Molecular engineering in homogeneous catalysis: One-phase catalysis coupled with biphase catalyst separation. The fluorous-soluble HRh(CO){P[CH2CH2(CF2)5CF3]3}3 hydroformylation system

Journal of the American Chemical Society

Volumn 120, Issue 13, 1998, Pages 3133-3143

  Horváth, István T ^a   Kiss, Gábor ^a   Cook, Raymond A ^a   Bond, Jeffrey E ^a   Stevens, Paul A ^a   Rábai, József ^a,b   Mozeleski, Edmund J ^a  

^a EXXONMOBIL UPSTREAM RESEARCH COMPANY   (United States)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 DECENE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; FLUORINE; FORMIC ACID DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ENGINEERING; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; PHASE TRANSITION; SYNTHESIS;

EID: 0038041352     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9738337     Document Type: Article

References (88)

1. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley: New York, 1992.
2. (b) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, 1996.
3. (c) Hermann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1049.
4. (a) Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1994, 475, 57.
5. (b) Zhang, X.-X.; Wayland, B. B. J. Am. Chem. Soc. 1994, 116, 7894.
6. (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217.
7. (b) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
8. (a) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
9. (b) Tsang, S. C.; Davis, J. J.; Green, M. L. H.; Hill, H. A. O.; Leung, Y. C.; Sadler, P. J. Chem. Commun. 1995, 1803.
10. (c) Bergbreiter, D. E.; Caraway, J. W. J. Am. Chem. Soc. 1996, 118, 6092.
11. (d) Neumann, R.; Cohen, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1738.
12. Bergbreiter, D. E.; Zhang, L.; Mariagnam, V. M. J. Am. Chem. Soc. 1993, 115, 9295.
13. Falbe, J. New Synthesis with Carbon Monoxide; Springer-Verlag: Berlin, 1980.
14. (a) O'Connor, C.; Yagupsky, G.; Evans, D.; Wilkinson, G. Chem. Commun. 1968, 420.
15. (b) Evans, D.; Yagupsky, G.; Wilkinson, G. J. Chem. Soc. A 1968, 2660.
16. (c) Evans, D.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 3133.
17. (d) Brown, C. K.; Wilkinson, G. J. Chem. Soc. A 1970, 2753.
18. (e) Pruett, R. L.; Smith, J. A. J. Org. Chem. 1969, 34, 327.
19. (f) Pruett, R. L. Adv. Organomet. Chem. 1979, 17, 1.
20. (g) Gregorio, G.; Montrasi, G.; Tampierei, M.; Cavaliezi d'Oro, P.; Pagani, G.; Andreetta, A. Chim. Ind. (Milan) 1980, 62, 389.
21. (h) Cavaliezi d'Oro, P.; Raimondi, L.; Pagani, G.; Montrasi, G.; Gregorio, G.; Andreetta, A. Chim. Ind. (Milan) 1980, 62, 572.
22. (i) Oswald, A. A.; Merola, J. S.; Mozeleski, E. J.; Kastrup, R. J.; Reisch, R. V. In Advances in Chemistry Series; Quin, L. D., Verkade, J. G., Eds.; American Chemical Society: Washington, DC, 1981; Vol. 171, p 503.
23. (j) Kastrup, R. J.; Merola, J. S.; Oswald, A. A. In Advances in Chemistry Series; Alyea, E. C., Meek, D. W., Eds.; American Chemical Society: Washington, DC, 1982; Vol. 196, p 43.
24. (k) Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. J.; Merola, J. S. Prepr. Pap., Am. Chem. Soc., Div. Pet. Chem. 1982, 27, 292.
25. (l) Brown, J. M.; Canning, L. R.; Kent, A. G.; Sidebottom, P. J. Chem. Commun. 1982, 721.
26. (m) Brown, J. M.; Kent, A. G. Chem. Commun. 1982, 723.
27. (n) Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597.
28. (o) Moser, W. R.; Papile, C. J.; Brannon, D. A.; Duwell, R. A.; Weininger, S. J. J. Mol. Catal. 1987, 41, 271.
29. (a) Jamerson, J. D.; Pruett, R. L.; Billig, E.; Fiato, R. A. J. Organomet. Chem. 1980, 193, C43.
30. (b) Morrell, D. G.; Sherman, P. D. U.S. Patent 4260 828, 1981.
31. (c) Bryant, D. R.; Billig, E. U.S. Patent 4277 627, 1981.
32. (d) Abatjoglou, A. G.; Billig, E.; Bryant, D. R. Organometallics 1984, 3, 923.
33. (e) Oswald, A. A.; Jermasen, T. G.; Westner, A. A.; Huang I. U.S. Patent 4668 809, 1987.
34. (f) Deshpande, R. M.; Divekar, S. S.; Gholap, R. V.; Chaudhari, R. V. J. Mol. Catal. 1991, 67, 333.
35. (a) Kuntz, E. G. CHEMTECH 1987, 17, 570.
36. (b) Herrmann, W. A.; Kohlpaintner, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
37. (a) Wiebus, E.; Cornus, B. Chem.-Ing.-Tech. 1994, 66, 916.
38. (b) Comils, B.; Wiebus, E. CHEMTECH 1995, 25, 33.
39. Horváth, I. T. Catal. Lett. 1990, 6, 43.
40. (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
41. (b) U.S. Patent 5463 082, 1995.
42. (a) Grosse, A. V.; Cady, G. H. Ind. Eng. Chem. 1947, 39, 367.
43. (b) Scott, R. L. J. Am. Chem. Soc. 1948, 70, 4090.
44. (c) Hildebrand, J. H.; Cochran, D. R. F. J. Am. Chem. Soc. 1949, 71, 22.
45. (d) Zadymova, N. M.; Markina, Z. N.; Yevseyeva, N. K.; Schukin, E. D. Kolloidn. Zh. 1988, 50, 825.
46. (e) Dorset, D. L. Macromolecules 1990, 23, 894.
47. (f) Kloubek, J Colloids Surf. 1991, 55, 191.
48. (a) Bergbreiter, D. E. Chemtracts Org. Chem. 1995, 8, 108.
49. (b) Curran, D. P. Chemtracts Org. Chem. 1996, 9, 75.
50. (c) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531.
51. (d) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312.
52. (e) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
53. (f) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583.
54. (g) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S. Y.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
55. (h) Horner, J. H.; Martinez, F. N.; Newcomb, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 2783.
56. (i) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
57. (j) Studer, A.; Curran, D. P. Tetrahedron 1997, 53, 6681.
58. (k) Bergbreiter, D. E.; Franchina, J. G. Chem. Commun. 1997, 1531.
59. (a) Pozzi, G.; Montanari, F.; Quic, S. Chem. Commun. 1997, 69.
60. (b) Klement, I.; Lutjens, H.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1454.
61. (c) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610.
62. (d) Vincent, J.-M.; Rabion, A.; Yachandra, V. K.; Fish, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2346.
63. (e) Betzemeier, B.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 2623.
64. (a) Tamborski, C. U.S. Patent 3499 041, 1970.
65. (b) Tamborski, C.; Snyder, C. E. U.S. Patent 4011 267, 1977.
66. (c) Tamborski, C.; Snyder, C. E.; Christian, J. B. U.S. Patent 4454 349, 1984.
67. (d) Gavezotti, P.; Strepparola, E. U.S. Patent 4681 693, 1987.
68. Filler, R. In Fluorine Containing Molecules; Liebman, J. F., Greenberg, A., Dolbier, W. R., Jr., Eds.; VCH: Weinheim, 1988; Chapter 2.
69. UniChem is a computational chemistry software package developed by Cray Research, Inc. Included within the package is the MNDO93 program developed by W. Thiel and co-workers.
70. James, J. P. S. In Reviews in Computational Chemisty; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1990; Vol. 1, p 45.
71. Tolman, C. A. Chem. Rev. 1977, 77, 313.
72. 21
73. Rauhut, M. M.; Currier, H. A.; Semsel, A. M.; Wystrach, V. P. J. Org. Chem. 1961, 26, 5138.
74. Juliette, J. J. J.; Gladysz, J. A. Personal communication, 1997.
75. Horváth, I. T.; Kastrup, R. V.; Oswald, A. A.; Mozeleski, E. J. Catal. Lett. 1989, 2, 85.
76. Li, C.; Nolan, S. P.; Horváth, I. T. Organometallics Submitted.
77. Tolman, C. A.; Faller, J. W. Mechanistic Studies of Catalytic Reactions Using Spectroscopic and Kinetic Techniques. In Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum: New York, 1983.
78. (a) Oliver, K. L.; Booth, F. B. Hydrocarbon Process. 1970, 49 (4), 112.
79. (b) Deshpande, R. M.; Bhanage, B. M.; Divekar, S. S.; Chaudhari, R. V. J. Mol. Catal. 1993, 78, L37.
80. (c) Claridge, J. B.; Douthwaite, R. E.; Green, M. L. H.; Lago, R. M.; Tsang, S. C.; York, A. P. E. J. Mol. Catal. 1994, 89, 113.
81. (d) Bartik, T.; Ding, H.; Bartik, B.; Hanson, B. E. J. Mol. Catal. A: Chem. 1995, 98, 117.
82. (e) Kurkin, V. I.; Sakulin, V. V.; Kobyakov, A. K.; Slivinskii, Ye. V.; Basner, M. Ye.; Aronovich, R. A.; Korneyeva, G. A.; Loktev, S. M. Petrol. Chem. 1994, 34 (5), 393.
83. (a) Deshpande, R. M.; Chaudhari, R. V. Ind. Eng. Chem. Res. 1988, 27, 1996.
84. (b) Deshpande, R. M.; Chaudhari, R. V. J. Catal. 1989, 115, 326.
85. (c) Divekar, S. S.; Deshpande, R. M.; Chaudhari, R. V. Catal. Lett. 1993, 21, 191.
86. (d) Deshpande, R. M.; Purwanto, Delmas, H.; Chaudhari, R. V. Ind. Eng. Chem. Res. 1996, 35, 3927.
87. (e) Bhanage, B. M.; Divekar, S. S.; Deshpande, R. M.; Chaudhari, R. V. J. Mol. Catal. A: Chem. 1997, 115, 247.
88. Horváth, I. T.; Ponce, E. C. Rev. Sci. Instrum. 1991, 62, 1104.