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Acetonitrile can also be produced by many other methods, but these are of no commercial importance as of 2002. Illustrative routes are by dehydration of acetamide or by hydrogenation of mixtures of carbon monoxide and ammonia. [16] In 1992, 14,700 tonnes (16,200 short tons) of acetonitrile were produced in the US.
A colorless liquid, it is derived from acetonitrile (CH 3 CN) by replacement of one H with Cl. In practice, it is produced by dehydration of chloroacetamide. [1] The compound is an alkylating agent, [2] and as such is handled cautiously. Chloroacetonitrile is also generated in situ by the reaction of acetonitrile with sulfur monochloride.
The aqueous solution consists of acrylonitrile, acetonitrile, hydrocyanic acid, and ammonium sulfate (from excess ammonia). A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation. One of the first useful catalysts was bismuth phosphomolybdate (Bi 9 PMo 12 O 52) supported on silica. [11]
The cation was first reported in 1923 with a nitrate anion as a byproduct of the reduction of silver nitrate with a suspension of copper powder in acetonitrile. [4] [Cu(CH 3 CN) 4]PF 6 is generally produced by the addition of HPF 6 to a suspension of copper(I) oxide in acetonitrile: [5] Cu 2 O + 2 HPF 6 + 8 CH 3 CN → 2 [Cu(CH 3 CN) 4]PF 6 + H 2 O
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Typical nitrile ligands are acetonitrile, propionitrile, and benzonitrile.The structures of [Ru(NH 3) 5 (NCPh)] n+ have been determined for the 2+ and 3+ oxidation states. Upon oxidation the Ru-NH 3 distances contract and the Ru-NCPh distances elongate, consistent with amines serving as pure-sigma donor ligands and nitriles functioning as pi-acceptors.