Kinetics of the homogeneous catalytic hydroformylation of 1-octene in supercritical carbon dioxide with HRh(CO)[P(p-CF3C6H4)3]3

Industrial and Engineering Chemistry Research

Volumn 38, Issue 10, 1999, Pages 3786-3792

  Palo, Daniel R ^a   Erkey, Can ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSIS; CATALYSTS; HYDROGEN; ORGANIC SOLVENTS; ORGANOMETALLICS; REACTION KINETICS; RHODIUM COMPOUNDS; SUPERCRITICAL FLUIDS;

HYDROFORMYLATION; OCTENE;

OLEFINS;

ALKENE; CARBON DIOXIDE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; LIGAND BINDING; REACTION ANALYSIS; SPECTROSCOPY; SUPERCRITICAL FLUID EXTRACTION; THERMODYNAMICS;

EID: 0033494687     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie990336l     Document Type: Article

References (48)

1. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; 2nd ed.; Wiley: New York, 1992.
2. Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, Germany, 1996; Vol. 1.
3. Kuntz, E. G. Homogeneous Catalysis in Water. CHEMTECH 1987, 17, 570.
4. Cornils, B.; Kuntz, E. Introducing TPPTS and Related Ligands for Industrial Biphasic Processes. J. Organomet. Chem. 1995, 502, 177.
5. McHugh, M. A.; Krukonis, V. J. Supercritical Fluid Extraction: Principles and Practice, 2nd ed.; Butterworth: Boston, 1994.
6. Jessop, P. G.; Ikariya, T.; Noyori, R. Homogeneous Catalysis in Supercritical Fluids. Chem. Rev. 1999, 99, 475.
7. Morgenstern, D. A.; LeLacheur, R. M.; Morita, D. K.; Borkowsky, S. L.; Feng, S.; Brown, G. H.; Luan, L.; Gross, M. F.; Burk, M. J.; Tumas, W. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T. C., Eds.; American Chemical Society: Washington, D.C., 1996.
8. Savage, P. E.; Gopalan, S.; Mizan, T. I.; Martino, C. J.; Brock, E. E. Reactions at Supercritical Conditions: Applications and Fundamentals. AIChE J. 1995, 41, 1723.
9. Kaupp, G. Reactions in Supercritical Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452; Angew. Chem. 1994, 106, 1519.
10. Kaupp, G. Reactions in Supercritical Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452; Angew. Chem. 1994, 106, 1519.
11. Subramaniam, B.; McHugh, M. A. Reactions in Supercritical Fluids - A Review. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 1.
12. Jessop, G. P.; Hsiao, Y.; Ikariya, T.; Noyori, R. Homogeneous Catalysis in Supercritical Fluids: Hydrogenation of Supercritical Carbon Dioxide to Formic Acid, Alkyl Formates, and Formamides. J. Am. Chem. Soc. 1996, 118, 344.
13. Jessop, P. G.; Ikariya, T.; Noyori, R. Selectivity for Hydrogenation or Hydroformylation of Olefins by Hydridopentacarbonylmanganese(I) in Supercritical Carbon Dioxide. Organometallics 1995, 14, 1510.
14. Jessop, G. P.; Ikariya, T.; Noyori, R. Homogeneous Catalysis in Supercritical Fluids. Science 1995, 269, 1065.
15. Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. Asymmetric Catalytic Hydrogenation Reactions in Supercritical Carbon Dioxide. J. Am. Chem. Soc. 1995, 117, 8278.
16. Jessop, G. P.; Ikariya, T.; Noyori, R. Homogeneous Catalytic Hydrogenation of Supercritical Carbon Dioxide. Nature 1994, 368, 231.
17. Morita, D. K.; Pesiri, D. R.; David, S. A.; Glaze, W. H.; Tumas, W. Palladium-Catalyzed Cross-Coupling Reactions in Supercritical Carbon Dioxide. Chem. Commun. 1998, 1397.
18. Carroll, M. A.; Holmes, A. B. Palladium-Catalyzed Carbon -Carbon Bond Formation in Supercritical Carbon Dioxide. Chem. Commun. 1998, 1395.
19. Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Olefin Metathesis in Compressed Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1997, 36, 2466; Angew. Chem. 1997, 109, 2562.
20. Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Olefin Metathesis in Compressed Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1997, 36, 2466; Angew. Chem. 1997, 109, 2562.
21. Rathke, J. W.; Klinger, R. J. United States Patent 5,198,589, 1993.
22. Rathke, J. W.; Klinger, R. J.; Krause, T. R. Thermodynamics for the Hydrogenation of Dicobalt Octacarbonyl in Supercritical Carbon Dioxide. Organometallics 1992, 11, 585.
23. Rathke, J. W.; Klingler, R. J.; Krause, T. R. Propylene Hydroformylation in Supercritical Carbon Dioxide. Organometallics 1991, 10, 1350.
24. Guo, Y.; Akgerman, A. Hydroformylation of Propylene in Supercritical Carbon Dioxide. Ind. Eng. Chem. Res. 1997, 36, 4581.
25. Guo, Y.; Akgerman, A. Determination of Selectivity for Parallel Reactions in Supercritical Fluids. J. Supercrit. Fluids 1999, 15, 63.
26. Bach, I.; Cole-Hamilton, D. J. Hydroformylation of Hex-1-ene in Supercritical Carbon Dioxide Catalyzed by Rhodium Trialklyphosphine Complexes. Chem. Commun. 1998, 1463.
27. Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Perfluoroalkyl-Substituted Arylphosphanes as Ligands for Homogeneous Catalysis in Supercritical Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699.
28. Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Perfluoroalkyl-Substituted Arylphosphanes as Ligands for Homogeneous Catalysis in Supercritical Carbon Dioxide. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699.
29. Koch, D.; Leitner, W. Rhodium-Catalyzed Hydroformylation in Supercritical Carbon Dioxide. J. Am. Chem. Soc. 1998, 120, 13398.
30. Palo, D. R.; Erkey, C. Homogeneous Catalytic Hydroformylation of 1-Octene in Supercritical Carbon Dioxide Using a Novel Rhodium Catalyst with Fluorinated Arylphosphine Ligands. Ind. Eng. Chem. Res. 1998, 37, 4203.
31. 3]. Ind. Eng. Chem. Res. 1999, 38, 2163.
32. Palo, D. R.; Erkey, C. In Reaction Engineering for Pollution Prevention; Hesketh, R., Abraham, M., Eds.; Elsevier Science: New York (accepted for publication).
33. Evans, D.; Yagupsky, G.; Wilkinson, G. The Reaction of Hydridocarbonyltris(triphenylphosphine)rhodium with Carbon Monoxide, and of the Reaction Products, Hydridodicarbonylbis(triphenylphosphine)rhodium and Dimeric Species, with Hydrogen. J. Chem. Soc. A 1968, 2660.
34. Evans, D.; Osborn, J. A.; Wilkinson, G. Hydroformylation of Alkenes by Use of Rhodium Complex Catalysts. J. Chem. Soc. A 1968, 3133.
35. Brown, C. K.; Wilkinson, G. Catalytic Hydroformylation of Unsaturated Compounds using Hydridocarbonyltris(triphenylphosphine)rhodium(I). Tetrahedron Lett. 1969, 22, 1725.
36. Yagupsky, M.; Brown, C. K.; Yagupsky, G.; Wilkinson, G. Further Studies on Hydridocarbonyltris(triphenylphosphine)rhodium(I). Part I. Nature of Inactivation of Catalytic Species. J. Chem. Soc. A 1970, 937.
37. Yagupsky, M.; Wilkinson, G. Further Studies on Hydridocarbonyltris(triphenylphosphine)rhodium(I). Part II. Isomerization of n-Pentenes and Hex-1-ene. J. Chem. Soc. A 1970, 941.
38. Brown, C. K.; Wilkinson, G. Homogeneous Hydroformylation of Alkenes with Hydridocarbonyltris(triphenylphosphine)rhodium(I) as Catalyst. J. Chem. Soc. A 1970, 2753.
39. Deshpande, R. M.; Bhanage, B. M.; Divekar, S. S.; Kanagasabapathy, S.; Chaudhari, R. V. Kinetics of Hydroformylation of Ethylene in a Homogeneous Medium: Comparison in Organic and Aqueous Systems. Ind. Eng. Chem. Res. 1998, 37, 2391.
40. 3 Catalyst. J. Mol. Catal. A: Chem. 1997, 115, 247.
41. Divekar, S. S.; Bhanage, B. M.; Deshpande, R. M.; Gholap, R. V.; Chaudhari, R. V. Selectivity in Hydroformylation of 1-Decene by Homogeneous Catalysis. J. Mol. Catal. 1994, 91, L1.
42. 3: Effect of PPh3 Addition on the Rate of Reaction. J. Mol. Catal. 1993, 78, L37.
43. 3 Catalyst in Hydroformylation of Allyl Alcohol: Effect of Second Immiscible Phase. J. Mol. Catal. 1992, 75, L19.
44. 3 Catalyst in Hydroformylation of 1-Hexene. J. Mol. Catal. 1991, 67, 333.
45. 3 Catalyst: A Kinetic Study. J. Catal. 1989, 115, 326.
46. 3 Catalyst: A Kinetic Study. J. Mol. Catal. 1989, 57, 177.
47. 3 Complex Catalyst. Ind. Eng. Chem. Res. 1988, 27, 1996.
48. Jardine, F. H. Carbonylhydridotris(triphenylphosphine)rhodium(I). Polyhedron 1982, 1, 569.