International Journal of Applied Science and Engineering
Published by Chaoyang University of Technology

Amanda J. Wrighta, Stephan Reyniera, Stanislaw Skoniecznyb, and Levente L. Diosadya∗

a Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, Canada 
b Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada


Download Citation: |
Download PDF


ABSTRACT


Dichlorodicarbonylbis (triphenylphosphine) ruthenium (II), a cis-selective and homogeneous catalyst, was immobilized on two types of inert solid supports: phosphinated polystyrenes and phosphinated silica gel. In both cases, spacer chains of different length were inserted between the phosphine attachment of the Ru complex and the support surface. Ru attachment efficiencies were determined by neutron activation analysis (NAA). The ability of the heterogenized catalysts to hydrogenate both 1-hexene and canola oil was also tested and the influence of linkage structure on activity was evaluated. In the case of the silica-supported catalysts, Ru dissociated from the support during hydrogenation. In contrast, the polymer-bound Ru remained immobilized during the catalytic reactions. Those polymer catalysts with the shortest linkage chains demonstrated the highest activity in the hydrogenation of 1-hexene. Despite this demonstrated activity, none of the polymer-bound Ru catalysts were active for canola oil hydrogenation.


Keywords: canola oil; hydrogenation; ruthenium; immobilization; 1-hexene; attachment efficien-cy.


Share this article with your colleagues

 


REFERENCES


  1. [1] American Oil Chemists’ Society. 1988. “Official Methods and Recommended Practices of the American Oil Chemists’ Society”. 3rd Ed., AOCS Press. Champaign, L.

  2. [2] Asherio, A., Katan, M. B., Zock, P. L., Stampfer, M. J., and Willett, W. C. 1999. Trans fatty acids and coronary heart disease. New England Journal of Medicine, 340: 1994-1998.

  3. [3] Azran, J., Buchman, O., Orchin, M., and Blum, J. 1984. Polymer-bound iridium catalysis. Hydrogen transfer from formic acid to unsaturated carbon-carbon bonds. Journal of Organometallic Chemistry, 49: 1327-1333.

  4. [4] Bello, C., Diosady, L. L., Graydon, W. F., and Rubin, L. J. 1985. Homogeneous catalytic hydrogenation of canola oil using a ruthenium catalyst. Journal of the American Oil Chemical Society, 62: 1587-1592.

  5. [5] Bailar, J. C. Jr. 1975. Heterogenizing homogeneous catalysts. Catalysis Reviews-Science and Engineering, 10: 17-36.

  6. [6] Capka, M. 1977. Catalysis by Metal Complexes. XLV. Selective phosphination of (2-chloropropyl) triethoxysilane, a new route to alkoxysilyl-substituted phosphines. Synthesis and Reactivity in Inorganic and Metal-organic Chemistry, 7: 347.

  7. [7] Czakova, M. and Capka, M. 1981. Hydogenation Activity of homogeneous and heterogenized rhodium (I) complexes containing {w-(triethoxysilyl) alkyl} aliphenylphosphines. Journal of Molecular Catalysis, 11: 313.

  8. [8] Evans, G. O., Pittman, C. U., McMillan, R., Beach, R. T., and Jones, R. 1974. Synthetic and catalytic studies of polymer-bound metal carbonyls. Journal of Organometallic Chemistry, 67: 295.

  9. [9] Grubbs, R. H., Kroll, L. C., LeRoy, C., and Sweet, E. M. 1973. Preparation and selectivity of a polymer-attached rhodium (I) olefin hydrogenation catalyst. Journal of Macromolecular Science-pure and Applied Chemistry, 7: 1047.

  10. [10] Hu, F. B., Stampfer, M. J., Manson, J. E., Rimm, E., Colditz, G. A., Rosner, B. A ., Hennekens, C. H., and Willett,W. C. 1997. Dietary fat intake and the risk of coronary heart disease in women. New England Journal of Medicine, 337: 1491-1499.

  11. [11] Mensik, R. P. and Katan, M. B. 1990. Effect of dietary trans fatty acids on High-density and Low-density lipoprotein cholesterol levels in healthy subjects. New England Journal of Medicine, 323: 439-445.

  12. [12] Michalska, Z. M., Capka, M., and Stoch, J. 1981. Silica-supported rhodium complexes. relation between catalyst structure and activity. Journal of Molecular Catalysis, 11: 321-330.

  13. [13] Pittman, C. U. and Evans, G. O. 1973. Polymer-bound catalysts and reagents. Chemiscal Technology: 560.

  14. [14] Pittman, C. U., Smith, L. R., and Hanes, R. M. 1975. Catalytic reactions using polymer-bound versus homogeneous complexes of nickel, rhodium, and ruthenium. Journal of the American Oil Chemical Society, 97: 1742-1748.

  15. [15] Sanchez-Delgado, R. A., Duran, , Monfort, J., and Rodriquez, E. 1981. A comparative study of the isomerization and hydrogenation of 1-hexene with soluble and silica-supported ruthenium catalysts. Journal of Molecular Catalysis, 11: 193.

  16. [16] Skupinski, W. and Malinowski, S. 1975. Catalytic systems containing nickel supported on silica and bonded with organic ligands and complexed by Lewis acids. Journal of Organometallic Chemistry, 99: 465.

  17. [17] Skupinski, W. and Malinowski, S. 1976. Investigations on catalytic systems containing nickel supported on silica gel and bonded with organic ligands and complexed by Lewis acids (II). Journal of Organometallic Chemistry: 117-183.

  18. [18] Strukul, G., Bonivento, M., Graziani, M., Cernia, E., and Palladino, N. 1975. Selective hydrogenation of ketones and olefins over polymer-bound rhodium catalysts. Inorganica Chimica Acta, 12: 15-21.

  19. [19] Williamson, K. L. 2003a. “Macroscale and Microscale Organic Experiments. Chapter 38: Grignard Synthesis of triphenylmethanol and benzoic acid”. 4th Ed., Houghton Mifflin Company, Boston, Massachusetts: 461-478.

  20. [20] Williamson, K. L. 2003b. “Macroscale and Microscale Organic Experiments. Chapter 24: Oxidation with pyridinium chlorochromate”. 4th Ed., Houghton Mifflin Company, Boston, Massachusets: 325-334.

  21. [21] Wright, A. J., Mihele, A. L., and Diosady, L. L. 2003. Cis selectivity of mixed catalyst systems in canola oil hydrogenation. Food Research International, 36: 797-804.


ARTICLE INFORMATION




Accepted: 2003-06-22
Available Online: 2003-09-01


Cite this article:

Wright, A.-J., Reynier, S., Skonieczny, S., DiosadyL.L. 2003. 
Immobilization of a homogeneous RU catalyst for hexene and canola oil hydrogenation: Synthesis and activity, International Journal of Applied Science and Engineering, 1, 89–100. https://doi.org/10.6703/IJASE.2003.1(2).89


We use cookies on this website to improve your user experience. By using this site you agree to its use of cookies.