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標題: Ultrasound-assisted phase-transfer catalysis: Benzoylation of sodium 4-acetylphenoxide by dual-site phase-transfer catalyst in a tri-liquid system
作者: Yang, H.M.
Chiu, C.C.
關鍵字: Dual-site phase-transfer catalyst;Third-liquid phase-transfer;catalysis;Ultrasound irradiation;Benzoylation;3rd-liquid phase;kinetics;1,7-octadiene;salt
Project: Ultrasonics Sonochemistry
期刊/報告no:: Ultrasonics Sonochemistry, Volume 18, Issue 1, Page(s) 363-369.
A novel dual-site phase-transfer catalyst (PTC) was prepared and used to conduct the benzoylation of sodium 4-acetylphenoxide by ultrasound-assisted third-liquid phase-transfer catalysis. The catalyst 1,4-bis(tributylammoniomethyl)benzene dibromide (BTBAMBB) was synthesized from the reaction of p-xylylene dibromide and tributylamine in toluene at 70 degrees C. The dual-site PTC was employed to form the third-liquid phase by extra addition of 0.04-0.05 mol of NaCl into 10 cm(3) of water. In the condition of 0.0425 mol of NaCl at 30 degrees C. the catalytic intermediate in the third-liquid phase reached a maximum value. Almost 80% of the catalyst was transferred from the aqueous phase into the third-liquid phase. The distributions of the catalytic intermediate and dual-site PTC between phases and the kinetics of benzoylation of sodium 4-acetylphenoxide catalyzed by BTBAMBB with ultrasound irradiation were performed. The pseudo-first-order kinetic equation was applied to describe the overall reaction. Under ultrasound irradiation (28 kHz/300 W) in a batch reactor, the yield of product 4-acetylphenyl benzoate in the organic phase was 98.1% in 2 min at 30 degrees C and 250 rpm with the apparent rate constant k(app) to be 0.0075 s(-1), which was 6 times faster than that without using ultrasound (yield = 14.4%, k(app) = 0.0013 s(-1)). The present study provides a green method to synthesize esters by ultrasound-assisted third-liquid phase-transfer catalysis. (C) 2010 Elsevier B.V. All rights reserved.
ISSN: 1350-4177
DOI: 10.1016/j.ultsonch.2010.06.017
Appears in Collections:化學工程學系所

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