Abstract
Critical to the success of phase-transfer catalytic (PTC) processes are (1) the maximization of the rate of transfer of reactant anions from the aqueous or solid phase to the organic phase, (2) the maximization of the rate of transfer of product anions from the organic phase to the aqueous or solid phase, and (3) the related equilibrium partitioning of the reactant and product anions between the organic and aqueous or solid phases. The common organic solvents employed in phase-transfer processes are usually relatively nonpolar and usually aprotic. Because anions do not have a great affinity for such solvents and prefer to reside in an aqueous environment, the desired transfer is not a particularly favorable process. The transfer of anions from an aqueous to an organic phase, however, may be achieved by choosing a phase-transfer cation that is not strongly solvated by water and that has organic-like characteristics and is thus compatible with the organic phase. For instance, the volume-to-charge ratio (as well as the organic-like nature) of quaternary ammonium and phosphonium salts can be adjusted over a wide range of values by simply changing the length of the alkyl (or aryl) substituents bonded to the quaternary heteroatom. Tetramethylammonium salts are highly soluble in aqueous media and only slightly soluble in most organic solvents, whereas tetradoecylammonium salts are soluble in most organic media but only slightly soluble in water.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
L. Pauling, The Naure of the Chemical Bond, Cornell University Press, Ithaca, New York, Appendix 3.1 (1940).
R. Alexander and A.J. Parker, J. Am. Chem. Soc., 89, 5549 (1967).
C.M. Starks and C.L. Liotta, Phase Transfer Catalysis: Principles and Techniques; Academic Press, New York (1978).
R. Bock and G.M. Beilstein, Z. Anal. Chem., 192, 45 (1963).
R.M. Diamond and D.G. Tuck, Prog. Inorg. Chem., 2, 109 (1960).
R. Bock and J. Jainz, Z. Anal. Chem, 198, 315 (1963).
Values of α for (C6H5)4Sb+X- have also been measured: Bock, R.; Gallath, E. Z. Anal. Chem., 222, 283 (1966).
C.J. Cotzee and H. Freisee, Anal. Chem., 41, 1128 (1969).
H.K. Bisivas and B.M. Mandai, Anal. Chem., 44, 1636 (1972).
R.B. Grieves, W. Charewicz, and P.J.W. The, Sep. Sci., 10, 77 (1975).
E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, 2nd ed; Verlag Chemie, Weinheim (1983).
N.A. Gibson and D.C. Weatherburn, Anal. Chim. Acta, 58, 159 (1972).
J.P. Antoine, I. de Aquirre, F. Janssens, and F. Thyrion, Bull. Soc. Chim. Fr., 207 (1980).
J. Czapkiewica, T. Czapkiewica, and D. Struk, Pol. J. Chem., 52, 2203 (1978).
E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, 2nd ed.; Verlag Chemie: Weinheim, p. 13 (1983).
B. Czapkiewicz-Tutaj and J. Czapkiewica, Rocz. Chem., 49, 1353 (1975).
E.V. Dehmlow and B. Vehre, J. Chem. Res. (S), 350 (1987).
Y. Inoue and O. Tochiyama, Bull. Chem. Soc. Jpn., 53, 1618 (1980).
C.M. Storks and R.M. Owens, J. Am. Chem. Soc., 95, 3613 (1973).
A.W. Herriott and D. Picker, J. Am. Chem. Soc, 97, 2345 (1975).
J. de la Zerda and Y. Sasson, J. Chem. Soc. Perkin Trans. II, 1147 (1987).
D. Landini, A. Maia, and A. Rampoldi, J. Am. Chem. Soc, 51, 5476 (1986).
E.V. Dehmlow, R. Thieser, Y. Sasson, and E. Pross, Tetrahedron, 41, 2927 (1985).
D.S. Allam and W.H. Lee, J. Chem. Soc. A, 426 (1966).
V.L. Kheifets, N.A. Yakovlova, and B. Ya Krasil’shchik, Khim. (Lenningrad), 46, 549 (1973).
D. Landini, A. Maia, and G. Podda, J. Org. Chem. 47, 2264 (1982).
D. Landini and A. Maia, J. Chem. Soc. Chem. Commun., 1041 (1984).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1994 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Starks, C.M., Liotta, C.L., Halpern, M.E. (1994). Phase-Transfer Catalysis: Fundamentals I. In: Phase-Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0687-0_2
Download citation
DOI: https://doi.org/10.1007/978-94-011-0687-0_2
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-4297-0
Online ISBN: 978-94-011-0687-0
eBook Packages: Springer Book Archive