Biotechnology Letters

, Volume 29, Issue 12, pp 1881–1885 | Cite as

Ionic liquids as a reaction medium for lipase-catalyzed methanolysis of sunflower oil

  • S. Sunitha
  • S. Kanjilal
  • P. S. Reddy
  • R. B. N. PrasadEmail author
Original Research Paper


Ionic liquids, 1-butyl-3-methyl imidazolium hexafluorophosphate ([BMIm][PF6]) and 1-ethyl-3-methyl imidazolium hexafluorophosphate ([EMIm][PF6]), were used for the methanolysis of sunflower oil using Candida antarctica lipase (Novozyme 435) and gave yields of fatty acid methyl esters at 98–99% within 10 h. The optimum conditions of methanolysis in hydrophobic ionic liquids are 2% (w/w) lipase, 1:1 (w/w) oil/ionic liquid and 1:8 (mol/mol) oil/methanol at 58–60°C. Methanolysis using hydrophilic ionic liquids, 3-methyl imidazolium tetrafluoroborate ([HMIm][BF4]) and 1-butyl-3-methyl imidazolium tetrafluoroborate ([BMIm][BF4]), gave very poor yields. A hydrophobic ionic liquid thus protects the lipase from methanol. Recovered ionic liquids and lipase were used for four successive reaction cycles without any significant loss of activity.


Fatty acid methyl ester Ionic liquid Lipase Methanolysis Sunflower oil 


  1. Christie WW (1982) Lipid Analysis. Pergamon press, Oxford, UKGoogle Scholar
  2. Diego DT, Lozano P, Gmouth S et al (2004) Fluorescence and CD spectroscopic analysis of the α-chymotrypsin stabilization by the ionic liquid, 1-ethyl-3-methylimidazolium bis [(trifluoromethyl) sulfonyl] amide. Biotehnol Bioeng 88:916–924CrossRefGoogle Scholar
  3. Fuller J, Carlin RT, de Long HC et al (1994) Structure of 1-ethyl-3-methylimidazolium hexafluorophosphate: model for room temperature molten state. J Chem Soc, Chem Commun 299–300Google Scholar
  4. Hua-Ping Z, Fan Y, Jie T et al (2003) Bronsted acidic ionic liquid methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification. Green Chem 5:38–39CrossRefGoogle Scholar
  5. Huddelston JG, Wiilauer HD, Swatloski RP et al (1998) Room temperature ionic liquids as novel media for “clean” liquid-liquid extraction. Chem Commun 1765–1766Google Scholar
  6. Jain N, Kumar A, Chauhan S et al (2005) Chemical and biochemical transformation in ionic liquids. Tetrahedron 61:1015–1060CrossRefGoogle Scholar
  7. Kaar JL, Jesionowski AM, Berberich JA et al (2003) Impact of ionic liquids physical properties on lipase activity and stability. J Am Chem Soc 125:4125–4131PubMedCrossRefGoogle Scholar
  8. Kwang-Wook K, Boyoung S, Min-Young C et al (2001) Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. Org Lett 3:1507–1509CrossRefGoogle Scholar
  9. Lau RM, Sorgedrager MJ, Carrea G et al (2004) Dissolution of Candida antartica lipase B in ionic liquids: effects of structure and activity. Green Chem 6:483–487CrossRefGoogle Scholar
  10. Lozano P, de Diego T, Carrie D et al (2001) Over-stabilization of Candida antartica lipase B by ionic liquids in ester synthesis. Biotehnol Lett 23:1529–1533CrossRefGoogle Scholar
  11. Modi MK, Reddy JRC, Rao BVSK et al (2007) Lipase mediated conversion of vegetable oils into biodiesel using ethyl acetate as the acyl acceptor. Biores Technol 98:1260–1264CrossRefGoogle Scholar
  12. Oliveira AC, Rosa MF (2006) Enzymatic transesterification of sunflower oil in an aqueous-oil biphasic system. J Am Oil Chem Soc 83:21–25CrossRefGoogle Scholar
  13. Park S, Kazlauskas J (2001) Improved preparation and use of room temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. J Org Chem 66:8395–8401PubMedCrossRefGoogle Scholar
  14. Sheldon RA, Lau RM, Sorgedrager MJ et al (2002) Biocatalysis in ionic liquids. Green Chem 4:147–151CrossRefGoogle Scholar
  15. Shimada Y, Watanabe Y, Samukawa T et al (1999) Conversion of vegetable oil to biodiesel using immobilized Candida antartica lipase. J Am Oil Chem Soc 76:789–793CrossRefGoogle Scholar
  16. Soumanou MM, Bornscheuer UT (2003) Improvement in lipase-catalysed synthesis of fatty acid methyl esters from sunflower oil. Enz Microbial Technol 33:97–103CrossRefGoogle Scholar
  17. Xu Y, Du W, Liu D (2005) Study on the kinetics of enzymatic interesterification of triglycerides for biodiesel production with methyl acetate as the acyl acceptor. J Mol Cat B: Enz 32:241–245CrossRefGoogle Scholar
  18. Zhang G, Xuebing X (2005) New opportunity for enzymatic modification of fats and oils with industrial potential. Org Biomol Chem 3:2615–2626CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2007

Authors and Affiliations

  • S. Sunitha
    • 1
  • S. Kanjilal
    • 1
  • P. S. Reddy
    • 1
  • R. B. N. Prasad
    • 1
    Email author
  1. 1.Lipid Science and Technology DivisionIndian Institute of Chemical TechnologyHyderabadIndia

Personalised recommendations