Abstract
Enzymatic synthesis of ethyl lactate was studied in organic solvents and in ionic liquids to determine optimal media for the reaction, and to investigate the effect of water content on the ester yield. Experiments proved that Cyphos 202 ionic liquid is the best solvent affording the highest ethyl lactate yields. Furthermore, 20 times less enzyme sufficed to carry out the reaction in this ionic liquid compared to organic solvents; ionic liquid could be applied as solvent. Using water removal, the ester yield decreased since a side reaction, dimerization of lactic acid, occurred as well. In contrast to these results, without water removal, the produced water was partly consumed by the decomposition of lactoyllactic acid to free lactic acid, increasing thus the substrate concentration of the mixture and enhancing the ester yield.
References
Bélafi-Bakó, K., Badr, A. K., Nemestóthy, N., Ehrenstein, U., & Gubicza, L. (2003). Kinetics of ethyl acetate formation by lipase in organic solvent and solvent-free system. Chemical Papers, 57, 278–281.
Delgado, P., Sanz, M. T., & Beltrán, S. (2008). Pervaporation study for different binary mixtures in the esterification system of lactic acid with ethanol. Separation and Purification Technology, 64, 78–87. DOI: 10.1016/j.seppur.2008.08.002.
Eugin, A., Haluk, H., & Gurkan, K. (2003). Production of lactic acid esters catalysed by heteropoly acid supported over ion-exchange resins. Green Chemistry, 5, 460–466. DOI: 10.1039/b303327a.
Fehér, E., Major, B., Bélafi-Bakó, K., & Gubicza, L. (2009). Semi-continuous enzymatic production and membrane assisted separation of isoamyl acetate in alcohol — ionic liquid biphasic system. Desalination, 241, 8–13. DOI: 10.1016/j.desal.2007.11.080.
Gubicza, L., Bélafi-Bakó, K., Fehér, E., & Fráter, T. (2008). Waste-free process for continuous flow enzymatic esterification in ionic liquid medium. Green Chemistry, 10, 1284–1287. DOI: 10.1039/b810009h.
Major, B., Kelemen-Horváth, I., Csanádi, Z., Bélafi-Bakó, K., & Gubicza, L. (2009). Microwave assisted enzymatic esterification of lactic acid and ethanol in phosphonium type ionic liquids as co-solvents. Green Chemistry, 11, 614–616. DOI: 10.1039/b820575b.
Roenne, T. H., Xu, X., & Tan, T. (2005). Lipase-catalysed esterification of lactic acid with straight-chain alcohols. Journal of the American Oil Chemists’ Society, 82, 881–884. DOI: 10.1007/s11746-005-1159-1.
Vu, D. T., Kolah, A. K., Asthana, N. S., Peereboom, L., Lira, C. T., & Miller, D. J. (2005). Oligomer distribution in concentrated lactic acid solutions. Fluid Phase Equilibria, 236, 125–135. DOI: 10.1016/j.fluid.2005.06.021.
Yang, Z., & Pan, W. (2005). Ionic liquids: Green solvents for nonaqueous biocatalysis. Enzyme and Microbial Technology, 37, 19–28. DOI: 10.1016/j.enzmictec.2005.02.014.
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Major, B., Németh, G., Bélafi-Bakó, K. et al. Unique role of water content in enzymatic synthesis of ethyl lactate using ionic liquid as solvent. Chem. Pap. 64, 261–264 (2010). https://doi.org/10.2478/s11696-009-0117-4
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DOI: https://doi.org/10.2478/s11696-009-0117-4