Hydrothermal reaction of saturated and unsaturated nitriles: Reactivity and reaction pathway analysis

The reactions of acrylonitrile, crotonitrile, propionitrile, and a small se t of related reaction products were investigated in high-temperature water. Hydrolysis of the cyano group yielded the corresponding amides, which unde rwent similar hydrolysis to yield the carboxylic acids. The conversion of a crylonitrile was more rapid than that of its saturated analogue propionitri le, as the unsaturated site of acrylonitrile provided a facile pathway for the formation of alcohols, amines, and ethers. Carbon-carbon bond cleavage pathways involving the hydration of the olefin moiety were also observed fo r acrylonitrile.