Synthesis of Benzenediols by Oxidation of Phenol with Peracetic Acid

Abstract

The oxidation of phenol with peracetic acid was investigated for the industrial preparation of benzenediols and the reaction conditions were optimized. The effect of additives was essentially important to improve the yield of the benzenediols. Effects of temperature, phenolperacid ratio were also investigated, and the optimum conditions were determined as carrying the reaction of phenol 1 mol with peracetic acid O.1 mol in the presence of O.2 g of additives at 60°C without solvent, where 85 mmol of phenol was converted into ca.45 mmol of catechol and ca.35 mmol of hydroquinone. The best additives were chelating agents, phosphates and condensed phosphates, which are well known peroxide stabilizers. As the simple stabilizing effect on peracid cannot interpret the whole phenomena, suppressing effect on the metal-catalyzedoxidation of benzenediol was estimated. Oxidation of cresols and aromatic ethers with peracetic acid was also investigated.