Several addition reactions of ethylenimine with various amino compounds, using water as a catalyst have been reported by Wilson (1). Substituted diamines have been prepared most commonly by a Gabriel Synthesis (2) from primary and secondary amines and B-bromoethylphthalimide, and through the reaction of ethylene oxide with amines to form ethanolamine from which the diamine could be prepared (3). However, the addition of primary and secondary amines to ethylenimine represents a direct and simple method for their preparation, providing satisfactory yields can be obtained. In the present work, a study of this addition reaction as catalyzed by aluminum chloride has been made. The use of aluminum chloride has certain advantages over the use of water since the reaction is carried out under anhydrous conditions and in many cases the isolation of products is more easily effected than when a large volume of water is used. So far as the present authors are aware, the catalysis by aluminum chloride of such an addition has not been previously reported.
Proceedings of the Iowa Academy of Science
©1946 Iowa Academy of Science, Inc.
Hicks, Zella A. and Coleman, George H.
"The Addition of Amines to Ethylenimine,"
Proceedings of the Iowa Academy of Science, 53(1), 207-209.
Available at: https://scholarworks.uni.edu/pias/vol53/iss1/25