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

摘要

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 deg 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.