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Optimisation of n-octyl oleate enzymatic synthesis over Rhizomucor miehei lipase

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Abstract

Octyl oleate is a useful organic compound with several applications in cosmetic, lubricant and pharmaceutical industry. At first, the enzymatic synthesis of n-octyl oleate by direct lipase-catalysed esterification of oleic acid and 1-octanol was investigated in a stirred batch reactor in solvent-free system. A systematic screening and optimisation of the reaction parameters were performed to gain insight into the kinetics mechanism. Particularly, enzyme concentration, reaction temperature, stirrer speed, water content, substrates concentration and molar ratio were optimised with respect to the final product concentration and reaction rate. The kinetics mechanism of the reaction was investigated. Finally, a comparison of the experimental results obtained in a solvent free-system with those using two different solvents, supercritical carbon dioxide (SC-CO2) and n-hexane, was proposed. It resulted that in SC-CO2 higher concentration of the desired product was attained, requiring lower enzyme concentrations to achieve comparable conversion of free fatty acid into fatty acid ester.

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Abbreviations

v i :

initial reaction rate (mol g−1 g −1enzyme  min−1)

T :

temperature (K)

E a :

activation energy (J mol−1)

R :

universal gas constant (J mol−1 K−1)

ΔH d :

deactivation enthalpy (J mol−1)

ΔS d :

deactivation entropy (J mol−1 K−1)

ΔG d :

deactivation Gibb’s free energy (J mol−1)

K d :

equilibrium constant

V max :

maximum initial reaction rate (mol g−1 g −1enzyme  min−1)

K m :

Michaelis constant (mol g−1)

a :

acid concentration (mol g−1)

b :

alcohol concentration (mol g−1)

FFA:

free fatty acid

FAE:

fatty acid ester

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Acknowledgements

This research was financially supported through a European Community Marie Curie Fellowship (Project HPMT–CT–2001–00418). The European Commission DG Research, Improving The Human Research Potential, is gratefully acknowledged. Further information is given in http://www.cordis.lu/improving.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, Laboratory for Separation Processes, University of Maribor, Smetanova ul. 17, 2000, Maribor, Slovenia

    Chiara Giulia Laudani, Maja Habulin, Mateja Primožič & Željko Knez

  2. Faculty of Engineering, Department of Chemical and Food Engineering, University of Salerno, Via Ponte Don Melillo 1, 84084, Fisciano (SA), Italy

    Chiara Giulia Laudani, Giovanna Della Porta & Ernesto Reverchon

Authors
  1. Chiara Giulia Laudani
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  2. Maja Habulin
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  3. Mateja Primožič
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  4. Željko Knez
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  5. Giovanna Della Porta
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  6. Ernesto Reverchon
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Correspondence to Željko Knez.

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Laudani, C.G., Habulin, M., Primožič, M. et al. Optimisation of n-octyl oleate enzymatic synthesis over Rhizomucor miehei lipase. Bioprocess Biosyst Eng 29, 119–127 (2006). https://doi.org/10.1007/s00449-006-0061-4

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  • DOI: https://doi.org/10.1007/s00449-006-0061-4

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