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Catalysis in Green Chemistry and Engineering

Published 4 issues per year

ISSN Print: 2572-9896

ISSN Online: 2572-990X

H-Index: 2

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HETEROGENEOUS SYNTHESIS OF ETHYL BUTYRATE: PARAMETER OPTIMIZATION AND KINETIC STUDIES

Volume 2, Issue 1, 2019, pp. 55-65
DOI: 10.1615/CatalGreenChemEng.2019030634
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ABSTRACT

This study investigates the reaction of butyric acid with ethanol using heterogeneous catalyst amberlyst-15. Experiments were conducted in a three-necked glass reactor in the temperature range of 323 to 353 K with provision for stirrer and condenser. Investigated experimental parameters were temperature, mole ratios of alcohol and acid used, loading of catalyst, stirrer speed, and amount of molecular sieves. The butyric acid equilibrium conversion reached 92.8% at 353 K at ethanol-to-butyric acid mole ratio of unity; amount of catalyst added, 3 g; molecular sieves, 4 g; and stirrer speed, 450 rpm. Equilibrium conversion and rate of forward reaction increased with temperature and catalyst loading. Addition of molecular sieves appeared to have a favorable effect on equilibrium conversion since it removed water formed in the reaction. Also, varying speeds of the stirrer showed the absence of resistance for external mass transfer during the reaction. The surface reaction rate constant was predicted using the Langmuir-Hinshelwood-Hougen-Watson model and was used to analyze thermodynamic parameters. Scanning electron microscopy and energy dispersive X-ray analysis of the resin catalyst after the esterification shows that the catalyst was thermally and mechanically stable for the reaction temperatures.

REFERENCES
  1. Aragao, V.C., Porto, M.R.A., Burkert, C.A.V., Kalil, S.J., and Burkert, J.F.D., Response Surface Methodology Approach for the Synthesis of Ethyl Butyrate, Food Technol. Biotechnol, vol. 49, pp. 103-110,2010.

  2. Chakrabarti, A. and Sharma, M.M., Cationic Ion Exchange Resins as Catalyst, Reactive Polymers, vol. 20, nos. 1-2, pp. 1-45, 1993.

  3. Clark, J.H., Solid Acid Catalysts for Green Chemistry, Accounts Chem. Res., vol. 35, pp. 791-797, 2002.

  4. Dange, P.N., Sharma, A., and Rathod, V.K., Synthesis of Methyl Butyrate Using Heterogeneous Catalyst: Kinetic Studies, Catal. Lett., vol. 144, pp. 1537-1546, 2014.

  5. de Jong, M.C., Feijt, R., Zondervan, E., Nijhuis, T.A., and de Haan, A.B., Reaction Kinetics of the Esterification of Myristic Acid with Isopropanol and n-Propanol Using p-Toluene Sulphonic Acid as Catalyst, Appl. Catal. A: General, vol. 365, pp. 141-147, 2009.

  6. De Silva, E.C.L., Bamunusingha, B.A.N.N., and Gunasekera, M.Y., Heterogeneous Kinetic Study for Esterification of Acetic Acid with Ethanol, Engineer, vol. 47, pp. 9-15, 2014.

  7. Dijs, I.J., van Ochten, H.L.F., van der Heijden, A.J.M., Geus, J.W., and Jenneskens, L.W., The Catalytic Performance of Sulphonated Cross-Linked Polystyrene Beads in the Formation of Isobornyl Acetate, Appl. Catal. A: General, vol. 241, pp. 185-203,2003.

  8. Edidiong, O., Habiba, S., and Gobina, E., Batch Process Esterification of Lactic Acid Catalysed by Cation-Exchange Resins for the Production of Environmental-Friendly Solvent, World Congress on Engineering and Computer Science Proc., San Francisco, pp. 590-594,2015.

  9. Fogler, S.H., Elements of Chemical Engineering, 3rd Edition, New Jersey: Prentice Hall, pp. 581-601, 1999.

  10. Fuchigami, Y., Hydrolysis of Methyl Acetate in Distillation Column Packed with Reactive Packing of Ion Exchange Resin, J. Chem. Eng. Japan, vol. 23, pp. 354-359, 1990.

  11. Gharat, N. and Rathod, V.K., Enzyme Catalyzed Trans-Esterification of Waste Cooking Oil with Di-Methyl Carbonate, J. Molecular Catal. B: Enzymatic, vol. 88, pp. 36-40,2013.

  12. Grob, S. and Hasse, H., Reaction Kinetics of the Homogeneously Catalyzed Esterification of 1-Butanol with Acetic Acid in a Wide Range of Initial Compositions, Industrial Eng. Chem. Res., vol. 45, no. 6, pp. 1869-1874, 2006.

  13. Jua, I.B., Limb, H.W., Jeona, W., Suha, D.J., Park, M.J., and Suh, Y.W., Kinetic Study of Catalytic Esterification of Butyric Acid and n-Butanol over Dowex 50Wx8-400, Chem. Eng. J, vol. 168, pp. 293-300,2011.

  14. Khire, S., Bhagwat, P.V., Fernandes, M., Gangundi, P.B., and Vadalia, H., Esterification of Lower Aliphatic Alcohols with Acetic Acid in Presence of Different Acid Catalysts, Indian J. Chem. Technol, vol. 19, pp. 342-350,2012.

  15. Kumar, A. and Kanwar, S.S., Synthesis of Ethyl Ferulate in Organic Medium Using Celite-Immobilized Lipase, Bio-Resour. Technol., vol. 102, no. 3, pp. 2162-2167, 2011.

  16. Larock, R.C., Comprehensive Organic Transformations, 2nd Edition, New York: VCH, pp. 563-583, 1999.

  17. Liaquat, M. and Apenten, R.K.O., Synthesis of Low Molecular Weight Flavor Esters Using Plant Seedling Lipases in Organic Media, J. FoodSci., vol. 65, pp. 295-299, 2000.

  18. Liu, Y.J., Lotero, E., and Goodwin Jr., J.G., Effect of Water on Sulfuric Acid Catalyzed Esterification, J. Molecular Catal. A: General, vol. 245, pp. 132-140, 2006.

  19. Liu, Y. J., Lotero, E., and Goodwin Jr., J.G., A Comparison of the Esterification of Acetic Acid with Methanol Using Heterogeneous versus Homogeneous Acid Catalysis, J. Catal., vol. 242, pp. 278-286, 2006.

  20. Lotero, E., Liu, Y. J., Lopez, D.E., Suwannakarn, K., Bruce, D.A., and Goodwin Jr., J.G., Synthesis of Biodiesel via Acid Catalysis, Industrial Eng. Chem. Resour., vol. 44, pp. 5353-5363, 2005.

  21. Lux, S., Winkler, T., Berger, G., and Siebenhofer M., Kinetic Study of the Heterogeneous Catalytic Esterification of Acetic Acid with Methanol Using Amberlyst-15, Chem. Biochem. Eng. Quart., vol. 29, pp. 549-557,2015.

  22. Paludo, N., Alves, J.S., Altmann, C., Ayub, M.A.Z., Lafuente, R.F., and Rodrigues, R.C., The Combined Use of Ultrasound and Molecular Sieves Improves the Synthesis of Ethyl Butyrate Catalyzed by Immobilized Thermomyces Lanuginosus Lipase, Ultrasonics Sonochem., vol. 9, pp. 89-94,2015.

  23. Pappu, V.K., Kanyi, S.V., Santhanakrishnan, A., Lira, C.T., and Miller, D.J., Butyric Acid Esterification Kinetics over Amberlyst Solid Acid Catalysts: The Effect of Alcohol Carbon Chain Length, Bio-Resour. Technol., vol. 130, pp. 793-797,2013.

  24. Ronnback, R., Salmi, T., Vuori, A., Haario, H., Lehtonen, J., Sundqvist, A., and Tirronen, E., Development of a Kinetic Model for the Esterification of Acetic Acid with Methanol in the Presence of a Homogenous Acid Catalyst, Chem. Eng. Sci, vol. 52, pp. 3369-3381, 1997.

  25. Sanchez, N., Coteron, A., Martinez, M., and Aracil, J., Kinetic Analysis and Modeling of the Esterification of Oleic Acid and Oleyl Alcohol Using Cobalt Chloride as Catalyst, Industrial Eng. Chem. Res, vol. 31, pp. 1985-1988, 1992.

  26. Savkovic-Stevanovic, J., Misic-Vukovik, M., Boncic-Caricic, G., Trisovic, B., and Jezdic, S., Reactive Distillation with Ion Exchanger, Separation Sci. Technol., vol. 27, pp. 613-630, 1992.

  27. Sharma, Y.C. and Singh, B., Advancements in Solid Acid Catalysts for Eco-Friendly and Economically Viable Synthesis of Biodiesel, Bio-Fuels, Bio-Products Bio-Refining, vol. 5, pp. 69-92, 2011.

  28. Smith, M.B. and March, J., Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th Edition, New York: John Wiley & Sons, 2001.

  29. Thomas, M. and John, S., Solid Acid Catalysts, Sci. American, vol. 266, no. 4, pp. 112-118, 1992.

  30. Vievelle, C., Moulooungui, Z., and Gaset, A., Kinetics of the Oleic Acid Esterification by Methanol in the Presence of Solid Catalyst, Industrial Eng. Chem. Res, vol. 32, pp. 2065-2068, 1993.

  31. Wang, J., Gu, S., Pang, N., Wang, F., and Wu, F., A Study of the Esterification of Caffeic Acid with Methanol Using p-Toluenesulfonic Acid as a Catalyst, J. Siberian Chem. Soc., vol. 78, pp. 1023-1034, 2013.

  32. Yadav, G.D. and Mehta, P.H., Heterogeneous Catalysis in Esterification Reactions: Preparation of Phenethyl Acetate and Cyclohexyl Acetate by Using a Variety of Solid Acidic Catalysts, Industrial Eng. Chem. Res., vol. 33, pp. 2198-2208, 1994.

  33. Yu, W., Hidajat, K., and Ray, A.K., Determination of Adsorption and Kinetic Parameters for Methyl Acetate Esterification and Hydrolysis Reaction Catalyzed by Amberlyst-15, Appl. Catal. A: General, vol. 260, pp. 191-205,2004.

  34. Zhang, Y., Ma, L., and Yang, J., Kinetics of Esterification of Lactic Acid with Ethanol Catalyzed by Cation-Exchange Resins, J. Reactive Functional Polymers, vol. 61, pp. 101-114, 2004.

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