Catalysis Letters, Vol.41, No.3-4, 181-187, 1996
Solvent Effects in Liquid-Phase Fries Rearrangement of Phenyl Acetate over a Hbea Zeolite
A kinetic study of phenyl acetate transformation was carried out in a batch reactor over a HBEA zeolite (framework Si/Al ratio of 11) at 160 degrees C, sulfolane or n-dodecane being used as solvents. Whatever the solvent, phenyl acetate undergoes a monomolecular rearrangement into o-hydroxyacetophenone, an autoacylation into p-acetoxyacetophenone plus phenol and a hydrolysis into phenol. p-hydroxyacetophenone which appears as a secondary product results from the acylation of phenol with phenyl acetate. The initial reaction rates and the product distribution depend very much on the solvent. This can be explained by the large difference in the strength of adsorption between the polar sulfolane and the non-polar dodecane solvents on the active acid sites.