Influence of the nature of the solvent on the direction of the catalytic reaction of aminoalkylation of unsymmetrical aliphatic diamines

Abstract

The influence of the solvent nature on the direction of the aminoalkylation reaction of asymmetric diamines under the conditions of basic catalysis is studied. A general mechanism of the process is proposed, including intermediate stages of formation of two types of quaternary ammonium centers (QAC), which have different reactivity in the subsequent stage of destruction. It is established that the ratio of the yields of the final reaction products, secondary triamines and triamines with a quaternary nitrogen atom, is determined by the degree of stabilizing effect of the solvent on the reaction center of QAC of different structures R1R2R3N+ and R1R2HN+.