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Cyanogen

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Title: Cyanogen  
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Subject: 96P/Machholz, Acetylene, Oxamide, Aminoacetonitrile, Thiocyanic acid
Collection: Cyanides, Inorganic Carbon Compounds, Inorganic Nitrogen Compounds
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Cyanogen

Cyanogen
Skeletal formula of cyanogen
Ball and stick model of cyanogen
Spacefill model of cyanogen
Names
IUPAC name
  • Ethanedinitrile[1] (substitutive)
  • Bis(nitridocarbon)(CC)[1] (additive)
Other names
  • Dicyan[2][3]
  • Carbon nitride[2]
  • Oxalic acid dinitrile[3]
  • Dicyanogen
  • Nitriloacetonitrile
  • Oxalonitrile[2]
  • Oxalyl cyanide
Identifiers
 YesY
1732464
ChEBI  YesY
ChemSpider  YesY
EC number 207-306-5
1090
Jmol-3D images Image
MeSH
PubChem
RTECS number GT1925000
UN number 1026
Properties
C2N2
Molar mass 52.04 g·mol−1
Appearance Colourless gas
Odor pungent, almond-like
Density 950 mg mL−1 (at −21 °C)
Melting point −28 °C (−18 °F; 245 K)
Boiling point −21.2 °C; −6.1 °F; 252.0 K
45 g/100 mL (at 20 °C)
Solubility soluble in ethanol, ethyl ether
Vapor pressure 5.1 atm (21 °C)[4]
1.9 μmol Pa−1 kg−1
1.327 (18 °C)
Thermochemistry
241.57 J K−1 mol−1
309.07 kJ mol−1
−1.0978–−1.0942 MJ mol−1
Hazards
Main hazards forms cyanide in the body; flammable[4]
Safety data sheet inchem.org
Extremely Flammable F+ Toxic T Dangerous for the Environment (Nature) N
R-phrases R50/53
S-phrases (S1/2), S16, S33, S45, S63
NFPA 704
4
4
2
Explosive limits 6.6–32%[4]
US health exposure limits (NIOSH):
PEL (Permissible)
none[4]
REL (Recommended)
TWA 10 ppm (20 mg/m3)[4]
N.D.[4]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY  (: YesY/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.[5] Certain derivatives of cyanogen are also called "cyanogen" even though they contain only one CN group. For example cyanogen bromide has the formula NCBr.[6]

Cyanogen is the anhydride of oxamide:

H2NC(O)C(O)NH2 → NCCN + 2 H2O

although oxamide is manufactured from cyanogen by hydrolysis:[7]

NCCN + 2 H2O → H2NC(O)C(O)NH2

Contents

  • Preparation 1
  • Paracyanogen 2
  • History 3
  • Safety 4
  • See also 5
  • References 6
  • External links 7

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.[8]

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.[9]

Paracyanogen

Paracyanogen can be best prepared by heating mercuric cyanide. It can also be prepared by heating silver cyanide, silver cyanate, cyanogen iodide or cyanuric iodide.[10] It can also be prepared by the polymerization of cyanogen at 300-500 °C in the presence of trace impurities. Paracyanogen can also be converted back to cyanogen by heating to 800 °C.[7] Based on experimental evidence, the structure of this polymeric material is thought to be rather irregular, with most of the carbon atoms being of sp2 type and localized domains of pi conjugation.[11]

History

Cyanogen was first synthesized in 1815 by Joseph Louis Gay-Lussac, who determined its empirical formula and named it. Gay-Lussac coined the word "cyanogène" from the Greek words κυανός (kyanos, blue) and γεννάω (gennao, I create), because cyanide was first isolated by the Swedish chemist Carl Wilhelm Scheele from the pigment "Prussian blue".[12] By the 1850s, cyanogen soap was used by photographers to remove silver stains from their hands. [13] 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 is a highly toxic compound, and in 1910 a spectroscopic analysis of Halley's Comet found cyanogen in the comet's tail. This led to public fear that the Earth would be poisoned as it passed through the tail. Because of the extremely diffuse nature of the tail, there was no effect when the planet passed through it.[14][15]

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.[16] Lethal dose through inhalation typically ranges from 100 to 150 mg. Inhalation of 900 ppm over a period of 10 min is considered lethal.[17]

Cyanogen produces the second hottest known natural flame (after carbon subnitride) with a temperature of over 4525 °C (or 8177 °F) when it burns in oxygen.[18][19]

See also

References

  1. ^ a b
  2. ^ a b c
  3. ^ a b
  4. ^ a b c d e f
  5. ^
  6. ^ ;
  7. ^ a b
  8. ^
  9. ^
  10. ^
  11. ^
  12. ^
  13. ^
  14. ^ Comet's Poisonous Tail
  15. ^ Halley's Comet 100 years Ago
  16. ^
  17. ^ p. 82.
  18. ^
  19. ^

External links

  • National Pollutant Inventory - Cyanide compounds fact sheet
  • PhysOrg.com
  • CDC - NIOSH Pocket Guide to Chemical Hazards
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