Solubilization of Benzyl Chloride and Rate Enhancement of Its Hydrolysis Reaction in Aqueous Sodium Cumenesulfonate Solutions

Alkaline hydrolysis of benzyl chloride (BzCl) in aqueous solutions of sodium cumenesulfonate (NaCS) is investigated for the hydrotropic effect. The presence of the hydrotrope, NaCS, increased the solubility of BzCl in aqueous solutions by an order of magnitude and consequently the rates of the reaction by 6-fold as compared to those in water. In addition, the hydrotropic medium increased the selectivity toward the formation of dibenzyl ether. Both of these effects have been attributed to the increased solubilization of BzCl, the microenvironment experienced by the reactants in the hydrotrope aggregates and proximity of the reactants for the subsequent condensation reaction.