Kinetic analysis of hydrogenation of cinnamaldehyde with a ruthenium complex catalyst in several solvents

Journal of Chemical Engineering of Japan

Volumn 36, Issue 2, 2003, Pages 155-160

  Fujita, Shin Ichiro ^a   Sano, Yoko ^a   Bhanage, Bhalchandra M ^a   Arai, Masahiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Cinnamaldehyde; Cinnamyl alcohol; Hydrocinnamaldehyde; Hydrocinnamyl alcohol; Ruthenium complex

Indexed keywords

HYDROGENATION; REACTION KINETICS; RUTHENIUM;

CINNAMALDEHYDE (CAL);

AROMATIC HYDROCARBONS;

HYDROGENATION;

EID: 0037312263     PISSN: 00219592     EISSN: None     Source Type: Journal    
DOI: 10.1252/jcej.36.155     Document Type: Article

References (24)

1. Bauer, K. and D. Garbe; Ullman Encyclopedia, 3rd ed., Vol. A11, p. 141, VCH, New York, USA (1988)
2. 2O): A Kinetic Investigation of the Salt Effect in Water," J. Mol. Catal., 72, 337-350 (1992)
3. Fache, E., C. Mercier, N. Pagnier, E. Despeyroux and P. Panster; "Selective Hydrogenation of α,β-Unsaturated Aldehydes Catalyzed by Supported Aqueous-Phase Catalysts and Supported Homogeneous Catalysts," J. Mol. Catal., 79, 117-131 (1993)
4. Farnetti, E., M. Pesce, J. Kaspar, R. Spogliarich and M. Graziani; "Selective Hydrogenation of Cinnamic Aldehyde to Unsaturated Alcohol Catalyzed by Iridium Phosphine Systems," J. Mol. Catal., 43, 35-40 (1987)
5. Fujita, S., K. Yuzawa, B. M. Bhanage, Y. Ikushima and M. Arai; "Palladium-Catalyzed Heck Coupling Reactions Using Different Fluorinated Phosphine Ligands in Compressed Carbon Dioxide and Conventional Organic Solvents," J. Mol. Catal. A: Chem., 180, 35-42 (2002)
6. Fukuzawa, S., T. Fujinami, S. Yamauchi and S. Sakai; "1,2-Regioselective Reduction of α,β-Unsaturated Carbonyl Compounds with Lithium Aluminium Hydride in the Presence of Lanthanoid Salts," J. Chem. Soc. Perkin Trans. I, 1929-1932 (1986)
7. Gallezot, P. and D. Richard; "Selective Hydrogenation of α,β-Unsaturated Aldehydes," Catal. Rev. Sci. Eng., 40, 81-126 (1998)
8. German, A. L. and J. L. Luche; "Lanthanoids in Organic Synthesis. 6. The Reduction of α-Enones by Sodium Borohydride in the Presence of Lanthanoid Chlorides: Synthetic and Mechanistic Aspects," J. Am. Chem. Soc., 103, 5454-5459 (1981)
9. Grosselin, J. M., C. Mercier, G. Allmang and F. Grass; "Selective Hydrogenation of α,β-Unsaturated Aldehydes in Aqueous Organic Two-Phase Solvent Systems Using Ruthenium or Rhodium Complexes of Sulfornated Phosphines," Organometallics, 10, 2126-2133 (1991)
10. Hernandez, M. and P. Kalck; "Study of the Hydrogenation of α,β-Unsaturated Carbonyl Compounds Catalyzed by Water-Soluble Ruthenium-TPPTS Complexes," J. Mol. Catal. A: Chem., 116, 131-146 (1997)
11. 3-HCI Catalyst," J. Mol. Catal., 29, 105-107 (1985)
12. Joo, F., J. Kovacs, A. C. Beyei and A. Katho; "The Effect 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," Catal. Today, 42, 441-445 (1998)
13. Levenspiel, O.; Chemical Reaction Engineering, 2nd ed., pp. 55-60, John Wiley, New York, USA (1972)
14. Li, R. X., K. C. Tin, N. B. Wong, T. C. W. Mak, Z. Y. Zhang and X. J. Li; "Synthesis of Noble Ruthenium Complexes of 2.2-Bis (diphenylphosphinomethyl)-1.1'-biphenyl and Their Catalytic Hydrogenation Recations of α,β-Unsaturated Aldehydes," J. Organomet. Chem., 557, 207-212 (1998a)
15. Li, R. X., N. B. Wong, X. J. Li, T. C. W. Mak, Q. C. Yang and K. C. Tin; "Synthesis and Characterization of Ruthenium Complexes of 1.8-Bis(diphenylphosphinomethyl)naphtalene (BDNA) and Their Catalytic Hydrogenation Recations of α,β-Unsaturated Aldehydes," J. Organomet. Chem., 571, 223-229 (1998b)
16. Li, R. X., X. J. Li, N. B. Wong, K. C. Tin, Z. Y. Zhou and T. C. W. Mak; "Synthesis and Characterization of Iridium Complexes Containing Bidentate Phophine Ligands and Their Catalytic Hydrogenation Recations of α,β-Unsaturated Aldehydes," J. Mol. Catal. A: Chem., 178, 181-190 (2002)
17. Lopez-Linares, F., M. G. Gonzalez and D. E. Paez; "The Regioselective Biphasic Hydrogenation of trans-Cinnamaldehyde by meta-Sulfonatophenyl-diphenylphosphine (TPPMS) Ru(II) and Os(II) Species. The Influence of Ionic Strength, Ligand Tensoactivity and Metal Nature in the Selective Production of the Unsaturated Alcohol," J. Mol. Catal. A: Chem., 145, 61-68 (1999)
18. Sanchez-Delgado, R. A., A. Andriollo and N. Valencia; "Homogeneous Hydrogenation of α,β-Unsaturated Aldehydes Catalyzed by Ruthenium and Osmium Complexes," J. Mol. Catal., 24, 217-220 (1984)
19. Sanchez-Delgado, R. A., M. Medina, F. Lopez-Linares and A. Fuentes; "The Chemistry and Catalytic Properties of Ruthenium and Osmium Compounds. Part 7. Regioselective Hydrogenation of Cinnamaldehyde Catalyzed by Ru and Os Triphenylphosphine Complexes in Homogeneous Solution and by Meta-Sulfornatophenylphosphine and Tris-Meta-Sulfornate-Phenylphosphine Derivatives in an Aqueous Biphasic System," J. Mol. Catal. A: Chem., 116, 167-177 (1997)
20. Shirai, M., T. Tanaka and M. Arai; "Selective Hydrogenation of α,β-Unsaturated Aldehyde to Unsaturated Alcohol with Supported Platinum Catalysts at High Pressure of Hydrogen," J. Mol. Catal. A: Chem., 168, 99-103 (2001)
21. 2(TRIPHOS)," J. Mol. Catal., 45, 335-344 (1988)
22. Tin, K. C., N. B. Wong, R. X. Li, Y. Z. Li, J. Y. Hu and X. J. Li; "Hydrogenation of Crotonaldehyde and Cinnamaldehyde Catalyzed by Water-Soluble Palladium Complex," J. Mol. Catal. A: Chem., 137, 121-125 (1999)
23. Zhao, F., B. M. Bhanage, M. Shirai and M. Arai; "Heck Reactions of Iodobenzene and Methyl Acrylate with Conventional Supported Palladium Catalysts in the Presence of Organic and/or Inorganic Bases without Ligands," Chem. Eur. J., 6, 843-848 (2000)
24. Zhao, F., M. Shirai, Y. Ikushima and M. Arai; "The Leaching and Re-deposition of Metal Species from and onto Conventional Supported Palladium Catalysts in the Heck Reactions of Iodobenzene and Methyl Acrylate in N-Methylpyrrolidone," J. Mol. Catal. A: Chem., 180, 211-219 (2002)