Difference between revisions of "Hydrogen cyanide" - New World Encyclopedia

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'''Hydrogen cyanide''' is a [[chemical compound]] with [[chemical formula]] HCN.  A [[solution]] of hydrogen cyanide in [[water (molecule)|water]] is called hydrocyanic acid.  Hydrogen cyanide is a [[color]]less, very [[poison]]ous, and highly [[volatility (chemistry)|volatile]] liquid that [[boiling|boils]] slightly above [[room temperature]] at 26 [[Celsius|°C]] (78.8 [[Fahrenheit|°F]]).  HCN has a faint, bitter, [[almond]]-like [[odor]] that some people are unable to [[olfactory system|detect]] due to a [[gene]]tic [[Trait (biological)|trait]].<ref>[[Online Mendelian Inheritance in Man]], [http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=304300 Cyanide, inability to smell]</ref>  Hydrogen cyanide is weakly [[acid]]ic and partly [[ionization|ionizes]] in solution to give the [[cyanide|cyanide anion]], CN<sup>&ndash;</sup>.  The [[salt]]s of hydrogen cyanide are known as [[cyanide]]s.  HCN is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.
+
'''Hydrogen cyanide''' is a [[chemical compound]] with [[chemical formula]] HCN.  A [[solution]] of hydrogen cyanide in [[water (molecule)|water]] is called hydrocyanic acid.  Hydrogen cyanide is a [[color]]less, very [[poison]]ous, and highly [[volatility (chemistry)|volatile]] liquid that [[boiling|boils]] slightly above [[room temperature]] at 26 [[Celsius|°C]] (78.8 [[Fahrenheit|°F]]).  HCN has a faint, bitter, [[almond]]-like [[odor]] that some people are unable to [[olfactory system|detect]] due to a [[gene]]tic [[Trait (biological)|trait]].<ref>[[Online Mendelian Inheritance in Man]], [http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=304300 Cyanide, inability to smell]</ref>  Hydrogen cyanide is weakly [[acid]]ic and partly [[ionization|ionizes]] in solution to give the [[cyanide|cyanide anion]], CN<sup>&ndash;</sup>.  The [[salt]]s of hydrogen cyanide are known as cyanides.  HCN is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.
 +
 
 +
==Occurrence ==
 +
 
 +
[[Fruit]]s that have a pit, such as [[cherry|cherries]] and [[apricot]]s, [[Almond#Sweet and bitter almond|bitter almond]]s and [[apples]], from which almond oil and flavoring are made, contain small amounts of [[cyanohydrin]]s such as [[mandelonitrile]] (CAS#532-28-5). Such molecules slowly release hydrogen cyanide.<ref>{{cite journal | author= J. Vetter| title= Plant cyanogenic glycosides | journal=Toxicon.  | year= 2000  | volume=38 | pages=11-36|doi=10.1016/S0041-0101(99)00128-2 }}</ref><ref>{{cite journal | author= D. A. Jones | title= Why are so many food plants cyanogenic? | journal=Phytochemistry  | year= 1998 | volume=47 | pages=155-162 |doi=10.1016/S0031-9422(97)00425-1 }}</ref> Some [[millipede]]s release hydrogen cyanide as a defense mechanism,<ref> {{cite journal | author= M. S. Blum, J. P. Woodring| title= Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede ''[[Pachydesmus crassicutis]]'' (Wood) | journal=[[Science]]  | year= 1962  | volume=138 | pages=512 - 513|doi=10.1126/science.138.3539.512 }}</ref> as do certain insects such as some [[Zygaenidae|burnet moth]]s. Hydrogen cyanide is contained in the exhaust of vehicles, in [[tobacco]] and wood smoke, and in smoke from burning nitrogen-containing [[plastics]].
 +
 
 +
==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.<ref>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.</ref>  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.<ref>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</ref>
  
 
==Production and synthesis==
 
==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.[http://www.the-innovation-group.com/ChemProfiles/Hydrogen%20Cyanide.htm]  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:<ref>{{cite journal
 
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.[http://www.the-innovation-group.com/ChemProfiles/Hydrogen%20Cyanide.htm]  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:<ref>{{cite journal
 
| title = The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide.   
 
| title = The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide.   
Line 73: Line 83:
  
 
In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of alkali metals:
 
In the laboratory, small amounts of HCN are produced by the addition of acids to cyanide salts of alkali metals:
−
::H<sup>+</sup>  +  NaCN →   HCN  +  Na<sup>+</sup>
+
::H<sup>+</sup>  +  NaCN → HCN  +  Na<sup>+</sup>
 
This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN.
 
This reaction is sometimes the basis of accidental poisonings because the acid converts a nonvolatile cyanide salt into the gaseous HCN.
  
 
==Reactions==
 
==Reactions==
 +
 
HCN adds to [[ketone]]s and [[aldehyde]]s to give [[cyanohydrin]]s.  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]].{{Fact|date=February 2007}}
 
HCN adds to [[ketone]]s and [[aldehyde]]s to give [[cyanohydrin]]s.  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]].{{Fact|date=February 2007}}
  
 
In [[hydrocyanation]], HCN adds to [[alkene]]s to give nitriles.  This reaction is employed to manufacture [[adiponitrile]], the precursor to [[Nylon|Nylon 66]].
 
In [[hydrocyanation]], HCN adds to [[alkene]]s to give nitriles.  This reaction is employed to manufacture [[adiponitrile]], the precursor to [[Nylon|Nylon 66]].
  
−
==Occurrence and applications==
+
== Applications ==
−
Cyanide is used in [[tempering]] [[steel]], [[dye]]ing, [[explosive]]s, [[engraving]], the production of [[Polymethyl methacrylate|acrylic resin plastic]], and other organic chemical products (eg: historically: [[formic acid]]). The less toxic [[ethyl acetate]] (C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>) has now largly replaced the use of cyanide in [[insect]] [[killing jar]]s. Cyanide is also being used for [[capital punishment]].
 
  
−
[[Fruit]]s that have a pit, such as [[cherry|cherries]] and [[apricot]]s, [[Almond#Sweet and bitter almond|bitter almond]]s and [[apples]], from which almond oil and flavoring are made, contain small amounts of [[cyanohydrin]]s such as [[mandelonitrile]] (CAS#532-28-5). Such molecules slowly release hydrogen cyanide.<ref>{{cite journal | author= J. Vetter| title= Plant cyanogenic glycosides | journal=Toxicon.  | year= 2000  | volume=38 | pages=11-36|doi=10.1016/S0041-0101(99)00128-2 }}</ref><ref>{{cite journal | author= D. A. Jones | title= Why are so many food plants cyanogenic? | journal=Phytochemistry  | year= 1998 | volume=47 | pages=155-162 |doi=10.1016/S0031-9422(97)00425-1 }}</ref> Some [[millipede]]s release hydrogen cyanide as a defense mechanism,<ref> {{cite journal | author= M. S. Blum, J. P. Woodring| title= Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede ''[[Pachydesmus crassicutis]]'' (Wood) | journal=[[Science]] | year= 1962  | volume=138 | pages=512 - 513|doi=10.1126/science.138.3539.512 }}</ref> as do certain insects such as some [[Zygaenidae|burnet moth]]s. Hydrogen cyanide is contained in the exhaust of vehicles, in [[tobacco]] and wood smoke, and in smoke from burning nitrogen-containing [[plastics]].
+
Cyanide is used in [[tempering]] [[steel]], [[dye]]ing, [[explosive]]s, [[engraving]], the production of [[Polymethyl methacrylate|acrylic resin plastic]], and other organic chemical products (eg: historically: [[formic acid]]). The less toxic [[ethyl acetate]] (C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>) has now largely replaced the use of cyanide in [[insect]] [[killing jar]]s. Cyanide is also being used for [[capital punishment]].
  
−
100 g of crushed apple seeds can yield 217 mg of Amygdalin which can generate ~10 mg of HCN.{{Fact|date=February 2007}}
+
===As a chemical weapon===
−
 
 
−
==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.<ref>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.</ref>  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.<ref>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</ref>
 
−
 
 
−
==Hydrogen cyanide as a chemical weapon==
 
−
:''See also: [[cyanide poisoning]]''
 
  
 
An HCN concentration of 300 parts per million in air will kill a [[homo sapiens|human]] within a few minutes.<ref>http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html</ref> 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 Germany|Nazi]] regime in mid-20th century as a method of mass murder. More recent examples include the usage of this gas in [[gas chamber]]s.
 
An HCN concentration of 300 parts per million in air will kill a [[homo sapiens|human]] within a few minutes.<ref>http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html</ref> 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 Germany|Nazi]] regime in mid-20th century as a method of mass murder. More recent examples include the usage of this gas in [[gas chamber]]s.
Line 98: Line 102:
 
Hydrogen cyanide is commonly listed amongst [[chemical warfare agent]]s which cause general poisoning.<ref>{{cite web | url = http://www.opcw.org/resp/html/hcn.html | title = Hydrogen Cyanide | work = Organization for the Prohibition of Chemical Weapons | accessdate = 2006-10-07}}</ref> As a substance listed under [[List of Schedule 3 substances (CWC)|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 [[Organization for the Prohibition of Chemical Weapons|OPCW]].
 
Hydrogen cyanide is commonly listed amongst [[chemical warfare agent]]s which cause general poisoning.<ref>{{cite web | url = http://www.opcw.org/resp/html/hcn.html | title = Hydrogen Cyanide | work = Organization for the Prohibition of Chemical Weapons | accessdate = 2006-10-07}}</ref> As a substance listed under [[List of Schedule 3 substances (CWC)|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 [[Organization for the Prohibition of Chemical Weapons|OPCW]].
  
−
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 [[Kurd]]s in northern Iraq during the [[1980s]]<ref name=http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp>[http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp]</ref>.
+
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 [[Kurd]]s in northern Iraq during the 1980s<ref name=http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp>[http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp]</ref>.
  
 
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]]<ref>{{cite web
 
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]]<ref>{{cite web
Line 109: Line 113:
 
Hydrogen cyanide gas in air is explosive at concentrations over 5.6%, equivalent to 56,000&nbsp;[[parts per million|ppm]]<ref name=http://www.cdc.gov/Niosh/idlh/74908.html>[http://www.cdc.gov/Niosh/idlh/74908.html]</ref>.
 
Hydrogen cyanide gas in air is explosive at concentrations over 5.6%, equivalent to 56,000&nbsp;[[parts per million|ppm]]<ref name=http://www.cdc.gov/Niosh/idlh/74908.html>[http://www.cdc.gov/Niosh/idlh/74908.html]</ref>.
  
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==Footnotes==
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==See also==
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<!--<nowiki>
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  See http://en.wikipedia.org/wiki/Wikipedia:Footnotes for an explanation of how
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* [[Chemical warfare]]
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  to generate footnotes using the<ref> and</ref> tags, and the template below
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* [[Cyanide]]
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</nowiki>—>
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{{reflist|2}}
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==Notes==
 +
<references/>
  
 
==References==
 
==References==
−
* Institut national de recherche et de sécurité (1997). "[http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf Cyanure d'hydrogène et solutions aqueuses]". ''Fiche toxicologique n° 4'', Paris:INRS, 5pp. (PDF file, ''in French'')
 
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==See also==
 
−
* [[Cyanide]]
 
−
* [[Hydrogen isocyanide]] (HNC)
 
  
 
==External links==
 
==External links==
Line 131: Line 131:
 
* [http://www.hpa.org.uk/infections/topics_az/deliberate_release/chemicals/cyanide.pdf#search=%22%22dicobalt%20edetate%22%22 Department of health review]
 
* [http://www.hpa.org.uk/infections/topics_az/deliberate_release/chemicals/cyanide.pdf#search=%22%22dicobalt%20edetate%22%22 Department of health review]
 
* [http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html OSHA: HCN Health Guidelines]
 
* [http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html OSHA: HCN Health Guidelines]
 +
* Institut national de recherche et de sécurité (1997). "[http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf Cyanure d'hydrogène et solutions aqueuses]." ''Fiche toxicologique n° 4'', Paris:INRS, 5pp. (PDF file, ''in French'')
  
 
{{Chemical warfare}}
 
{{Chemical warfare}}

Revision as of 18:16, 7 December 2007


Hydrogen cyanide
Hydrogen-cyanide-2D.png
Hydrogen-cyanide-3D-vdW.png
IUPAC name Hydrogen cyanide
Other names Hydrocyanic acid
prussic acid,
formonitrile
formic anammonide
carbon hydride nitride
cyclon
Identifiers
CAS number [74-90-8]
RTECS number MW6825000
Properties
Molecular formula HCN
Molar mass 27.03 g/mol
Appearance Colorless gas or pale blue
highly volatile liquid
Density 0.687 g/cm³, liquid.
Melting point

-13.4°C (259.75 K, 7.88°F)

Boiling point

26°C (299.15 K, 78.8°F)

Solubility in water Completely miscible.
Acidity (pKa) 9.2 - 9.3
Structure
Molecular shape Linear
Dipole moment 2.98 D
Hazards
Main hazards Highly toxic, highly flammable.
NFPA 704

NFPA 704.svg

4
4
2
 
R-phrases R12, R26, R27, R28, R32.
S-phrases (S1), S2, S7, S9, S13, S16,
S28, S29, S45.
Flash point −17.78 °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)

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.

Occurrence

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). Such molecules slowly release hydrogen cyanide.[2][3] Some millipedes release hydrogen cyanide as a defense mechanism,[4] 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.

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.[5] 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.[6]

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:[7]

CH4 + NH3 + 1.5O2 → HCN + 3H2O

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:[8]

CH4 + NH3 → HCN + 3H2

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:

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.

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]

In hydrocyanation, HCN adds to alkenes to give nitriles. This reaction is employed to manufacture adiponitrile, the precursor to Nylon 66.

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 largely replaced the use of cyanide in insect killing jars. Cyanide is also being used for capital punishment.

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.

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.

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].

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]

Hydrogen cyanide gas in air is explosive at concentrations over 5.6%, equivalent to 56,000 ppm[14].

See also

Notes

  1. ↑ Online Mendelian Inheritance in Man, Cyanide, inability to smell
  2. ↑ J. Vetter (2000). Plant cyanogenic glycosides. Toxicon. 38: 11-36.
  3. ↑ D. A. Jones (1998). Why are so many food plants cyanogenic?. Phytochemistry 47: 155-162.
  4. ↑ M. S. Blum, J. P. Woodring (1962). Secretion of Benzaldehyde and Hydrogen Cyanide by the Millipede Pachydesmus crassicutis (Wood). Science 138: 512 - 513.
  5. ↑ 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.
  6. ↑ 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
  7. ↑ L. Andrussow (1935). The catalytic oxydation of ammonia-methane-mixtures to hydrogen cyanide.. Angewandte Chemie 48: 593-595.
  8. ↑ F. Endter (1958). Die technische Synthese von Cyanwasserstoff aus Methan und Ammoniak ohne Zusatz von Sauerstoff. Chemie Ingenieur Technik 30 (5): 281-376.
  9. ↑ http://www.osha.gov/SLTC/healthguidelines/hydrogencyanide/recognition.html
  10. ↑ Hydrogen Cyanide. Organization for the Prohibition of Chemical Weapons. Retrieved 2006-10-07.
  11. ↑ http://www.bt.cdc.gov/agent/cyanide/basics/facts.asp
  12. ↑ Chronology of Aum Shinrikyo's CBW Activities (pdf).
  13. ↑ http://www.time.com/time/magazine/article/0,9171,1205478,00.html
  14. ↑ [1]

References
ISBN links support NWE through referral fees

External links

WMD-chemical.svg
Agents of Chemical Warfare
Blood agents: Cyanogen chloride (CK) – Hydrogen cyanide (AC)
Blister agents: Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3)
Nerve agents: G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) | V-Agents: VE – VG – VM – VX
Pulmonary agents: Chlorine – Chloropicrin (PS) – Phosgene (CG) – Diphosgene (DP)
Incapacitating agents: Agent 15 (BZ) – KOLOKOL-1
Riot control agents: Pepper spray (OC) – CS gas – CN gas (mace) – CR gas

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