KINETIC STUDY OF SYNTHESIZING 1-PHENYl-3-PROPYL ETHER UNDER LIQUID-LIQUID PHASE-TRANSFER CATALYTIC CONDITIONS

The etherification of 1-bromo-3-phenylpropane with phenol to synthesize 1-phenyl-3-propyl ether by phase-transfer catalytic conditions was successfully carried out in an alkaline solution of KOH/organic solvent two-phase medium. In this work, quaternary ammonium salts acted as the phase-transfer catalysts. The main purpose of this study was to investigate the kinetic behavior, mechanism, and activation energy of the reaction system. A rational mechanism for the etherification is proposed according to the experimental evidence. The reaction follows a pseudo first-order rate law. A pseudo steady-state hypothesis (PSSH) was proposed to describe the kinetic behaviors from which the apparent rate constant of the two-phase reaction (kapp) was obtained via experimental data. Kinetics of the reaction including the effects of agitation speed, amount of potassium hydroxide, volume of water, temperature, amount of tetrabutylammonium bromide, quaternary ammonium salts, volume of chlorobenzene, and organic solvents on the reaction rate were investigated in detail. Rational explanations to account for the unique results, especially for the water volume effect on the reaction rate, are also provided.