Synthesis of cationic surfactants with alkenyl group

Abstract

Quaternary ammonium chlorides with long chain alkenyl groups were synthesized by the reaction of tert-amines with alkylallyl chloride which, in turn, were obtained by the allylic chlorination of l-olefins with N-tert-butyl-or N-cyclohexyl-N-ehloro-ethanesulfonamides. Of the two kinds of alkylallyl chlorides prepared by the allylic chlorination of 1-olefins, the 7-alkylallyt ctflorides(I), were found to be reactive with tert-amines, while the secondary chlorides, 0~-alkylallyl chlorides(II), were not so reactive and, when the allylic chloride mixture was reacted with tert-amine under suitable reaction conditions, the 7-alkylallyl chloride could be selectively converted to a quaternary ammonium chloride while the a-alkylallyl chloride was recovered unreacted. The quaternary ammonium chlorides thus obtained were identified as 7-alkylallyl ammonium chlorides from their spectra, and they were shown to possess almost the same surface tension lowering ability as their saturated homologs, although larger critical micelle concentration values and greater water solubilities were observed.