Abstract
The acid catalyzed hydrolysis of MTBE using p-toluenesulfonic acid was studied in nonpolar medium to ascertain the effect of nucleophile upon reaction. NMR measurements showed protonation of both MTBE and methanol by p-toluenesulfonic acid in nonpolar medium but no nucleophile-electrophile interaction of MTBE with p-toluenesulfonic acid methyl ester as potential nucleophile. Addition or in situ generation of a nucleophile did not accelerate the reaction. At low conversions and low catalyst concentration the reaction exhibited pseudo zero order with respect to reactant concentration and second order with respect to catalyst concentration. The results suggest protonation of MTBE in a fast preequilibrium step in which the acid catalyst exhibits cooperative effect. No nucleophilic assistance in the transition state of MTBE hydrolysis in nonpolar medium occurs.
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