Lipase-catalyzed Transesterification in Several Reaction Systems: An Application of Room Temperature Ionic Liquids for Bi-phasic Production of n-Butyl Acetate

  • Park Suk-Chan (Department of Biological Engineering, Inha University) ;
  • Chang Woo-Jin (ERC for Advanced Bioseparation Technology, Inha University) ;
  • Lee Sang-Mok (Department of Biological Engineering, Inha University) ;
  • Kim Young-Jun (ERC for Advanced Bioseparation Technology, Inha University) ;
  • Koo Yoon-Mo (Department of Biological Engineering, Inha University, ERC for Advanced Bioseparation Technology, Inha University)
  • Published : 2005.02.01

Abstract

Organic solvents are widely used in biotransformation systems. There are many efforts to reduce the consumption of organic solvents because of their toxicity to the environment and human health. In recent years, several groups have started to explore novel organic solvents called room temperature ionic liquids in order to substitute conventional organic solvents. In this work, lipase-catalyzed transesterification in several uni- and bi-phasic systems was studied. Two representative hydrophobic ionic liquids based on 1-butyl-3-methylimidazolum coupled with hexafluorophosphate ([BMIM][$PF_6$]) and bis[{trifluoromethylsulfonyl} imide] ([BMIM] [$Tf_{2}N$]) were employed as reaction media for the transesterification of n-butanol. The commercial lipase, Novozym 435, was used for the transesterification reaction with vinyl acetate as an acyl donor. The conversion yield was increased around $10\%$ in a water/[BMIM][$Tf_{2}N$] bi-phasic system compared with that in a water/hexane system. A higher distribution of substrates into the water phase is believed to enhance the conversion yield in a water/[BMIM][$Tf_{2}N$] system. Partition coefficients of the substrates in the water/[BMIM][$Tf_{2}N$] bi-phasic system were higher than three times that found in the water/hexane system, while n-butyl acetate showed a similar distribution in both systems. Thus, RTILs appear to be a promising substitute of organic solvents in some biotransformation systems.

Keywords

References

  1. Bradoo, S., R.K. Saxena, and R. Gupta (1999) Partitioning and resolution of mixture of two lipase from Bacillus stearothermophilus SB-1 in aqueous two-phase system. Process Biochem. 35: 57-62 https://doi.org/10.1016/S0032-9592(99)00032-1
  2. Lee, J.-H., N.-H. Loc, T.-H. Kwon, and M.-S. Yang (2004) Partitioning of recombinant human granulocytemacrophage colony stimulating factor (hGM-CSF) from plant cell suspension culture in PEG/sodium phosphate aqueous two-phase systems. Biotechnol. Bioprocess Eng. 9:12-16 https://doi.org/10.1007/BF02949316
  3. Villeneuve, P., J. M. Muderhwa, J. Graille, and M. J. Haas (2000) Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Molec. Catal. B: Enzymatic B9: 113-148 https://doi.org/10.1016/S1381-1177(99)00107-1
  4. Murty, V. R., J. Bhat, and P. K. A. Muniswaran (2002) Hydrolysis of oils by using immobilized lipase enzyme. Biotechnol. Bioprocess Eng. 4: 57-66 https://doi.org/10.1007/BF02935881
  5. Chen, C. S. and C. J. Sih (1989) General aspects and optimization of enantioselective biocatalysis in organic solvents: The use of lipase. Angew. Chem. Int. Ed. Eng. 28: 695-707 https://doi.org/10.1002/anie.198906951
  6. Cull, S. G., J. D. Holbrey, V. Vargas-Mora, K. R. Seddon, and G. J. Lye (2000) Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. Biotechnol. Bioeng. 69: 227-233 https://doi.org/10.1002/(SICI)1097-0290(20000720)69:2<227::AID-BIT12>3.0.CO;2-0
  7. Park, S. and R. J. Kazlauskas (2003) Biocatalysis in ionic liquids–advantages beyond green technology. Curr. Opin. Biotechnol. 14: 432-437 https://doi.org/10.1016/S0958-1669(03)00100-9
  8. Itoh, T., Y. Nishimura, N. Ouchi, and S. Hayase (2003) 1- Butyl-2,3-dimethylimidazolium tetrafluoroborate: The most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor. J. Molec. Catal. B: Enzymatic B26: 41-45 https://doi.org/10.1016/S1381-1177(03)00147-4
  9. Park, S. and R. J. Kazlauskas (2001) Improved preparation and use of room-temperature ionic liquid in lipasecatalyzed enantio- and regioselective acylations. J. Org. Chem. 66: 8395-8401 https://doi.org/10.1021/jo015761e
  10. van Rantwijk, F., R. M. Lau, and R. A. Sheldon (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol. 21: 131-138 https://doi.org/10.1016/S0167-7799(03)00008-8
  11. Carmichael, A. J. and K. R. Seddon (2000) Polarity study of some 1-alkyl-3-methylimidazolium ambient-temperature ionic liquids with the solvatochromic dye, Nile Red. J. Phys. Org. Chem. 13: 591-595 https://doi.org/10.1002/1099-1395(200010)13:10<591::AID-POC305>3.0.CO;2-2
  12. Lozano, P., T. De Diego, D. Carrié, M. Vaultier, and J. L. Iborra (2001) Over-stabilization of Candida antarctica lipase B by ionic liquids in ester synthesis. Biotechnol. Lett. 23: 1529-1533 https://doi.org/10.1023/A:1011697609756
  13. Persson, M. and U. T. Bornscheuer (2003) Increased stability of an esterase from Bacillus stearothermophilus in ionic liquids as compared to organic solvents. J. Molec. Catalysis B: Enzymatic B22: 21-27 https://doi.org/10.1016/S1381-1177(02)00294-1
  14. Yadav, G. D. and A. H. Trivedi (2003) Kinetic modeling of immobilized-lipase catalyzed transesterification of noctanol with vinyl acetate in non-aqueous media. Enzyme Microb. Technol. 32: 783-789 https://doi.org/10.1016/S0141-0229(03)00064-4
  15. Belafi-Bako, K., N. Dormo, O. Ulbert, and L. Gubicza (2002) Application of pervaporation for removal of water produced during enzymatic esterification in ionic liquids. Desalination 149: 267-268 https://doi.org/10.1016/S0011-9164(02)00781-6
  16. Murty, V. R., J. Bhat, and PK. A. Muniswaran (2002) Hydrolisys of rice bran oil using immobilized lipase in a stirred batch reactor. Biotechnol. Bioprocess Eng. 7: 367-370 https://doi.org/10.1007/BF02933523
  17. Seo, W.-Y. and K. Lee (2004) Optimized conditions for in situ immobilization of lipase in aldehyde-silica packed columns. Biotechnol. Bioprocess Eng. 9: 465-470 https://doi.org/10.1007/BF02933487