Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents
International audience Four Deep Eutectic Solvents (DES) based on choline chloride (ChCl) and different hydrogen bond donors (1,4‐butanediol, glycerol, isosorbide, and urea) were tested as reaction medium for the immobilized Candida antarctica B (iCALB) lipase‐catalyzed esterification of fatty acids...
Published in: | Journal of the American Oil Chemists' Society |
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Online Access: | https://hal.science/hal-04288317 https://doi.org/10.1002/aocs.12784 |
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ftinstagro:oai:HAL:hal-04288317v1 2024-10-13T14:02:15+00:00 Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents Maurente, Lorena Callejas, Nicolás Volonterio, Elisa Baréa, Bruno Barouh, Nathalie Bourlieu-Lacanal, Claire Durand, Erwann Villeneuve, Pierre Figueroa-Espinoza, Maria Cruz Jachmanián, Iván Universidad de la República Montevideo (UDELAR) Démarche intégrée pour l'obtention d'aliments de qualité (UMR QualiSud) Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut de Recherche pour le Développement (IRD)-Avignon Université (AU)-Université de La Réunion (UR)-Institut Agro Montpellier Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Université de Montpellier (UM) Département Performances des systèmes de production et de transformation tropicaux (Cirad-PERSYST) Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad) Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE) Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut Agro Montpellier ECOS Sud—UdelaR No U17E02 cooperation program for financing research missionsand Agencia Nacional de Investigacion e Innovacion (ANNI) 2024 https://hal.science/hal-04288317 https://doi.org/10.1002/aocs.12784 en eng HAL CCSD Springer Verlag info:eu-repo/semantics/altIdentifier/doi/10.1002/aocs.12784 hal-04288317 https://hal.science/hal-04288317 doi:10.1002/aocs.12784 WOS: 001104993900001 ISSN: 0003-021X EISSN: 1558-9331 Journal of the American Oil Chemists' Society https://hal.science/hal-04288317 Journal of the American Oil Chemists' Society, 2024, 101 (4), pp.407-417. ⟨10.1002/aocs.12784⟩ Candida antarctica B lipase choline chloride deep eutectic solvents esterification saturated fattyacid [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2024 ftinstagro https://doi.org/10.1002/aocs.12784 2024-09-18T23:37:56Z International audience Four Deep Eutectic Solvents (DES) based on choline chloride (ChCl) and different hydrogen bond donors (1,4‐butanediol, glycerol, isosorbide, and urea) were tested as reaction medium for the immobilized Candida antarctica B (iCALB) lipase‐catalyzed esterification of fatty acids with n‐butanol. Although the strong hydrogen bonds between DES components were expected to lower their reactivity, all except urea, competed in the esterification reaction. To study the effect of acyl group donor and water, different chain length of saturated fatty acids (ranging from 6:0 to 18:0) and water content (ranging from 0, 1, 2 or 3 molar ratio of water/ChCl) were tested in the lipase‐catalyzed esterification with n‐butanol in ChCl:urea (1:2, molar ratio). When the incubation was performed in the absence of water, the shorter the fatty acid chain length, the higher the conversion. Upon water addition, a drastic increase in the esterification rate of all the fatty acids was observed and, conversely to what occurred in the anhydrous media, the longer the fatty acid chain length, the higher the conversion. Results suggest that water concentration in the DES medium possesses a multifactorial effect, as it influences the enzyme activity, the solvent viscosity, the DES structure, and the interaction between DES components, substrates, and enzymes, thus determining the efficiency and yield of the esterification reaction. Article in Journal/Newspaper Antarc* Antarctica Portail HAL Institut Agro Journal of the American Oil Chemists' Society |
institution |
Open Polar |
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Portail HAL Institut Agro |
op_collection_id |
ftinstagro |
language |
English |
topic |
Candida antarctica B lipase choline chloride deep eutectic solvents esterification saturated fattyacid [CHIM]Chemical Sciences |
spellingShingle |
Candida antarctica B lipase choline chloride deep eutectic solvents esterification saturated fattyacid [CHIM]Chemical Sciences Maurente, Lorena Callejas, Nicolás Volonterio, Elisa Baréa, Bruno Barouh, Nathalie Bourlieu-Lacanal, Claire Durand, Erwann Villeneuve, Pierre Figueroa-Espinoza, Maria Cruz Jachmanián, Iván Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
topic_facet |
Candida antarctica B lipase choline chloride deep eutectic solvents esterification saturated fattyacid [CHIM]Chemical Sciences |
description |
International audience Four Deep Eutectic Solvents (DES) based on choline chloride (ChCl) and different hydrogen bond donors (1,4‐butanediol, glycerol, isosorbide, and urea) were tested as reaction medium for the immobilized Candida antarctica B (iCALB) lipase‐catalyzed esterification of fatty acids with n‐butanol. Although the strong hydrogen bonds between DES components were expected to lower their reactivity, all except urea, competed in the esterification reaction. To study the effect of acyl group donor and water, different chain length of saturated fatty acids (ranging from 6:0 to 18:0) and water content (ranging from 0, 1, 2 or 3 molar ratio of water/ChCl) were tested in the lipase‐catalyzed esterification with n‐butanol in ChCl:urea (1:2, molar ratio). When the incubation was performed in the absence of water, the shorter the fatty acid chain length, the higher the conversion. Upon water addition, a drastic increase in the esterification rate of all the fatty acids was observed and, conversely to what occurred in the anhydrous media, the longer the fatty acid chain length, the higher the conversion. Results suggest that water concentration in the DES medium possesses a multifactorial effect, as it influences the enzyme activity, the solvent viscosity, the DES structure, and the interaction between DES components, substrates, and enzymes, thus determining the efficiency and yield of the esterification reaction. |
author2 |
Universidad de la República Montevideo (UDELAR) Démarche intégrée pour l'obtention d'aliments de qualité (UMR QualiSud) Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut de Recherche pour le Développement (IRD)-Avignon Université (AU)-Université de La Réunion (UR)-Institut Agro Montpellier Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Université de Montpellier (UM) Département Performances des systèmes de production et de transformation tropicaux (Cirad-PERSYST) Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad) Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE) Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut Agro Montpellier ECOS Sud—UdelaR No U17E02 cooperation program for financing research missionsand Agencia Nacional de Investigacion e Innovacion (ANNI) |
format |
Article in Journal/Newspaper |
author |
Maurente, Lorena Callejas, Nicolás Volonterio, Elisa Baréa, Bruno Barouh, Nathalie Bourlieu-Lacanal, Claire Durand, Erwann Villeneuve, Pierre Figueroa-Espinoza, Maria Cruz Jachmanián, Iván |
author_facet |
Maurente, Lorena Callejas, Nicolás Volonterio, Elisa Baréa, Bruno Barouh, Nathalie Bourlieu-Lacanal, Claire Durand, Erwann Villeneuve, Pierre Figueroa-Espinoza, Maria Cruz Jachmanián, Iván |
author_sort |
Maurente, Lorena |
title |
Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
title_short |
Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
title_full |
Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
title_fullStr |
Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
title_full_unstemmed |
Effect of the water content and the lengthening of fatty acids chain on the iCALB ‐catalyzed esterification in deep eutectic solvents |
title_sort |
effect of the water content and the lengthening of fatty acids chain on the icalb ‐catalyzed esterification in deep eutectic solvents |
publisher |
HAL CCSD |
publishDate |
2024 |
url |
https://hal.science/hal-04288317 https://doi.org/10.1002/aocs.12784 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 0003-021X EISSN: 1558-9331 Journal of the American Oil Chemists' Society https://hal.science/hal-04288317 Journal of the American Oil Chemists' Society, 2024, 101 (4), pp.407-417. ⟨10.1002/aocs.12784⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1002/aocs.12784 hal-04288317 https://hal.science/hal-04288317 doi:10.1002/aocs.12784 WOS: 001104993900001 |
op_doi |
https://doi.org/10.1002/aocs.12784 |
container_title |
Journal of the American Oil Chemists' Society |
_version_ |
1812815850784161792 |