The Hydrodimerization of Acrylonitrile

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Abstract
During the course of our studies of the dimerization of such vinyl monomers as acrylonitrile or acrolein with various Ziegler-type catalysts or metal carbonyls, it has been found that acrylonitrile is converted at an elevated temperature in an iron or cobalt carbonyl-alkali-water system, an iron or cobalt carbonyl-sodium borohydride or -lithium aluminum hydride system, or a cobalt carbonyl - H2 system to hydrodimers of acrylonitrile composed of adiponitrile and 2-methylglutaronitrile as well as propionitrile. Some iron carbonyl hydrides, which are presumably formed as intermediates in these reactions, were therefore prepared and subjected to reaction with acrylonitrile, 3-chloropropionitrile, or ethyl acrylate. On the basis of these experimental results, a reaction mechanism containing a cyanoethyl complex as an intermediate was proposed for the formation of hydrodimers of acryionitrile.