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Synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on a magnetic polymer support in continuous flow

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Abstract

This study investigated the synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on magnetic poly(styrene-co-divinylbenzene) particles in a continuous packed-bed bioreactor. Runs were carried out in a solvent-free system at 50 °C. The performance of the reactor was evaluated for substrates composed by oleic acid and 2-ethylhexanol at five molar ratios (1:4–4:1), determining its operation limits in terms of substrate flow rate. The system performance was quantified for three different flow rates corresponding to space-time between 3 and 12 h. For each condition, the influence of the space-time in the ester formation, esterification yield and productivity was determined. The molar ratio of acid-to-alcohol interfered, in a remarkable way, in the formation of 2-ethylhexyl oleate and the best performance was attained for substrate at equimolar ratio running at 12 h space-time. Under this condition, average 2-ethylhexyl oleate concentration was 471.65 ± 2.98 g L−1 which corresponded to ester productivity of 23.16 ± 0.49 mmol g−1 L−1 h−1. This strategy also gave high biocatalyst operational stability, revealing a half-life time of 2063 h. A model based on the ping-pong Bi–Bi mechanism was developed to describe the kinetics of the esterification reaction and validated using experimental data. The goodness of fit of the model was satisfactory (R2 = 0.9310–0.9952).

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Acknowledgements

This work was supported by the São Paulo Research Foundation (FAPESP) (Grant Numbers #2016/17833-3, #2016/10636-8 and #2017/04934-9) and CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior-Brazil)—Finance Code 001.

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Authors and Affiliations

  1. Department of Chemical Engineering, Engineering School of Lorena, University of São Paulo, Lorena, SP, 12602-810, Brazil

    Mateus V. C. da Silva, Amanda B. Souza, Heizir F. de Castro, Leandro G. Aguiar, Pedro C. de Oliveira & Larissa de Freitas

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  1. Mateus V. C. da Silva
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  2. Amanda B. Souza
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  3. Heizir F. de Castro
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  4. Leandro G. Aguiar
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  5. Pedro C. de Oliveira
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  6. Larissa de Freitas
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Correspondence to Larissa de Freitas.

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da Silva, M.V.C., Souza, A.B., de Castro, H.F. et al. Synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on a magnetic polymer support in continuous flow. Bioprocess Biosyst Eng 43, 615–623 (2020). https://doi.org/10.1007/s00449-019-02257-9

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