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Cyanogen
From Wikipedia, the free encyclopedia
| Cyanogen | |
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| Chemical name | Ethanedinitrile |
| Other names | Cyanogen Carbon nitride Dicyan Dicyanogen Nitriloacetonitrile Oxalic acid dinitrile Oxalonitrile Oxalyl cyanide |
| Chemical formula | C2N2 |
| Molecular mass | 52.04 g mol−1 |
| CAS number | [460-19-5] |
| Density | 0.95 g cm−3 at −21 °C |
| Melting point | −28 °C |
| Boiling point | −21 °C |
| SMILES | N#CC#N |
| NFPA 704 |
4
4
2
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| Disclaimer and references | |
Cyanogen is a chemical compound (CN)2. The CN entity behaves like a halogen. Cyanogen molecules consist of two CN groups (analogous to diatomic halogen molecules, such as F2, Cl2, Br2, or I2). The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N. The word “cyanogen” may refer to a single cyano group in some molecules that are considered derivatives of cyanogen. Cyanogen chloride (NCCl), for example, is considered (for the purposes of naming) to be cyanogen with one cyano group replaced with a chlorine atom.
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At room temperature cyanogen is a colorless gas with a pungent odor. Its melting point is −27.9°C (−18.2°F) & its boiling point is −20.1°C (−4.2°F). Its density is approximately twice that of air at the same temperature and pressure. Like most cyanides, it 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.
2 Hg(CN)2 → NCCN + 2 HgCN
Cyanogen can be prepared in the laboratory by heating mercuric cyanide . 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. Cyanogen is also formed when nitrogen (N2) and acetylene (C2H2) are made to react by an electrical spark or discharge.
2 CuSO4 + 4 KCN → 2 Cu(CN)2 + 2 K2SO4 → NCCN + 2 CuCN + 2 K2SO4
On mixing 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.[1]
Cyanogen has a long history and was probably first synthesised around 1782 by Carl Scheele when he studied hydrogen cyanide.[2] It had definitely been synthesised by 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.
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.[3]
- ^ T. K. Brotherton, J. W. Lynn (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews 59 (5): 841 - 883. DOI:10.1021/cr50029a003.
- ^ H. Bauer (1980). "Die ersten organisch-chemischen Synthesen". Naturwissenschaften 67 (1): 1 -6. DOI:10.1007/BF00424496.
- ^ Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of Chemistry, London.
- J. Gay-Lussac (1815). ".". Ann. chim. et phys. 96: 175.
- 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.