Book contents
- Intensification of Liquid–Liquid Processes
- Cambridge Series in Chemical Engineering
- Intensification of Liquid–Liquid Processes
- Copyright page
- Contents
- 1 Introduction
- 2 Droplets and Dispersions
- 3 Mass Transfer
- 4 Membrane-Based and Emulsion-Based Intensifications
- 5 High Gravity Fields
- 6 Electrically Driven Intensification of Liquid–Liquid Processes
- 7 Intensification of Liquid–Liquid Coalescence
- 8 Ionic Liquid Solvents and Intensification
- 9 Liquid–Liquid Phase-Transfer Catalysis
- Index
- References
9 - Liquid–Liquid Phase-Transfer Catalysis
Published online by Cambridge University Press: 12 May 2020
Book contents
- Intensification of Liquid–Liquid Processes
- Cambridge Series in Chemical Engineering
- Intensification of Liquid–Liquid Processes
- Copyright page
- Contents
- 1 Introduction
- 2 Droplets and Dispersions
- 3 Mass Transfer
- 4 Membrane-Based and Emulsion-Based Intensifications
- 5 High Gravity Fields
- 6 Electrically Driven Intensification of Liquid–Liquid Processes
- 7 Intensification of Liquid–Liquid Coalescence
- 8 Ionic Liquid Solvents and Intensification
- 9 Liquid–Liquid Phase-Transfer Catalysis
- Index
- References
Summary
Phase-transfer catalysis involves chemical reactions which occur in a two-phase liquid–liquid system and it has been shown to provide an effective method for organic synthesis. Phase-transfer catalytic reactions can facilitate high conversions and reaction selectivity and thus are consistent with the principles of green chemistry and process intensification. The basic mechanisms involved in phase-transfer catalysis and the related suite of reactions that involve catalytic transfer hydrogenations are briefly described and reviewed. The requirements and benefits of phase-transfer catalytic systems are summarized. Organic syntheses which exploit the principles of phase-transfer catalysis are described as examples of intensification. These include: synthesis of phenyl alkyl acetonitriles, transfer hydrogenations, alkyl oxidation and sulfonation reactions, etherification of cresols in a three-phase system, organic oxidations, nitrations, polymerizations, and organic condensation reactions. The enhancement of phase-transfer catalysis using other intensification methods, such as ultrasonics, is also described.
Keywords
- Type
- Chapter
- Information
- Intensification of Liquid–Liquid Processes , pp. 341 - 364Publisher: Cambridge University PressPrint publication year: 2020
References
Benjamin, I. (2013). Dissociation and transport of ion pairs across the liquid/liquid interface. Implications for phase transfer catalysis. Journal of Physical Chemistry B, 117, 4325–4331.CrossRefGoogle ScholarPubMed
Bogdal, D. and Loupy, A. (2008). Application of microwave irradiation to phase-transfer catalyzed reactions. Organic Process Research & Development, 12, 710–722.Google Scholar
Bogdal, D, and Lukasiewicz, M. (2000). Microwave-assisted oxidation of alcohols using aqueous hydrogen peroxide. Synlett, 1, 143–145.Google Scholar
Bogdal, D., Galica, M., Bartus, G., Wolinski, J., and Wronski, S. (2010). Preparation of polymers under phase-transfer catalytic conditions. Organic Process Research & Development, 14, 669–683.CrossRefGoogle Scholar
Casagrande, M., Storaro, L., Talon, A., et al. (2002). Liquid phase acetophenone hydrogenation on Ru/Cr/B catalysts supported on silica. Journal of Molecular Catalysis A: Chemical, 188, 133–139.CrossRefGoogle Scholar
Chatel, G., Monniera, C., Kardosa, N., et al. (2014) Green, selective and swift oxidation of cyclic alcohols to corresponding ketones. Applied Catalysis A: General, 478, 157–164.Google Scholar
Demmans, K. Z., Ko, O. W. K., and Morris, R. H. (2016). Aqueous biphasic iron-catalyzed asymmetric transfer hydrogenation of aromatic ketones. RSC Advances, 6(91), 88580–88587.Google Scholar
Fleming, F. F., Yao, L., Ravikumar, P. C., Funk, L., and Shook, B. C. (2010). Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore. Journal of Medicinal Chemistry, 53(22), 7902–7917.Google Scholar
Gonzalez-Galvez, D., Lara, P., Rivada-Wheelaghan, O., et al. (2013). NHC-stabilized ruthenium nanoparticles as new catalysts for the hydrogenation of aromatics. Catalysis Science and Technology, 3, 99–105.CrossRefGoogle Scholar
Makosza, M. (2000). Phase-transfer catalysis. A general green methodology in organic synthesis. Pure and Applied Chemistry, 72(7), 1399–1403.Google Scholar
Meshechkina, A. E., Mel’nik, L. V., Rybina, G. V., Srednev, S. S., and Shevchuk, A. S. (2012). Efficiency of phase-transfer catalysis in cyclopentene epoxidation with hydrogen peroxide. Russian Journal of Applied Chemistry, 85(4), 661–665.CrossRefGoogle Scholar
Reichart, B., Kappe, T., and Glasnov, T. N. (2013). Phase-transfer catalysis: mixing effects in continuous-flow liquid/liquid O- and S-alkylation processes. Synlett, 24, 2393–2396.Google Scholar
Tsai, H. B. and Lee, Y. D. (1987a). Polyarylates (I): Investigation of the interfacial polycondensation reaction by UV. Journal of Polymer Science, 25, 1505–1515.Google Scholar
Tsai, H. B. and Lee, Y. D. (1987b). Polyarylates. II. The molecular weight distribution measured by GPC. Journal of Polymer Science, 25, 1709–1712.Google Scholar
Tsai, H. B. and Lee, Y. D. (1987c). Polyarylates III. Kinetics studies of interfacial polycondensation. Journal of Polymer Science, 25, 2195–2206.Google Scholar
Tsai, H. B., Lee, Y. D., Jeng, J. T. (1988). Polyarylates V. The influence of phase transfer agents on the interfacial polycondensation. Journal of Polymer Science, 26, 2039–2046.Google Scholar
Tsai, H. B., Jeng, J. T., and Tsai, R. S. (1990) Reaction kinetics of interfacial polycondensation of polyarylate. Journal of Applied Polymer Science, 39, 471–476.Google Scholar
Wang, L., Hongxia Ma, H., Song, L., et al. (2014). Transfer hydrogenation of acetophenone in an organic-aqueous biphasic system containing double long-chain surfactants. RSC Advances, 4, 1567–1569.Google Scholar
Wang, P., Lu, M., Zhu, J., Song, Y., and Xiong, X. (2011). Regioselective nitration of aromatics under phase-transfer catalysis conditions. Catalysis Communications, 14, 42–47.Google Scholar
Wolinski, J. and Wronski, S. (2009). Interfacial polycondensation of polyarylate in Taylor-Couette-Reactor. Chemical Engineering and Processing, 48, 1061–1071.CrossRefGoogle Scholar
Yadav, G. D. and Badure, O. V. (2008). Selective engineering in O-alkylation of m-cresol with benzyl chloride using liquid–liquid–liquid phase transfer catalysis. Journal of Molecular Catalysis A: Chemical, 288, 33–41.Google Scholar
Yadav, G. D. and Jadhav, Y. B. (2003). Kinetics and modeling of liquid–liquid phase transfer catalyzed synthesis of p-chlorophenyl acetonitrile: role of co-catalyst in intensification of rates and selectivity. Journal of Molecular Catalysis A: Chemical, 192, 41–52.Google Scholar
Yadav, G. D. and Kadam, A. A. (2012). Atom-efficient benzoin condensation in liquid–liquid system using quaternary ammonium salts: pseudo-phase transfer catalysis. Organic Process Research and Development, 16, 755–763.Google Scholar
Zhu, M. (2014). Integration of phase transfer catalysis into aqueous transfer hydrogenation. Applied Catalysis A – General, 479, 45–48.Google Scholar
Zyuzin, I. (2013). Alkylation of 1,1-bis(methoxy-NNO-azoxy)alkanes under phase-transfer catalysis. Russian Journal of Organic Chemistry, 49(4), 536–544.CrossRefGoogle Scholar