Abstract
Esterifications of n-amyl alcohol with propionic acid catalyzed by macroporous (Amberlyst-15) and microporous (Dowex 50 W and Amberlite IR-120) polymeric ion-exchange resins were carried out between 333–348 K. When these catalysts were used as commercially available, Amberlyst-15 was observed to be the most effective catalyst with respect to rate constants, but after drying it became the less effective one. The reaction rate increased with increase in catalyst concentration and reaction temperature. Stirrer speed and different mesh sizes had virtually no effect on the rate under the experimental conditions. The effect of divinylbenzene content was examined for the microporous resin Dowex 50W, and the results showed that the propionic acid conversion decreased as the divinylbenzene content was increased. The rate data were correlated with a second-order homogeneous reaction model. The apparent activation energies, reaction enthalpies and entropy values were calculated for each catalyst. Reaction monitoring is simple and fast by volumetric method and the reproducibility of this method was the order of ± %2.54.
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References
Chakrabarti, A. and Sharma, M.M., “Cationic ion exchange resins as catalyst,” Reactive Polymers, 20, 4 (1993).
Coutinho, F.M.B., Souza, R.R. and Gomes, A. S., “Synthesis, characterization and evaluation of sulfonic resins as catalysts,” European Polymer Journal, 40, 1531 (2004).
Gerasimov, Ya., Dreving, V. and Eremin, E., Physical chemistry, Volume: 1, MIR Publishers, Moscow, 507 (1974).
Hart, M., Fuller, G., Brown, D. R., Dale, J.A. and Plant, S., “Sulfonated poly(styrene-co-divinylbenzene) ion-exchange resins: acidities and catalytic activities in aqueous reactions,” Journal of Molecular Catalysis A: Chemical, 182–183, 445 (2002).
Hause, J. E., Principles of chemical kinetics, Wm.C. Brown Publishers, USA, 61 (1997).
Kırbaşlar, Ş. I., Baykal, Z. B. and Dramur, U., “Esterification of acetic acid with ethanol catalysed by an acidic ion-exchange resin,” Turk J. Engin. Environ. Science, 25, 570 (2001).
Kırbaşlar, Ş. I., Terzioğlu, H. and Dramur, U., “Catalytic esterification of methyl alcohol with acetic acid,” Chinese Journal of Chem. Engineering, 9, 93 (2001).
Levenspiel, O., Chemical reaction engineering, John Wiley & Sons, Inc., Canada, 63 (1972).
Lilja, J., Aumo, J., Salmi, T., Murzin, D.Yu., Maki-Arvela, P., Sundell, M., Ekman, K., Peltonen, R. and Vainio, H., “Kinetics of esterification of propanoic acid with methanol over a fibrous polymer-supported sulphonic acid catalyst,” Applied Catalysis A: General, 228, 255 (2002).
Lilja, J., Murzin, D.Yu., Salmi, T., Aumo, J., Maki-Arvela, P. and Sundell, M., “Esterification of different acids over heterogeneous and homogeneous catalysts and correlation with the Taft equation,” Journal of Molecular Catalysis A: Chemical, 182–183, 556 (2002).
Liu, W. T. and Tan, C. S., “Liquid-phase esterification of propionic acid with n-butanol,” Ind. Eng. Chem. Research, 40, 3281 (2001).
Mahajani, S.M., “Reactions of glyoxylic acid with aliphatic alcohols using cationic exchange resins as catalysts,” Reactive & Functional Polymers, 43, 254 (2000).
Park, S.W., Cho, H. B., Suh, D. S. and Kim, C.W., “Esterification of lauric acid with isopropyl alcohol by tricaprylylmethylammonium chloride as a catalyst in a liquid-liquid heterogeneous systems,” Korean J. Chem. Eng., 16, 221 (1999).
Rodriguez, O. and Setinek, K., “Dependence of esterification rates on crosslinking of ion exchange resins used as solid catalysts,” Journal of Catal., 39, 449 (1975).
Roy, R. and Bhatia, S., “Kinetics of esterification of benzyl alcohol with acetic acid catalysed by cation-exchange resin,” Journal of Chem. Technology Biotechnol., 37, 6 (1987).
Weissermel, K. and Arpe, H. J., Industrial organic chemistry, 2nd revised and extended edition, VCH Publishers Inc., New York, 289 (1993).
Xu, Z. P. and Chuang, K. T., “Kinetics of acetic acid esterification over ion exchange catalysts,” The Canadian Journal of Chemical Engineering, 74, 494 (1996).
Yadav, G. D. and Bhagat, R. D., “Experimental and theoretical analysis of Friedel-Crafts acylation of thioanisol to 4-(methythio) actophenone using solid acids,” Journal of Molecular Catalysis A: Chemical, 235, 101 (2005).
Yadav, G. D. and Kulkarni, H. B., “Ion-exchange resin catalysis in the synthesis of isopropyl lactate,” Reactive & Functional Polymers, 44, 164 (2000).
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. Research, 33, 2198 (1994).
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Erdem, B., Cebe, M. Kinetics of esterification of propionic acid with n-amyl alcohol in the presence of cation exchange resins. Korean J. Chem. Eng. 23, 896–901 (2006). https://doi.org/10.1007/s11814-006-0005-3
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DOI: https://doi.org/10.1007/s11814-006-0005-3