Enzymatic esterification of free fatty acids in vegetable oils utilizing different immobilized lipases

Abstract

Different immobilized lipases were screened for their ability to esterify free fatty acids (FFA) with monoacylglycerol (MAG) as acyl-group acceptor. A lipase from Rhizomucor miehei (Lipozyme RMIM) was the most suitable for lipase-catalyzed de-acidification—a promising alternative to conventional neutralization. A reduction of the FFA content to 0.6 % (w/w) was achieved by applying a substrate with an initial FFA-content of 6 % (w/w), the reaction at 50 °C for 22 h as well as the stepwise addition of a quadruple stoichiometric amount of MAG.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3

Abbreviations

AN:

Acid number

M(KOH) :

Molar mass of KOH

c(KOH) :

Concentration of KOH solution

V(KOH) :

Volume KOH solution applied during titration

m(oil) :

Mass of the oil sample

M(FFA) :

Average molecular weight of the free fatty acids (with regard to the fatty acid composition of rapeseed oil)

ρ(oil) :

Density of rapeseed oil

References

  1. Bellot JC, Choisnard L, Castillo E, Marty A (2001) Combining solvent engineering and thermodynamic modeling to enhance selectivity during monoglyceride synthesis by lipase-catalyzed esterification. Enzym Microb Technol 28:362–369

    CAS  Article  Google Scholar 

  2. Bhattacharyya S, Bhattacharyya DK (1989) Biorefining of high acid rice bran oil. J Am Oil Chem Soc 66:1809–1811

    CAS  Article  Google Scholar 

  3. Bhosle BM, Subramanian R (2005) New approaches in deacidification of edible oils—a review. J Food Eng 69:481–494

    Article  Google Scholar 

  4. Bockisch M (1993) Handbuch der Lebensmitteltechnologie. Ulmer

  5. Bousquet-Dubouch MP, Graber M, Sousa N, Lamare S, Legoy MD (2001) Alcoholysis catalyzed by Candida antarctica lipase B in a gas/solid system obeys a ping pong Bi Bi mechanism with competitive inhibition by the alcohol substrate and water. Biochim Biophys Acta 1550:90–99

    CAS  PubMed  Article  Google Scholar 

  6. Chulalaksananukul W, Condoret JS, Delorme P, Willemot RM (1990) Kinetic/study of esterification by immobilized lipase in n-hexane. FEBS Lett 276:181–184

    CAS  PubMed  Article  Google Scholar 

  7. Cmolik J, Pokorny J (2000) Physical refining of edible oils. Eur J Lipid Sci Technol 102:472–486

    CAS  Article  Google Scholar 

  8. De Maria L, Vind J, Oxenboll KM, Svendsen A, Patkar S (2007) Phospholipases and their industrial applications (vol 74, pg 290, 2007). Appl Microbiol Biotechnol 76:235

    CAS  Article  Google Scholar 

  9. Ducret A, Pina M, Montet D, Graille J (1992) Biocatalyzed deacidification—reaction optimization on a model hyperacid oil. Biotechnol Lett 14:185–188

    CAS  Article  Google Scholar 

  10. Fettforschung DGf (2012) Bestimmung der Säurezahl und freien Fettsäuren (Azidität). In: e.V. DGfF (ed) DGF-Einheitsmethoden zur Untersuchung von Fetten, Fettprodukten, Tensiden und verwandten Stoffen. Wissenschaftliche Verlagsgesellschaft, Stuttgart

  11. Herbst D, Peper S, Niemeyer B (2012) Enzyme catalysis in organic solvents: influence of water content, solvent composition and temperature on Candida rugosa lipase catalyzed transesterification. J Biotechnol 162:398–403

    CAS  PubMed  Article  Google Scholar 

  12. Somashekar BR, Lohith K, Manohar B, Divakar S (2007) Inhibition of Rhizomucor miehei and Candida rugosa lipases by d-glucose in esterification between l-alanine and -glucose. J Biosci Bioeng 103:122–128

    CAS  PubMed  Article  Google Scholar 

  13. Zaks A, Klibanov AM (1985) Enzyme-catalyzed processes in organic solvents. Proc Natl Acad Sci USA 82:3192–3196

    CAS  PubMed Central  PubMed  Article  Google Scholar 

Download references

Acknowledgments

The present work was funded by the Federal Ministry of Education and Research in line with a cooperation program “Programme Inter Carnot Fraunhofer (PICF 2010)”.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Daniela von der Haar.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

von der Haar, D., Stäbler, A., Wichmann, R. et al. Enzymatic esterification of free fatty acids in vegetable oils utilizing different immobilized lipases. Biotechnol Lett 37, 169–174 (2015). https://doi.org/10.1007/s10529-014-1668-1

Download citation

Keywords

  • Enzymatic de-acidification
  • Esterification
  • Free fatty acids
  • Lipase
  • Oil refining
  • Rapeseed oil refining