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01-06-2009 | Original Paper

Liquid–liquid–liquid phase-transfer catalysis for cleaner and selective etherification of p-hydroxy-biphenyl with benzyl chloride to 1,1′-biphenyl-4-(phenylmethoxy)

Authors: Ganapati D. Yadav, Omprakash V. Badure

Published in: Clean Technologies and Environmental Policy | Issue 2/2009

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Abstract

Conversion of bi-liquid phase transfer catalysis (PTC) into a tri-liquid PTC system presents several advantages in terms of enhancement of reaction rates and selectivity. These improvements lead to a minimization of waste, reduction in reactor volume and processing times by orders of magnitude in comparison with a liquid–liquid PTC process. The O-alkylation (etherification) of 4-hydroxybiphenyl with benzyl chloride to 1,1′-biphenyl-4-(phenylmethoxy) was carried out under L-L-L PTC system with 100% selectivity at 50°C. The resulting product is commercially used in fine chemical industry and to produce novel materials. The catalyst-rich third phase can be recycled many times, thereby leading to profitability and waste minimization. A reaction mechanism and kinetic model are developed and validated against experimental data, which include the effect of different variables on reaction rates and selectivity.

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Literature
go back to reference Barluenga J, Alonso-Cires L, Campos PJ, Asensio G (1983) Mercury (II) oxide/tetrafluoroboric acid: enhancedalkylating ability of alkyl bromide: a general synthesis of alcohol and ethers. Synthesis 1:53CrossRef Barluenga J, Alonso-Cires L, Campos PJ, Asensio G (1983) Mercury (II) oxide/tetrafluoroboric acid: enhancedalkylating ability of alkyl bromide: a general synthesis of alcohol and ethers. Synthesis 1:53CrossRef
go back to reference Benedict DR, Bianchi TA, Cate LA (1979) Synthesis of simple unsymmetrical ethers from alcohols and alkylhalides or sulfates: the potassium hydroxide/dimethyl sulfoxide system. Synthesis 6:428CrossRef Benedict DR, Bianchi TA, Cate LA (1979) Synthesis of simple unsymmetrical ethers from alcohols and alkylhalides or sulfates: the potassium hydroxide/dimethyl sulfoxide system. Synthesis 6:428CrossRef
go back to reference Dehmlow EV, Dehmlow SS (1993) Phase transfer catalysis, monographs in modern chemistry, vol II. Verlag Chemie Weinheim, Germany Dehmlow EV, Dehmlow SS (1993) Phase transfer catalysis, monographs in modern chemistry, vol II. Verlag Chemie Weinheim, Germany
go back to reference Huang CC, Yang HM (2005) Kinetics for benzoylation of sodium 4-acetylphenoxide via third-liquid phase in the phase-transfer catalysis. Appl Catal A Gen 290:65CrossRef Huang CC, Yang HM (2005) Kinetics for benzoylation of sodium 4-acetylphenoxide via third-liquid phase in the phase-transfer catalysis. Appl Catal A Gen 290:65CrossRef
go back to reference Kensuke I, Akira I, Takekatsu S, Hiroharu M (1984) Heat-sensitive recording materials. US 4471073 Kensuke I, Akira I, Takekatsu S, Hiroharu M (1984) Heat-sensitive recording materials. US 4471073
go back to reference Masaharu N (1986) Thermal recording materials. JP 61272189 Masaharu N (1986) Thermal recording materials. JP 61272189
go back to reference Masahiro T, Masataka Y, Shosei M, Shinichi N, Kenji S, Kazuharu K (1992) Liquid crystal apparatus and chiral smectic liquid crystal composition for use therein. US 5119219 Masahiro T, Masataka Y, Shosei M, Shinichi N, Kenji S, Kazuharu K (1992) Liquid crystal apparatus and chiral smectic liquid crystal composition for use therein. US 5119219
go back to reference Masson D, Magdassi S, Sasson Y (1991) Role of a third liquid phase in phase transfer catalysis. J Org Chem 56:7229CrossRef Masson D, Magdassi S, Sasson Y (1991) Role of a third liquid phase in phase transfer catalysis. J Org Chem 56:7229CrossRef
go back to reference Neumann R, Sasson Y (1984) Mechanism of base-catalyzed reactions in phase-transfer system with poly(ethylene glycols) as catalyst: the isomerization of allylanisole. J Org Chem 49:3448CrossRef Neumann R, Sasson Y (1984) Mechanism of base-catalyzed reactions in phase-transfer system with poly(ethylene glycols) as catalyst: the isomerization of allylanisole. J Org Chem 49:3448CrossRef
go back to reference Sasson Y, Neumann R (eds) (1997) Handbook of phase transfer catalysis. Blackie Academic and Professional, London Sasson Y, Neumann R (eds) (1997) Handbook of phase transfer catalysis. Blackie Academic and Professional, London
go back to reference Starks CM, Liotta C, Halpern M (1994) Phase transfer catalysis: fundamentals, applications and perspectives. Chapman and Hall, New York Starks CM, Liotta C, Halpern M (1994) Phase transfer catalysis: fundamentals, applications and perspectives. Chapman and Hall, New York
go back to reference Wang DH, Weng HS (1995) Solvents and salts effects on the formation of third liquid phase and the reaction mechanism in the phase transfer catalysis system-reaction between n-butyl bromide and sodium phenolate. Chem Eng Sci 50:3477CrossRef Wang DH, Weng HS (1995) Solvents and salts effects on the formation of third liquid phase and the reaction mechanism in the phase transfer catalysis system-reaction between n-butyl bromide and sodium phenolate. Chem Eng Sci 50:3477CrossRef
go back to reference Wang DH, Weng HS (1988) Preliminary study on the role played by the third liquid phase in phase transfer catalysis. Chem Eng Sci 43:2019CrossRef Wang DH, Weng HS (1988) Preliminary study on the role played by the third liquid phase in phase transfer catalysis. Chem Eng Sci 43:2019CrossRef
go back to reference Yadav GD (2004a) Insight into green phase transfer catalysis. Topics Catal 29(3–4):145CrossRef Yadav GD (2004a) Insight into green phase transfer catalysis. Topics Catal 29(3–4):145CrossRef
go back to reference Yadav GD (2004b) Production of greener and safer chemicals by clean and benign processes. Chem Ind Dig 17(1):52 Yadav GD (2004b) Production of greener and safer chemicals by clean and benign processes. Chem Ind Dig 17(1):52
go back to reference Yadav GD, Desai NM (2006) Novelties of low energy microwave irradiation in tri-phase vis-à-vis bi-liquid phase transfer catalysis in selective etherification aromatic phenols. Catal Commun 7:325CrossRef Yadav GD, Desai NM (2006) Novelties of low energy microwave irradiation in tri-phase vis-à-vis bi-liquid phase transfer catalysis in selective etherification aromatic phenols. Catal Commun 7:325CrossRef
go back to reference Yadav GD, Bisht PM (2004) Selectivity engineering in multiphase transfer catalysis in the preparation of aromatic ethers. J Mol Catal A Chem 223:93CrossRef Yadav GD, Bisht PM (2004) Selectivity engineering in multiphase transfer catalysis in the preparation of aromatic ethers. J Mol Catal A Chem 223:93CrossRef
go back to reference Yadav GD, Desai NM (2005) Selectivity engineering of phase transfer catalyzed alkylation of 2′-hydroxy-acetophenone: enhancement in rates and selectivity by creation of a third liquid phase. Org Proc Res Dev 9(6):749CrossRef Yadav GD, Desai NM (2005) Selectivity engineering of phase transfer catalyzed alkylation of 2′-hydroxy-acetophenone: enhancement in rates and selectivity by creation of a third liquid phase. Org Proc Res Dev 9(6):749CrossRef
go back to reference Yadav GD, Jadhav YB (2003) Cascade engineered phase transfer catalysis: a novel concept in green chemistry. Clean Tech Environ Policy 6:32CrossRef Yadav GD, Jadhav YB (2003) Cascade engineered phase transfer catalysis: a novel concept in green chemistry. Clean Tech Environ Policy 6:32CrossRef
go back to reference Yadav GD, Lande SV (2005a) Novelties of reaction in the middle liquid phase in tri-liquid phase transfer catalysis: kinetics of selective O-alkylation of vanillin with benzyl chloride. Appl Catal A Gen 287(2):267CrossRef Yadav GD, Lande SV (2005a) Novelties of reaction in the middle liquid phase in tri-liquid phase transfer catalysis: kinetics of selective O-alkylation of vanillin with benzyl chloride. Appl Catal A Gen 287(2):267CrossRef
go back to reference Yadav GD, Lande SV (2005b) Liquid-liquid-liquid phase transfer catalysis: a novel and green concept for selective reduction of substituted nitroaromatics. Adv Synth Catal 347(9):1235CrossRef Yadav GD, Lande SV (2005b) Liquid-liquid-liquid phase transfer catalysis: a novel and green concept for selective reduction of substituted nitroaromatics. Adv Synth Catal 347(9):1235CrossRef
go back to reference Yadav GD, Naik SS (2001) Novelties of liquid-liquid-liquid phase transfer catalysis: alkoxylation of p-chloronitrobenzene. Catal Today 66(2–4):345CrossRef Yadav GD, Naik SS (2001) Novelties of liquid-liquid-liquid phase transfer catalysis: alkoxylation of p-chloronitrobenzene. Catal Today 66(2–4):345CrossRef
go back to reference Yadav GD, Reddy CA (1999) Kinetics of the n-butoxylation of p-chloronitrobenzene under liquid-liquid-liquid phase transfer catalysis. Ind Eng Chem Res 38(6):2245CrossRef Yadav GD, Reddy CA (1999) Kinetics of the n-butoxylation of p-chloronitrobenzene under liquid-liquid-liquid phase transfer catalysis. Ind Eng Chem Res 38(6):2245CrossRef
Metadata
Title
Liquid–liquid–liquid phase-transfer catalysis for cleaner and selective etherification of p-hydroxy-biphenyl with benzyl chloride to 1,1′-biphenyl-4-(phenylmethoxy)
Authors
Ganapati D. Yadav
Omprakash V. Badure
Publication date
01-06-2009
Publisher
Springer-Verlag
Published in
Clean Technologies and Environmental Policy / Issue 2/2009
Print ISSN: 1618-954X
Electronic ISSN: 1618-9558
DOI
https://doi.org/10.1007/s10098-008-0161-8