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Received March 6, 2012
Accepted March 29, 2012
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Effects of physicochemical properties of ionic liquids on butyl acetate synthesis using Candida antarctica lipase B
Department of Biological Engineering, Inha University, Incheon 402-751, Korea
Korean Journal of Chemical Engineering, November 2012, 29(11), 1610-1614(5), 10.1007/s11814-012-0043-y
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Abstract
Butyl acetate synthesis in imidazolium ring-based ionic liquids (ILs) containing trifluoromethanesulfonate, [TfO]. using Candida antarctica lipase B was demonstrated. Among the ILs tested, the highest butyl acetate production and its initial rate was achieved in [Bmim][TfO]. Compared with tert-butanol, which has been the conventional solvent for transesterification reactions, the initial reaction and conversion rate were approximately 1.4 and 1.1 times, respectively, higher. Some physicochemical parameters, such as viscosity, hydrophobicity, and partial charge of ILs were examined to find the relations which influence reaction rates. Although only weak correlations between each parameter and enzyme activity were found, it shed a light on understanding the generalization complexity of ILs for enzyme reaction.
References
Venimadhavan G, Malone MF, Doherty MF, Ind. Eng. Chem. Res., 38(3), 714 (1999)
Steinigeweg S, Gmehling J, Ind. Eng. Chem. Res., 41(22), 5483 (2002)
Welsh FW, Murray WD, Williams RE, Crit. Rev. Biotechnol., 9, 105 (1989)
Ben Salah R, Ghamghui H, Miled N, Mejdoub H, Gargouri Y, J. Biosci. Bioeng., 103(4), 368 (2007)
Leblanc D, Morin A, Gu D, Zhang XM, Bisaillon JG, Paquet M, Dubeau H, Biotechnol. Lett., 20(12), 1127 (1998)
BourgGarros S, Razafindramboa N, Pavia AA, J. Am. Oil.Chem. Soc., 74, 1471 (1997)
Krishna SH, Manohar B, Divakar S, Prapulla SG, Karanth NG, Enzyme Microb. Technol., 26(2-4), 131 (2000)
Janssen AEM, Vanderpadt A, Vantriet K, Biotechnol. Bioeng., 42, 953 (1993)
Anderson EM, Karin M, Kirk O, Biocatal. Biotransfor., 16, 181 (1998)
Rotticci D, Rotticci-Mulder JC, Denman S, Norin T, Hult K, Chembiochem., 2, 766 (2001)
Welton T, Chem. Rev., 99(8), 2071 (1999)
Sheldon RA, Lau RM, Sorgedrager MJ, van Rantwijk F, Seddon KR, Green Chem., 4, 147 (2002)
Seddon KR, J. Chem. Technol. Biotechnol., 68(4), 351 (1997)
Van Gerpen J, Fuel Process. Technol., 86(10), 1097 (2005)
Flores MV, Naraghi K, Engasser JM, Halling PJ, Biotechnol. Bioeng., 78(7), 814 (2002)
Moon YH, Lee SM, Ha SH, Koo YM, Korean J. Chem. Eng., 23(2), 247 (2006)
Ha SH, Menchavez RN, Koo YM, Korean J. Chem. Eng., 27(5), 1360 (2010)
Lee SH, Dang DT, Ha SH, Chang WJ, Koo YM, Biotechnol. Bioeng., 99(1), 1 (2008)
Ha SH, Lan MN, Lee SH, Hwang SM, Koo YM, Enzyme Microb. Technol., 41(4), 480 (2007)
Lee SH, Koo YM, Ha SH, Korean J. Chem. Eng., 25(6), 1456 (2008)
Widegren JA, Laesecke A, Magee JW, Chem. Commun., 1610 (2005)
Tetko IV, Tanchuk VY, J. Chem. Inf. Comp. Sci., 42, 1136 (2002)
Machatha SG, Yalkowsky SH, Int. J. Pharm., 294, 185 (2005)
Chrzanowski L, Stasiewicz M, Owsianiak M, Szulc A, Piotrowska-Cyplik A, Olejnik-Schmidt AK, Wyrwas B, Biodegradation., 20, 661 (2009)
Sambasivarao SV, Acevedo O, J. Chem. Theory Comput., 5, 1038 (2009)
Lee ME, van der Vegt NFA, J. Chem. Phys., 122, 114509 (2005)
Ganske F, Bornscheuer UT, J. Mol. Catal. B-Enzym., 36, 40 (2005)
Ganske F, Bornscheuer UT, Organic. Lett., 7, 3097 (2005)
Yang Z, Pan WB, Enzyme Microb. Technol., 37(1), 19 (2005)
Ha SH, Koo YM, Korean J. Chem. Eng., 28(11), 2095 (2011)
Berthod A, Ruiz-Angel M, Carda-Broch S, J. Chromatogr. A., 1184, 6 (2008)
Lee SH, Lee SB, Chem. Commun., 3469 (2005)
Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168 (1996)
Ha SH, Mai NL, Koo YM, Process. Biochem., 45, 1899 (2010)
Martinez S, Garriga R, Perez P, Gracia M, J. Chem. Eng. Data., 45, 1182 (2000)
Lozano P, De Diego T, Carrie D, Vaultier M, Iborra JL, Biotechnol. Lett., 23(18), 1529 (2001)
Villela M, Stillger T, Muller M, Liese A, Wandrey C, Angew.Chem. Int. Ed., 42, 2993 (2003)
Weingartner H, Cabrele C, Herrmann C, Physical Chemistry Chemical Physics, 14, 415 (2012)
Laane C, Boeren S, Vos K, Veeger C, Biotechnol. Bioeng., 102(1), 2 (2009)
Lau RM, Sorgedrager MJ, Carrea G, Van Rantwijk F, Secundo F, Sheldon RA, Green Chem., 6, 483 (2004)
Degoede ATJW, Benckhuijsen W, Vanrantwijk F, Maat L, Vanbekkum H, Recl. Trav. Chim. Pay. B., 112, 567 (1993)
Ha SH, Lee SH, Dang DT, Kwon MS, Chang WJ, Yu YJ, Byun IS, Koo YM, Korean J. Chem. Eng., 25(2), 291 (2008)
Anderson JL, Ding J, Welton T, Armstrong DW, J. Am. Chem. Soc., 124(47), 14247 (2002)
Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ, J. Am. Chem. Soc., 125(14), 4125 (2003)
Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD, Green Chem., 5, 443 (2003)
Steinigeweg S, Gmehling J, Ind. Eng. Chem. Res., 41(22), 5483 (2002)
Welsh FW, Murray WD, Williams RE, Crit. Rev. Biotechnol., 9, 105 (1989)
Ben Salah R, Ghamghui H, Miled N, Mejdoub H, Gargouri Y, J. Biosci. Bioeng., 103(4), 368 (2007)
Leblanc D, Morin A, Gu D, Zhang XM, Bisaillon JG, Paquet M, Dubeau H, Biotechnol. Lett., 20(12), 1127 (1998)
BourgGarros S, Razafindramboa N, Pavia AA, J. Am. Oil.Chem. Soc., 74, 1471 (1997)
Krishna SH, Manohar B, Divakar S, Prapulla SG, Karanth NG, Enzyme Microb. Technol., 26(2-4), 131 (2000)
Janssen AEM, Vanderpadt A, Vantriet K, Biotechnol. Bioeng., 42, 953 (1993)
Anderson EM, Karin M, Kirk O, Biocatal. Biotransfor., 16, 181 (1998)
Rotticci D, Rotticci-Mulder JC, Denman S, Norin T, Hult K, Chembiochem., 2, 766 (2001)
Welton T, Chem. Rev., 99(8), 2071 (1999)
Sheldon RA, Lau RM, Sorgedrager MJ, van Rantwijk F, Seddon KR, Green Chem., 4, 147 (2002)
Seddon KR, J. Chem. Technol. Biotechnol., 68(4), 351 (1997)
Van Gerpen J, Fuel Process. Technol., 86(10), 1097 (2005)
Flores MV, Naraghi K, Engasser JM, Halling PJ, Biotechnol. Bioeng., 78(7), 814 (2002)
Moon YH, Lee SM, Ha SH, Koo YM, Korean J. Chem. Eng., 23(2), 247 (2006)
Ha SH, Menchavez RN, Koo YM, Korean J. Chem. Eng., 27(5), 1360 (2010)
Lee SH, Dang DT, Ha SH, Chang WJ, Koo YM, Biotechnol. Bioeng., 99(1), 1 (2008)
Ha SH, Lan MN, Lee SH, Hwang SM, Koo YM, Enzyme Microb. Technol., 41(4), 480 (2007)
Lee SH, Koo YM, Ha SH, Korean J. Chem. Eng., 25(6), 1456 (2008)
Widegren JA, Laesecke A, Magee JW, Chem. Commun., 1610 (2005)
Tetko IV, Tanchuk VY, J. Chem. Inf. Comp. Sci., 42, 1136 (2002)
Machatha SG, Yalkowsky SH, Int. J. Pharm., 294, 185 (2005)
Chrzanowski L, Stasiewicz M, Owsianiak M, Szulc A, Piotrowska-Cyplik A, Olejnik-Schmidt AK, Wyrwas B, Biodegradation., 20, 661 (2009)
Sambasivarao SV, Acevedo O, J. Chem. Theory Comput., 5, 1038 (2009)
Lee ME, van der Vegt NFA, J. Chem. Phys., 122, 114509 (2005)
Ganske F, Bornscheuer UT, J. Mol. Catal. B-Enzym., 36, 40 (2005)
Ganske F, Bornscheuer UT, Organic. Lett., 7, 3097 (2005)
Yang Z, Pan WB, Enzyme Microb. Technol., 37(1), 19 (2005)
Ha SH, Koo YM, Korean J. Chem. Eng., 28(11), 2095 (2011)
Berthod A, Ruiz-Angel M, Carda-Broch S, J. Chromatogr. A., 1184, 6 (2008)
Lee SH, Lee SB, Chem. Commun., 3469 (2005)
Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168 (1996)
Ha SH, Mai NL, Koo YM, Process. Biochem., 45, 1899 (2010)
Martinez S, Garriga R, Perez P, Gracia M, J. Chem. Eng. Data., 45, 1182 (2000)
Lozano P, De Diego T, Carrie D, Vaultier M, Iborra JL, Biotechnol. Lett., 23(18), 1529 (2001)
Villela M, Stillger T, Muller M, Liese A, Wandrey C, Angew.Chem. Int. Ed., 42, 2993 (2003)
Weingartner H, Cabrele C, Herrmann C, Physical Chemistry Chemical Physics, 14, 415 (2012)
Laane C, Boeren S, Vos K, Veeger C, Biotechnol. Bioeng., 102(1), 2 (2009)
Lau RM, Sorgedrager MJ, Carrea G, Van Rantwijk F, Secundo F, Sheldon RA, Green Chem., 6, 483 (2004)
Degoede ATJW, Benckhuijsen W, Vanrantwijk F, Maat L, Vanbekkum H, Recl. Trav. Chim. Pay. B., 112, 567 (1993)
Ha SH, Lee SH, Dang DT, Kwon MS, Chang WJ, Yu YJ, Byun IS, Koo YM, Korean J. Chem. Eng., 25(2), 291 (2008)
Anderson JL, Ding J, Welton T, Armstrong DW, J. Am. Chem. Soc., 124(47), 14247 (2002)
Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ, J. Am. Chem. Soc., 125(14), 4125 (2003)
Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD, Green Chem., 5, 443 (2003)
