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Esterification of oleic acid with glycerol in the presence of sulfated iron oxide catalyst

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Journal of the American Oil Chemists’ Society

Abstract

Esterification of oleic acid with glycerol was investigated in view of the reaction kinetics, using “superacidic” sulfated iron oxide catalysts. A series of different sulfate contents were prepared and characterized by a multitude of techniques prior to their use as catalysts. The sulfated iron oxide reaction was carried out with equivalent amounts of reactants in the temperature range of 180–240°C. Effects of the sulfate content and the catalyst amount on reaction kinetics at different temperatures were evaluated.

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References

  1. Swern, D. (ed.),Bailey’s Industrial Oil and Fat Products, 4th edn., Vol. 2, John Wiley and Sons, New York, 1982, pp. 113–118.

    Google Scholar 

  2. Johnson, R.W., and E. Fritz,Fatty Acids in Industry, Marcel Dekker Inc., New York, 1989, pp. 139–152.

    Google Scholar 

  3. Markley, K.S. (ed.),Faity Acids, Their Chemistry, Properties, Production, and Uses, Vol. 2, Robert E. Krieger Publishing Company, Malabar, 1983, pp. 797–826.

    Google Scholar 

  4. —, Vol. 5, pp. 3476–3492.

    Google Scholar 

  5. Goldsmith, H.A., Polyhydric Alcohol Esters of Fatty Acids,Chem. Rev. 22:257–349 (1945).

    Google Scholar 

  6. Hartman, L., Advances in the Synthesis of Glycerides of Fatty Acids,,58:845–867 (1958).

    Article  CAS  Google Scholar 

  7. Formo, M.W., Ester Reactions of Fatty Materials,J. Am. Oil. Chem. Soc. 31:548–559 (1954).

    CAS  Google Scholar 

  8. Feuge, R.O., E.A. Kraemer, and A.E. Bailey, Modification of Vegetable Oils. IV. Reesterification of Fatty Acids with Glycerol.Oil and Soap 22:202–207 (1945).

    CAS  Google Scholar 

  9. Hilditch, T.P., and J.G. Rigg, Experiments on the Direct Esterification of Higher Fatty Acids with Glycerol and with Ethylene Glycol,J. Chem. Soc., 1774–1778 (1935).

  10. Hilditch, T.P., and J.G. Rigg (to Imperial Chemical Industries Ltd.), U.S. Patent 2,073, 797 (1937);Chem. Abs. 31:3724 (1937).

  11. Ivanoff, N., Esterification of Fatty Acids by Glycerol,Chim. Ind. 1945:41 (1945);Chem. Abs. 40:1785 (1946).

    Google Scholar 

  12. Patrick Jr., T.J. and K.G. Johnson (to Monsanto Chemical Co.), U.S. Patent 3,060, 224 (1962);Chem. Abs. 58:11282d (1963).

  13. Gross, A.T., and R.O. Feuge, Preparation of Partial Glycerides by Direct Esterification,J. Am. Oil Chem. Soc. 41:727–731 (1964).

    Google Scholar 

  14. Feuge, R.O., R.K. Willich, and W.A. Guice, Preparation of Glycerides by Controlled Esterification,40:260–264 (1963).

    CAS  Google Scholar 

  15. Bhattacharya, R., and T.P. Hilditch, The Structure of Synthetic Mixed Triglycerides,Proc. Roy. Soc. (London) 129A:468–476 (1930);Chem. Abs. 25:1801 (1931).

    CAS  Google Scholar 

  16. Mohan, A.G., and W.R. Christian (to Nopco Chemical Co.), U.S. Patent 3,071,604 (1963);Chem. Abs. 58:8154a (1963).

  17. Biswas, S.K., and D. Ganguly, Esterification of Fatty Acids with Glycerol,Nature 188:56–57 (1960).

    Article  CAS  Google Scholar 

  18. Choudhury, R.B.R., The Preparation and Purification of Monoglycerides. II. Direct Esterification of Fatty Acids with Glycerol,J. Am. Oil Chem. Soc. 39:345–347 (1962).

    CAS  Google Scholar 

  19. Christian, H., and P. Uwe (Henkel K.-G.a.A.), Ger Offen. 3,011,881 (1981);Chem. Abs. 95:202316e (1981).

  20. Wlodzimierz, Z., J. Krzysztof, S. Halina, and M. Janina (Politechnika Gdanska) Pol PL 152,300 (1990);Chem. Abs. 115:138677a (1991).

    Google Scholar 

  21. Dunlop, L.H., and J.S. Heckles, Catalyzed Esterification of Oleic Acid,J. Am. Oil Chem. Soc. 37:281–285 (1960).

    Google Scholar 

  22. Hartman, L., Esterification Rates of Some Saturated and Unsaturated Fatty Acids with Glycerol,,43:536–538 (1966).

    CAS  Google Scholar 

  23. Kazushige, M., and Y. Chizuo, Reactions and Reaction Products in the Synthesis of Glycerol Monooleate,Yukaguku 31:1021–1026 (1982).

    Google Scholar 

  24. Markman, A.L., M. Mirzabaeva, and A.I. Glushenkova, Kinetics of the Esterification of Aliphatic Acids by Alcohols,Uzb. Khim. Zh. 12:28–30 (1968);Chem. Abst. 70:36763k (1969).

    CAS  Google Scholar 

  25. Tanizaki, Y., and T. Yoshida, Kinetics of Elementary Reactions in Alkyd Synthesis,Shikizai Kyakaishi 45:83–87 (1972);Chem. Abs. 77:114933b (1972).

    CAS  Google Scholar 

  26. Schuch, R., R. Baruffaldi, and L.A. Gioielli, Kinetics of Zinc Cloride-Catalyzed Esterification of Glycerol with Palmitic Acid,Rev. Farm. Bioquim. Univ. Sao Paulo 20:51–55 (1984);Chem. Abs. 102:26793k (1985).

    CAS  Google Scholar 

  27. Eckey, E.W., and A.S. Richardson, U.S. Patent 2,251,693 (1941);Chem. Abs. 35:6977 (1941).

  28. Osman, F., A.E. Ashour, and A.M. Gad, Monoglycerides. I. Synthesis by Direct Esterification of Fatty Acids and Glycerol.Fette Seifen Anstrichm. 70:331–333 (1968).

    Article  CAS  Google Scholar 

  29. Erciyes, A.T., and H. Civelekoglu, A Simple Laboratory Method for the Esterification of Fatty Acids in the Presence of a Co-Solvent,Bull. Tech. Univ. Istanbul 35:255–266 (1982).

    CAS  Google Scholar 

  30. Emtir, M.M., F.S. Guner, O.S. Kabasakal, A.T. Erciyes, and E. Ekinci, Kinetics of Esterification Reaction Between Glycerol and Oleic Acid in the Presence of Pyridine,Fat Sci. Technol. 97:347–351 (1995).

    CAS  Google Scholar 

  31. Pradhan, V.R., J.W. Tierney, I. Wender, and G.P. Huffman, Catalysis in Direct Coal Luquefaction by Sulfated Metal Oxides,Energy and Fuels 5:497–407 (1991).

    Article  CAS  Google Scholar 

  32. Pradhan, V.R., D.E. Herrick, J.W. Tierney, and I. Wender, Finely Dispersed Iron, Iron-Molybdenum, and Sulfated Iron Oxides as Catalysts for Coprocessing Reactions,5:712–720 (1991).

    Article  CAS  Google Scholar 

  33. Pradhan, V.R., J. Hu, J.W. Tierney, and I. Wender, Activity and Characterization of Anion-Modified Iron (III) Oxides as Catalyst for Direct Liquefaction of Low Pyrite Coals,7:446–454 (1993).

    Article  CAS  Google Scholar 

  34. Lee, J.S., and D.S. Park, Interaction of Pyridine and Ammonia with a Sulfate-Promoted Iron Oxide Catalyst,J. of Catalysis 120:46–54 (1989).

    Article  CAS  Google Scholar 

  35. Jin, T., T. Yamaguchi, and K. Tanabe, Mechanism of Acidity Generation on Sulfur-Promoted Metal Oxides,J. Phys. Chem. 90:4794–4796 (1986).

    Article  CAS  Google Scholar 

  36. Kayo, A., T. Yamaguchi, and K. Tanabe, The Effect of Preparation Method on the Acidic and Catalytic Properties of Iron Oxide,J of Catalysis 83:99–106 (1983).

    Article  CAS  Google Scholar 

  37. Cocks, L.V., and C. van Rede,Laboratory Handbook for Oil and Fat Analysts, Academic Press, London, 1966.

    Google Scholar 

  38. Guner, F.S., A.T. Erciyes, and A. Erdem-Senatalar, Kinetics of Esterification Reaction Between Glycerol and Oleic Acid, inIX.Chemistry and chemical Engineering Symposium, edited by A. Ikizler, Karadeniz Technical University Publications, Trabzon, 1993, p. 446.

    Google Scholar 

  39. Erdem-Senatalar, A., E. Erencek, M. Tuter, and A.T. Erciyes, Effects of Lewis Acid Catalysts on the Esterification Reaction Kinetics of Castor Oil with Oleic Acid,J. Am. Oil Chem. Soc. 71:1035–1037 (1994).

    CAS  Google Scholar 

  40. Erdem-Senatalar, A., E. Erencek, and A.T. Erciyes, Mechanism and Kinetics of the CoCl2-Catalyzed Esterification Reaction of Castor Oil with Oleic Acid,72:891–894 (1995).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Chemical Engineering Department, Istanbul Technical University, Maslak, 80626, Istanbul, Turkey

    F. S. Guner, A. Sirkecioglu, S. Yilmaz, A. T. Erciyes & A. Erdem-Senatalar

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  1. F. S. Guner
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  2. A. Sirkecioglu
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  3. S. Yilmaz
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  4. A. T. Erciyes
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  5. A. Erdem-Senatalar
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Guner, F.S., Sirkecioglu, A., Yilmaz, S. et al. Esterification of oleic acid with glycerol in the presence of sulfated iron oxide catalyst. J Am Oil Chem Soc 73, 347–351 (1996). https://doi.org/10.1007/BF02523429

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  • DOI: https://doi.org/10.1007/BF02523429

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