Asymmetric hydroformylation of styrene in supercritical carbon dioxide

Industrial and Engineering Chemistry Research

Volumn 45, Issue 4, 2006, Pages 1324-1330

  Kleman, Angela M ^a   Abraham, Martin A ^a  

^a Toledo   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PHENYLPROPIONALDEHYDE; ASYMMETRIC HYDROFORMYLATION; FINE CHEMICALS; SUPERCRITICAL CARBON DIOXIDE;

ALDEHYDES; CARBON DIOXIDE; CATALYSTS; DRUG PRODUCTS; IN SITU PROCESSING; ORGANIC SOLVENTS; RECYCLING; RHODIUM; SUPERCRITICAL FLUIDS;

STYRENE;

ALDEHYDES; CARBON DIOXIDE; CATALYSTS; DRUG PRODUCTS; IN SITU PROCESSING; ORGANIC SOLVENTS; RECYCLING; RHODIUM; STYRENE; SUPERCRITICAL FLUIDS;

EID: 33644748238     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie0509701     Document Type: Article

References (24)

1. van Leeuwen, P. W. N. M.; Claver, C. Rhodium Catalyzed Hydroformylation; Kluwer Academic Publishers: Boston, 2000.
2. Reinius. H. K.; Krause, A. O. I. Hydroformylation of Functional Alkenes with Heterodonor Phosphine Rhodium Catalysts: Substrate or Ligand Directed Regioselectivity? Catal. Lett. 2000, 70, 149-154.
3. Abatjoglou, A. G.; Bryant. D. R. Ionic phosphites and their use in homogeneous transition metal catalyzed processes. U.S. Patent 5,059.710, 1991.
4. Buhling, A.; Elgersma, J. W.; Nkrumah. S.; Kamer, P. C. J.; van Leeuwen. P. W. N. M. Novel amphiphilic diphosphines: Synthesis, rhodium complexes, use in hydroformylation and rhodium recycling. J. Chem Soc., Dalton Trans. 1996, 10, 2143-2154.
5. van der Slot, S. C.; Duran, J.; Luten, L.; Kamer. P. C. J.; van Leeuwen, P. W. N. M. Rhodium-Catalyzed Hydroformylation and Deuterioformylation with Pyrrolyl-Based Phosphorus Amidite Ligands: Influence of Electronic Ligand Properties. Organometatlics 2002, 21, 3873-3883.
6. Bunten, K. A.; Farrar, D. H.; Poe, A. J.; Lough. A. Stoichiometric and Catalytic Oxidation of BINAP by Dioxygen in Rhodium(I) Complex. Organometallics 2002, 21, 3344-3350.
7. Shibahara, F.; Nozaki, K.; Hiyama, T. Solvent-free asymmetric olefin hydroformylation catalyzed by highly cross-linked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complex. J. Am. Chem. Soc. 2003, 125 (28), 8555-8560.
8. Dieguez, M.; Pamies. O.; Claver. C. Recent advances in Rh-catalyzed asymmetric hydroformylation using phosphite ligands. Tetrahedron: Asvmmelry 2004, 15 (14). 2113-2122.
9. 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.
10. Koch, D.; Leitner, W. Rhodium-Catalyzed Hydroformylation in Supercritical Carbon Dioxide. J. Am. Chem. Soc. 1998, 120, 13398-13404.
11. Kani, I.; Flores, R.; Fackler. J. P.; Akgerman, A. Hydroformylation of styrene in supercritical carbon dioxide with fluoroacrylate polymer supported rhodium catalysts. J. Supercrit. Fluids 2004, 31 (3), 287-294.
12. Lin, B.; Akgerman, A. Styrene hydroformylation in supercritical carbon dioxide: Rate and selectivity control. Ind. Eng. Chem. Res. 2001, 40 (4), 1113-1118.
13. Kainz, S.; Leitner, W. Catalytic asymmetric hydroformylation in the presence of compressed carbon dioxide. Catal. Lett. 1998, 55 (3-4). 223-225.
14. Matsuda, T.; Kanamaru, R.; Watanabe, K.; Harada, T.; Nakamura. K. Control on Enantioselectivity with Pressure for Lipase-Catalyzed Esterification in Supercritical Carbon Dioxide. Tetrahedron Lett. 2001, 42, 8319-8321.
15. Jessop, P. G.; Ikariya, T.; Noyori. R. Homogeneous Catalysis in Supercritical Fluids. Chem. Rev. 1999, 99, 475.
16. Simmons, M. S. The Role of Catalysts in Environmentally Benign Synthesis of Chemicals. In Green Chemistry: Designing Chemistry for the Environment', Anastas, P. T., Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC. 1996: Chapter 10.
17. Ojima, I. Catalytic Asvmmetric Synthesis; Wiley-VCH: New York, 2000.
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. 1. Effect of process parameters. J. Supercrit. Fluids 2003, 25 (2), 183-196.
19. Giordano, G.; Crabtree, R. H. Di-μ-chloro-bis(η-4-1.5-cyclooctadiene) dirhodium(I). Inorg. Synth. 1990, 28, 88-90.
20. Gassman, P. G.; Macomber, D. W.; Willging, S. M. Isolation and Characterization of Reactive Intermediates and Active Catalysts in Homogeneous Catalysis. J. Am. Chem. Soc. 1985, 107, 2380-2388.
21. Marteel, A. E. Development of Heterogeneous Catalysts for Hydroformylation of 1-Hexene in Supercritical Carbon Dioxide. Ph.D. Dissertation, The University of Toledo, Toledo, OH, 2003.
22. Bunten, K. A.; Farrar, D. H.; Poe, A. J.; Lough, A. Stoichiometric and Catalytic Oxidation of BINAP by Dioxygen in Rhodium(I) Complex. Organometallics 2002, 21, 3344-3350.
23. Bensaid, L. F. Rhodium-Catalyzed Hydroformylation of 1-Hexene Using Acidic Phosphines and Synthesis of a New Phosphine Ligand for Use in Supercritical Carbon Dioxide. M.S. Thesis, The University of Toledo. Toledo, OH, 2002.
24. Hegedus, C.; Madarasz, J.; Gergely, I.; Szollosy, A.; Monsees, A.; Riermeier, T. Bakos, J. Electronic and Steric Effects of Ligands as Control Elements for Rhodium-Catalyzed Asymmetric Hydroformylation. Part 3: Highly Active Hydroformylation of Styrene. Tetrahedron: Asymmetry-2004, 75, 2507-2513.