Abstract
The cathodic crossed hydrocoupling of acetone with acrylonitrile, which occurs at about −1·20 V(sce) in aqueous sulphuric acid, has been investigated.At mercury the yield ana the current efficiency for the hydrocoupling product were both over 70 per cent based on acrylonitrile. However, at lead and at cadmium, both decreased, with increasing hydrocarbon formation. It was also observed that benzophenone could hardly be hydrocoup led with acrylonitrile under the same conditions. The results support a tentative mechanism of this process, in which the reaction of a hydroacetone anion with an acrylonitrile molecule was proposed. This reaction was found to be applicable to methylethylketone and diethylketone with 60 and 30 per cent current efficiency respectively.In aqueous quaternary ammonium salt solution, the same reaction may be obtained at −1·90 V though the yield of the product is not as good. This may be the reaction of a hydroacrylonitrile anion with an acetone molecule.The formation at the cathode of terebic acid from a mixture of acetone and maleic acid is also reported.
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