Capronitrile

Capronitrile, also known as hexanenitrile, is an aliphatic nitrile with six carbon atoms in the molecule (the nitrile carbon plus a five-carbon alkyl chain), giving the formula C6H11N. It is a straight-chain nitrile and is primarily encountered as an industrial chemical used as an intermediate in organic synthesis.

Production and applications

Capronitrile is typically produced by nitrile-forming routes such as hydrocyanation of 1-hexene or related hydrocarbon precursors. In commerce it is used as a chemical intermediate in the synthesis of more complex compounds and as a solvent for certain organic reactions. Its role is largely as a building block in the production of specialty chemicals rather than a bulk commercial product.

Physical and chemical properties

Capronitrile is usually described as a colorless to pale liquid with a characteristic acrid odor. It is immiscible with water and is soluble in many organic solvents. It has a relatively high boiling point compared with smaller nitriles, reflecting its longer hydrocarbon chain. The nitrile group is relatively stable but can undergo hydrolysis under acidic or basic conditions to give hexanoic acid (caproic acid) and ammonia.

Safety and handling

Capronitrile is an irritant and should be handled with appropriate protective equipment in a well-ventilated area. Like other nitriles, it can pose health hazards if inhaled, ingested, or absorbed through the skin, and it may release cyanide under certain hydrolytic conditions. It should be stored away from heat, flames, and strong oxidizers.

See also

Nitriles, hexanenitrile, caproic-related chemistry.