Evaluation of pressure and correlation to reaction rates during homogeneously catalyzed hydroformylation in supercritical carbon dioxide

Journal of Supercritical Fluids

Volumn 46, Issue 1, 2008, Pages 47-56

  Koeken, Ard C J ^a   de Bakker, Stefan J M ^a   Costerus, Hester M ^a   van den Broeke, Leo J P ^a   Deelman, Berth Jan ^b   Keurentjes, Jos T F ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b ARKEMA   (France)

Author keywords

1 Octene; Homogeneous catalysis; Hydroformylation; Phosphine ligand; Rhodium catalyst; Supercritical carbon dioxide

Indexed keywords

CATALYSIS; ESTERS; HYDROFORMYLATION; PRESSURE EFFECTS;

HOMOGENEOUS CATALYSIS; PHOSPHINE LIGAND; RHODIUM CATALYST; SUPERCRITICAL CARBON DIOXIDE;

CORRELATION METHODS;

EID: 44249127447     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2008.02.012     Document Type: Article

References (59)

1. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook. second ed. vol. 1 (2002), Wiley-VCH, Weinheim
2. In: Jessop P.G., and Leitner W. (Eds). Chemical Synthesis Using Supercritical Fluids (1999), Wiley-VCH, Weinheim
3. Jessop P.G., Ikariya T., and Noyori R. Homogeneous catalysis in supercritical fluids. Chem. Rev. 99 (1999) 475-493
4. 2 in green chemical synthesis and processing. J. Supercrit. Fluids 28 (2004) 121-191
5. Bektesevic S., Kleman A.M., Marteel-Parrish A.E., and Abraham M.A. Hydroformylation in supercritical carbon dioxide: catalysis and benign solvents. J. Supercrit. Fluids 38 (2006) 232-241
6. Jessop P.G. Homogeneous catalysis using supercritical fluids: recent trends and systems studied. J. Supercrit. Fluids 38 (2006) 211-231
7. Oakes R.S., Clifford A.A., and Rayner C.M. The use of supercritical fluids in synthetic organic chemistry. J. Chem. Soc., Perkin Trans. 1 (2001) 917-941
8. Tzschucke C.C., Markert C., Bannwarth W., Roller S., Hebel A., and Haag R. Modern separation techniques for the efficient workup in organic synthesis. Angew. Chem. Int. Ed. 41 (2002) 3964-4000
9. Prajapati D., and Gohain M. Recent advances in the application of supercritical fluids for carbon-carbon bond formation in organic synthesis. Tetrahedron 60 (2004) 815-833
10. Liu S., and Xiao J. Toward green catalytic synthesis-transition metal-catalyzed reactions in non-conventional media. J. Mol. Catal. A 270 (2007) 1-43
11. Rayner C.M. The potential of carbon dioxide in synthetic organic chemistry. Org. Proc. Res. Dev. 11 (2007) 121-132
12. Examples of integration of reaction and separation:
13. Sellin M.F., Webb P.B., and Cole-Hamilton D.J. Continuous flow homogeneous catalysis: hydroformylation of alkenes in supercritical fluid-ionic liquid biphasic mixtures. Chem. Commun. (2001) 781-782
14. Cole-Hamilton D.J. Homogeneous catalysis-new approaches to catalyst separation, recovery, and recycling. Science 299 (2003) 1702-1706
15. Webb P.B., Kunene T.E., and Cole-Hamilton D.J. Continuous flow homogeneous hydroformylation of alkenes using supercritical fluids. Green Chem. 7 (2005) 373-379
16. For an example of a pressure profile during hydroformylation:. Patcas F., Maniut C., Ionescu C., Pitter S., and Dinjus E. Supercritical carbon dioxide as an alternative reaction medium for hydroformylation with integrated catalyst recycling. Appl. Catal. B 70 (2007) 630-636
17. Rathke J.W., Klingler R.J., and Krause T.R. Propylene hydroformylation in supercritical carbon dioxide. Organometallics 10 (1991) 1350-1355
18. 2 in supercritical carbon dioxide: ligand substitution, hydrogenation, and hydroformylation reactions. Organometallics 23 (2004) 2701-2707
19. de Vries T.J., Kemmere M.F., and Keurentjes J.T.F. Characterization of polyethylenes produced in supercritical carbon dioxide by a late-transition-metal catalyst. Macromolecules 37 (2004) 4241-4246
20. van Schilt M., Kemmere M., and Keurentjes J. Process development for the catalytic conversion of cyclohexene oxide and carbon dioxide into poly(cyclohexene carbonate). Catal. Today 115 (2006) 162-169
21. Mueller P.A., Storti G., and Morbidelli M. Detailed modeling of MMA dispersion polymerization in supercritical carbon dioxide. Chem. Eng. Sci. 60 (2005) 1911-1925
22. Guo Y., and Akgerman A. Hydroformylation of propylene in supercritical carbon dioxide. Ind. Eng. Chem. Res. 36 (1997) 4581-4585
23. Peng D.-Y., and Robinson D.B. A new two-constant equation of state. Ind. Eng. Chem. Fundam. 15 (1976) 59-64
24. Guo Y., and Akgerman A. Determination of selectivity for parallel reactions in supercritical fluids. J. Supercrit. Fluids 15 (1999) 63-71
25. 2. J. Am. Chem. Soc. 123 (2001) 3661-3670
26. Stradi B.A., Kohn J.P., Stadtherr M.A., and Brennecke J.F. Phase behavior of the reactants, products and catalysts involved in the allylic epoxidation of trans-2-hexen-1-ol to (2R,3R)-(+)-3-propyloxiranemethanol in high pressure carbon dioxide. J. Supercrit. Fluids 12 (1998) 109-122
27. Westerterp K.R., van Swaaij W.P.M., and Beenackers A.A.C.M. Chemical Reactor Design and Operation. second ed. (1984), John Wiley & Sons, Chichester
28. Palo D.R., and 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. 37 (1998) 4203-4206
29. Olivier K.L., and Booth F.B. Make aldehydes by new oxo process. Hydrocarbon Process 49 4 (1970) 112-114
30. 3 addition on the rate of reaction. J. Mol. Catal. 78 (1993) L37-L40
31. Cavalieri d'Oro P., Raimondi L., Pagani G., Montrasi G., Gregorio G., and Andreetta A. Propene hydroformylation with rhodium carbonyls and triphenylphosphine. II. Kinetics of butyraldehydes formation. Chim. Ind. 62 (1980) 572-579
32. 3. Ind. Eng. Chem. Res. 39 (2000) 3671-3678
33. Haji S., and Erkey C. Investigation of rhodium catalyzed hydroformylation of ethylene in supercritical carbon dioxide by in situ FTIR spectroscopy. Tetrahedron 58 (2002) 3929-3941
34. van Leeuwen P.W.N.M. Homogenous Catalysis: Understanding the Art (2004), Kluwer Academic Publishers pp. 139-174
35. Fujita S.-I., Fujisawa S., Bhanage B.M., and Arai M. Rhodium-tris(3,5-bis(trifluoromethyl)phenyl)phosphine catalyzed hydroformylation of dienes to dialdehydes in supercritical carbon dioxide with high activity. Tetrahedron Lett. 45 (2004) 1307-1310
36. Kainz S., Koch D., Baumann W., and Leitner W. Perfluoroalkyl-substituted arylphosphanes as ligands for homogeneous catalysis in supercritical carbon dioxide. Angew. Chem. Int. Ed. Engl. 36 (1997) 1628-1630
37. Koch D., and Leitner W. Rhodium-catalyzed hydroformylation in supercritical carbon dioxide. J. Am. Chem. Soc. 120 (1998) 13398-13404
38. Palo D.R., and Erkey C. Effect of ligand modification on rhodium-catalyzed homogeneous hydroformylation in supercritical carbon dioxide. Organometallics 19 (2000) 81-86
39. 3. Ind. Eng. Chem. Res. 38 (1999) 3786-3792
40. 2. J. Chem. Soc., Dalton Trans. (2000) 4052-4055
41. Giménez-Pedrós M., Aghmiz A., Ruiz N., and Masdeu-Bultó A.M. New ligands for Rh-catalysed hydroformylation of 1-octene in supercritical carbon dioxide-X-ray structure of [Rh{PPh2(OC9H19)}4]PF6. Eur. J. Inorg. Chem. (2006) 1067-1075
42. Bach I., and Cole-Hamilton D.J. Hydroformylation of hex-1-ene in supercritical carbon dioxide catalysed by rhodium trialkylphosphine complexes. Chem. Commun. (1998) 1463-1464
43. Giménez-Pedrós M., Masdeu-Bultó A.M., Bayardon J., and Sinou D. Hydroformylation of alkenes with rhodium catalyst in supercritical carbon dioxide. Catal. Lett. 107 (2006) 205-208
44. Tadd A.R., Marteel A., Mason M.R., Davies J.A., and 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. 41 (2002) 4514-4522
45. Lopez-Castillo Z.K., Flores R., Kani I., Fackler Jr. J.P., and Akgerman A. Evaluation of polymer-supported rhodium catalysts in 1-octene hydroformylation in supercritical carbon dioxide. Ind. Eng. Chem. Res. 42 (2003) 3893-3899
46. Moser W.R., Papile C.J., Brannon D.A., and Duwell R.A. The mechanism of phosphine modified rhodium catalyzed hydroformylation studied by CIR-FTIR. J. Mol. Catal. 41 (1987) 271-292
47. Casey C.P., Paulsen E.L., Beuttenmueller E.W., Proft B.R., Petrovich L.M., Matter B.A., and Powell D.R. Electron withdrawing substituents on equatorial and apical phosphines have opposite effects on the regioselectivity of rhodium catalyzed hydroformylation. J. Am. Chem. Soc. 119 (1997) 11817-11825
48. Koeken A.C.J., van Vliet M.C.A., van den Broeke L.J.P., Deelman B.-J., and Keurentjes J.T.F. Hydroformylation of 1-octene in supercritical carbon dioxide and organic solvents using trifluoromethyl-substituted triphenylphosphine ligands. Adv. Synth. Catal. 348 (2006) 1553-1559
49. Koeken A.C.J., van Vliet M.C.A., van den Broeke L.J.P., Deelman B.-J., and Keurentjes J.T.F. Selectivity of rhodium-catalyzed hydroformylation of 1-octene during batch and semi-batch reaction using trifluoromethyl-substituted ligands. Adv. Synth. Catal. 350 (2008) 179-188
50. Burgemeister K., Franciò G., Gego V.H., Greiner L., Hugl H., and Leitner W. Inverted supercritical carbon dioxide/aqueous biphasic media for rhodium-catalyzed hydrogenation reactions. Chem. Eur. J. 13 (2007) 2798-2804
51. Frisch A.C., Webb P.B., Zhao G., Muldoon M.J., Pogorzelec P.J., and Cole-Hamilton D.J. "Solventless" continuous flow homogeneous hydroformylation of 1-octene. Dalton Trans. 47 (2007) 5531-5538
52. Sellin M.F., Bach I., Webster J.M., Montilla F., Rosa V., Avilés T., Poliakoff M., and Cole-Hamilton D.J. Hydroformylation of alkenes in supercritical carbon dioxide catalysed by rhodium trialkylphosphine complexes. J. Chem. Soc., Dalton Trans. 24 (2002) 4569-4576
53. 2-expanded solvent media. Chem. Eng. Sci. 59 (2004) 4887-4893
54. Jessop P.G., and Subramaniam B. Gas-expanded liquids. Chem. Rev. 107 (2007) 2666-2694
55. 2-expanded media. AIChE J. 52 (2006) 2575-2581
56. 2 + 1-hexene + heptanal. Fluid Phase Equilib. 215 (2004) 85-89
57. Jiménez-Gallegos R., Galicia-Luna L.A., and Elizalde-Solis O. Experimental vapor-liquid equilibria for the carbon dioxide + octane and carbon dioxide + decane systems. J. Chem. Eng. Data 51 (2006) 1624-1628
58. Valderrama J.O. The state of the cubic equations of state. Ind. Eng. Chem. Res. 42 (2003) 1603-1618
59. For example:. Meehan N.J., Sandee A.J., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M., and Poliakoff M. Continuous, selective hydroformylation in supercritical carbon dioxide using an immobilised homogeneous catalyst. Chem. Commun. (2000) 1497-1498