Tetramethylammonium neodecanoate as a recyclable catalyst for acidolysis reaction of epichlorohydrin with neodecanoic acid

Abstract

The acidolysis of epoxides is an important series reaction applied in the polymer industry including coating and rubber. Glycidyl neodecanoate, which is a green material of environmentally friendly coatings, is synthesized through the acidolysis reaction of epichlorohydrin (ECH) with neodecanoic acid. We developed a green catalyst named tetramethylammonium neodecanoate (TMAN) for this reaction. TMAN is totally recyclable and the reaction system can be homogeneous, thus combining the advantages of tertiary amines and quaternary ammonium salts, meanwhile eliminating their drawbacks. Comparing with tetramethylammonium chloride (TMAC) which is a traditional industrial catalyst, the amount of side product dichlorohydrin can be reduced by more than 50%, effective utilization of ECH and yield of the main product can be increased by 5% and 2% respectively, and the reaction time can be reduced by 20% or more. We suggested a main catalytic reaction network including the conversion of TMAN to TMAC at the late stage of the reaction, and TMAC can be easily recycled and reused to prepare TMAN. More importantly, after the replacement of material acid and the carboxylic anion of catalyst, this efficient catalytic system and the mechanism network can be applied to other acidolysis reactions of epoxides.