Patent ID: 8309755

Claim:
A process of making a compound R 1 COOR 3 (I) comprising: (i) reacting an ester compound R 1 COOR 2 (II) with an alcohol R 3 OH (III) in the presence of a transesterification catalyst in a transesterification reaction, wherein R 1 is H or C 1-4 alkyl or CH 2 ═CR 4 —, R 2 is C 1-4 alkyl, R 3 is selected from the group consisting of alkyl having at least 4 carbon atoms, cycloalkyl having at least 5 carbon atoms, aryl, aralkyl, alkaryl and amino alkyl, and R 4 is —H or —C 1-4 alkyl; (ii) forming alcohol R 2 OH (IV) as a byproduct; and (iii) removing said byproduct (IV) by distillation in the presence of an entrainer, wherein the entrainer is a compound that suppresses the formation of an azeotrope between compound (II) and byproduct (IV), wherein the entrainer is selected from the group consisting of ethers, alkanes of at least eleven carbon atoms, and chlorinated alkanes, wherein the entrainer brings about a separation factor between the ester compound (II) and the byproduct (IV) at infinite dilution of greater than 2.5 when measured at 345 K, wherein the separation factor is a measure of the relative volatilities between the byproduct (IV) and the ester compound (II), and wherein the transesterification reaction is carried out in the presence of the entrainer and byproduct (IV) is substantially the only compound removed from the reaction by distillation.