Abstract
The problem of bringing together two substances of markedly different polarities is one which has been a continual challenge to chemists. The traditional solution has been the use of dipolar aprotic solvents, such as dimethylsulfoxide or N,N-dimethylformamide, in which both covalent and ionic substances are soluble. These solvents, however, are expensive, toxic, and their low volatilities can make product purification tricky. Environmental pressure means that many of the ‘better’ organic solvents are becoming unacceptable, and industry is being forced to look for cleaner alternative technologies.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
J. Zhu and M.M. Kayser, Synth. Commun., 1994, 24, 1179.
C.M. Starks, J. Am. Chem. Soc., 1971, 93, 195.
M. Makosza, Pure Appl. Chem., 1975, 43, 439.
A. Brändström, Pure Appl. Chem., 1982, 54, 1769.
Y. Goldberg, Phase Transfer Catalysis: Selected Problems and Applications, Gordon and Breach Science Publishers, Yverdon, Switzerland, 1992. Cites 1333 references; our own survey found 2253 references published since 1981.
C.M. Starks and C. Liotta, Phase Transfer Catalysis: Principles and Techniques, Academic Press Inc., 1978.
Y. Goldberg, Phase Transfer Catalysis: Selected Problems and Applications, Gordon and Breach Science Publishers, Yverdon, Switzerland, 1992.
M. Makosza and M. Fedoryñski, Advances in Catalysis, 1987, 35, 375.
M. Rabinovitz, Y. Cohen and M. Halpbern, Angew. Chem. Int. Ed. Engl., 1986, 25, 960.
A. Gobbi, D. Landini, A. Maia, G. Delogu and G. Podda, J. Org. Chem., 1994, 59, 5059.
M. Ouchi, Y. Inoue, T. Kanzaki and T. Hakushi, Bull. Chem. Soc. Jpn., 1984, 57, 887.
B.P. Czech, M.J. Pugia and R.A. Bartsch, Tetrahedron, 1985, 41, 5439.
P. Tundo, J. Org. Chem., 1979, 44, 2048.
A. Loupy, P. Pigeon, M. Ramdani and P. Jacquault, Synth. Commun., 1994, 24, 159.
P.M. Wovkulich, K. Shankaran, K. Kiegiel and M.R. Uskovic, J. Org. Chem., 1993, 58, 832.
Y.C. Yang, J.A. Baker and J.R. Ward, Chem. Rev., 1992, 92, 1729.
D. Landini, A. Maia and F. Montanari, J. Am. Chem. Soc., 1978, 100, 2796.
D. Landini, S. Quinci and F. Rolla, Synthesis, 1975, 430.
M. Makosza and M. Fedoryñski, Advances in Catalysis, 1987, 35, 375.
P. Balcerzak and A. Joñczyk, J. Chem. Research (S), 1994, 200.
M. Fedoryñski and A. Joñczyk, J. Chem. Research (S), 1994, 150.
M. Makosza, Pure Appl. Chem., 1975, 43, 439.
C. Sarangi and Y.R. Rao, J. Chem. Research (S), 1994, 392.
S.N. Tan, R.A. Dryfe and H.H. Girault, Helvetica Chimica Acta, 1994, 77, 231.
J.H. Clark and D.J. Macquarrie, Tetrahedron Lett., 1987, 28, 111.
H. Suzuki, N. Yazawa, Y. Toshida, O. Furusawa and Y. Kimura, Bull. Chem. Soc. Jpn., 1990, 63, 2010.
J. Dakka and Y. Sasson, J. Chem. Soc., Chem. Commun., 1987, 19, 1421.
S. Gervat, E. Leonel, J.Y. Barraud and V. Ratovelomanana, Tetrahedron Lett., 1993, 34, 2115.
J. Correia, J. Org. Chem., 1992, 57, 4555.
S. Snipes and A.W. Herriott, J. Am. Chem. Soc., 1979, 101, 6441.
H. Iwamoto, H. Kabayashi, P. Murer, T. Sonoda and H. Zollinger, Bull. Chem. Soc. Jpn., 1993, 66, 2590.
S.L. Regen, J. Am. Chem. Soc., 1975, 97, 5956.
S.L. Regen, J. Am. Chem. Soc., 1976, 98, 6270.
M. Cinouini, S. Colonna, H. Molinari, F. Montanari and P. Tundo, J. Chem. Soc., Chem. Commun., 1976, 394.
H. Molinari, F. Montanari, S. Quici and P. Tundo, J. Am. Chem. Soc., 1979, 101, 3920.
P. Tundo, J. Chem. Soc., Chem. Commun., 1977, 641.
P. Tundo, P. Venturello and E. Angeletti, J. Am. Chem. Soc., 1982, 104, 6551.
P. Tundo and P. Venturello, J. Am. Chem. Soc., 1979, 101, 6066.
Y. Gotoh, Y. Kohno, W. Fukuda and M. Tomoi, J. Poly. Sci., Pt A: Poly. Chem., 1994, 32, 1543.
T. Tsanov, R. Stamenova and C. Tsvetanov, Polymer, 1993, 34, 616.
M.S. Chou and J.S. Shih, Can. J. Chem., 1994, 72, 1614.
A.W. Herriott and D. Picker, J. Am. Chem. Soc., 1975, 97, 2345.
C.M. Starks and C. Liotta, Phase Transfer Catalysis: Principles and Techniques, Academic Press, Inc, 1978, 61.
E.V. Dehmlow and J. Wilkenloh, J. Chem. Ber., 1990, 123, 583.
M. Fedoryñski, W. Ziólkowska and A. Joñczyk, J. Org. Chem., 1993, 58, 6120.
E.V. Dehmlow, R. Richter and A.B. Zhivich, J. Chem. Research (S), 1993, 504.
U.T. Bhalerao, S.N. Mathur and S. Nagabhushan Rao, Synth. Comm., 1992, 22, 1645.
D. Landini, A. Maia and F. Montanari, J. Am. Chem. Soc., 1978, 100, 2796.
D. Mason, S. Magdassi and Y. Sasson, J. Org. Chem., 1991, 56, 7229.
O.I. Danilova and S.S. Yufit, Mendeleev Commun., 1993, 165.
T.W. Bentley, R.V.H. Jones, A.H. Larder and S.J. Lock, J. Chem. Soc., Chem. Commun., 1994, 2309.
Y. Sasson, O. Arrad, S. Dermeik, H.A. Zahalka, M. Weiss and H. Wiener, Mol. Cry st. Liq. Cryst. Inc. Nonlin. Opt., 1988, 161, 495.
D. Landini, A. Maia and A. Rampoldi, J. Org. Chem., 1986, 51, 5476.
Y. Sasson and H.A. Zahalka, J. Chem. Soc., Chem. Commun., 1983, 1347.
U. Hoffmann, F. Helmer-Metzmann, M. Klapper and K. Müllen, Macromolecules, 1994, 27, 3573.
T. Balakrishnan and K. Arivalagan, J. Poly. Sci, Pt A: Poly. Chem., 1994, 32, 1909.
S. Banerjee, S.K. Palit and S. Maiti, J. Poly. Sci., Pt A: Poly. Chem., 1994, 32, 219.
G. Schill and H. Zollenkopf, Nachr. Chem. Tech., 1967, 79, 149.
Y.X. Shen, D. Xie and H.W. Gibson, J. Am. Chem. Soc., 1994, 116, 537.
M.S. Urdea and T. Horn, Science, 1993, 261, 534.
J.J. Lee, W.T. Ford, J.A. Moore and Y. Li, Macromolecules, 1994, 27, 4632.
M. Shi and Y. Masaki, J. Chem. Research (S), 1994, 250.
H.H. Freedman, Pure Appl. Chem., 1986, 58, 857.
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1995 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Tavener, S.J., Clark, J.H. (1995). Phase transfer catalysis. In: Clark, J.H. (eds) Chemistry of Waste Minimization. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0623-8_5
Download citation
DOI: https://doi.org/10.1007/978-94-011-0623-8_5
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-4273-4
Online ISBN: 978-94-011-0623-8
eBook Packages: Springer Book Archive