Abstract
Hexyl acetate, a short-chain ester with fruity odor, is a significant green note flavor compound that is widely used in the food industry. The ability of immobilized lipase from Rhizomucor miehei (Lipozyme IM-77) to catalyze the transesterification of hexanol with triacetin in supercritical carbon dioxide was investigated in this study. Response surface methodology and a 3-level-3-factor fractional factorial design were adopted to evaluate the effects of synthesis variables, such as reaction time (30 to 90 min), temperature (35 to 55°C), and pressure (1500 to 3500 psi), on percent molar conversion of hexyl acetate. The results showed that reaction time and pressure were the most important parameters and temperature had less effect on percent molar conversion. Based on canonical analysis, optimal synthesis conditions were as follows: reaction time 69.0 min, synthesis temperature 46.7°C, pressure 2640 psi. The predicted value was 75.6% and the actual value was 77.3% molar conversion.
Similar content being viewed by others
References
Bauer, K., D. Garbe, and H. Surburg, Common Fragrance and Flavor Materials, VCH Publishers, New York, 1990.
Bourg-Garros, S., N. Razafindramboa, and A.A. Pavia, Synthesis of (Z)-3-Hexen-1-yl Butyrate in Hexane and Solvent-Free Medium Using Mucor miehei and Candida antarctica Lipases, J. Am. Oil Chem. Soc. 74:1471–1475 (1997).
Bourg-Garros, S., N. Razafindramboa, and A.A. Pavia, Optimization of Lipase-Catalyzed Synthesis of (Z)-3-Hexen-1-yl Acetate by Direct Esterification in Hexane and Solvent-Free Medium, Enzyme Microb. Technol. 22:240–245 (1998).
Bornscheuer, U.T., and R.J. Kazlauskas, Hydrolases in Organic Synthesis—Rogio- and Stereoselective Biotransformations, Wiley-VCH, Weinheim, 1999.
Miyawaki, O., and K. Nakamura, Enzymatic Reaction in Supercritical Fluid, in Lipid Biotechnology, edited by T.-M. Kuo and H.W. Gardner, Marcel Dekker, New York, 2002, pp. 698–702.
Chulalaksananukul, W., J.-S. Condoret, and D. Combes, Geranyl Acetate Synthesis by Lipase-Catalyzed Transesterification in Supercritical Carbon Dioxide, Enzyme Microb. Technol. 15:691–698 (1993).
Sereti, V., H. Stamatis, and F.N. Kolisis, Improved Stability and Reactivity of Fusarium solani Cutinase in Supercritical CO2, Biotechnol. Tech. 11:661–665 (1997).
Krishna Hari, S., B. Manohar, S. Divakar, and N.G. Karanth, Lipase-Catalyzed Synthesis of Isoamyl Butyrate: Optimization by Response Surface Methodology, J. Am. Oil Chem. Soc. 76:1483–1488 (1999).
Krishna, S.H., B. Manohar, S. Divakar, S.G. Prapulla, and N.G. Karanth, Optimization of Isoamyl Acetate Production by Using Immobilized Lipase from Mucor miehei by Response Surface Methodology, Enzyme Microb Technol. 26:131–136 (2000).
Shieh, C.-J., and S.-W. Chang, Optimized Synthesis of Lipase-Catalyzed Hexyl Acetate in n-Hexane by Response Surface Methodology, J. Agric. Food Chem. 49:1203–1207 (2001).
Yan, Y., U.T. Bornscheuer, G. Stadler, S. Lutz-Wahl, M. Reuss, and R.D. Schmid, Production of Sugar Fatty Acid Esters by Enzymatic Esterification in a Stirred-Tank Membrane Reaction: Optimization of Parameters by Response Surface Methodology, J. Am. Oil Chem. Soc. 78:147–152 (2001).
Cochran, W.G., and G.M. Cox, Experimental Designs, John Wiley & Sons, New York, 1992.
SAS, SAS User’s Guide, SAS Institute, Inc., Cary, NC, 1990.
Krishna, S.H., and N.G. Karanth, Lipase-Catalyzed Synthesis of Isoamyl Butyrate—A Kinetic Study, Biochim. Biophys. Acta 1547:262–267 (2001).
Ott, L, An Introduction to Statistical Methods and Data Analysis, PWS-Kent Publishing, Boston, 1988.
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Yu, ZR., Chang, SW., Wang, HY. et al. Study on synthesis parameters of lipase-catalyzed hexyl acetate in supercritical CO2 by response surface methodology. J Amer Oil Chem Soc 80, 139–144 (2003). https://doi.org/10.1007/s11746-003-0666-4
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-003-0666-4