ADIPONITRILE (NC(CH₂)₄CN)

Adiponitrile, a colorless liquid, is slightly soluble in water but soluble in alcohol. The main use of adiponitrile is to make nylon 6/6. The production of adiponitrile from butadiene starts by a free radical chlorination, which produces a mixture of 1,4-dichloro-2-butene and 3,4- dichloro-l-butene:

The vapor-phase chlorination reaction occurs at approximately 200–300°C. The dichlorobutene mixture is then treated with NaCN or HCN in presence of copper cyanide. The product 1,4-dicyano-2-butene is obtained in high yield because allylic rearrangement to the more thermodynamically stable isomer occurs during the cyanation reaction:

Adiponitrile may also be produced by the electrodimerization of acrylonitrile or by the reaction of ammonia with adipic acid followed by two-step dehydration reactions: