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Esterification of Sodium 4-hydroxybenzoate by Ultrasound-Assisted Solid-Liquid Phase-Transfer Catalysis Using Dual-Site Phase-Transfer Catalyst

Esterification of Sodium 4-hydroxybenzoate by Ultrasound-Assisted Solid-Liquid Phase-Transfer Catalysis Using Dual-Site Phase-Transfer Catalyst

Hung-Ming Yang, Wei-Ming Chu

Ultrason Sonochem. 2014 Jan;21(1):395-400.

PMID: 23972326

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP94188	Benzyl 4-hydroxybenzoate		94-18-8	Price

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