Advertisement

Journal of the American Oil Chemists' Society

, Volume 89, Issue 11, pp 1991–1998 | Cite as

Biocatalytic Conversion of Coconut Oil to Natural Flavor Esters Optimized with Response Surface Methodology

  • Jingcan SunEmail author
  • Jin Hua Chin
  • Weibiao Zhou
  • Bin Yu
  • Philip Curran
  • Shao-Quan Liu
Original Paper

Abstract

Lipase (Lipozyme TL IM)-mediated biocatalysis in a solvent-free system was effectively employed to convert coconut oil and fusel oil to flavor-active octanoic acid esters (mainly ethyl-, butyl-, isobutyl- and (iso)amyl octanoate). Response surface methodology based on five-level-three-factor central composite design was applied to investigate the effects of single and multiple interactive factors on the conversion. Results indicated that the studied independent parameters including reactant molar ratio, enzyme loading and shaking speed were all significant factors that affected the formation of octanoic acid esters during transesterification reaction. According to the developed polynomial model (R 2 = 0.947), the optimum transesterification conditions were determined as follows: molar ratio of 3.25:1 (alcohol/oil), enzyme loading of 16.7 % (wt%) and shaking speed of 160 rpm. Under the optimized reaction conditions an average conversion of 62.0 % was achieved which was in reasonable agreement with the predicted value of 64.1 % and about 9.4 mg of ethyl octanoate, 14.4 mg of isobutyl octanoate, 0.3 mg of butyl octanoate and 49.2 mg of (iso)amyl octanoate were produced per gram of coconut oil.

Keywords

Coconut oil Flavor esters Lipase Fusel oil Solvent-free transesterification Biocatalysis 

References

  1. 1.
    Metzger J, Bornscheuer U (2006) Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol 71:13–22CrossRefGoogle Scholar
  2. 2.
    Schrader J, Etschmann M, Sell D, Hilmer JM, Rabenhorst J (2004) Applied biocatalysis for the synthesis of natural flavour compounds: current industrial processes and future prospects. Biotechnol Lett 26:463–472CrossRefGoogle Scholar
  3. 3.
    Jaeger K-E, Eggert T (2002) Lipases for biotechnology. Curr Opin Biotechnol 13:390–397CrossRefGoogle Scholar
  4. 4.
    Güvenç A, Kapucu N, Mehmetoğlu Ü (2002) The production of isoamyl acetate using immobilized lipases in a solvent-free system. Process Biochem 38:379–386CrossRefGoogle Scholar
  5. 5.
    Soumanou MM, Bornscheuer UT (2003) Lipase-catalyzed alcoholysis of vegetable oils. Eur J Lipid Sci Technol 105:656–660CrossRefGoogle Scholar
  6. 6.
    Jitputti J, Kitiyanan B, Rangsunvigit P, Bunyakiat K, Attanatho L, Jenvanitpanjakul P (2006) Transesterification of crude palm kernel oil and crude coconut oil by different solid catalysts. Chem Eng J 116:61–66CrossRefGoogle Scholar
  7. 7.
    Kumar D, Kumar G, Singh C (2010) Fast, easy ethanolysis of coconut oil for biodiesel production assisted by ultrasonication. Ultrason Sonochem 17:555–559CrossRefGoogle Scholar
  8. 8.
    Nemestóthy N, Gubicza L, Fehér E, Bélafi-Bakó K (2008) Biotechnological utilisation of fusel oil, a food industry by-product. Food Technol Biotech 46:44–50Google Scholar
  9. 9.
    Du W, Xu YY, Liu DH (2003) Lipase-catalysed transesterification of soya bean oil for biodiesel production during continuous batch operation. Biotechnol Appl Biochem 38:103–106CrossRefGoogle Scholar
  10. 10.
    Yahya ARM, Anderson WA, Moo-Young M (1998) Ester synthesis in lipase-catalyzed reactions. Enzyme Microb Technol 23:438–450CrossRefGoogle Scholar
  11. 11.
    Bezerra MA, Santelli RE, Oliveira EP, Villar LS, Escaleira LA (2008) Response surface methodology (RSM) as a tool for optimization in analytical chemistry. Talanta 76:965–977CrossRefGoogle Scholar
  12. 12.
    Mahapatra P, Kumari A, Kumar Garlapati V, Banerjee R, Nag A (2009) Enzymatic synthesis of fruit flavor esters by immobilized lipase from Rhizopus oligosporus optimized with response surface methodology. J Mol Catal B Enzym 60:57–63CrossRefGoogle Scholar
  13. 13.
    Al-Khalifa A (1996) Physicochemical characteristics, fatty acid composition, and lipoxygenase activity of crude pumpkin and melon seed oils. J Agric Food Chem 44:964–966CrossRefGoogle Scholar
  14. 14.
    Sampranpiboon P, Jiraratananon R, Uttapap D, Feng X, Huang R (2000) Pervaporation separation of ethyl butyrate and isopropanol with polyether block amide (PEBA) membranes. J Memb Sci 173:53–59CrossRefGoogle Scholar
  15. 15.
    Chulalaksananukul W, Condoret JS, Combes D (1993) Geranyl acetate synthesis by lipase-catalyzed transesterification in supercritical carbon dioxide. Enzyme Microb Technol 15:691–698CrossRefGoogle Scholar
  16. 16.
    Wang Y, Wu H, Zong M (2008) Improvement of biodiesel production by lipozyme TL IM-catalyzed methanolysis using response surface methodology and acyl migration enhancer. Bioresour Technol 99:7232–7237CrossRefGoogle Scholar
  17. 17.
    Yadav G, Trivedi A (2003) Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media. Enzyme Microb Technol 32:783–789CrossRefGoogle Scholar
  18. 18.
    Rodrigues RC, Volpato G, Wada K, Ayub MAZ (2008) Enzymatic synthesis of biodiesel from transesterification reactions of vegetable oils and short chain alcohols. J Am Oil Chem Soc 85:925–930CrossRefGoogle Scholar
  19. 19.
    Huang Y, Zheng H, Yan Y (2010) Optimization of lipase-catalyzed transesterification of lard for biodiesel production using response surface methodology. Appl Biochem Biotechnol 160:504–515CrossRefGoogle Scholar
  20. 20.
    Yadav GD, Lathi PS (2005) Lipase catalyzed transesterification of methyl acetoacetate with n-butanol. J Mol Catal B Enzym 32:107–113CrossRefGoogle Scholar

Copyright information

© AOCS 2012

Authors and Affiliations

  • Jingcan Sun
    • 1
    Email author
  • Jin Hua Chin
    • 1
  • Weibiao Zhou
    • 1
  • Bin Yu
    • 2
  • Philip Curran
    • 2
  • Shao-Quan Liu
    • 1
  1. 1.Food Science and Technology Programme, Department of ChemistryNational University of SingaporeSingaporeSingapore
  2. 2.Firmenich Asia Pte LtdSingaporeSingapore

Personalised recommendations