Published procedures for the reaction of primary aromatic amines with epihalohydrins to give 1:1 addition compounds are not generally applicable, and we have found that they frequently lead to impure products. The reactions were investigated in water, alcohol and bromobenzene solutions. A number of techniques were used to follow the reaction. Infrared spectroscopy gave qualitative data since significant changes occur in the 2.5 μ - 3.0 μ and the 10 μ - 11 μ regions of the spectrum. Thin layer chromatography made it possible to detect the formation of by-products and to determine the purity of the addition compounds. The best quantitative measure of the rate of the reaction was obtained by means of an oxirane titration with HBr. The reaction of epichlorohydrin with p-anisidine, p-toluidine and aniline in bromobenzenc solution exhibited an induction period believed to be due to the catalytic effect of HCI split out from the addition compound by unreacted amine.
Proceedings of the Iowa Academy of Science
©1964 Iowa Academy of Science, Inc.
Aniline, Orm and Pennington, F. C.
"Reaction of Aromatic Amines with Epihalohydrins,"
Proceedings of the Iowa Academy of Science, 71(1), 172-176.
Available at: https://scholarworks.uni.edu/pias/vol71/iss1/27