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Cyanogen



Cyanogen
IUPAC name Ethanedinitrile
Other names Cyanogen
Carbon nitride
Dicyan
Dicyanogen
Nitriloacetonitrile
Oxalic acid dinitrile
Oxalonitrile
Oxalyl cyanide
Identifiers
CAS number 460-19-5
SMILES N#CC#N
Properties
Molecular formula C2N2
Molar mass 52.04 g mol−1
Density 0.95 g cm−3 at −21 °C
Melting point

−28 °C

Boiling point

−21 °C

Hazards
NFPA 704
4
4
2
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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 it far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N, although other isomers have been detected. Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example Cyanogen bromide is the compound with the structure NCBr.[1]

Cyanogen is the anhydride of oxamide:

H2NC(O)C(O)NH2 → NCCN + 2 H2O

Additional recommended knowledge

Contents

Preparation

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

2 Hg(CN)2 → (CN)2 + 2 HgCN

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.[2]

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

Industrially, it is made 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 (N2) and acetylene (C2H2) are made to react by an electrical spark or discharge.[3]

History

Cyanogen has a long history and was probably first generated by Carl Scheele around 1782 in the course of his studies of hydrogen cyanide.[4] [5]The first confirmed synthesis was reported 1802, when it was used to make what we now know as cyanogen chloride. 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 undergoes reduction to cyanide, which binds more strongly than oxygen to 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.[6]

Cyanogen produces the second hottest known natural flame (after Carbon subnitride) with a temperature of over 4525°C (8180°F) when it burns in oxygen.[7]

See also

References

  1. ^ Hartman W. W.; Dreger, E. E. "Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf
  2. ^ T. K. Brotherton, J. W. Lynn (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews 59 (5): 841 - 883. doi:10.1021/cr50029a003.
  3. ^ A. A. Breneman (1959). "Showing the Progress and Development of Processes for the 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.
  4. ^ H. Bauer (1980). "Die ersten organisch-chemischen Synthesen". Naturwissenschaften 67 (1): 1 -6. doi:10.1007/BF00424496.
  5. ^ J. Gay-Lussac (1815). "?". Ann. chim. et phys. 96: 175.
  6. ^ Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of Chemistry, London.
  7. ^ Thomas, N. & Gaydon, A. G.; Brewer, L. (March 1952), " ", The Journal of Chemical Physics 20 (3): 369-374,
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cyanogen". A list of authors is available in Wikipedia.
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