple-bonded to a The salts of hydrogen cyanide are known as cyanides. Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants A cyanide is any Chemical compound that contains the cyano group (C≡N which consists of a Carbon Atom triple-bonded to a HCN is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.
Contents |
Production and synthesis
Hydrogen cyanide is currently produced in large quantities by three processes. In the year 2000, 1. 615 billion pounds (732,552 tons) were produced in the US. [1] 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]
- 2CH4 + 2NH3 + 3O2 → 2HCN + 6H2O
The energy needed for the reaction is provided by the part oxidation of methane and ammonia. The Andrussov Oxidation is an Organic reaction describing the Oxidation of Methane in the presence of Oxygen, Ammonia, and a Leonid Andrussow (*28 November 1896 in Riga; †15 December 1988 near Paris) was a German chemical engineer Methane is a Chemical compound with the molecular formula. It is the simplest Alkane, and the principal component of Natural gas. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Platinum (ˈplætɪnəm is a Chemical element with the Atomic symbol Pt and an Atomic number of 78
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]
- CH4 + NH3 → HCN + 3H2
This reaction is akin to steam reforming, the reaction of methane and water. Steam reforming (SR hydrogen reforming or catalytic oxidation, is a method of producing Hydrogen from Hydrocarbons. Methane is a Chemical compound with the molecular formula. It is the simplest Alkane, and the principal component of Natural gas. In another process, practiced at BASF, formamide is heated and split into hydrogen cyanide and water:
- 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. BASF SE () is a German chemical company and the largest chemical company in the world Formamide, also known as methanamide is an Amide derived from Formic acid.
History
The first source for hydrogen cyanide was the reaction of acid on ferrocyanides. Ferrocyanide is the name of the Anion Fe ( C[[Nitrogen N]]64− The rising demand due to the use of cyanides for mining operations in the 1890s was met by the Bleiby process. George Thomas Beilby patented a method to produce hydrogen cyanide by passing ammonia over glowing coal in 1892. George Thomas Beilby ( 17 November 1850 &ndash 1 August 1924 was a British Chemist. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor 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. Hamilton Young Castner ( 11 September 1858 &mdash 11 October 1899) was an American industrial Chemist. Sodium (ˈsoʊdiəm is an element which has the symbol Na( Latin natrium, from Arabic natrun) atomic number 11 atomic mass 22
Reactions
HCN adds to ketones and aldehydes to give cyanohydrins. 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 An aldehyde is an organic compound containing a terminal Carbonyl group. A cyanohydrin is a Functional group in Organic compounds Cyanohydrins have the formula R2C(OHCN where R is H Alkyl, or Aryl. Amino acids are prepared by this reaction; the essential amino acid methionine is manufactured by this route. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Methionine ( abbreviated as Met or M) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH2CH2SCH3 The cyanohydrin of acetone is a precursor to methyl methacrylate. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Methyl methacrylate is an Organic compound with the formula CH2=C(CH3CO2CH3
In hydrocyanation, HCN adds to alkenes to give nitriles. Hydrocyanation is most fundamentally the process whereby H+ and &ndashCN Ions are added to a molecular substrate In Organic chemistry, an alkene, olefin, or olefine is an unsaturated Chemical compound containing at least one Carbon This reaction is employed to manufacture adiponitrile, the precursor to Nylon 66. Adiponitrile is the Chemical compound with the formula (CH24(CN2 Overview Nylon is a Thermoplastic silky material first used commercially in a nylon- Bristled Toothbrush (1938 followed more famously by
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). Tempering is a Heat treatment technique for metals and Alloys In Steels tempering is done to "toughen" the metal by transforming brittle Steel is an Alloy consisting mostly of Iron, with a Carbon content between 0 A dye can generally be described as a Colored substance that has an affinity to the substrate to which it is being applied An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied Engraving is the practice of incising a design onto a hard usually flat surface by cutting grooves into it Poly(methyl methacrylate ( PMMA) or poly(methyl 2-methylpropenoate is a Thermoplastic and transparent Plastic. Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. The less toxic ethyl acetate (C4H8O2) has now largely replaced the use of cyanide in insect killing jars. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Insects ( Class Insecta) are a major group of Arthropods and the most diverse group of Animals on the Earth with over a million described A killing jar is a device used by Entomologists to kill captured Insects quickly humanely and with minimum damage Cyanide is also being used for capital punishment. Capital punishment, the death penalty or execution, is the Killing of a person by judicial process as Punishment.
Fruits that have a pit, 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). The term fruit has different meanings dependent on context and the term is not synonymous in Food preparation and Biology. This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. The Apricot ( Prunus armeniaca, "Armenian plum" in Latin syn The Almond ( Prunus dulcis, syn Prunus amygdalus Batsch Amygdalus communis L The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. A cyanohydrin is a Functional group in Organic compounds Cyanohydrins have the formula R2C(OHCN where R is H Alkyl, or Aryl. 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. Millipedes (Class Diplopoda, previously also known as Chilognatha are Arthropods that have two pairs of legs per segment (except for the first segment behind The Zygaenidae are a family of Lepidoptera ( Moths typically day-flying with a slow fluttering flight and with rather clubbed antennae They generally Hydrogen cyanide is contained in the exhaust of vehicles, in tobacco and wood smoke, and in smoke from burning nitrogen-containing plastics. Tobacco is an Agricultural product recognized as an addictive drug processed from the fresh Leaves of plants in the genus Nicotiana. Plastic is the general common term for a wide range of synthetic or semisynthetic organic solid materials suitable for the manufacture of industrial products
100 g of crushed apple seeds can yield 219 mg of Amygdalin which can generate ~10 mg of HCN. Amygdalin (from Greek: grc-Latn amygdálē “almond” C20H27NO11 is a Glycoside initially isolated from the seeds
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. In the Natural sciences, Abiogenesis, or origin of life, is the study of how Life on Earth emerged from Inanimate Organic Leslie Orgel, among many researchers, has written extensively on the condensation of HCN. Leslie Eleazer Orgel FRS ( January 12, 1927 &ndash October 27, 2007) was a British chemist [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]
Hydrogen cyanide as a poison and chemical weapon
- See also: cyanide poisoning
An HCN concentration of 300 mg/m3 in air will kill a human within a few minutes. Cyanide poisoning occurs when a living organism is exposed to Cyanide. Human beings, humans or man (Origin 1590–1600 L homō man OL hemō the earthly one (see Humus [9] The toxicity is caused by the cyanide ion, which prevents cellular respiration. A cyanide is any Chemical compound that contains the cyano group (C≡N which consists of a Carbon Atom triple-bonded to a Cellular respiration is the set of the metabolic reactions and processes that take place in Organisms cells to convert biochemical energy from Hydrogen cyanide (under the brand name Zyklon B) was perhaps most infamously employed by the Nazi regime in mid-20th century. Zyklon B (tsykloːn ˈbeː also spelled Cyclon B or Nazi Germany and the Third Reich are the common English names for Germany under the regime of Adolf Hitler and the National Socialist German Workers
Hydrogen cyanide is commonly listed amongst chemical warfare agents that cause general poisoning. Chemical warfare involves using the toxic properties of Chemical substances to kill injure or incapacitate an enemy. [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. Schedule 3 substances, in the sense of the Chemical Weapons Convention, are chemicals which can either be used as toxic chemical weapons themselves or used in the manufacture The Chemical Weapons Convention ( CWC) is an Arms control agreement which outlaws the production stockpiling and use of chemical weapons Its full name is The Organisation for the Prohibition of Chemical Weapons (OPCW is an international agency located in The Hague, The Netherlands.
Hydrogen cyanide gas in air is explosive at concentrations over 5. 6%, equivalent to 56,000 ppm[11]. "Parts-per" notation is used especially in Science and Engineering, to denote Ratios (relative proportions in measured quantities particularly
Footnotes
- ^ Online Mendelian Inheritance in Man, Cyanide, inability to smell
- ^ L. The Mendelian Inheritance in Man project is a Database that catalogues all the known Diseases with a genetic component, and—when possible—links them 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:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ J. Vetter (2000). "Plant cyanogenic glycosides". Toxicon. 38: 11-36. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ D. A. Jones (1998). "Why are so many food plants cyanogenic?". Phytochemistry 47: 155-162. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ M. S. Blum, J. P. Woodring (1962). "Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood)". Science 138: 512 - 513. Science (from the Latin scientia, meaning " Knowledge " or "knowing" is the effort to discover, and increase human understanding doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ Matthews, C. N. "The HCN World: Establishing Protein-Nucleic Augucid 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
- ^ Hydrogen Cyanide
- ^ Hydrogen Cyanide. Organisation for the Prohibition of Chemical Weapons. Retrieved on 2006-10-07. Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 3761 BC - The epoch (origin of the modern Hebrew calendar ( Proleptic Julian calendar)
- ^ Documentation for Immediately Dangerous to Life or Health Concentrations (IDLHs) - 74908
References
- 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)
See also
External links
- 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
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