Hydroformylation of 1-octene in supercritical carbon dioxide: Can alkylation of arylphosphines with tertbutyl groups lead to soluble and active catalytic systems?

Journal of Supercritical Fluids

Volumn 46, Issue 1, 2008, Pages 63-70

  Galia, Alessandro ^a   Cipollina, Andrea ^a   Filardo, Giuseppe ^a   Scialdone, Onofrio ^a   Ferreira, Michel ^b   Monflier, Eric ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITÉ D'ARTOIS   (France)

Author keywords

Alkenes; Homogeneous catalysis; Hydroformylation; Phosphine ligands; Rhodium; Supercritical carbon dioxide

Indexed keywords

CARBON DIOXIDE; CATALYST ACTIVITY; FUNCTIONAL GROUPS; GAS MIXTURES; HYDROFORMYLATION; LIGANDS;

HOMOGENEOUS CATALYSIS; PHOSPHINE LIGANDS; SUPERCRITICAL CARBON DIOXIDE;

SUPERCRITICAL FLUIDS;

EID: 44249085113     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2008.02.019     Document Type: Article

References (36)

1. Jessop P.J. Homogeneous catalysis using supercritical fluids: recent trends and systems studied. J. Supercrit. Fluids 38 (2006) 211-231
2. O. Roelen, German Patent 849548 (1938).
3. Trzeciak A.M., and Ziolkowski J.J. Perspectives of rhodium organometallic catalysis. Fundamental and applied aspects of hydroformylation. Coord. Chem. Rev. 190-192 (1999) 883-900
4. Jessop P.G., and Leitner W. In: Jessop P.G., and Leitner W. (Eds). Metal Complex-catalyzed Reactions in Chemical Synthesys Using Supercritical Fluids (1999), Wiley-VCH Verlag GmbH, Weinheim 365
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. 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
7. Koch D., and Leitner W. Rhodium-catalyzed hydroformylation in supercritical carbon dioxide. J. Am. Chem. Soc. 120 (1998) 13398-13404
8. 3. Ind. Eng. Chem. Res. 38 (1999) 3786-3792
9. 2. J. Chem. Soc., Dalton Trans. (2000) 4052-4055
10. 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
11. 2 down to low pressures. Nature 405 (2000) 165-168
12. 2-philes. Ind. Eng. Chem. Res. 39 (2000) 4678-4683
13. 2. Organometallics 20 (2001) 3206-3208
14. 6. Eur. J. Inorg. Chem. (2006) 1067-1075
15. Ryoo W., Webber S.E., and Johnston K.P. Water in carbon dioxide microemulsions with methylated branched hydrocarbon surfactants. Ind. Eng. Chem. Res. 42 (2003) 6348-6358
16. Eastoe J., Paul A., Nave S., Steytler D.C., Robinson B.H., Rumsey E., Thorpe M., and Heenan R.K. Micellization of hydrocarbon surfactants in supercritical carbon dioxide. J. Am. Chem. Soc. 123 (2001) 988-989
17. 2 dispersants. Colloid Polym. Sci. 284 (2006) 1333-1337
18. Smart N.G., Carleson T.E., Elshani S., Wang S., and Wai C.M. Extraction of toxic heavy metals using supercritical fluid carbon dioxide containing organophosphorus reagents. Ind. Eng. Chem. Res. 36 (1997) 1819-1826
19. Filardo G., Di Blasi M., Galia A., Ponchel A., Bricout H., Sayede A.D., and Monflier E. Peracetylated β-cyclodextrin as solubilizer of arylphosphines in supercritical carbon dioxide. J. Supercrit. Fluids 36 (2006) 173-181
20. Caron L., Bricout H., Tilloy S., Landy D., Fourmentin S., and Monflier E. Molecular recognition between a water-soluble organometallic complex and a β-cyclodextrin: first example of second-sphere coordination adducts possessing a catalytic activity. Adv. Synth. Catal. 346 (2004) 1449-1456
21. Caron L., Canipelle M., Tilloy S., Bricout H., and Monflier E. Convenient synthesis of new amphiphilic triphenylphosphine analogues for aqueous biphasic catalysis. Tetrahedron Lett. 42 (2001) 8837-8840
22. Kosolapoff G.M., and Maier L. Organic Phosphorus Compounds vol. 1 (1972), Wiley Interscience, New York
23. Brune H.A., Falck M., Hemmer R., Schmidtberg G., and Alt H.G. Chem. Ber. 117 9 (1984) 2791-2802
24. Wagner K.D., Dahmen N., and Dinjus E. Solubity of triphenylphosphine, tris(p-fluorophenyl)phosphine, tris(pentaflorophenyl)phosphine, and tris(p-trifluoromethylphenyl)phosphine in liquid and supercritical carbon dioxide. J. Chem. Eng. Data 45 (2000) 672-677
25. Barton A. Handbook of Solubility Parameters and Other Cohesion Parameters. 2nd ed. (1991), CRC Press, Boca Raton (Chapter 2)
26. Allada S.R. Solubilty parameters of supercritical fluids. Ind. Eng. Chem. Process Des. Dev. 23 (1984) 344-348
27. Cipollina A., Anselmo A., Scialdone O., Filardo G., and Galia A. Experimental P-T-ρ measurements of supercritical mixtures of carbon dioxide, carbon monoxide, and hydrogen and semiquantitative estimation of their solvent power using the solubility parameter concept. J. Chem. Eng. Data 52 (2007) 2291-2297
28. Tolman C.A. Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis. Chem. Rev. 77 (1977) 313-348
29. Tucci E.R. Hydroformylating terminal olefins, influence of organophosphine ligands. Ind. Eng. Chem. Prod. Res. Dev. 9 (1970) 516-521
30. Moser W.R., Papile C.J., Brannon D.A., Duwell R.A., and Weininger S.J. The mechanism of phosphine-modified rhodium-catalyzed hydroformylation studied by CIR-FTIR. J. Mol. Catal. 41 (1987) 271-292
31. Palo D.R., and Erkey C. Effect of ligand modification on rhodium-catalyzed homogeneous hydroformylation in supercritical carbon dioxide. Organometallics 19 (2000) 81-86
32. Allen D.W., and Taylor B.F. The chemistry of heteroarylphosphorus compounds. Part 15. Phosphorus-31 nuclear magnetic resonance studies of the donor properties of heteroarylphosphines towards selenium and platinum(II). J. Chem. Soc., Dalton Trans. (1982) 51-54
33. Montilla F., Galindo A., Rosa V., and Avilés T. Effect of trimethylsilyl substitution on the chemical properties of triarylphosphines and their corresponding metal-complexes: solubilising effect in supercritical carbon dioxide. J. Chem. Soc., Dalton Trans. (2004) 2588-2592
34. Sellin M.F., Bach I., Webster J.M., Montilla F., Rosa V., Aviles 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. (2002) 4569-4576
35. Cavalieri d'Oro P., Raimondi L., Pagani G., Montrasi G., Gregorio G., and Andreetta A. Propene hydroformylation with rhodium carbonyls and triphenylphosphine. Chim. Ind. 62 (1980) 572-579
36. Kainez 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