Abstract
Synthesis of a fatty acid ethyl ester via the lipase-catalyzed transesterification of acid oil and ethanol was investigated in a continuous reactor. Lipozyme TL IM was employed as the immobilized lipase. This immobilized lipase derived from Thermomyces lanuginosus was purchased from Novozymes (Seoul, Korea). The acid oil was prepared by the acidification of soapstock formed as a by-product during the refining of rice bran oil. The parameters investigated were water content, temperature, and molar ratio of substrates. The relative activity of Lipozyme TL IM was assessed during the repeated use of the immobilized lipase. The water content of the substrate had a considerable effect on the yield and the optimum water content was 4 %. The optimum temperature and molar ratio of acid oil to ethanol were 20 °C and 1:4, respectively. The maximum yield of approximately 92 % was achieved under the optimum conditions. The corresponding compositions were 92 % fatty acid ethyl esters, 3 % fatty acids, and 5 % acylglycerols. When glycerol formed during the reaction was removed by intermittent washing with ethanol, the relative activity of lipase was maintained over 82 % for a total usage of 27 cycles. For a mean residence time of 4 h, the half-life times of Lipozyme TL IM on the control (unwashed) and treatment (washed) were 39 and 45 cycles, respectively.
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References
Robles-Medina A, González-Moreno PA, Esteban-Cerdán L, Molina-Grima E (2009) Biocatalysis: towards ever greener biodiesel production. Biotechnol Adv 27:398–408
Körbitz W (1999) Biodiesel production in Europe and North America, an encouraging prospect. Renew Energ 16:1078–1083
Tan T, Lu J, Nie K, Deng L, Wang F (2010) Biodiesel production with immobilized lipase: a review. Biotechnol Adv 28:628–634
Vasudevan PT, Briggs M (2008) Biodiesel production-current state of the art and challenges. J Ind Microbiol Biot 35:421–430
Al-Zuhair S (2007) Production of biodiesel: possibilities and challenges. Biofuel Bioprod Bior 1:57–66
Salis A, Pinna M, Monduzzi M, Solinas V (2005) Biodiesel production from triolein and short chain alcohols through biocatalysis. J Biotechnol 119:291–299
Akoh CC, Swanson BG (1988) Base catalyzed transesterification of vegetable oils 1. J Food Process Pres 12:139–149
Freedman B, Pryde EH, Mounts TL (1984) Variables affecting the yields of fatty esters from transesterified vegetable oils. J Am Oil Chem Soc 61:1638–1643
Szczęsna Antczak M, Kubiak A, Antczak T, Bielecki S (2009) Enzymatic biodiesel synthesis–Key factors affecting efficiency of the process. Renew Energ 34:1185–1194
Ognjanovic N, Bezbradica D, Knezevic-Jugovic Z (2009) Enzymatic conversion of sunflower oil to biodiesel in a solvent-free system: process optimization and the immobilized system stability. Bioresource Technol 100:5146–5154
Du W, Xu Y, Liu D, Zeng J (2004) Comparative study on lipase-catalyzed transformation of soybean oil for biodiesel production with different acyl acceptors. J Mol Catal B Enzym 30:125–129
Al-Zuhair S, Jayaraman KV, Krishnan S, Chan W-H (2006) The effect of fatty acid concentration and water content on the production of biodiesel by lipase. Biochem Eng J 30:212–217
Kaieda M, Samukawa T, Kondo A, Fukuda H (2001) Effect of methanol and water contents on production of biodiesel fuel from plant oil catalyzed by various lipases in a solvent-free system. J Biosci Bioeng 91:12–15
Wang L, Du W, Liu D, Li L, Dai N (2006) Lipase-catalyzed biodiesel production from soybean oil deodorizer distillate with absorbent present in tert-butanol system. J Mol Catal B Enzym 43:29–32
Lara Pizarro AV, Park EY (2003) Lipase-catalyzed production of biodiesel fuel from vegetable oils contained in waste activated bleaching earth. Process Biochem 38:1077–1082
Tüter M, Aksoy HA, Gılbaz EE, Kurşun E (2004) Synthesis of fatty acid esters from acid oils using lipase B from Candida antarctica. Eur J Lipid Sci Tech 106:513–517
Xu X, Balchen S, Hoy CE, Adler-Nissen J (1998) Production of specific-structured lipids by enzymatic interesterification in a pilot continuous enzyme bed reactor. J Am Oil Chem Soc 75:1573–1579
Chen HC, Ju HY, Wu TT, Liu YC, Lee CC, Chang C, Chung YL, Shieh CJ (2011) Continuous production of lipase-catalyzed biodiesel in a packed-bed reactor: optimization and enzyme reuse study. J Biomed Biotechnol 2011. doi:10.1155/2011/950725
Sdana A (1980) A deactivation model for immobilized and soluble enzymes. Biotechnol Lett 2:279–284
Kusdiana D, Saka S (2004) Effects of water on biodiesel fuel production by supercritical methanol treatment. Bioresource Technol 91:289–295
He Y, Shahidi F (1997) Enzymatic esterification of θ-3 fatty acid concentrates from seal blubber oil with glycerol. J Am Oil Chem Soc 74:1133–1136
Kvittingen L, Sjursnes B, Anthonsen T, Halling P (1992) Use of Salt Hydrates to buffer optimal water level during lipase catalyzed synthesis in organic media—a practical procedure for organic chemists. Tetrahedron 48:2793–2802
Reslow M, Adlercreutz P, Mattiasson B (1988) On the importance of the support material for bioorganic synthesis. Eur J Biochem 172:573–578
Arroyo M, Sánchez-Montero MS, Sinisterra JV (1999) Thermal stabilization of immobilized lipase B from Candida antarctica on different supports: effect of water activity on enzymatic activity in organic media. Enzyme Microb Technol 24:3–12
Piyatheerawong W, Iwasaki Y, Xu XB, Yamane T (2004) Dependency of water concentration on ethanolysis of trioleoylglycerol by lipases. J Mol Catal B Enzym 28:19–24
Deng L, Xu XB, Haraldsson GG, Tan TW, Wang F (2005) Enzymatic production of alkyl esters through alcoholysis: a critical evaluation of lipases and alcohols. J Am Oil Chem Soc 82:341–347
Watanabe Y, Pinsirodom P, Nagao T, Kobayashi T, Nishida Y, Takagi Y, Shimada Y (2005) Production of FAME from acid oil model using immobilized Candida antarctica lipase. J Am Oil Chem Soc 82:825–831
Fjerbaek L, Christensen KV, Norddahl B (2009) A review of the current state of biodiesel production using enzymatic transesterification. Biotechnol Bioeng 102:1298–1315
Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409:241–246
Yang TK, Xu XB, He C, Li LT (2003) Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chem 80:473–481
Vikbjerg AF, Mu H, Xu X (2005) Parameters affecting incorporation and by-product formation during the production of structured phospholipids by lipase-catalyzed acidolysis in solvent-free system. J Mol Catal B Enzym 36:14–21
Sim JH, Kamaruddin AH, Bhatia S (2010) Biodiesel (FAME) productivity, catalytic efficiency and thermal stability of Lipozyme TL IM for crude palm oil transesterification with methanol. J Am Oil Chem Soc 87:1027–1034
Khor GK, Sim JH, Kamaruddin AH, Uzir MH (2010) Thermodynamics and inhibition studies of lipozyme TL IM in biodiesel production via enzymatic transesterification. Bioresource Technol 101:6558–6561
Dizge N, Keskinler B (2008) Enzymatic production of biodiesel from canola oil using immobilized lipase. Biomass Bioenerg 32:1274–1278
Corrêa INdS, Lorena de Souza S, Catran M, Bernardes OL, Portilho MF, Langone MAP (2011) Enzymatic biodiesel synthesis using a byproduct obtained from palm oil refining. Enzyme Res 2011. doi:10.4061/2011/814507
Shao P, Meng XH, He JZ, Sun PL (2008) Analysis of immobilized Candida rugosa lipase catalyzed preparation of biodiesel from rapeseed soapstock. Food Bioprod Process 86:283–289
Selmi B, Thomas D (1998) Immobilized lipase-catalyzed ethanolysis of sunflower oil in a solvent-free medium. J Am Oil Chem Soc 75:691–695
Millqvist A, Adlercreutz P, Mattiasson B (1994) Lipase-catalyzed alcoholysis of triglycerides for the preparation of 2-monoglycerides. Enzyme Microb Tech 16:1042–1047
Laane C, Boeren S, Vos K, Veeger C (1987) Rules for optimization of biocatalysis in organic-solvents. Biotechnol Bioeng 30:81–87
Lai CC, Zullaikah S, Vali SR, Ju YH (2005) Lipase-catalyzed production of biodiesel from rice bran oil. J Chem Technol Biot 80:331–337
Hernández-Martín E, Otero C (2008) Different enzyme requirements for the synthesis of biodiesel: novozym 435 and Lipozyme TL IM. Bioresoure Technol 99:277–286
Rodrigues R, Volpato G, Wada K, Ayub M (2008) Enzymatic synthesis of biodiesel from transesterification reactions of vegetable oils and short chain alcohols. J Am Oil Chem Soc 85:925–930
Xu Y, Du W, Liu D, Zeng J (2003) A novel enzymatic route for biodiesel production from renewable oils in a solvent-free medium. Biotechnol Lett 25:1239–1241
Salis A, Monduzzi M, Solinas V (2007) Use of lipases for the production of biodiesel. In: Polaina J, MacCabe A (eds) Industrial Enzymes. Springer, Netherlands, pp 317–339
Li L, Du W, Liu D, Wang L, Li Z (2006) Lipase-catalyzed transesterification of rapeseed oils for biodiesel production with a novel organic solvent as the reaction medium. J Mol Catal B Enzym 43:58–62
Watanabe Y, Shimada Y, Sugihara A, Noda H, Fukuda H, Tominaga Y (2000) Continuous production of biodiesel fuel from vegetable oil using immobilized Candida antarctica lipase. J Am Oil Chem Soc 77:355–360
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This work was carried out with the support of “Cooperative Research Program for Agriculture Science & Technology Development (Project No. PJ01103701)” Rural Development Administration, Republic of Korea.
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Choi, N., Kim, Y., Lee, JS. et al. Synthesis of Fatty Acid Ethyl Ester from Acid Oil in a Continuous Reactor via an Enzymatic Transesterification. J Am Oil Chem Soc 93, 311–318 (2016). https://doi.org/10.1007/s11746-016-2786-9
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DOI: https://doi.org/10.1007/s11746-016-2786-9