title: Esterification of sodium 4-hydroxybenzoate by ultrasound-assisted solid-liquid phase-transfer catalysis using dual-site phase-transfer catalyst.
abstract: The catalytic esterification of sodium 4-hydroxybenzoate with benzyl bromide by ultrasound-assisted solid-liquid phase-transfer catalysis (U-SLPTC) was investigated using the novel dual-site phase-transfer catalyst 4,4'-bis(tributylammoniomethyl)-1,1'-biphenyl dichloride (BTBAMBC), which was synthesized from the reaction of 4,4'-bis(chloromethyl)-1,1'-biphenyl and tributylamine. Without catalyst and in the absence of water, the product yield at 60 °C was only 0.36% in 30 min of reaction even under ultrasound irradiation (28 kHz/300 W) and 250 rpm of stirring speed. When 1cm(3) of water and 0.5 mmol of BTBAMBC were added, the yield increased to 84.3%. The catalytic intermediate 4,4'-bis(tributylammoniomethyl)-1,1'-biphenyl di-4-hydroxybenzoate was also synthesized to verify the intrinsic reaction which was mainly conducted in the quasi-aqueous phase locating between solid and organic phases. Pseudo-first-order kinetic equation was used to correlate the overall reaction, and the apparent rate coefficient with ultrasound (28 kHz/300 W) was 0.1057 min(-1), with 88% higher than that (0.0563 min(-1)) without ultrasound. The esterification under ultrasonic irradiation using BTBAMBC by solid-liquid phase-transfer catalysis was developed.
authors: Department of Chemical Engineering, National Chung Hsing University, 250 Kuo-Kuang Road, Taichung 402, Taiwan, ROC. Electronic address: hmyang@dragon.nchu.edu.tw.
authors: Hung-Ming
authors: HM
authors: Yang
authors: Wei-Ming
authors: WM
authors: Chu
keywords: Benzyl 4-hydroxybenzoate; Dual-site phase-transfer catalyst; Esterification; Solid–liquid phase-transfer catalysis; Ultrasound irradiation