Novelties of solid-liquid phase transfer catalysed synthesis of p-toluenesulfonyl fluoride from p-toluenesulfonyl chloride |
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Authors: | Ganapati D Yadav Priyanvada M Paranjape |
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Institution: | Department of Chemical Engineering, University Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai 400019, India |
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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 SN2 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. |
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Keywords: | Solid-liquid phase transfer catalysis p-Toluenesulfonyl fluoride KF PEG-400 Rate constant Equilibrium constant Modeling |
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