A green route for the acylation of resorcinol with acetic acid

Abstract

2',4'-Dihydroxyacetophenone, also known as resoacetophenone, is a commercially important intermediate which is generally prepared by the acylation of resorcinol with acetic acid in the presence of a molar excess of zinc chloride, which leads to waste disposal problems. The most frequently used acylating agents such as acetic anhydride and acetyl chloride have several disadvantages and need to be replaced by cheap and benign agents. In this connection, acetic acid is a better choice but with a non-polluting and reusable catalyst. The synthesis of 2',4'-dihydroxyacetophenone from resorcinol and acetic acid was carried out in the presence of a variety of solid acid catalysts such as montmorillonite clay (K-10), dodecatungstophosphoric acid (DTP) supported on K-10, sulfated zirconia and ion exchange resins. Amongst these catalysts, Amberlyst-36, an ion exchange resin, was found to be the most effective. The effects of various parameters on the rate of reaction and selectivity were investigated to establish the intrinsic kinetics of the reaction. It was possible to deduce the adsorption equilibrium constant and rate constant simultaneously for the reaction including the corresponding energies of activation. The catalyst is reusable. The process is in consonance with the principles of green chemistry.