New approaches to rate enhancement in heterogeneous catalysis

Abstract

Rate enhancement, or promotion, of heterogeneous catalysts has long been viewed as an empirical subject, and many catalysts have been designed on the basis of large catalyst screening programmes. This paper addresses recent advances in this topic and indicates that much progress is being made on the basis of a molecular approach, in contrast to the previous empirical methodology, and in particular highly effective enantioselective heterogeneous catalysts can be designed. Two catalyst systems are selected for detailed discussion, namely enantioselective hydrogenation using cinchona-modified platinum catalysts and the modification of zeolites with chiral molecules.

References

1. M. V. Twigg, Catalyst Handbook, Wolfe, London, 2nd edn., 1989.
2. G. J. Hutchings, Appl. Catal., 1991, 72, 1.
3. G. J. Hutchings, Catal. Today, 1993, 16, 139.
4. G. J. Hutchings, C. J. Kiely, M. T. Sananes and J. C. Volta, Catal. Today, 1998, 40, 273.
5. C. J. Kiely, A. Burrows, S. Sajip, G. J. Hutchings, M. T. Sananes, A. Tuel and J. C. Volta, J. Catal., 1996, 162, 31.
6. G. J. Hutchings, A. Desmartin-Chomel, R. Olier and J. C. Volta, Nature, 1994, 368, 41.
7. H. U. Blaser, H. P. Jalett, D. M. Monti, A. Baiker and J. T. Wherli, Stud. Surf. Sci. Catal., 1991, 67, 147.
8. A. Biaker, Stud. Surf. Sci. Catal., 1996, 101, 51.
9. G. Webb and P. B. Wells, Catal. Today, 1992, 12, 319.
10. T. J. Hall, P. Johnston, W. A. H. Vermeer, S. R. Watson and P. B. Wells, Stud. Surf. Sci. Catal., 1996, 101, 221; I. M. Sutherland, A. Ibbotson, R. B. Moyes and P. B. Wells, J. Catal., 1990, 125, 77; P. A. Meheux, A. Ibbotson and P. B. Wells, J. Catal., 1991, 128, 387; K. E. Simons, A. Ibbotson, P. Johnston, H. Plum and P. B. Wells, J. Catal., 1994, 150, 321; G. Bond and P. B. Wells, J. Catal., 1994, 150, 329.
11. Y. Orito, S. Imai, S. Niwa and G.-H. Nguyen, J. Synth. Org. Chem. Jpn., 1979, 37, 173.
12. Y. Orito, S. Imai and S. Niwa, Nippon Kagaku Kaishi, >1979, 1118.
13. Y. Orito, S. Imai and S. Niwa, Nippon Kagaku Kaishi, 1980, 670.
14. Y. Orito, S. Imai and S. Niwa, Nippon Kagaku Kaishi, 1982, 137.
15. Y. Izumi, Adv Catal., 1983, 32, 215.
16. H. U. Blaser, H. P Jalett, M. Müller and M. Studer, Catal. Today, 1997, 37, 441.
17. H. U. Blaser, Tetrahedron: Asymmetry, 1991, 2, 843.
18. H. U. Blaser and M. Müller, Stud. Surf. Sci. Catal., 1991, 59, 73.
19. H. U. Blaser, H. P. Jalett, D. M. Monti, J. F. Reber and J. T. Wherli, Stud. Surf. Sci. Catal., 1988, 41, 153.
20. U. Böhmer, K. Morgenschweiss and W. Reschetilowski, Catal. Today, 1995, 24, 195.
21. W. Reschetilowski, U. Böhmer and K. Morgenschweiss, Chem.-Ing.-Tech., 1995, 67, 205.
22. W. Reschetilowski, U. Böhmer and J. Wiehl, in Chiral Reactions in Heterogeneous Catalysis, ed. G. Jannes and V. Dubois, Plenum Press, New York, 1995, p. 111.
23. R. L. Augustine, S. K. Tanielyan and L. K. Doyle, Tetrahedron: Asymmetry, 1993, 4, 1803.
24. A. Baiker, J. Mol. Catal. A, 1997, 115, 473.
25. D. G. Blackmond, J. Catal., 1998, 176, 267.
26. T. Mallat and A. Baiker, J. Catal., 1998, 176, 271.
27. K. E. Simons, G. Wang, T. Heinz, T. Giger, T. Mallat, A. Pfaltz and A. Baiker, Tetrahedron: Asymmetry, 1995, 6, 505.
28. A. Baiker, T. Mallat, B. Minder, O. Schwalm, K. E. Simons and J. Weber, in Chiral Reactions in Heterogeneous Catalysis, ed. G. Jannes and V. Dubois, Plenum Press, New York, 1995, p. 95.
29. O. Schwalm, B. Minder, J. Weber and A. Baiker, Catal. Lett., 1994, 23, 271.
30. O. Schwalm, J. Weber, B. Minder and A. Baiker, J. Mol. Struct. (THEOCHEM), 1995, 330, 353.
31. J. L. Margitfalvi, M. Hegedüs and E. Tfirst, Tetrahedron: Asymmetry, 1996, 7, 571.
32. J. L. Margitfalvi, M. Hegedüs and E. Tfirst, Stud. Surf. Sci. Catal., 1996, 101, 241.
33. G. J. Hutchings and D. J. Willock, Top. Catal., 1998, 5, 177.
34. P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, London, 1979.
35. S. B. Chang, J. M. Galvin and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 6937.
36. G. J. Hutchings, F. King, I. P. Okoye, M. B. Padley and C. H. Rochester, J. Catal., 1994, 148, 453; F. King, I. P. Okoye, M. B. Padley and C. H. Rochester, J. Catal., 1994, 148, 463; M. B. Padley, C. H. Rochester, G. J. Hutchings and F. King, J. Catal., 1994, 148, 438.
37. A. Corma, M. Iglesias, C. del Pino and F. Sànchez, Proc. 10th Int. Cong. Catal., Elsevier, Amsterdam, 1993, p. 2293.
38. R. Noyari, Chem. Soc. Rev., 1989, 187.
39. A. Corma, M. Iglesias, F. Mohino and F. Sönchez, J. Organometal. Chem., 1977, 544, 147.
40. J. M. Thomas, Nature, 1994, 368, 289.
41. J. M. Thomas and G. N. Greaves, Science, 1994, 265, 1675.
42. T. Maschmeyer, F. Rey, G. Sankar and J. M. Thomas, Nature, 1995, 378, 159.
43. R. Oldroyd, J. M. Thomas, T. Maschmeyer, P. A. MacFaul, D. W. Snelgrove, K. I. Ingold and D. M. Wayner, Angew. Chem. Int. Ed. Engl., 1996, 35, 2787.
44. T. Maschmeyer, R. D. Oldroyd, G. Sankar, J. M. Thomas, I. J. Shannon, J. A. Klepetko, A. F. Masters, J. K. Beattie and C. R. A. Catlow, Angew. Chem., Int. Ed. Engl., 1997, 36, 1639.
45. A. Corma, J. L. Jorda, M. T. Navarro and R. Rey, Chem. Commun., 1998, 1899.
46. R. F. Parton, L. Uytterhoeven and P. A. Jacobs, in Heterogeneous Catalysis and Fine Chemicals ed. M. Guisnet), Elsevier, Amsterdam, 1995, p. 395.
47. P. P. Knops-Gerrits, D. De Vos, F. Thibault-Starzyk and P. A. Jacobs, Nature, 1994, 369, 543.
48. S. B. Ogunmumi and T. Bein, Chem. Commun., 1997, 901.
49. M. J. Sabater, A. Corma, A. Domenech, V. Fornés and H. Garcia, Chem. Commun., 1997, 1285.
50. G. Sundarababu, M. Leibovitch, D. R. Corbin, J. R. Scheffer and V. Ramamurphy, Chem. Commun., 1996, 2159.
51. S. Feast, D. Bethell, P. C. B. Page, F. King, C. H. Rochester, M. R. H. Siddiqui, D. J. Willock and G. J. Hutchings, J. Chem. Soc., Chem. Commun., 1995, 2409.
52. S. Feast, M. R. H. Siddiqui, R. Wells, D. J. Willock, F. King, C. H. Rochester, D. Bethell, P. C. B. Page and G. J. Hutchings, J. Catal., 1997, 167, 533.
53. W. O. Haag and R. M. Lago, US Pat., 1982, 4326994.
54. C. Mirodatos and D. Bartemeuf, J. Chem. Soc., Chem. Commun., 1981, 39.
55. P. O. Fritz and J. H. Lunsford, J. Catal., 1989, 118, 85.
56. S. Feast, D. Bethell, P. C. B. Page, M. R. H. Siddiqui, D. J. Willock, G. J. Hutchings, F. King and C. H. Rochester, Stud. Surf. Sci. Catal., 1996, 101, 211.
57. D. J. Willock and G. J. Hutchings, Top. Catal., 1998, 5, 177.
58. C. Langham, P. Piaggio, D. Bethell, D. F. Lee, P. McMorn, P. C. B. Page, D. J. Willock, C. Sly, F. E. Hancock, F. King and G. J. Hutchings, Chem. Commun., 1998, 1601.
59. P. Piaggio, P. McMorn, C. Langham, D. Bethell, P. C. B. Page, F. E. Hancock and G. J. Hutchings, J. Nouv. Chem., in press.
60. D. J. Berrisford, C. Bolm and B. Sharpless, Angew. Chem., Int. Ed. Engl., 1995, 34, 1059.