Phase-transfer catalysis of a new cationic gemini surfactant with ester groups for nucleophilic substitution reaction

A highly effective phase transfer of a quaternary ammonium gemini surfactant with ester groups ((diethylhexanedioate) diyl-alpha,omega-bis(dimethyl dodecyl ammonium bromide) referred to as 12-10-12) was synthesized with high yield and characterized by infrared spectroscopy, elemental analysis and H-1-NMR. Then, 12-10-12 was used as a phase transfer catalyst to study the catalytic effect on the reaction of anhydrous sodium acetate and 4-methylbenzyl chloride. The possible catalytic mechanism and the influence of surfactant concentration, temperature and type are also discussed. The experimental results showed that the catalysis efficiency was more active than the traditional, single-chained surfactant, tetrabutyl ammonium bromide. It also revealed that the reaction was first-order with respect to the concentration of 4-methylbenzyl chloride. The concentration of 4-methylbenzyl chloride grew linearly with the concentration of 12-10-12 and as the reaction temperature increased. The optimum reaction time was 7 h. (C) 2014 Zhong-Wen Pan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.