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==Safety==
==Safety==
Like other inorganic [[cyanide]]s, cyanogen is very toxic, as it undergoes reduction to [[cyanide]], which binds more strongly than oxygen to the [[cytochrome c oxidase]] complex, thus interrupting the [[mitochondrion|mitochondrial]] [[electron transfer chain]]. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions, and death, depending on exposure.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref>
Like other inorganic [[cyanide]]s, cyanogen is very toxic, as it readily undergoes reduction to [[cyanide]], which poisons the [[cytochrome c oxidase]] complex, thus interrupting the [[mitochondrion|mitochondrial]] [[electron transfer chain]]. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions, and death, depending on exposure.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref>


Cyanogen produces the second hottest known natural flame (after [[Dicyanoacetylene|carbon subnitride]]) with a temperature of over 4525&nbsp;°C when it burns in oxygen.<ref>{{Cite journal
Cyanogen produces the second hottest known natural flame (after [[Dicyanoacetylene|carbon subnitride]]) with a temperature of over 4525&nbsp;°C when it burns in oxygen.<ref>{{Cite journal

Revision as of 05:36, 27 March 2012

This article is about the chemical compound. For the Android firmware, see CyanogenMod.
Cyanogen
Cyanogen
Names
IUPAC name
Ethanedinitrile
Other names
Cyanogen
Carbon nitride
Dicyan
Dicyanogen
Nitriloacetonitrile
Oxalic acid dinitrile
Oxalonitrile
Oxalyl cyanide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.643 Edit this at Wikidata
EC Number
  • 207-306-5
RTECS number
  • GT1925000
UN number 1026
  • InChI=1S/C2N2/c3-1-2-4 checkY
    Key: JMANVNJQNLATNU-UHFFFAOYSA-N checkY
  • InChI=1/C2N2/c3-1-2-4
    Key: JMANVNJQNLATNU-UHFFFAOYAS
  • N#CC#N
Properties
C2N2
Molar mass 52.036 g·mol−1
Density 0.95 g/cm3 (liquid, −21 °C)
Melting point −28 °C (−18 °F; 245 K)
Boiling point −21 °C (−6 °F; 252 K)
450 mL/100 mL (20 °C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
4
2
Flash point Flammable gas
Explosive limits 6.6–42.6%
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cyanogen is the chemical compound with the formula (CN)2. It is a colorless, toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups — analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N, although other isomers have been detected.[1] Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example cyanogen bromide has the formula NCBr.[2]

Cyanogen is the anhydride of oxamide:

H2NC(O)C(O)NH2 → NCCN + 2 H2O

Preparation

Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide:

2 Hg(CN)2 → (CN)2 + Hg2(CN)2

Alternatively, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.[3]

2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4

Industrially, it is created by the oxidation of hydrogen cyanide, usually using chlorine over an activated silicon dioxide catalyst or nitrogen dioxide over a copper salt. It is also formed when nitrogen and acetylene are reacted by an electrical spark or discharge.[4]

Paracyanogen

Paracyanogen is produced by polymerization of cyanogen through pyrolysis of heavy metal cyanides.[5]

Astronomy

Cyanogen is used to measure the temperature of interstellar gas clouds[6].

Cyanogen is found in many comets and gives them their greenish halo[7].

History

Cyanogen was first synthesized in 1815 by Joseph Louis Gay-Lussac, who determined its empirical formula and named it.[8] It attained importance with the growth of the fertilizer industry in the late nineteenth century and is still an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of nitrocellulose.

Safety

Like other inorganic cyanides, cyanogen is very toxic, as it readily undergoes reduction to cyanide, which poisons the cytochrome c oxidase complex, thus interrupting the mitochondrial electron transfer chain. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions, and death, depending on exposure.[9]

Cyanogen produces the second hottest known natural flame (after carbon subnitride) with a temperature of over 4525 °C when it burns in oxygen.[10]

See also

References

  1. ^ Ringer, Ashley (Jan 15). "Low-lying singlet excited states of isocyanogen". International Journal of Quantum Chemistry. Vol. 106, no. 6. Wiley. pp. 1137–1140. {{cite news}}: Check date values in: |date= and |year= / |date= mismatch (help)
  2. ^ Hartman W. W.; Dreger, E. E. "Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf
  3. ^ T. K. Brotherton, J. W. Lynn (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews. 59 (5): 841–883. doi:10.1021/cr50029a003.
  4. ^ A. A. Breneman (1959). "Showing the Progress and Development of Processes for the manufacture of Cyanogen and its Derivates (in: THE FIXATION OF ATMOSPHERIC NITROGEN". Journal of the American Chemical Society. 11 (1): 2–28. doi:10.1021/ja02126a001.
  5. ^ Paracyanogen Paracyanogen
  6. ^ http://www.mendeley.com/research/interstellar-cyanogen-temperature-cosmic-microwave-background-radiation/
  7. ^ http://science.nasa.gov/science-news/science-at-nasa/2009/04feb_greencomet/
  8. ^ Joseph Louis Gay-Lussac (1815) "Recherches sur l'acide prussique," Annales de chimie, vol. 95, pages 136-231. On page 163 of this article, Gay-Lussac coined the word "cyanogène" from the Greek words κύανος (kyanos, blue) and γεννάω (gennao, I create), because cyanide was first isolated by the Swedish chemist Carl Wilhelm Scheele from the pigment "Prussian blue".
  9. ^ Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of Chemistry, London.
  10. ^ Thomas, N.; Gaydon, A. G.; Brewer, L., A. G.; Brewer, L. (March 1952). "Cyanogen Flames and the Dissociation Energy of N2". The Journal of Chemical Physics. 20 (3): 369–374. Bibcode:1952JChPh..20..369T. doi:10.1063/1.1700426.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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