Reactions of organic peroxides. Part X. Amino-peroxides from cyclohexanone

Abstract

Reaction of cyclohexanone with hydrogen peroxide and ammonia gives either 1,1′-peroxydicyclohexylamine or 1-hydroperoxycyclohexylamine, depending on the ketone to hydrogen peroxide ratio. The reactions of these peroxy-amines studied include (i) base-catalysed conversion of 1,1′-peroxydicyclohexylamine into caprolactam and cyclohexanone, (ii) vapour-phase pyrolysis of 1,1′-peroxydicyclohexylamine to decane-1,10-dicarbonimide, 11-cyanoundecanoic acid, caprolactam, and cyclohexanone, and (iii) conversion of 1-hydroperoxycyclohexylamine into cyclohexanone oxime with tungstate catalysts.