Preparation of Quaternary Ammonium Salts Containing Ester Groups from Epichlorohydrin

Abstract

Abstract:A series of quaternary ammonium salts containing ester groups in their alkyl chains were prepared effectively from the one-pot reaction of alkylamine with epichlorohydrin and fatty acid. The reaction of alkylamine, epichlorohydrin and fatty acid was investigated by measuring the acid and amine values of the intermediates. It is considered to be a two step reaction: One is the formation of alkyl chloride containing an ester group from the reaction of fatty acid with epichlorohydrin. The other is the quaternarization of alkylamine with alkyl chloride containing an ester group. It was also found that the formation of alkyl chloride is greatly assisted by alkylamine, which is the raw material for the quaternary ammonium salt. The surface-active properties of prepared quaternary ammonium salts were measured and compared with the conventional quaternary ammonium salts.

Effect of Spacer Structures on the Interfacial Adsorption and Micelle Properties of Quaternary Ammonium Salt-Based Gemini Surfactants

“…The surface tension of the gemini surfactants increased with the length of the spacer. The γ CMC of the 2C 12 (Spacer) surfactants with long spacers were comparable to those of conventional monomeric surfactants, such as C 12 TAB (38.6 mN m –1 ) and C 12 TAC (39.0 mN m –1 ) . The Γ values of 2C 12 (Spacer) were (1.17–1.50) × 10 –6 mol m –2 , which were smaller than those of the corresponding monomeric surfactants such as C 12 TAB (3.42 × 10 –6 mol m –2 ) and C 12 TAC (1.87 × 10 –6 mol m –2 ) .…”

“…The γ CMC of the 2C 12 (Spacer) surfactants with long spacers were comparable to those of conventional monomeric surfactants, such as C 12 TAB (38.6 mN m −1 ) 35 and C 12 TAC (39.0 mN m −1 ). 37 The Γ values of 2C 12 (Spacer) were (1.17− 1.50) × 10 −6 mol m −2 , which were smaller than those of the corresponding monomeric surfactants such as C 12 TAB (3.42 × 10 −6 mol m −2 ) 35 and C 12 TAC (1.87 × 10 −6 mol m −2 ). 36 The A values of 2C 12 (Spacer) were 1.11−1.42 nm 2 , which were larger than those of the corresponding monomeric surfactants such as C 12 TAB (0.490 nm 2 ) 35 and C 12 TAC (0.889 nm 2 ).…”

“… a CMC determined from surface tension measurement. b CMC determined from conductivity measurement. c –: not obtained. d Ref . e Ref . f Ref . g Ref . …”