Dual catalytic systems for consecutive isomerization-hydroformylation reactions

Chemistry - A European Journal

Volumn 5, Issue 4, 1999, Pages 1301-1305

  Beller, Matthias ^a   Zimmermann, Burkhard ^b   Geissler, Holger ^c  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c CLARIANT PRODUKTE DEUTSCHLAND GMBH   (Germany)

Author keywords

Homogeneous catalysis; Hydroformylations; Isomerizations; Phosphanophosphite ligands; Rhodium

Indexed keywords

ALKENE; POLYVINYLCHLORIDE; RHODIUM;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ISOMERISM; LIGAND BINDING; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032952227     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990401)5:4<1301::AID-CHEM1301>3.0.CO;2-Y     Document Type: Article

References (63)

1. Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996.
2. a) Aqueous-Phase Organometallic Catalysis: Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1998;
3. b) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, John Wiley, New York, 1992.
4. For major reviews see: a) F. Ungvary, Coord. Chem. Rev. 1997, 167, 233;
5. b) C. D. Frohning, C. W. Kohlpaintner in ref. [1], p. 29;
6. c) M. Lenarda, L. Storaro, R. Ganzerla, J. Mol. Catal. 1996, 111, 203;
7. M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpaintner, J. Mol. Catal. 1995, 104, 17;
8. e) B. Cornils, in New Synthesis with Carbon Monoxide (Ed.: J. Falbe), Springer, Berlin, 1980, p. 1.
9. a) B. Cornils, E. Wiebus, Chemtech (1) 1995, 33;
10. b) E. Wiebus, B. Cornils, Chem. Ing. Tech. 1994, 66, 916.
11. Chem. Ind. 1998, 18 May, 379.
12. a) E. Drent, D. H. L. Pello, J. C. L. J. Swuykerbuyk, J. van Gogh (Shell), PCT Int. WO 95/05.354, 1995; Chem. Abstr. 1995, 123, 313386u;
13. a) E. Drent, D. H. L. Pello, J. C. L. J. Swuykerbuyk, J. van Gogh (Shell), PCT Int. WO 95/05.354, 1995; Chem. Abstr. 1995, 123, 313386u;
14. b) K. D. Tau (Celanese Corp.), US 4605781, 1986; Chem. Abstr. 1986, 105, 193347m;
15. b) K. D. Tau (Celanese Corp.), US 4605781, 1986; Chem. Abstr. 1986, 105, 193347m;
16. c) J. F. Knifton, R. A. Grigsby (Texaco Dev. Corp.), US 4469895, 1984; Chem. Abstr. 1984, 101, 72273t.
17. J. F. Knifton, R. A. Grigsby (Texaco Dev. Corp.), US 4469895, 1984; Chem. Abstr. 1984, 101, 72273t.
18. a) A. Macaluso, O. W. Rigdon (Texaco Dev. Corp.), US 3907909, 1973; Chem. Abstr. 1976, 84, 58609f;
19. a) A. Macaluso, O. W. Rigdon (Texaco Dev. Corp.), US 3907909, 1973; Chem. Abstr. 1976, 84, 58609f;
20. b) A. Macaluso, O. W. Rigdon (Texaco Dev. Corp.), US 3984486, 1976; Chem. Abstr. 1977, 86, 43169e.
21. b) A. Macaluso, O. W. Rigdon (Texaco Dev. Corp.), US 3984486, 1976; Chem. Abstr. 1977, 86, 43169e.
22. E. R. Tucci, Ing. Eng. Chem. Prod. Res. Develop. 1968, 7, 227.
23. C. Botteghi, R. Ganzerla, M. Lenarda, G. Moretti, J. Mol. Catal. 1987, 40, 129.
24. a) P. W. N. M. van Leeuwen, C. F. Roobeek, J. Organomet. Chem. 1983, 258, 343;
25. b) A. van Rooy, E. N. Orij, P. C. J. Kamer, F. v. d. Aardweg, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1991, 1096.
26. a) E. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), US 4769498, 1988; Chem. Abstr. see ref. [11c];
27. a) E. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), US 4769498, 1988; Chem. Abstr. see ref. [11c];
28. b) E. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), EP 0213639, 1987; Chem. Abstr. 1987, 107, 7392r;
29. b) E. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), EP 0213639, 1987; Chem. Abstr. 1987, 107, 7392r;
30. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), EP 0214622, 1987; Chem. Abstr. 1987, 107, 25126m.
31. Billig, A. G. Abatjoglou, D. R. Bryant (UCC Corp.), EP 0214622, 1987; Chem. Abstr. 1987, 107, 25126m.
32. J. P. Kennedy, T. Otsu, Adv. Polym. Sci. 1979, 7, 369.
33. K. Huthmacher, S. Krill, in ref. [1], p. 465.
34. a) Y. Ishii, K. Miyashita, K. Kamita, M. Hidai, J. Am. Chem. Soc. 1997, 119, 6448;
35. b) Y. Ishii, M. Sato, H. Matsuzaka, M. Hidai, J. Mol. Catal. 1989, 54, L13;
36. c) M. Hidai, H. Matsuzaka, Polyhedron 1988, 7, 2369;
37. M. Hidai, A. Fukuoka, Y. Koyasu, Y. Uchida, J. Chem. Soc. Chem. Commun. 1984, 516.
38. For recent reviews see: a) W. A. Herrmann in ref. [1], p. 980;
39. b) ref. [2b], p. 9.
40. a) C. A. Tolman, J. Am. Chem. Soc. 1970, 92, 2956;
41. b) C. A. Tolman, J. Am. Chem. Soc. 1972, 94, 2994;
42. c) G. Fachinetti, A. Stefani, Angew. Chem. 1982, 94, 937; Angew. Chem. Int. Ed. Engl. 1982, 21, 925; Angew. Chem. Suppl. 1982, 1967;
43. c) G. Fachinetti, A. Stefani, Angew. Chem. 1982, 94, 937; Angew. Chem. Int. Ed. Engl. 1982, 21, 925; Angew. Chem. Suppl. 1982, 1967;
44. G. Fachinetti, A. Stefani, Angew. Chem. 1982, 94, 937; Angew. Chem. Int. Ed. Engl. 1982, 21, 925; Angew. Chem. Suppl. 1982, 1967;
45. d) P. S. Hallman, D. Evans, J. A. Osborn, G. Wilkinson, J. Chem. Soc. Chem. Commun. 1967, 305;
46. e) G. C. Bond, R. A. Hillyard, Discuss. Faraday Soc. 1968, 46, 20.
47. a) L. Kollar, E. Farkas, J. Batiu, J. Mol. Catal. A 1997, 115, 283;
48. b) A. Stefani, G. Consiglio, C. Botteghi, P. Pino, J. Am. Chem. Soc. 1977, 99, 1058;
49. C. P. Casey, C. R. Cyr, J. Am. Chem. Soc. 1973, 95, 2240 and 2248;
50. P. Pino, S. Pucci, F. Piacenti, G. Dell'Amico, J. Chem. Soc. C 1971, 1640;
51. e) M. Orchin, W. Rupilius, Catal. Rev. 1972, 6, 85;
52. f) M. Orchin, Adv. Catal. 1966, 16, 1.
53. H. Bahrmann, C. D. Frohning, P. Heymanns, H. Kalbfell, P. Lappe, D. Peters, E. Wiebus, J. Mol. Catal. 1997, 116, 35.
54. a) F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 2485;
55. b) K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413.
56. N. Sakai, K. Nozaki, H. Takaya, J. Chem. Soc. Chem. Commun. 1994, 395.
57. 4; it gave less than 5% conversion (within 2 h) and a n:i selectivity of 1:99.
58. 3 system generated aldehydes with an n/i ratio of 62:58. However, these results could not be reproduced.
59. 3 system generated aldehydes with an n/i ratio of 62:58. However, these results could not be reproduced.
60. P. Kalck, Y. Peres, J. Jenck, Adv. Organomet. Chem. 1991, 32, 121.
61. G. J. H. Buisman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron Asymmetry, 1993, 4, 1625.
62. Prepared according to literature procedures: a) L. Kurz, G. Lee, D. Morgans, M. J. Waldyke, T. Ward, Tetrahedron Lett. 1990, 44, 6321;
63. b) H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629.