Jump to ContentJump to Main Navigation
Show Summary Details
More options …

International Journal of Chemical Reactor Engineering

Ed. by de Lasa, Hugo / Xu, Charles Chunbao

12 Issues per year

IMPACT FACTOR 2017: 0.881
5-year IMPACT FACTOR: 0.908

CiteScore 2017: 0.86

SCImago Journal Rank (SJR) 2017: 0.306
Source Normalized Impact per Paper (SNIP) 2017: 0.503

See all formats and pricing
More options …
Volume 16, Issue 7


Volume 9 (2011)

Volume 8 (2010)

Volume 7 (2009)

Volume 6 (2008)

Volume 5 (2007)

Volume 4 (2006)

Volume 3 (2005)

Volume 2 (2004)

Volume 1 (2002)

A Green Process for Synthesis of Geraniol Esters by Immobilized Lipase from Candida Antarctica B Fraction in Non-Aqueous Reaction Media: Optimization and Kinetic Modeling

Ganapati D. Yadav
  • Corresponding author
  • Department of Chemical Engineering, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400019, India
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Manoj P. Kamble
  • Department of Chemical Engineering, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400019, India
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2018-05-30 | DOI: https://doi.org/10.1515/ijcre-2017-0179


Enzymatic synthesis of molecules such as flavors, perfumes and fragrances has a great commercial advantage of being marketed as “natural” and also it offers exquisite selectivity of enzymes that can be superior over chemical catalysis. The current work focuses on the enzymatic synthesis of geranyl acetate as model compound, including optimization of reaction conditions such as nature of catalyst, reaction media, speed of agitation, mole ratio and temperature. A variety of esters were also synthesized. Geraniol was esterified with various acids, aromatic esters and vinyl esters in 1:4 molar ratio. Among all vinyl ester was the best giving in good yield (77–100 %) as compared to aromatic esters (5–82 %) and acids (7–31 %). Novozym 435 was found to be most active catalyst with ~96 % conversion and 100 % selectivity in 60 min at 55 °C in n-heptane as solvent for geranyl acetate. The maximum reaction rate was estimated (Vmax = 0.2712 mol L−1 min-1) by using the double reciprocal plot. It is a ternary complex (ordered bi-bi) mechanism with inhibition by geraniol.

This article offers supplementary material which is provided at the end of the article.

Keywords: biotransformation; candida antarctica lipase B; enzyme kinetics; geraniol esters; ternary complex


  • Abbas, H., and L. Comeau. 2003. “Aroma Synthesis by Immobilized Lipase from Mucor Sp.” Enzyme Microbial Technology 32: 589–595. DOI: .CrossrefGoogle Scholar

  • Akacha, B. N., and M. Gargouri. 2015. “Microbial and Enzymatic Technologies Used for the Production of Natural Aroma Compounds: Synthesis, Recovery Modeling, and Bioprocesses.” Food & Bioproducts Processing 94: 675–706. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Claon, P.A., and C.C. Akoh. 1994. “Enzymatic Synthesis of Geranyl Acetate Inn-Hexane withCandida Antarctica Lipases.” Journal of American Oil Chemists Society 71: 575–578. DOI: .CrossrefGoogle Scholar

  • Dhake, K.P., K.M. Deshmukh, Y.P. Patil, R.S. Singhal, and B.M. Bhanage. 2011. “Improved Activity and Stability of Rhizopus Oryzae Lipase via Immobilization for Citronellol Ester Synthesis in Supercritical Carbon Dioxide.” Journal of Biotechnology 156: 46–51. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Domínguez De María, P., J. V. Sinisterra, J.M. Sánchez-Montero, M. Lotti, F. Valero, and A.R. Alcántara. 2006. “Acyl Transfer Strategy for the Biocatalytical Characterisation of Candida Rugosa Lipases in Organic Solvents.” Enzyme Microbial Technology 38: 199–208. DOI: .CrossrefGoogle Scholar

  • Gupta, S.M., M.P. Kamble, and G.D. Yadav. 2017. “Insight into Microwave Assisted Enzyme Catalysis in Process Intensification of Reaction and Selectivity: Kinetic Resolution of (R,S)-Flurbiprofen with Alcohols.” Molecular Catalysis 440: 50–56. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Kamble, M.P., S.A. Chaudhari, R.S. Singhal, and G.D. Yadav. 2017. “Synergism of Microwave Irradiation and Enzyme Catalysis in Kinetic Resolution of (R,S)-1-Phenylethanol by Cutinase from Novel Isolate Fusarium ICT SAC1.” Biochemical Engineering Journal 117: 121–128. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Kamble, M.P., S.D. Shinde, and G.D. Yadav. 2016. “Kinetic Resolution of (R,S)- -Tetralol Catalyzed by Crosslinked Candida Antarctica Lipase B Enzyme Supported on Mesocellular Foam: A Nanoscale Enzyme Reactor Approach.” Journal of Molecular Catalysis B: Enzymatic 132: 61–66. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Kamble, M.P., and G.D. Yadav. 2017. “Kinetic Resolution of (R,S)-α-Tetralol by Immobilized Candida Antarctica Lipase B: Comparison of Packed-Bed over Stirred-Tank Batch Bioreactor.” Industrial & Engineering Chemistry Research 56: 1750–1757. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Kamble, M.P., and G.D. Yadav. 2018. “Biocatalytic Resolution of (R,S)-Styrene Oxide Using a Novel Epoxide Hydrolase from Red Mung Beans.” Catalysis Today 309: 236–241. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Khan, N.R., and V.K. Rathod. 2015. “Enzyme Catalyzed Synthesis of Cosmetic Esters and Its Intensification: A Review.” Process Biochem 50: 1793–1806. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Kramer, M., J.C. Cruz, P.H. Pfromm, M.E. Rezac, and P. Czermak. 2010. “Enantioselective Transesterification by Candida Antarctica Lipase B Immobilized on Fumed Silica.” Journal of Biotechnology 150: 80–86. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Lozano, P., J.M. Bernal, and A. Navarro. 2012. “A Clean Enzymatic Process for Producing Flavour Esters by Direct Esterification in Switchable Ionic Liquid/Solid Phases.” Green Chemistry 14: 3026–3033. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Mohamad, N.R., N.A. Buang, N.A. Mahat, J. Jamalis, F. Huyop, H.Y. Aboul-Enein, and R.A. Wahab. 2015. “Simple Adsorption of Candida Rugosa Lipase onto Multi-Walled Carbon Nanotubes for Sustainable Production of the Flavor Ester Geranyl Propionate.” Journal of Industrial & Engineering Chemistry 32: 99–108. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Oguntimein, G.B., W.A. Anderson, and M. Moo-Young. 1995. “Synthesis of Geraniol Esters in a Solvent-Free System Catalysed by Candida Antarctica Lipase.” Biotechnology Letters 17: 77–82. DOI: .CrossrefGoogle Scholar

  • Romero, M.D., L. Calvo, C. Alba, A. Daneshfar, and H.S. Ghaziaskar. 2005. “Enzymatic Synthesis of Isoamyl Acetate with Immobilized Candida Antarctica Lipase in N-Hexane.” Enzyme & Microbial Technology 37: 42–48. DOI: .CrossrefGoogle Scholar

  • Salvi, H.M., M.P. Kamble, and G.D. Yadav. 2018. “Synthesis of Geraniol Esters in a Continuous-Flow Packed-Bed Reactor of Immobilized Lipase: Optimization of Process Parameters and Kinetic Modeling.” Applied Biochemsitry & Biotechnology 184: 630–643. DOI: .CrossrefGoogle Scholar

  • Sheldon, R.A., and P.C. Pereira. 2017. “Biocatalysis Engineering: The Big Picture.” Chemical Society Reviews 46: 2678–2691. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Shinde, S.D., and G.D. Yadav. 2014. “Process Intensification of Immobilized Lipase Catalysis by Microwave Irradiation in the Synthesis of 4-Chloro-2-Methylphenoxyacetic Acid (MCPA) Esters.” Biochemical Engineering Journal 90: 96–102. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Sontakke, J.B., and G.D. Yadav. 2014. “Microwave Assisted Synthesis of Ethyl 2-(4-Aminophenyl) Acetate Using Novozyme 435.” Current Catalysis 3 (1): 27–34.CrossrefGoogle Scholar

  • Trusek-Holownia, A., and A. Noworyta. 2007. “An Integrated Process: Ester Synthesis in an Enzymatic Membrane Reactor and Water Sorption.” Journal of Biotechnology 130: 47–56. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Varma, M.N., and G. Madras. 2010. “Kinetics of Enzymatic Synthesis of Geranyl Butyrate by Transesterification in Various Supercritical Fluids.” Biochemical Engineering Journal 49: 250–255. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Villalba, M., C.M. Verdasco-Martín, J.C.S. Dos Santos, R. Fernandez-Lafuente, and C. Otero. 2016. “Operational Stabilities of Different Chemical Derivatives of Novozym 435 in an Alcoholysis Reaction.” Enzyme & Microbial Technology 90: 35–44. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Xiong, J., Y. Huang, H. Zhang, and L. Hou. 2014. “Lipase-Catalyzed Transesterification Synthesis of Geranyl Acetate in Organic Solvents and Its Kinetics.” Food Science & Technology Research 20: 207–216. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Yadav, G.D., and I.V. Borkar. 2008. “Kinetic and Mechanistic Investigation of Microwave-Assisted Lipase Catalyzed Synthesis of Citronellyl Acetate.” Industrial & Engineering Chemistry Research 48: 7915–792. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Yadav, G.D., and S. Devendran. 2012. “Lipase Catalyzed Synthesis of Cinnamyl Acetate via Transesterification in Non-Aqueous Medium.” Process Biochemistry 47: 496–502. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Yadav, G.D., and S. Devendran. 2015. “Microwave Assisted Enzyme Catalysis: Practice and Perspective, Chapter 4.” In White Biotechnology for Sustainable Catalysis, edited by Alice Z Maria, 2015. RSC, London: Coelho and Bernardo Dias Ribeiro. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and K.M. Devi. 2004. “Immobilized Lipase-Catalysed Esterification and Transesterification Reactions in Non-Aqueous Media for the Synthesis of Tetrahydrofurfuryl Butyrate: Comparison and Kinetics.” Chemical Engineering Science 59: 373–383. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., M.P. Hude, and A.D. Talpade. 2015. “Microwave Assisted Process Intensification of Lipase Catalyzed Transesterification of 1,2 Propanediol with Dimethyl Carbonate for the Green Synthesis of Propylene Carbonate: Novelties of Kinetics and Mechanism of Consecutive Reactions.” Chemical Engineering Journal 281: 199–208. DOI: .CrossrefWeb of ScienceGoogle Scholar

  • Yadav, G.D., and S.R. Jadhav. 2005. “Synthesis of Reusable Lipases by Immobilization on Hexagonal Mesoporous Silica and Encapsulation in Calcium Alginate: Transesterification in Non-Aqueous Medium.” Microporous Mesoporous Materials 86: 215–222. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and H.B. Kulkarni. 2000. “Ion-Exchange Resin Catalysis in the Synthesis of Isopropyl Lactate.” Reactive & Functional Polymers 44: 153–165. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and P.S. Lathi. 2003. “Kinetics and Mechanism of Synthesis of Butyl Isobutyrate over Immobilised Lipases.” Biochemical Engineering Journal 16: 245–252. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and P.S. Lathi. 2004. “Synthesis of Citronellol Laurate in Organic Media Catalyzed by Immobilized Lipases: Kinetic Studies.” Journal of Molecular Catalysis B: Enzymatic 27: 113–119. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and P.S. Lathi. 2005. “Lipase Catalyzed Transesterification of Methyl Acetoacetate with N-Butanol, Journal of Molecular Catalysis B.” Enzymatic 32: 107–113. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and P.S. Lathi. 2006. “Intensification of Enzymatic Synthesis of Propylene Glycol Monolaurate from 1,2-Propanediol and Lauric Acid under Microwave Irradiation: Kinetics of Forward and Reverse Reactions.” Enzyme Microb. Technol. 38: 814–820. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and P.H. Mehta. 1994. “Heterogeneous Catalysis in Esterification Reactions: Preparation of Phenethyl Acetate and Cyclohexyl Acetate by Using a Variety of Solid Acidic Catalysts.” Industrial & Engineering Chemistry Research 33: 2198–2208. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and M.S.M.M. Rahuman. 2003. “Synthesis of Fragrance and Flavour Grade Esters: Activities of Different Ion Exchange Resins and Kinetic Studies.” Clean Technologies & Environmental Policy 5: 128–135. DOI: .CrossrefGoogle Scholar

  • Yadav, G.D., and A.H. Trivedi. 2003. “Kinetic Modeling of Immobilized-Lipase Catalyzed Transesterification of N-Octanol with Vinyl Acetate in Non-Aqueous Media.” Enzyme & Microbial Technology 32: 783–789. DOI: .CrossrefGoogle Scholar

About the article

Received: 2017-09-24

Accepted: 2018-05-05

Revised: 2018-01-21

Published Online: 2018-05-30

Competing interests: Both authors declare that they have no conflict of interest and have contributed equally.

Citation Information: International Journal of Chemical Reactor Engineering, Volume 16, Issue 7, 20170179, ISSN (Online) 1542-6580, DOI: https://doi.org/10.1515/ijcre-2017-0179.

Export Citation

© 2018 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Supplementary Article Materials

Comments (0)

Please log in or register to comment.
Log in