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Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters

Biocatalytic synthesis of 2-ethylhexyl 2-methylhexanoate is described in this work for the first time. This branched-chain ester is suitable for use at low temperatures in numerous applications. The immobilized lipase Novozym(®) 435 has demonstrated its ability to catalyze the ester synthesis from 2...

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Autores principales: Montiel, María Claudia, Asensi, Miguel, Gimeno-Martos, Silvia, Máximo, Fuensanta, Bastida, Josefa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8625366/
https://www.ncbi.nlm.nih.gov/pubmed/34832249
http://dx.doi.org/10.3390/ma14226847
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author Montiel, María Claudia
Asensi, Miguel
Gimeno-Martos, Silvia
Máximo, Fuensanta
Bastida, Josefa
author_facet Montiel, María Claudia
Asensi, Miguel
Gimeno-Martos, Silvia
Máximo, Fuensanta
Bastida, Josefa
author_sort Montiel, María Claudia
collection PubMed
description Biocatalytic synthesis of 2-ethylhexyl 2-methylhexanoate is described in this work for the first time. This branched-chain ester is suitable for use at low temperatures in numerous applications. The immobilized lipase Novozym(®) 435 has demonstrated its ability to catalyze the ester synthesis from 2-ethylhexanol and 2-methylhexanoic acid in a solvent-free medium. The high reaction times that are required result in a loss of alcohol by evaporation, which must be compensated for with an excess of this substrate if high conversions are to be achieved. Therefore, two strategies are established: 70 °C with a 10% excess of alcohol, which requires a longer operating time and provides conversions of 97%, and 80 °C with a 20% excess of alcohol, which allows for the achievement of a 99% conversion in a shorter time. The optimal reaction conditions have been chosen based on reusability of the enzyme, process productivity, green metrics and preliminary economic study. When the synthesis is carried out under the best conditions (70 °C, 10% molar excess of alcohol and six uses of the immobilized enzyme) a productivity of 203.84 kg product × kg biocatalyst(−1) is attained. The biocatalytic procedure matches many of the objectives of “green chemistry” and is suitable to be scaled up and used in industrial manufacturing.
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spelling pubmed-86253662021-11-27 Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters Montiel, María Claudia Asensi, Miguel Gimeno-Martos, Silvia Máximo, Fuensanta Bastida, Josefa Materials (Basel) Article Biocatalytic synthesis of 2-ethylhexyl 2-methylhexanoate is described in this work for the first time. This branched-chain ester is suitable for use at low temperatures in numerous applications. The immobilized lipase Novozym(®) 435 has demonstrated its ability to catalyze the ester synthesis from 2-ethylhexanol and 2-methylhexanoic acid in a solvent-free medium. The high reaction times that are required result in a loss of alcohol by evaporation, which must be compensated for with an excess of this substrate if high conversions are to be achieved. Therefore, two strategies are established: 70 °C with a 10% excess of alcohol, which requires a longer operating time and provides conversions of 97%, and 80 °C with a 20% excess of alcohol, which allows for the achievement of a 99% conversion in a shorter time. The optimal reaction conditions have been chosen based on reusability of the enzyme, process productivity, green metrics and preliminary economic study. When the synthesis is carried out under the best conditions (70 °C, 10% molar excess of alcohol and six uses of the immobilized enzyme) a productivity of 203.84 kg product × kg biocatalyst(−1) is attained. The biocatalytic procedure matches many of the objectives of “green chemistry” and is suitable to be scaled up and used in industrial manufacturing. MDPI 2021-11-13 /pmc/articles/PMC8625366/ /pubmed/34832249 http://dx.doi.org/10.3390/ma14226847 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Montiel, María Claudia
Asensi, Miguel
Gimeno-Martos, Silvia
Máximo, Fuensanta
Bastida, Josefa
Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title_full Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title_fullStr Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title_full_unstemmed Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title_short Sustainable Biocatalytic Procedure for Obtaining New Branched Acid Esters
title_sort sustainable biocatalytic procedure for obtaining new branched acid esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8625366/
https://www.ncbi.nlm.nih.gov/pubmed/34832249
http://dx.doi.org/10.3390/ma14226847
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