Abstract
From the standpoint of the process engineer, the advantages of phase transfer catalysis are:
high yield (often >90%);
-
increased reaction rates, sometimes leading to enhanced selectivity;
-
mild reactions conditions, which increase process reliability and flexibility;
-
viability in the presence of water and avoidance of run-away conditions;
-
the ability to use NaOH as a base rather than the more expensive and hazardous organic bases such as sodium methoxide;
-
compatibility with a broad range of solvents.
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
Freedman, H.H. (1986) Pure Appl. Chem.,58,857.
O’Donnell, M.J. (1993) in Catalytic Asymmetric Synthesis (ed. I. Ojima), VCH, New York, p. 389.
Yadav, G.D. and Sharma, M.M. (1981) Ind. Eng. Chem. Process Des. Dev., 20, 385.
Sugimato, N., Fugita, T., Shigenmatsu, N. and Ayada, A. (1962) Chem. Pharm. Bull., 10427.
Wang, M. and Yang, H. (1990) Ind. Eng. Chem. Res., 29, 522.
Wang, T.T. and Huang, T.C. (1990) Chem. Eng. Commun., 92, 139.
Gove, E.S. (1990) Platinum Met. Rev., 34, 2.
Cassar, L., Foa, M. and Gardano, A. (1976) J. Organomet. Chem., 121(3), C55.
Yadav, G.D. and Mistry, C.K. (1995) J. Mol. Catal., 102, 67.
Pradhan, N.C. and Sharma, M.M. (1992) Ind. Eng. Chem. Res., 31, 1610.
Yang, J and Yu, S. (1994) Huazue Shiji, 16, 316; Chem. Abstr., 122, 213693.
Huang, D. and Lin, S. (1988) Chin. J. Ind. Chem. Eng., 19, 193.
Makosza, M. and Serafin, B. (1965) Rocz. Chem., 39, 1401.
Gower, C. (1983) US Pat., 4 387 253; Chem. Abstr., 97, 5961.
Pradhan, N.C. and Sharma, M.M. (1990) Ind. Eng. Chem. Res., 29, 1103.
Pradhan, N.C. and Sharma, M.M. (1992) Ind. Eng. Chem. Res., 31, 1606.
Dakka, J., Zoran, A. and Sasson, Y. (1989) Eur. Pat., Appl., EP 300,921; Chem. Abstr., Ill, 23218.
Neumann, R. and Sasson, Y. (1985) J. Chem. Soc., Chem. Commun., 616.
Sasson, Y., Zappi, G.D. and Neumann, R. (1986) J. Org. Chem., 51, 2880.
Lindblom, L. and Elander, M. (1980) Pharm. Technol., 4(10), 59.
Jonezyk, A., Ludwikow, M. and Makosza, M. (1979) Org. Prep. Proced. Int., 11, 275.
Yamada, T. and Onishi, M. (1992) Jpn. Kokai Tokkyo Koho, JP 04 18 090; Chem. Abstr., 116,255631.
Gozlan, I., Ladkani, D. Helpern, M. et al. (1984) J. Heterocycl. Chem., 21, 613.
Suzuki, K., Yoshida, K. and Otaka, H. (1992) Jpn. Kokai Tokkyo Koho, JP 04 164 078; Chem. Abstr., 117,212525.
Hayes, S.F. and Mitchell, M.B. (1993) Chem. Br., 1037.
Fex, H.J., Kristensson, S.K. and Stamvik, A.R. (1978) Ger. Offen.,2 629 657; Chem. Abstr., 86, 189570.
Schwart, S. and Weber, G. (1975) East Ger. Pat., 114 806; Chem. Abstr., 85, 63238.
Koziara, A., Zowadzki, S. and Zwierzak, A. (1979) Synthesis, 521.
Hodkova, J., Vesely, Z. and Trojanek, J. (1990) Czech Pat., CS-266 942; Chem. Abstr., 115, 183648.
Vasndort, H.M. and Geursen, H.J. (1967) Reel. Trav. Chim. Pays-Bas, 86, 520.
Broda, W. and Dehmlow, E.V. (1985) Isr. J. Chem., 26, 219.
Hermann, C.K.F., Sachdeva, Y.P. and Wolfe, J.F. (1987) Heterocycl. Chem., 24, 1061.
Starks, C.M., Liotta, C.L. and Halpern, M. (1994) Phase Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives, Chapman & Hall, London, p. 383.
Koch, M. and Magni, A. (1985) US Pat., 4 501 919; Chem. Abstr., 102, 204296.
Heiszmann, J., Bitter, I., Harsanyi, K. and Toke, L. (1987) Synthesis, 738.
Plonka, J.H. and Pews, R.G. (1976) US Pat., 3 974 199; Chem. Abstr., 86, 55053.
Sane, P.V. and Sharma, M.M. (1988) Org. Prep. Proced. Int., 20, 598.
Maggioni, P. (1980) Ger. Offen., DE 2 703 640; Chem. Abstr., 87, 167715.
Dakka, J. and Sasson, Y. (1987) J. Chem. Soc., Chem. Commun., 1421.
Szabo, G.T., Aranyoso, K., Csiba, M. and Toke, L. (1987) Synthesis, 565.
Jovanovic, S.S., Misic-Vukovic, M.M., Djokovic, D.D. and Bajic, D.S. (1992) J. Mol Catal., 73, 9.
Ziang, H. and Zongyuan, Y. (1995) Yingyong Huaxue, 12(3), 113.
Schubert, H. and Baessler, K. (1984) US Pat., 4 454 355; Chem. Abstr., 98, 106961.
Yuam, Y., Gao, D. and Jiang, Y. (1992) Synth. Commun., 22,2117.
Folz, G., Papenfus, T. and Schubert, H. (1992) Eur. Pat. Appl, EP 496 370; Chem. Abstr., 117,150684.
Write, C.R. (1987) US Pat., 4 642 399; Chem. Abstr., 106, 138076; Ger. Offen., DE 2 938 939 (1980); Chem. Abstr., 93, 185932.
Hagedorn, F., Fiege, H., Soellner, R. and Helm, R. (1995) Eur. Pat, Appl, EP 658 544; Chem. Abstr., 123, 82939.
Hiroshi, S., Shuji, O. and R’yuichi, M. (1993) Jpn. Kokai Tokkyo Koho, JP07 126 198; Chem. Abstr., 123, 169226.
Hampl, F., Smid, I., Votava, V. et al. (1990) Czech. Pat., CS-265 360; Chem. Abstr., 114, 20680.
Angeletti, E., Tundo, P., Venturello, P. and Trotta, F. (1984) Br. Polym. J., 16, 219.
Liu, B.L., Jin, Y.T., Lin, Z.H. et al. (1985) Int. J. Appl Radiat. Isot., 36, 561.
Aragao dos Santos, H., Espindola, L., Ferreise, V.F. and Nakamura, T. (1991) Braz. Pat., 9 102 022; Chem. Abstr., 118, 134747.
Ranganekar, D.W. and Lokhande, S.B. (1986) Indian J. Chem. B, 25,485.
Ranganekar, D.W. and Shenoy, G.R. (1988) Dyes Pigments, 10, 69.
Ranganekar, D.W. and Shenoy, G.R. (1988) Dyes Pigments, 10, 165.
Hattori, M., Taguma, A., Morimitsu, T. and Takeshite, A. (1984) Eur. Pat. Appl, EP 105 762; Chem. Abstr., 101, 173037.
Stern, M.K. and Cheng, B.K. (1993) J. Org. Chem., 58, 6883.
Mauran, L., (1983) US Pat., 4 418 232; Chem. Abstr., 100, 52179.
Reed, D.J. and Snedecor, T.G., Jr (1993) PCTInt. Pat. Appl, WO 95 05 352; Chem. Abstr., 123,199636.
Nanba, H., Abe, K. and Saito, M. (1988) Jpn. Kokai Tokkyo Koho, JP 63 196 550; Chem. Abstr., 110, 23361.
Krishna Kumar, V.K. and Sharma, M.M. (1983) Synthesis, 558.
Glasser, W.G., Olivera, W., Kelley, S.S. and Nich, L.S. (1990) US Pat., 4 918 167; Chem. Abstr., 113, 99698.
Wang, M. and Yang, H. (1990) J. Mol. Catal., 57, 271.
General Electric (1985) Jpn. Kokai Tokkyo Koho, JP 60 188 368; Chem. Abstr., 104, 130428.
Qin, D. and Wang, G. (1990) Faming Shuanli Shenqing Gongkai Shuomingshu, CN 1 039413; Chem. Abstr., 113, 230791.
Kochler, M., Roemer, M. and Herz, C. (1986) Ger. Offen., DE 3 512 541; Chem. Abstr., 106, 32575.
Osborn, M.E. (1995) Speciality Chem., 215.
Zupanicic, B.G. and Sopcic, M. (1982) Synthesis, 942.
Dow Chemical (1977) Neth. Pat. Appl, 75 09 2021; Chem. Abstr., 88, 22642.
Gore, S.T., Goel, R.N. and Sobti, R.R. (1980) Indian Pat., 148 068; Chem. Abstr., 97, 97854.
Garganu, R., Perez, D. and Williams, D. (1982) US Pat., 4 326 059; Chem. Abstr., 92, 163900.
Kroposki, L.M., Yoshimine, M. and Freedman, H.H. (1975) US Pat., 3 917 621; Chem. Abstr., 84, 121436.
Freedman, H.H. (1976) US Pat., 3 969 360; Chem. Abstr., 86, 53174.
Botar, S., Szekely, I., Bertok, B. et al. (1992) PCT Int. Appl, WO 92 02 492; Chem. Abstr., 116,214743.
Sheldon, R.A., Been, P., Wood, D.A. and Mason, R.F. (1977) Ger. Offen., 2 708 590; Chem. Abstr., 88, 6563.
Henneke, K., Diehn, H. and Wedemeyer, K. (1986) US Pat., 4 594 467; Chem. Abstr., 105, 42451.
Koenig, K.E. and Weber, W.P. (1974) Tetrahedron Lett., 2275.
Lantzsch, R. and Krall, H. (1988) Ger. Offen., DE 3 626 411, Chem. Abstr., 109, 54497.
Wei, T. and Chen, J. (1994) Huaxue Shijie, 35, 538; Chem. Abstr., 123, 202861.
Merz, A. (1974) Synthesis, 124.
Brokke, M.E. and Magee, W.L. (1985) Eur. Pat. Appl., EP 140 454; Chem. Abstr., 103, 143568.
Mark, H.W. (1988) Eur. Pat. Appl, 268 261; Chem. Abstr., 109, 230275.
Suzuki, H., Kawashima, M., Kawamura, Y. and Ogura, T. (1986) Jpn. Kokai Tokkyo Koho, JP 62 294 652; Chem. Abstr., 109, 92460.
Imamura, K., Miura, H., Uno, Y. and Watanabe, E. (1990) Jpn. Kokai Tokkyo Koho, JP 02 304 061; Chem. Abstr., 114, 206583.
Kumala, K., Ankner, K., Rintala, L. et al. (1993) PCT Int. Pat. Appl, WO 95 07 254; Chem. Abstr., 122, 290330.
Landini, D., Montanari, F. and Rolla, F. (1974) Synthesis, 1, 34.
Shinozaki, H., Imaizumi, M. and Tajima, M. (1983) Chem. Lett., 929.
Krbechek, L.O. (1995) PCT Int. Pat. Appl., WO 95 01 957; Chem. Abstr., 122, 213748.
Weissien, B., Andreasson, E. and Holmberg, K. (1989) J. Am. Oil Chem. Soc., 66,1107.
Quinn, R. (1995) Chem. Eng. News, 17 April, 26.
Jablokoff, H., Lorch, B and Engelmann, H. (1982) East Ger. Pat., DD 154 813; Chem. Abstr., 98,4274.
Dehmlow, E.V., Raths, H.C. and Soufi, J. (1988) J. Chem. Res., 384.
Rigterink, R.H. and Kenaga, E.E. (1966) J. Agric. Food. Chem., 14, 304.
Sarkar, A., Dey, P.K. and Datta, K. (1986) Indian J. Chem. B, 25, 656.
Kumala, K., Ankner, K., Rintala, L. et al. (1995) PCT Int. Pat. Appl, WO 95 07 254; Chem. Abstr., 122, 290330.
Kumala, K., Anker, K. and Rintala, L. (1995) PCT Int. Pat. Appl, WO 95 00 464; Chem. Abstr., 122, 132576.
Bram, B.G., Sansoulet, J., Golons, H. and Micgue, M. (1988) Synth. Commun., 18, 376.
Hales, B.F., Hachey, C. and Robaire, B. (1980) Biochem. J., 189, 135.
Fedorynski, M., Wojciechowski, K., Matacz, Z. and Makosza, M. (1978) J. Org. Chem., 43,4682.
Dehmlow, E.V. and Kinning, J. (1995) J. Prakt. ChemJChem.-Z, 337, 153.
Lu, W., Yan, C., Ding, Y. and Gu, H. (1995) Huzxue Shiji, 17, 110,120; Chem. Abstr., 123, 198244.
Branko, J. (1988) Tetrahedron, 44, 6677.
Dehmlow, E.V. and Naranjo, S.B. (1981)J Chem. Res., 142.
Dehmlow, E.V. and Naranjo, S.B. (1981)J. Chem. Res., 143.
Sasson, Y. and Yonovich, M. (1979) Tetrahedron Lett., 39, 3753.
Kajigaeshi, S., Asano, K., Fujiaki, A. etal. (1989) Chem. Lett., 463.
Kajigaeshi, S., Murakawa, K. Asano, K. etal (1989)J. Chem. Soc., Perkin Trans. 1, 1702.
Rane, D.S. and Sharma, M.M. (1994) J Chem. Technol. Biotechnol., 59, 271.
Zaidman, B., Sasson, Y. and Neumann, R. (1985) Ind. Eng. Chem. Prod Res. Dev., 24, 390.
Lin, C.L. and Pinnavaia, T.J. (1991) Chem. Mater., 3, 213.
Chaudhary, B.M., Rao, Y.V.S. and Prasad, B.P. (1991) Clays Clay Miner, 39, 329.
Boyd, G.E. and Larson, Q.V. (1967) J. Am. Chem. Soc., 89, 6038.
Pahari, P. (1991) PhD Thesis, University of Bombay.
Ledon, H. (1974) Synthesis, 347.
Bram, G., Loupy, A. and Sansoulet, J. (1985) Isr. J. Chem., 26, 291; Chem. Abstr., 105, 96660.
Sjoberg, K. (1980) Aldrichim. Acta, 13, 55.
Hampl, F., Hajek, J. Votava, V. et al. (1989) Czech. Pat., CS-265 560; Chem. Abstr., 114, 207024.
Berris, B.C. (1991) US Pat., 5 030 757; Chem. Abstr., 115, 114015.
Maurin, L. (1983) US Pat., 4 418 232; Chem. Abstr., 100, 52179.
Taracon, E.M. (1992) Span. Pat., ES-1 023 606; Chem. Abstr., 117,48107.
Brunelle, D. (1982) US Pat., 4 363 905; Chem. Abstr., 98, 72918.
Nanba, H., Takahashi, N., Abe, K. and Saito, M. (1988) Jpn. Kokai Tokkyo Koho, JP 63 196 549; Chem. Abstr., 110, 23360.
Liotta, C.L., Starks, C.M. and Halpern, M.E. (1994) Phase Transfer Catalysis: Fundamentals, applications and industrial perspectives, Chapman & Hall, p. 26.
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Chapman & Hall
About this chapter
Cite this chapter
Sharma, M. (1997). Application of phase transfer catalysis in the chemical industry. In: Sasson, Y., Neumann, R. (eds) Handbook of Phase Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0023-3_5
Download citation
DOI: https://doi.org/10.1007/978-94-009-0023-3_5
Publisher Name: Springer, Dordrecht
Print ISBN: 978-0-7514-0258-2
Online ISBN: 978-94-009-0023-3
eBook Packages: Springer Book Archive