Kinetic Study of Synthesizing 1-(3-Phenylpropyl)pyrrolidine-2,5-dione under Solid−Liquid Phase-Transfer Catalytic Conditions Assisted by Ultrasonic Irradiation

Abstract

The synthesis of 1-(3-phenylpropyl)pyrrolidine-2,5-dione (SUC-R) (1) was successfully carried out by reacting succinimide (SUC-H) (2) with 1-bromo-3-phenylpropane (RBr) (3) in a small amount of KOH and organic solvent solid−liquid phase medium under phase-transfer catalysis (PTC) and almost anhydrous conditions assisted by ultrasonic irradiation. The main purpose of this work was to obtain the kinetic behavior, activation energy, and the related parameters in the solid−liquid PTC reaction combined with the ultrasonic irradiation. Based on the experimental data, a rational mechanism for the reaction is proposed. The reaction followed a pseudo-first-order rate law. A rate expression was developed to describe the kinetic behaviors from which the apparent rate constant (kapp) of the organic-phase solution was obtained via experimental data. Kinetics of the reaction, including the effects of agitation speed, ultrasonic energy, amount of water, amount of potassium hydroxide, temperature, amount of tetrabutylammonium bromide (TBAB), volume of cyclohexanone, amount of SUC-H, quarternary ammonium salts, and organic solvents on the conversion of RBr and the apparent rate constant (kapp) were investigated in detail. Rational explanations to account for the resulting phenomena were provided.