Specific Effects in Acid Catalysis by Ion Exchange Resins. II. Hydrolysis of Esters in Water Solution

Abstract

In water solution a lightly cross-linked ion exchange resin of the polystyrenesulfonic acid type is a better catalyst for the hydrolysis of aliphatic esters of low molecular weight than is dilute hydrochloric acid, and the effectiveness is somewhat greater for ethyl acetate than for methyl acetate. A tightly cross-linked resin, however, behaves in water solution in the same way as all such resins do in aqueous acetone solution, namely, the resin is less effective than the homogeneous strong acid, and the relative effectiveness of the resin decreases with increasing chain length of the ester. Within the experimental error both energy and entropy of activation are the same for all resin catalysts as for hydrochloric acid and are identical for methyl and ethyl acetates. © 1953, American Chemical Society. All rights reserved.