Nitriles

Abstract Nitriles are cyano‐substituted organic compounds, ie, organic derivatives of hydrogen cyanide. The combination of unique physical properties imparted by the nitrile group and the ease with which nitrile groups can be converted to other functional groups has made organonitrile compounds commercially important substances. Organonitriles may be prepared by a variety of methods including metathesis of organohalides, ammoxidation of hydrocarbons, dehydration of amides, and addition of hydrogen cyanide to unsaturated organic compounds such as aldehydes, ketones, and olefins. Some of the more common transformations include hydrolysis or alcoholysis to produce amides, acids and esters, and hydrogenation to produce amines, which are intermediates for the production of polyurethanes and polyamides. Nitriles are generally toxic to the extent that they may be metabolized in the body to liberate cyanide, and care in the body to liberate cyanide and care should be taken to prevent skin contact, oral ingestion or inhalation of vapors. This article addresses the following organonitrile compounds in some detail: acetonitrile, adiponitrile, a‐aminonitriles, azobisnitriles, benzonitrile, cyanoacetic acid (and esters), isophthalonitrile, methylglutaronitrile, pentenenitriles, and fatty acid nitriles.