Analysis of the hydroformylation reaction over an immobilized catalyst in supercritical carbon dioxide

Industrial and Engineering Chemistry Research

Volumn 44, Issue 14, 2005, Pages 4973-4981

  Bektesevic, Selma ^a   Tack, Timothy ^a   Mason, Mark R ^b   Abraham, Martin A ^a  

^a The University of Toledo   (United States)

^b UNIVERSITY OF TOLEDO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST IMMOBILIZATION; CATALYST RECOVERY; HYDROFORMYLATION; PHASE-TRANSFER EFFECT;

CARBON DIOXIDE; CATALYSTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; REACTION KINETICS; RECOVERY; SUPERCRITICAL FLUIDS;

CATALYSIS;

SUPERCRITICAL CARBON DIOXIDE;

EID: 22944455210     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie049125t     Document Type: Article

References (35)

1. Applied Homogeneous Catalysis with Organometallic Compounds; Cornus, B., Herrnann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol.1, p 49.
2. Reinius, H. K.; Suomalainen, P.; Riihimaki, H.; Karvinen, E.; Pursiainen, J. Hydroformylation of 1-hexene and propene with in situ formed rhodium phosphine catalysts. J. Catal. 2001, 199 (2), 302-308.
3. Karlsson, M.; Andersson, C.; Hjortkjaer, J. Hydroformylation of propene and 1-hexene catalysed by a a-zirconium phosphate supported rhodium-phosphine complex. J. Mol. Catal. A: Chem. 2001, 166 (2), 337-343.
4. Shibahara, P.; Nozaki, K.; Matsuo, T.; Hiyama, T. Asymmetric hydroformylation with highly cross-linked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complexes: The effect of immobilization position. Biol. Inorg. Chem. Lett. 2002, 12 (14), 1825-1827.
5. Nozaki, K.; Shibahara, F.; Hiyama, T. Vapor-phase asymmetric hydroformylation. Chem. Lett. 2000, (6), 694-695.
6. 3RhH-(CO). J. Am. Chem. Soc. 1976, 5402-5405.
7. 2-EDAX, FTIR AND Kinetic Study. J. Mol. Catal. 1990, 61, 27-39.
8. Allum, K. G.; Hancock, R. D.; Howell, I. V.; Pitkethly, R. C.; Robinson, P. J. Supported Transition Metal Complexes IV. Rhodium Catalysts for the Liquid-Phase Hydroformylation of Hexene-1. J. Catal. 1976, 43, 322-330.
9. Sandee, A. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. A silica-supported, switchable, and recyclable hydroformylation-hydrogenation catalyst. J. Am. Chem. Soc. 2001, 123, 8468-8476.
10. Rathke, J. W.; Klinger, R. J.; Krause, T. R. Propylene Hydroformylation in Supercritical Carbon Dioxide. Organometallics 1991, 10, 1350-1355.
11. Palo, D. R.; Erkey, C. Effect of ligand modification on rhodium-catalyzed homogeneous hydroformylation in supercritical carbon dioxide. Organometallics 2000, 19, 81-86.
12. Sellin, M. F.; Cole-Hamilton, D. J. Hydroformylation reactions in supercritical carbon dioxide using insoluble metal complexes. J. Chem. Soc., Dalton Trans. 2000, 1681-1683.
13. Sellin, M. F.; Bach, I.; Webster, J. M.; Montilla, F.; Rosa, V.; Aviles, T.; Poliakoff, M.; Cole-Hamilton, D. J. Hydroformylation of alkenes in supercritical carbon dioxide catalysed by rhodium trialkylphosphine complexes" J. Chem. Soc., Dalton Trans. 2002, 4569-4576.
14. Koch, D.; Leitner, W. Rhodium-catalyzed hydroformylation in supercritical carbon dioxide" J. Am. Chem. Soc. 1998, 720, 13398-13404.
15. Hemminger, O.; Marteel, A.; Mason, M. R.; Davies, J. A.; Tadd, A. R.; Abraham, M. A. Hydroformylation of 1-hexene in supercritical carbon dioxide using a heterogeneous rhodium catalyst. 3. Evaluation of solvent effects. Green Chem. 2002, 4, 507-512.
16. Tadd, A. R.; Marteel, A.; Mason, M. R.; Davies, J. A.; Abraham, M. A. Hydroformylation of 1-hexene in supercritical carbon dioxide using a heterogeneous rhodium catalyst. 1. Effect of process parameters. J. Supercrit. Fluids 2003, 25 (2), 183-196.
17. 2. Ind. Eng. Chem. Res. 2001, 40 (23), 5317-5325.
18. Tadd, A. R.; Marteel, A.; Mason, M. R.; Davies, J. A.; Abraham, M. A. Hydroformylation of 1-hexene in supercritical carbon dioxide using a heterogeneous rhodium catalyst. 2. Evaluation of reaction kinetics. Ind. Eng. Chem. Res. 2002, 41, 4514-4522.
19. Beck, J. S.; Vartuli, J. C.; Roth, W. J.; Leonowicz, M. E.; Kresge, C. T.; Schmitt, K. D.; Chu, C. T. W.; Olson, D. H.; Sheppard, E. W.; McCullen, S. B.; Higgins, J. B.; Schlenker, J. L. A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates. J. Am. Chem. Soc. 1992, 114, 10834-10843.
20. Marteel, A.; Davies, J. A.; Mason, M. R.; Abraham, M. A.; Tack, T.; Bektesevic, S. Supported platinum/tin complexes as catalysts for hydroformylation of 1-hexene in supercritical carbon dioxide. Catal. Commun. 2003, 4 (7), 309-314.
21. Tack, T. T. Performance of Rhodium and Platinum Supported Catalysts for Hydroformylation in Supercritical Carbon Dioxide. M.S. Thesis, The University of Toledo, Toledo, OH, 2003.
22. Sanger, A. R.; Schallig, L. R. The Structures and Hydroformylation Catalytic Activities of Polyphosphine Complexes of Rhodium(I), and Related Complexes Immobilised on Polymer Supports. J. Mol. Catal. 1977/1978, 3, 101-109.
23. Evans, D.; Yagupski, G.; Wilkinson, G. The Reaction of Hydridocarbonyltris(triphenylphosphine)rhodiuin with Carbon Monoxide, and of the Reaction Products, Hydridodicarbonylbis(triphenylphosphine)rhodium and Dimeric Species, with Hydrogen J. Chem. Soc. A 1968, 2660-2664.
24. Luchetti, A.; Wieserman, L. F.; Hercules, D. M. A Study of Supported Chlorocarbonylbis(triphenylphosphine)rhodiumd(I) and Its Reactions with CO. J. Phys. Chem. 1981, 85, 549-556.
25. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals; John Wiley & Sons: New York, 2001; p 282.
26. Yang, A. C.; Garland, C. W. Infrared Studies of Carbon Monoxide Chemisorbed on Rhodium. J. Phys. Chem. 1957, 61, 1504-1512.
27. Allum, K. G.; Hancock, R. D.; Howell, I. V.; McKenzie, S.; Pitkethly, R. C.; Robinson, P. J. Supported Transition Metal Complexes II. Silica as the Support. J. Organomet. Chem. 1975, 87, 203-216.
28. Yagupski, G.; Brown, C. K.; Wilkinson, G. Further Studies on Hydridocarbonyltris(triphenylphosphine)rhodium(I); Intermediate Species in Hydroformylation; Rhodium and Iridium Analogues. J. Chem. Soc. A 1970, 1392-1401.
29. Evans, D.; Osborn, J. A.; Wilkinson, G. Hydroformylation of Alkenes by Use of Rhodium Complex Catalysts. J. Chem. Soc. A 1968, 3133-3142.
30. Moser, W. R.; Papile, C. J.; Brannon, D. A.; Duwell, R. A.; Weininger, S. J. The Mechanism of Phosphine-modified Rhodium catalyzed Hydroformylation Stuided by CIR FTIR. J. Mol. Catal. 1087, 41, 271-292.
31. Liu, G. W.; Garland, M. The homogeneous rhodium catalyzed hydroformylation of ethylene starting with tetrarhodium dodecacarbonyl - the observation of a new type of rhodium carbonyl spectrum. J. Organomet. Chem. 2000, 613, 124-127.
32. Morris, D. E.; Tinker, H. B. Infrared Examination of a Catalyst in Action. CHEMTECH 1972, 554-559.
33. Haji, S.; Erkey, C. Investigation of rhodium catalyzed hydroformylation of ethylene in supercritical carbon dioxide by in situ FTIR spectroscopy. Tetrahedron 2002, 3929-3941.
34. Marteel, A. E. Development of Heterogeneous Catalyst for Hydroformylation of 1-Hexene in Supercritical Carbon Dioxide. PhD. Dissertation, The University of Toledo, Toledo, OH, 2003.
35. van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. Electronic effect on rhodium diphosphine catalyzed hydroformylation: The bite angle effect reconsidered. J. Am. Chem. Soc. 1998, 120, 11616-11626.