Novelties of solid–liquid phase transfer catalysed synthesis of p-toluenesulfonyl fluoride from p-toluenesulfonyl chloride

Abstract

Organic sulfonyl fluorides are of interest owing to their insecticidal, germicidal and enzyme inhibitory properties. In the current work synthesis of p-toluenesufonyl fluoride was accomplished by reacting p-toluenesulfonyl chloride with solid potassium fluoride using PEG-400 as a catalyst under solid–liquid phase transfer catalysis (S–L PTC) at 30 °C. p-Toulenesulfonyl fluoride is used as peroxygen bleach activator. It also finds use in the treatment of Alzheimer's disease. The mechanism is based on homogeneous solubilization of solid. PEG forms a complex with metal cation which associates with the nucleophile and it participates in S_N² type reaction. The reaction is intrinsically kinetically controlled. A complete theoretical analysis is done to determine both the rate constant and equilibrium constant from the same set of data. The activation energy and Gibbs free energy are also calculated.