Cyanogen
Chemical compound
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Through Chemical formula, Carbon and Nitrogen
Cyanogen is the anhydride of oxamide:
- H2N−C(=O)−C(=O)−NH2 → N≡C−C≡N + 2 H2O
Oxamide is manufactured from cyanogen by hydration:
- N≡C−C≡N + 2 H2O → H2N−C(=O)−C(=O)−NH2
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
Or, 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.
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.
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Reactions
Addition of disulfur dichloride to cyanogen gives 3,4-dichloro-1,2,5-thiadiazole.
Paracyanogen
Paracyanogen is a polymer of cyanogen. It can be best prepared by heating mercury(II) cyanide. It can also be prepared by heating silver cyanide, silver cyanate, cyanogen iodide or cyanuric iodide. It can also be prepared by the polymerization of cyanogen at 300 to 500 °C (572 to 932 °F) in the presence of trace impurities. Paracyanogen can also be converted back to cyanogen by heating to 800 °C (1,470 °F). 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 π conjugation.
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, to create), because cyanide was first isolated by Swedish chemist Carl Wilhelm Scheele from the pigment Prussian blue. It attained importance with the growth of the fertilizer industry in the late 19th century and remains an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of nitrocellulose.
Cyanogen is commonly found in comets. In 1910 a spectroscopic analysis of Halley's Comet found cyanogen in the comet's tail, which led to public fear that the Earth would be poisoned as it passed through the tail. People in New York wore gas masks, and merchants sold quack "comet pills" claimed to neutralize poisoning. Because of the extremely diffuse nature of the tail, there was no effect when the planet passed through it.
Interstellar medium
While cyanogen is believed to be abundant in the interstellar medium, it is not able to be directly detected via radio astronomy, as its lack of a dipole moment means it has no rotational microwave spectrum. Its protonated derivative NCCNH+ has been detected, as has its less stable isomer isocyanogen (cyanogen cyanide), −C≡N+−C≡N.
Dimerization of cyanide radicals can also produce a third, even less stable, isomer, diisocyanogen (C=N−N=C), which has been captured via matrix isolation in solid argon at 12 K. As of 2022, it is not known to be present in the interstellar medium.
Safety
Like other 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. Lethal dose through inhalation typically ranges from 100 to 150 milligrams (1.5 to 2.3 grains).
Cyanogen produces the second-hottest-known natural flame (after dicyanoacetylene aka carbon subnitride) with a temperature of over 4,525 °C (8,177 °F) when it burns in oxygen.