Abstract
The lipase Candida antarctica (Novozyme 435) immobilized on acrylic resin was used as an unconventional catalyst for in situ epoxidation of soybean oil. The reactions were carried out in toluene. The peracid used for converting TG double bonds to oxirane groups was formed by reaction of FFA and hydrogen peroxide. The reaction conditions were optimized by varying the lipase concentration, solvent concentration, molar ratio of hydrogen peroxide to double bond, oleic acid concentration, and reaction temperature. The kinetic study showed that 100% conversion of double bonds to epoxides can be obtained after 4 h. The addition of free acids was not required for the reaction to proceed to conversions exceeding 80%, presumably owing to generation of FFA by hydrolysis of soybean oil. The enzyme catalyst was found to deteriorate after repeated runs.
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References
La Scala, J., and R.P. Wool, The Effect of Fatty Acid Composition on the Acrylation Kinetics of Epoxidized Triacylglycerols, J. Am. Oil Chem. Soc. 79:59–63 (2002).
Hutchinson, G.H., Traditional and New Uses for Vegetable Oils in the Surface Coatings and Allied Industries, Surf. Coat. Int. Part B: Coat. Trans. 85, B1:1–78 (2002).
Dusek, K., M. Duskova-Smrckova, A. Zlatanic, and Z. Petrovic, Formation of Polyurethane Networks from Polyols Based on Vegetable Oils, Polym. Mat. Sci. Eng. 86:381–382 (2002).
Wu, X., H. Zhang, S. Yang, H. Chen, and D. Wang, The Study of Epoxidized Rapeseed Oil Used as a Potential Biodegradable Lubricant, J. Am. Oil Chem. Soc. 77:561–563 (2000).
Petrovic, Z.S., A. Zlatanic, C.C. Lava, and S. Sinadinovic-Fiser, Epoxidation of Soybean Oil in Toluene with Peroxoacetic and Peroxoformic Acids—Kinetics and Side Reactions, Eur. J. Lipid Sci. Technol. 104:293–299 (2002).
Gerbase, A.E., J.R. Gregorio, M. Martinelli, M.C. Brasil, and A.N.F. Mendes, Epoxidation of Soybean Oil by the Methyltrioxorhenium-CH2Cl2/H2O2 Catalytic Biphasic System, J. Am. Oil Chem. Soc. 79:179–181 (2002).
Mannari, V.M., and J.L. Massingill, Jr., Two-component Highsolid Polyurethane Coating Systems Based on Soy Polyols, International Waterborne, High-Solid, and Powder Coating Symposium, New Orleans, February 6–8, 2002.
Refvik, M.D., and R.C. Larock, The Chemistry of Metathesized Soybean Oil, J. Am. Oil Chem. Soc. 76:99–102 (1999).
Zlatanic, A., Z.S. Petrovic, and K. Dusek, Structure and Properties of Triolein-based Polyurethane Networks Biomacromolecules 3:1048–1056 (2002).
Sinadinovic-Fiser, S., M. Jankovic, and Z.S. Petrovic, Kinetics of in situ Epoxidation of Soybean Oil in Bulk Catalyzed by Ion Exchange Resin, J. Am. Oil Chem. Soc. 78:725–731 (2001).
Sherringham, J.A., A.J. Clark, and B.R.T. Keene, New Chemical Feedstocks from Unsaturated Oils, Lipid Technol. 12:129–132 (2000).
Hilke, I., D. Bothe, J. Pruss, and H.-J. Warnecke, Chemo-enzymatic Epoxidation of Unsaturated Plant Oils, Chem. Eng. Sci. 56:427–432 (2001).
Piazza, G.J., T.A. Foglia, and A. Nuñez, Optimizing Reaction Parameters for the Enzymatic Synthesis of Epoxidized Oleic Acid with Oat Seed Peroxygenase, J. Am. Oil Chem. Soc. 78:589–592 (2001).
Björkling, F., S.E. Gadtfredsen, and O. Kirk, Lipase-Mediated Formation of Peroxycarboxylic Acids Used in Catalytic Epoxidation of Alkenes, J. Chem. Soc. Chem. Commun.:1301–1303 (1990).
WASDE Modifies Forecasts, inform 16:285 (2005).
Paquot, C., and A. Hautfenne, Standard Methods for the Analysis of Oils, Fats and Derivatives, Blackwell Scientific, London, 1987, pp. 118–119.
Paquot, C., and A. Hautfenne, Ibid., pp. 88–93.
AOCS, Acid Value, in Official Methods and Recommended Practices of the AOCS, AOCS Press, Champaign 2004, Official Method Cd 3d-63.
Rüsch gen. Klaas, M., and S. Warwel, Chemoenzymatic Epoxidation of Unsaturated Fatty Acid Esters and Plant Oils, J. Am. Oil Chem. Soc. 73:1453–1457 (1996).
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Vlček, T., Petrović, Z.S. Optimization of the chemoenzymatic epoxidation of soybean oil. J Amer Oil Chem Soc 83, 247–252 (2006). https://doi.org/10.1007/s11746-006-1200-4
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DOI: https://doi.org/10.1007/s11746-006-1200-4