Study on Bis-cyanoethylation of Fatty Amines. II

Synthesis of Bis- (β-cyanoethyl) -hexyl amine and Bis- (β-cyanoethyl) -nonylamine

Abstract

In the previous report, authors described on the bis-cyanoethylation of cetyl amine. In this paper, studies on the bis-cyanoethylation of hexyl amine and nonyl amine are reported.
In this experiment, the relation between the reaction in polar solvent or in non-polar solvent and the composition of cyanoethylate was investigated.
As a result, cyanoethylation to form mono-compound and his-compound was a successive reaction and bis-compound was obtained with a yield of about 90% under the suitable condition in methanol solvent, whereby a mixture of 2 parts of solvent per part of amine and 3 mol of acrylonitrile per mol of amine was used and the mixture was refluxed at reaction temperature of 70°C in atmospheric pressure and maintained at reflux for 48 hr. Optimum conditions in the reaction to hexyl amine and to that of nonyl amine were nearly the same except that the reaction velocity of the former was something fast. At the reaction in benzene solvent, under the same condition abovementioned, mono-compound obtained from the both amines was at yield from 94 to 97%, and bis-compound from the both was at yield of about 3% respectively. In the case of non-solvent, under the same condition, mono-compounds from the both amines were at yield of about 85%, and about 15% for his-compounds.
Authors found it as the difference in reaction velocity between those amines and cetyl amine in the bis-cyanoethylation, that the change in reaction temperature ranging from 20 to 70°C had no exceeding influence upon the yield of the bis-compounds of the both amines, and that the reaction velocity to form bis-compound with both amines in the methanol was slower than that of cetyl amine.