ULTRASOUND-ASSISTED N-ALKYLATION OF PHTHALIMIDE UNDER PHASE-TRANSFER CATALYSIS CONDITIONS AND ITS KINETICS

In this work, N-butylation of potassium phthalimide was carried out under ultrasonic-assisted phase-transfer catalysis condition using n-bromobutane as an alkylating agent. The mechanism of the solid-liquid reaction of alkyl halide and potassium salt of phthalimide in an organic solvent was verified in this work. The kinetics of the reaction depends on the amount of catalyst, agitation speed, type of quaternary ammonium salts, volume of water, type of organic solvent, volume of organic solvents, temperature, and the frequency of the ultrasound. Five different onium salts were examined for the reaction and tetrahexylammonium bromide showed maximum catalytical activity. An improvement of the reaction outcome (yield and reaction time) was achieved through the immersion of the reactor into an ultrasound bath. The rate of the reaction is two times faster under ultrasonic condition (k_app = 10.7 × 10^?3 min^?1) than silent condition (k_app = 5.5 × 10^?3 min^?1) and is five times faster when the reaction is carried out in acetonitrile medium than in cyclohexane medium. The reaction is very fast under anhydrous condition. Based on the experimental data, a rational mechanism for the reaction is proposed.