SYNTHESIS OF POLYESTERS BY REACTION OF CARBOXYLIC-ACID QUATERNARY AMMONIUM-SALTS WITH ALKYL-HALIDES OR ALKYL TOSYLATES

The synthesis of polyesters by the reaction of dicarboxylic acid salts with bis halides or bis tosylates or by the self-condensation of salt s of omega-bromocarboxylic acids, has been investigated under two diff erent types of conditions. When benzyltrimethylammonium salts and hali des were reacted together in acetonitrile at ca. 82 degrees C the resu lts obtained were similar to those reported in the literature for expe riments using sodium or potassium salts. Thus, the yields of polyester s were generally modest, with degrees of polymerization (DPs) being in the range from 17 to 47. Using liquid-liquid phase-transfer catalysis procedures the yields were high and the DPs were usually in the range from 22 to 161. This is the first time that the liquid-liquid phase-t ransfer catalysed synthesis of polyesters has produced such high DP va lues.