Cobalt-catalyzed hydroformylation of olefins in the presence of additional "inert" gases

Organometallics

Volumn 16, Issue 20, 1997, Pages 4235-4236

  Piacenti, Franco ^a   Calderazzo, Fausto ^b   Blanchi, Mario ^a   Rosi, Luca ^a   Fredian, Piero ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000422419     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9704713     Document Type: Article

References (62)

1. (a) Sacco, A.; Rossi, M. J. Chem. Soc., Chem. Commun. 1967, 316.
2. (b) Jolly, P. W.; Jonas, K. Angew. Chem., Int. Ed. Engl. 1968, 80, 705.
3. (c) Aresta, M.; Giannoccaro, P.; Rossi, M.; Sacco, A. Inorg. Chim. Acta 1971, 5, 203.
4. (d) Banister, J. A.; George, M. W.; Grubert, S.; Howdle, S. M.; Jobling, M.; Johnson, F. P. A.; Morrison, S. L.; Poliakoff, M.; Schubert, U.; Westwell, J. R. J. Organomet. Chem. 1994, 484, 129.
5. (e) Gambarotta, S. J. Organomet. Chem. 1995, 500, 117.
6. (f) Hidai, M.; Mizobe, Y. Chem. Rev. 1995, 95, 1115.
7. (g) Bazhenova, T. A.; Kulikov, A. V.; Shestakov, A. F.; Shilov, A. E.; Antipin, M. Yu.; Lyssenko, K. A.; Struchkov, Yu. T.; Makhaev, V. D. J. Am. Chem. Soc. 1995, 117, 12176.
8. (a) Kubas, G. J. Acc. Chem. Res. 1988, 21, 120.
9. (b) Gonzales, A. A.; Zhang, K.; Nolan, S. P.; Lopez de la Vega, R.; Mukerjee, S. L.; Hoff, C. D.; Kubas, G. J. Organometallics 1988, 7, 2429.
10. (c) Haward, M. T.; George, M. W.; Howdle, S. M.; Poliakoff, M. J. Chem. Soc., Chem. Commun. 1990, 913.
11. (d) Heinekey, D. M.; Oldham, W. J. Chem. Rev. 1993, 93, 913.
12. (e) Sabo-Etienne, S.; Chaudret, B.; el Makarim, H. A.; Barthelat, J.-C.; Daudey, J.-P.; Moïse, C.; Leblanc, G. J. J. Am. Chem. Soc. 1994, 116, 9335.
13. (f) Kubas, G. J.; Nelson, J. E.; Bryan, J. C.; Eckert, J.; Wisniewski, L.; Zilm, K. Inorg. Chem. 1994, 33, 2954.
14. (g) Li, Z.-W.; Taube, H. J. Am. Chem. Soc. 1994, 116, 11584.
15. (h) Li, J.; Dickson, R. M.; Ziegler, T. J. Am. Chem. Soc. 1995, 117, 11482.
16. (i) Ma, B.; Collins, C. L.; Schaefer H. F., III. J. Am. Chem. Soc. 1996, 118, 870.
17. (j) Bianchini, C.; Mealli, C.; Peruzzini, M.; Zanobini, F. J. Am. Chem. Soc. 1992, 114, 5905.
18. (k) Bianchini, C.; Mealli, C.; Peruzzini, M.; Zanobini, F. J. Am. Chem. Soc. 1987, 109, 5548.
19. (l) Bianchini, C.; Farnetti, E.; Graziani, M.; Kaspar, J.; Vizza, F. J. Am. Chem. Soc. 1993, 115, 1753.
20. (m) Heinekey, D. M.; Liegeois, A.; van Roon, M. J. Am. Chem. Soc. 1994, 116, 8388.
21. (n) Gusev, D. G.; Notheis, J. U.; Rambo, J. R.; Hauger, B. E.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1994, 116, 7409.
22. (a) Billups, W. E.; Chang, S.-C.; Hauge, R. H.; Margrave, J. L. J. Am. Chem. Soc. 1993, 115, 2039.
23. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987.
24. (c) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7332.
25. (d) Graham, M. A.; Perutz, R. N.; Poliakoff, M.; Turner, J. J. J. Organomet. Chem. 1972, 34, C34.
26. (e) Welch, J. A.; Peters, K. S.; Vaida, V. J. Phys. Chem. 1982, 86, 1941.
27. (a) Cotton, F. A.; LaCour, T.; Stanislowski, A. G. J. Am. Chem. Soc. 1974, 96, 754.
28. (b) Cotton, F. A.; Stanislowski, A. G. J. Am. Chem. Soc. 1974, 96, 5074.
29. (c) Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
30. (d) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1.
31. (a) Laverty, D. T.; Rooney, J. J. J. Chem. Soc., Faraday Trans, 1 1983, 79, 869.
32. (b) Krauledat, H.; Brintzinger, H. H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1412.
33. (c) Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377.
34. (d) Brookhardt, M.; Volpe, A. F. Jr.; Lincoln, D. M.; Horvàth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634.
35. (e) Janiak, C. J. Organomet. Chem. 1993, 452, 63.
36. (f) Pellecchia, C.; Grassi, A.; Zambelli, A. Organometallics 1994, 13, 298.
37. (g) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
38. (h) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
39. (i) Støvneng, J. A.; Rytter, E. J. Organomet. Chem. 1996, 519, 277.
40. (j) Fan, L.; Krzywicki, A.; Somogyvari, A.; Ziegler, T. Inorg. Chem. 1996, 35, 4003.
41. (a) Simpson, M. B.; Poliakoff, M.; Turner, J. J.; Maier, W. B.; McLuaghlin, I. G. J. Chem. Soc., Chem. Commun. 1983, 1355.
42. (b) Wells, J. R.; Weitz, E. J. Am. Chem. Soc. 1992, 114, 2783.
43. (c) Weiller, B. H. J. Am. Chem. Soc. 1992, 114, 10910.
44. (d) Bengali, A. A.; Bergman, R. G.; Moore, C. B. J. Am. Chem. Soc. 1995, 117, 3879.
45. (a) Calderazzo, F.; Ercoli, R.; Natta, G. Metal Carbonyls: Preparation, Structure and Properties. In Organic Syntheses via Metal Carbonyls; Wender, I., Pino, P., Eds.; Interscience Publishers: New York, London, and Sidney, 1967; Vol. 1.
46. (b) Natta, G.; Ercoli, R. Chim. Ind. (Milan) 1952, 34, 503.
47. (c) Natta, G.; Ercoli, R.; Castellano, S.; Barbieri, F. H. J. Am. Chem. Soc. 1954, 76, 4049.
48. (d) Natta, G.; Ercoli, R.; Castellano, S. Chim. Ind. (Milan) 1955, 37, 6.
49. (e) Pino, P.; Piacenti, F.; Bianchi, M. Reactions of Carbon Monoxide and Hydrogen with Olefinic Substrates: The Hydroformylation (OXO) Reactions. In Organic Syntheses via Metal Carbonyls; Wender, I., Pino, P., Eds.; Interscience Publishers: New York, London, and Sidney, 1977; Vol. 2, pp 43-231.
50. (f) Piacenti, F.; Bianchi, M. Carbonylation of Saturated Oxygenated Compounds. In Organic Syntheses via Metal Carbonyls; Wender, I., Pino, P., Eds.; Interscience Publishers: New York, London, and Sydney, 1977; Vol. 2, pp 1-42.
51. (g) Martin, A. R. Chem Ind. (London) 1954, 1536.
52. (h) Greenfield, H.; Metlin, S.; Wender, I. Abstracts of Papers, 126th Meeting of the American Chemical Society, New York, September 12-17, 1954; American Chemical Society: Washington, DC, 1954.
53. (a) Pino, P.; Ercoli, R.; Calderazzo, F. Chim. Ind. (Milan) 1955, 37, 782.
54. (b) Ungvàry, F. J. Organomet. Chem. 1972, 36, 363.
55. (c) Alemdaroglu, N. H.; Penninger, J. M.; Oltay, E. Monatsh. Chem. 1976, 107, 1043.
56. 4
57. Sweany, R. L. J. Am. Chem. Soc. 1982, 104, 3739. Sweany, R. L.; Russel, F. N. Organometallics 1988, 7, 719.
58. Sweany, R. L. J. Am. Chem. Soc. 1982, 104, 3739. Sweany, R. L.; Russel, F. N. Organometallics 1988, 7, 719.
59. 3 and distilled under dinitrogen before use, bp 356 K. C. Erba reagent grade toluene was refluxed over sodium and distilled under dinitrogen before use.
60. The hydroformylation experiments were performed in a stainless steel rocking autoclave, 25 mL capacity, capable of withstanding a pressure of several thousand bar, electrically heated with a temperature control (±1 K). Pressures were measured with a transducer with an accuracy of ±1 bar (transducer model Z Absolute, Sensotec). Molar ratios of liquid and gaseous reagents were chosen in such a way as to avoid a relevant pressure decrease. Solid catalyst was introduced under dinitrogen into the autoclave, which was then evacuated; solvent and olefin were introduced by suction, and then carbon monoxide was pressurized up to 5 bar. Rocking and heating were then started, and at 373 K the carbon monoxide pressure was increased to 70 atm. Within 1 min, dihydrogen up to a total pressure of 160 bar (85 ± 2 bar of dihydrogen from control experiments) and the additional gas up to the required pressure (see Table 1) were introduced into the still autoclave, which was rocked again immediately after. After 3 h, the autoclave was rapidly cooled by immersion into water. Gases were vented through a condenser, and the clear yellow solution was subjected to GLC chromatography to determine the conversion to cyclohexanecarboxaldehyde based on both residual cyclohexene and formed aldehyde. Olefin hydrogenation was always low, below 1%. Compressibilities of both dinitrogen and argon were estimated, with an accuracy sufficient for our purpose, by volumetric measurements, as a function of pressure, of the gas released at atmospheric pressure from an empty autoclave maintained at 373 K. Similar experiments performed in the presence of a known volume of solvent provided sufficient data for an evaluation of the amount of dissolved gas.
61. Dinitrogen (99.996% pure), argon, (99.998% pure), CO (99.3% pure), and hydrogen (99.85% pure) were supplied by SOL. Octacarbonyldicobalt, supplied by Strem Chemicals, was recrystallized before use.
62. Wilhelm, E.; Battino, R. Chem. Rev. 1973, 73, 1.