Soybean Oil Epoxidation by Heterogeneous Catalyst of Silica Sulfuric Acid

Document Type : Research Article

Authors

Chemical, Polymer & Petrochemical Technology Development Division, RIPI, Tehran, I.R. IRAN

Abstract

In situ epoxidation reaction of soybean oil from the raw materials of acetic acid and hydrogen peroxide was performed for the first time in the presence of a heterogeneous catalyst, namely silica sulfuric acid within the temperature of 30-75 °C. By altering the molar ratios of soybean oil, acetic acid and hydrogen peroxide and also the reaction temperature and percent of catalyst, the optimum condition of the epoxidation reaction for obtaining the highest value of epoxy percent in epoxidized soybean oil was achieved. The maximum oxirane value obtained in he product was 6% which was achieved at the optimum condition of the reaction, involving the molar ratio of soybean oil, acetic acid and hydrogen peroxide of 1:0.5:1.1 respectively, at the temperature of 60 °C and in the presence of 5% catalyst. Moreover, in comparison with the other acid liquid catalysts usually used for epoxidation reactions, silica sulfuric acid have several advantages including ease of usage, being inexpensive, having high chemical activity and safety and being environmentally friendly.

Keywords

Main Subjects

References

[1]  Bueno-Ferrer C., Garrigós M.C., Jiménez A.,Characterization and Thermal Stability of Poly(Vinyl Chloride) Plasticized with Epoxidized Soybean Oil for Food Packaging , Polymer Degradation and Stability, 95(11): 2207-2212 (2010).
[2] معتمد، س.؛ عالم­زاده، ا.؛ تخلیص پراکسید از سویا و بررسی ویژگی­های آن، نشریه شیمی و مهندسی شیمی ایران، (3)28: 33 تا 40 (1388).
[3] Ernesto Salzano, Anita Garcia Agreda, Vincenzo Russob, Martino Di Serio, Elio Santacesaria, Safety Criteria for the Epoxydation of Soybean Oil in Fed-Batch Reactor, Chemical Engineering Transactions, 26: 39-44 (2012).
[4] Goud V.V., Pradhan N.C., Patwardhan A.V, Epoxidation of Karanja (Pongamia Glabra) Oil by H2O2, Journal of American Oil Chem Soc., 83: 635-640 (2006).
[5] Sylvain Caillol1, Myriam Desroches1, Gilles Boutevin, Cédric Loubat, Rémi Auvergne, Bernard Boutevin, Synthesis of New Polyester Polyols from Epoxidized Vegetable Oils and Biobased Acids, Journal of European Lipid Science and Technology, 114(12): 1447-1459 (2012).
[6] Okieimen F.E, Pavithran C., Bakare I.O., Epoxidation and Hydroxylation of Rubber Seed Oil:One-Pot Multi Step Reactions, Euro. J. Lipid Sci. &Tech., 107: 864-870 (2005).
[7] Carlson K.D., Kleiman R., Bagby M.O, Epoxidation of Lesquerella and Limmanthes (Meadowfoam ) Oil, J. Am. Oil Chem. Soc., 71: 175-182 (1995).
[8] Marcel S.F., Lei K. J. and Mohammad K.P., Epoxidation Reactions of Unsaturated Fatty Esterswith Peroxomonosulphate, Lipids, 33: 633-637 (1998).
[9] Sonnet P.E., Foglia T., Epoxidation of Natural Triglycerides with Ethydioxyrane, J. Am. Oil Chem. Soc., 83: 835-840 (1996).
[10] Aerts A.J., Jacob P.A., Epoxide Yield Determination of Oils and Fatty Acid Methyl Esters Using 1H NMR, J. Am. Oil Chem. Soc., 81: 841-846 (2004).
[11] Snezana Sinadinovic-Fiser, Milovan Jankovic, Zoran S. Petrovic, Kinetic of in Situ Epoxidation of Soybean Oil in Bulk Catalyzed by Ion Exchange Resin, JAOCS, 78(7): 725-731 (2001).
[12] Goud, V.V., Patwardhan A.V., Pradhan N.C., Studies on the Epoxidation of Mahua Oil (Madhumica Indica) by Hydrogen Peroxide, Bioresour. Technol., 97: 1365-1371 (2006).
[13] Dinda S., Patwardhan A.V., Goud V.V, Pradhan N.C,Epoxidation of Cottonseed Oil by Aqueous Hydrogen Peroxide Catalysed by Liquid Lnorganic Acids, Bioresour Technol, 99: 3737-3744 (2008).
[14] Campanella, A., Fontanini C., Baltanas, M.A.,High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in Situ, Chem. Eng. J., 144: 466-475 (2008).
[15] Mungroo R., Paradhan N.C., Goud V.V.,Dalai A.K., Epoxidation of Canola Oil with Hydrogen Peroxide Catalysed by Acidic Ion Exchange Resin, J Am. Oil Chem Soc, 85: 887-896 (2008).
[16] Varma R.S., "Fundamental of Aqueous Microwave Chemistry", Springer, 43, Chapter. 1, (1999).
[17]  Salehi P., Zolfigol M.A., Shirini F., Baghbanzadeh M., Silica Sulfuric Acid and Silica Chloride as Efficient Reagents for Organic Reactions, Curr. Org. Chem., 10: 2171-2189 (2006).
[18]  Zolfigol M.A., Silica Sulfuric Acid/NaNO2 as a Novel Heterogeneous System for Production of Thionitrites and Disulfides under Mild Conditions, Tetrahedron, 57: 9509-9511 (2001).
[19] Salehi P., Dabiri M., Zolfigol M.A., Bodaghi Fard M.A., Silica Sulfuric Acid as an Efficient and Reusable Reagent for Crossed-Aldol Condensation of Ketones with Aromatic Aldehydes under Solvent-Free Conditions, Heterocycles, 60: 2435-      (2003).
[20] Salehi P., Dabiri M., Zolfigol M.A., Baghbanzadeh M., A New Approach to the Facile Synthesis of Mono- and Disubstituted Quinazolin-4(3H)-Ones under Solvent-Free Conditions, Tetrahedron Lett, 46:7051-7053 (2005).
[21]  Salehi P., Dabiri M., Zolfigol M.A., Otokesh S., Baghbanzadeh M., Selective Synthesis of 2-Aryl-1-Arylmethyl-1H-1,3-Benzimidazoles in Water at Ambient Temperature, Tetrahedron Lett., 47: 2557-2560 (2006).
[22] Minoo Dabiri, Peyman Salehi, Mostafa Baghbanzadeh, Mohammd Ali Zolfigol,Silica Sulfuric Acid: An Efficient Reusable Heterogeneous Catalyst, Catalysis Communications, 9: 785-788 (2008).
[23] Foster D.S., Leslie S.E., Determination of Oxirane Content in Epoxy Compounds, "Encyclopedia of Industrial Chemical Analysis", Interscience Publishers, A Division of John Willey & Sonc, Inc, 12: 206-207 (1971).
[24] Wijs Method, Iodine Value of Fats and Oils, pp. 1-25, AOCS Method Cd (1994).

Files

Share

How to cite

Statistics