Journal of Japan Oil Chemists' Society
Online ISSN : 1884-2003
ISSN-L : 0513-398X
Syntheses of Tetra- (β-cyanoethyl) -ethylene-diamine and Nonamethylene-diamine
Studies on Bis-cyanoethylation of Fatty Amines. V.
Seimei NITANAI
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1964 Volume 13 Issue 7 Pages 374-378

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Abstract
In this paper, the synthesis of tetracyanoethylate in the reaction of ethylene diamine or nonamethylene diamine with acrylonitrile were studied.
Molratio of acrylonitril to amine, solvents, weight ratio of solvent to amine, reaction temperature and reaction time were investigated.
As a result, it was found that the reaction carried out in methanol containing water was effective in the tetra-cyanoethylation of ethylene diamine, that the reaction carried out in methanol or methanol containing water were very effective in the tetra-cyanoethylation of nonamethylene diamine, and that the reactivity in cyanoethylation varied with the length of carbon chain of diamines, but nonamethylene diamine indicated approximately the same reactivity as that of hexamethylene diamine which was reported in previous papers.
N, N, N', N'-tetra (β-cyanoethyl) -alkylene diamine was obtained in stoichiometric quantity under the optimum condition that twice methanol or methanol containing water by weight for the amine and six moles of acrylonitrile to one mol of amine was refluxed at the reaction temperature of 70°C for 24hrs or 48hrs.
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