The hydrogenation of cinnamaldehyde by supported aqueous phase (SAP) catalyst of RhCl(TPPTS)3: Selectivity, kinetic and mass transfer aspects

Chemical Engineering Science

Volumn 61, Issue 18, 2006, Pages 5944-5953

  Nuithitikul, Kamchai ^a   Mike Winterbottom, John ^b  

^a KING MONGKUT'S UNIVERSITY OF TECHNOLOGY NORTH BANGKOK   (Thailand)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Catalyst selectivity; Kinetics; Mass transfer; Multiphase reactions; SAP catalyst; TPPTS

Indexed keywords

CATALYST SELECTIVITY; CHEMICAL BONDS; CONCENTRATION (PROCESS); HYDROGENATION; MASS TRANSFER; REACTION KINETICS;

KINETICS; MULTIPHASE REACTIONS; SUPPORTED AQUEOUS PHASE (SAP) CATALYST; TPPTS;

ALDEHYDES;

ALDEHYDES; CATALYST SELECTIVITY; CHEMICAL BONDS; CONCENTRATION (PROCESS); HYDROGENATION; MASS TRANSFER; REACTION KINETICS;

EID: 33746825907     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ces.2006.05.015     Document Type: Article

References (28)

1. Andriollo A., Carrasquel J., Mariño J., López F.A., Páez D.E., and Valencia I.R.N. On the synthesis and characterization of two ruthenium water-soluble complexes: preliminary results on the hydrogenation of cinnamaldehyde in a biphasic system. Surface activity of the ligands TPPMS and TPPTS. Journal of Molecular Catalysis A: Chemical 116 (1997) 157-165
2. Arhancet J.P., Davis M.E., Merola J.S., and Hanson B.E. Supported aqueous-phase catalysts. Journal of Catalysis 121 (1990) 327-339
3. Bhanage B.M., Ikushima Y., Shirai M., and Arai M. Multiphase catalysis using water-soluble metal complexes in supercritical carbon dioxide. Chemical Communications (1999) 1277-1278
4. Choplin A., and Quignard F. From supported homogeneous catalysts to heterogeneous molecular catalysts. Coordination Chemistry Reviews 178-180 (1998) 1679-1702
5. Choplin A., Santos S.D., Quignard F., Sigismondi S., and Sinou D. Palladium (0) allylic alkylation in a two-phase system or with a supported aqueous phase catalyst. Catalysis Today 42 (1998) 471-478
6. Davis M.E. Transitions to heterogeneous techniques (SAPC and variations). In: Cornils B., and Herrmann W.A. (Eds). Aqueous-phase Organometallic Catalysis, Concepts and Applications (1998), Wiley-vch, Weinheim
7. Doraiswamy, L.K., Sharma, M.M., 1984. Heterogeneous Reactions: Analysis, Examples and Reactor Design, Volume 2: Fluid-fluid-solid Reactions. Wiley, USA, pp. 277-316.
8. Dror Y., and Manassen J. Hydrogenation of olefins with rhodium-phosphine complexes, having substrate and catalyst in two different immiscible phases. Journal of Molecular Catalysis 2 (1977) 219-222
9. Frémy G., Monflier E., Carpentier J.F., Castanet Y., and Mortreux A. Expanded scope of supported aqueous phase catalysis: efficient rhodium-catalyzed hydroformylation of α, β-unsaturated esters. Journal of Catalysis 162 (1996) 339-348
10. Fujita S., Sano Y., Bhanage B.M., and Arai M. Supported liquid-phase catalysts containing ruthenium complexes for selective hydrogenation of α, β-unsaturated aldehyde: importance of interfaces between liquid film solvent and support for the control of product selectivity. Journal of Catalysis 225 1 (2004) 95-104
11. Grosselin, J.M., Mercier, C., 1990. Process for the preparation of unsaturated alcohols. US Patent, 4925990.
12. Grosselin J.M., Mercier C., Allmang G., and Grass F. Selective hydrogenation of α, β-unsaturated aldehydes in aqueous organic two-phase solvent systems using ruthenium or rhodium complexes of sulfonated phosphines. Organometallics 10 7 (1991) 2126-2133
13. 2, in a supported aqueous phase for the hydroformylation of 1-hexene. Journal of Organometallic Chemistry 403 (1991) 221-227
14. Hernandez M., and Kalck P. Study of the hydrogenation of α, β-unsaturated carbonyl compounds catalyzed by water-soluble ruthenium-TPPTS complexes. Journal of Molecular Catalysis A: Chemical 116 (1997) 131-146
15. Herrmann W.A., and Kohlpaintner C.W. Water-soluble ligands metal complexes, and catalysis: synergism of homogeneous and heterogeneous catalysis. Angewandte Chemie-International Edition in English 32 (1993) 1524-1544
16. Jáuregui-Haza U.J., Dessoudeix M., Kalck Ph., Wilhelm A.M., and Delmas H. Multifactorial analysis in the study of hydroformylation of oct-1-ene using supported aqueous phase catalysis. Catalysis Today 66 (2001) 297-302
17. Joó F., Kovács J., Bényei A.Cs., and Kathó A. The effects of pH on the molecular distribution of water soluble ruthenium (II) hydrides and its consequences on the selectivity of the catalytic hydrogenation of unsaturated aldehydes. Catalysis Today 42 (1998) 441-448
18. Kalck P., and Dessoudeix M. Inter-facial catalysts using various water compatible ligands in supramolecular systems. Coordination Chemistry Reviews 190-192 (1999) 1185-1198
19. Kuntz E.G. Homogeneous catalysis in water. Chemtech 17 (1987) 570-575
20. Lal P., Kumar S., Upadhyay S.N., and Upadhyay Y.D. Solid-liquid mass transfer in agitated Newtonian and non-Newtonian fluids. Industrial & Engineering Chemistry Research 27 (1988) 1246-1259
21. Lashdaf M., Krause A.O.I., Lindblad M., Tiitta M., and Venäläinen T. Behaviour of palladium and ruthenium catalysts on alumina and silica prepared by gas and liquid phase deposition in cinnamaldehyde hydrogenation. Applied Catalysis A: General 241 (2003) 65-75
22. Li Z., Peng Q., and Yuan Y. Aqueous phosphine-Rh complexes supported on non-porous fumed-silica nanoparticles for higher olefin hydroformylation. Applied Catalysis A: General 239 (2003) 79-86
23. 3. Chemical Engineering Science 59 (2004) 5439-5447
24. Sánchez-Delgado R.A., Medina M., López-Linares F., and Fuentes A. The chemistry and catalytic properties of ruthenium and osmium compounds, part 7: regioselective hydrogenation of cinnamaldehyde (3-phenyl-2-propenal) catalyzed by Ru and Os triphenylphosphine complexes in homogeneous solution and by meta-sulfonatophenyl-diphenylphosphine (TPPMS) and tris-meta-sulfonato-phenylphosphine (TPPTS) derivatives in an aqueous biphasic system. Journal of Molecular Catalysis A: Chemical 116 (1997) 167-177
25. Sandee A.J., Slagt V.F., Reek J.N.H., Kamer P.C.J., and Van Leeuwen P.W.N.M. A stable and recyclable supported aqueous phase catalyst for highly selective hydroformylation of higher olefins. Chemical Communications (1999) 1633-1634
26. Santos S.D., Tong Y., Quignard F., Choplin A., Sinou D., and Dutasta J.P. Supported aqueous-phase palladium catalysts for the reaction of allylic substitution: toward an understanding of the catalytic system. Organometallics 17 (1998) 78-89
27. Tóth I., Guo I., and Hanson B.E. Alternative supported aqueous-phase catalyst systems. Journal of Molecular Catalysis A: Chemical 116 (1997) 217-229
28. Winterbottom J.M., and King M.B. Reactor Design for Chemical Engineers (1999), Stanley Thornes (Publishers) Ltd, Cheltenham pp. 344-375