Industrial & Engineering Chemistry Research, Vol.34, No.5, 1572-1580, 1995
Phase-Transfer Catalytic Kinetics of the Synthesis of Phenyl Benzoate
The reaction kinetics of the phase-transfer synthesis of phenyl benzoate from benzoyl chloride and phenol is studied using quaternary ammonium salts as well as tertiary amines as catalysts in a well-stirred batch reactor. Polar organic solvents promote high conversion from benzoyl chloride to phenyl benzoate and fast overall reaction, such as dichloromethane and chlorobenzene. Using nonpolar organic solvents such as n-hexane, benzene, and toluene, the conversion is lower and the overall reaction rate becomes slower. The order of catalytic activity for various quaternary ammonium chloride is benzyltributylammonium bromide > tetrabutylammonium hydrogensulfate > tetrabutylammonium bromide > benzyltriethylammonium chloride. When tertiary amines are used as catalysts, for the overall reaction rate the order of the catalytic activity is alkyldimethylamine > triethylamine > tributylamine > trimethylamine. As for the conversion the order is triethylamine > tributylamine > alkyldimethylamine > trimethylamine. The order of the effectiveness of organic solvents is dichloromethane > n-hexane > chlorobenzene > toluene.