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Lipase-catalyzed transesterification synthesis of citronellyl acetate in a solvent-free system and its reaction kinetics

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Abstract

The lipase-catalyzed citronellol synthesis of citronellyl acetate via transesterification was investigated in a solvent-free system. After screening several lipases, the lipase from Pseudomonas fluorescens was identified as the optimal enzyme for the system. The optimal reaction temperature was 40 °C. The external diffusion limitation could be greatly reduced by increasing the agitation speed to 200 rpm. A linear relationship between the initial reaction rate and an enzyme load of up to 6 mg mL−1 demonstrated that the internal diffusion limitations could be minimized. Substrate inhibition was absent when the substrate concentration was below 500 mmol L−1, but the experimental results indicated that the product inhibition effect should be considered. The results from the reaction kinetics analysis showed that the reaction obeys the ping-pong bi–bi mechanism that is inhibited by citronellyl acetate. Matlab was used to simulate the model parameters. The experimental values could be satisfactorily fitted to the simulated values with a relative error of 11.98 %.

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Abbreviations

A :

Substrate, vinyl acetate

B :

Substrate, citronellal

E :

Enzyme

EA:

Enzyme–vinyl acetate compound

EQ:

Enzyme–citronellyl acetate compound

F :

Acyl-enzyme

FB, FP:

Acyl-enzyme intermediate

k i :

Rate constant (i = ±1, ±2, ±3, ±4)

K IQ :

Inhibition constant of citronellyl acetate

K x :

Parameters of kinetics modeling (x = A, B, QA, BQA)

P :

Product, vinyl alcohol

Q :

Product, citronellyl acetate

V :

Reaction rate

V m :

Maximal rate of reaction

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Acknowledgments

We gratefully acknowledge the Chinese National Natural Science Foundation (No. 21006051) and A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions for their financial support.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225000, Jiangsu Province, People’s Republic of China

    Jian Xiong, Ya-Juan Huang & Hua Zhang

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  1. Jian Xiong
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  2. Ya-Juan Huang
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Correspondence to Jian Xiong.

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Xiong, J., Huang, YJ. & Zhang, H. Lipase-catalyzed transesterification synthesis of citronellyl acetate in a solvent-free system and its reaction kinetics. Eur Food Res Technol 235, 907–914 (2012). https://doi.org/10.1007/s00217-012-1819-3

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  • DOI: https://doi.org/10.1007/s00217-012-1819-3

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