Enzymatic Synthesis of Sugar Fatty Acid Esters

In Sang Yoo; Sang Joon Park; Hyon Hee Yoon

Journal of Industrial and Engineering Chemistry, Vol.13, No.1, 1-6, January, 2007

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Enzymatic Synthesis of Sugar Fatty Acid Esters

In Sang Yoo , Sang Joon Park , and Hyon Hee Yoon^†

Department of Chemical Engineering, Kyungwon University, Kyunggi 461-701, Korea

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Enzymatic synthesis of sugar fatty acid esters was performed in an organic solvent using an immobilized Candida antartica lipase and various sugars and oleic acid as substrates. A high solubility of the sugar in the solvent was needed for a high sugar ester yield. Among the sugars and solvents tested in this study, the highest yield (98 %) was obtained when xylitol and 2-methyl 2-butanol were used as the sugar and solvent, respectively. The optimal sugar-to-fatty acid ratio was in the range from 2:1 to 3:1 for a high conversion and minimization of the residual fatty acid concentration. The water content in the reaction medium was critical and had to be kept below 0.15 % to obtain a high sugar ester yield. The half life cycle of the enzyme used in this study was observed after 9-repeated uses. In a pilot reaction test, water formed during the reaction was effectively removed by recycling the reaction medium through a molecular sieve column outside the reactor; thus, a high sugar ester yield was obtained.

Keywords:sugar ester;Candida antartica lipase;solubility;water content;enzyme stability

[References]

Akoh CC, Swanson BG, Carbohydrate Polyesters as Fat Substitutes, Marcel Dekker, Inc,. New York, 37 (1994)
Sarney DB, Vulfson EV, Trends Biotechnol., 13, 164 (1995)
Seino H, Uchibori T, Nishitani T, Inamasu S, J. Am. Oil Chem. Soc., 61, 1761 (1984)
Therisod M, Klibanov AM, J. Am. Ceram. Soc., 108, 5638 (1986)
Oguntimein OB, Erdmann H, Schmid RD, Biotechnol. Lett., 15, 175 (1993)
Lay L, Panza L, Khitri S, Tirendi S, Carbohydr. Res., 291, 197 (1996)
Coulon D, Ismail A, Girardin M, Ghoul M, Trends Biotechnol., 51, 115 (1996)
Adachi S, Kobayashi T, J. Biosci. Bioeng., 99(2), 87 (2005)
Halling PJ, Enzyme Microb. Technol., 16(3), 178 (1994)
Chamouleau F, Coulon D, Girardin M, Ghoul M, J. Mol. Catal. B-Enzym., 11, 949 (2001)
Ducret A, Giroux A, Trani M, Lortie R, Biotechnol. Bioeng., 48(3), 214 (1995)
Yan YC, Bornscheuer UT, Cao LQ, Schmid RD, Enzyme Microb. Technol., 25(8-9), 725 (1999)
Rich JO, Bedell BA, Dordick JS, Biotechnol. Bioeng., 45(5), 426 (1995)

[Referenced By]

[Related Articles]

[1] Akoh CC, Swanson BG, Carbohydrate Polyesters as Fat Substitutes, Marcel Dekker, Inc,. New York, 37 (1994)

[2] Sarney DB, Vulfson EV, Trends Biotechnol., 13, 164 (1995)

[3] Seino H, Uchibori T, Nishitani T, Inamasu S, J. Am. Oil Chem. Soc., 61, 1761 (1984)

[4] Therisod M, Klibanov AM, J. Am. Ceram. Soc., 108, 5638 (1986)

[5] Oguntimein OB, Erdmann H, Schmid RD, Biotechnol. Lett., 15, 175 (1993)

[6] Lay L, Panza L, Khitri S, Tirendi S, Carbohydr. Res., 291, 197 (1996)

[7] Coulon D, Ismail A, Girardin M, Ghoul M, Trends Biotechnol., 51, 115 (1996)

[8] Adachi S, Kobayashi T, J. Biosci. Bioeng., 99(2), 87 (2005)

[9] Halling PJ, Enzyme Microb. Technol., 16(3), 178 (1994)

[10] Chamouleau F, Coulon D, Girardin M, Ghoul M, J. Mol. Catal. B-Enzym., 11, 949 (2001)

[11] Ducret A, Giroux A, Trani M, Lortie R, Biotechnol. Bioeng., 48(3), 214 (1995)

[12] Yan YC, Bornscheuer UT, Cao LQ, Schmid RD, Enzyme Microb. Technol., 25(8-9), 725 (1999)

[13] Rich JO, Bedell BA, Dordick JS, Biotechnol. Bioeng., 45(5), 426 (1995)