Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach
BACKGROUND: Applications of chemical and enzymatic methods of esterification have been limited by low selectivity of chemical catalysts and low productivity and high cost of enzymes. The objective of this study was to produce eugenol esters with high productivity and selectivity using a microwave technique without adding any catalyst or solvent. Specific focus was given to reaction temperature and molar ratio to establish the kinetics and mechanism of eugenol auto‐catalytic acylation using microwave radiation. RESULTS: Reaction conversion was observed to increase in response to higher temperatures. The optimum molar ratio of eugenyl/acetic anhydride was 1:6, while the optimum molar ratio of eugenyl/butyric anhydride was 1:4.5. A high degree of selectivity (of over 97%) occurred under all conditions of the reaction. Based on modelling studies, it can be concluded that the intended reaction follows second‐order kinetics for both eugenyl acetate and eugenyl butyrate. Microwave heating at 70 °C led to an increase of rate constant by 3.71‐ and 3.83‐fold for eugenyl acetate and eugenyl butyrate, respectively, as compared to the conventional method. This was associated with a decrease in the activation energy (4.38% for eugenyl acetate and 3.11% for eugenyl butyrate) and an increase in the frequency factor (42.31% for eugenyl acetate and 49.84% for eugenyl butyrate) and entropy (4.71% for eugenyl acetate and 5.22% for eugenyl butyrate) as a result of using microwave radiation. CONCLUSIONS: The microwave technique can be considered as a green, low‐cost and quick process for auto‐catalytic production of eugenol esters.
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Subjects: | Q02 - Traitement et conservation des produits alimentaires, Q04 - Composition des produits alimentaires, F60 - Physiologie et biochimie végétale, micro-ondes, butyrate, butyrate (ester), acétate (ester), Activité catalytique, http://aims.fao.org/aos/agrovoc/c_4815, http://aims.fao.org/aos/agrovoc/c_1167, http://aims.fao.org/aos/agrovoc/c_32023, http://aims.fao.org/aos/agrovoc/c_32018, http://aims.fao.org/aos/agrovoc/c_1382, |
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dig-cirad-fr-5967932024-01-29T03:07:01Z http://agritrop.cirad.fr/596793/ http://agritrop.cirad.fr/596793/ Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach. Keramat Malihe, Golmakani Mohammad-Taghi, Durand Erwann, Villeneuve Pierre, Hashem Hosseini Seyed Mohammad. 2021. Journal of Chemical Technology and Biotechnology, 96 (3) : 704-713.https://doi.org/10.1002/jctb.6583 <https://doi.org/10.1002/jctb.6583> Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach Keramat, Malihe Golmakani, Mohammad-Taghi Durand, Erwann Villeneuve, Pierre Hashem Hosseini, Seyed Mohammad eng 2021 Journal of Chemical Technology and Biotechnology Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 BACKGROUND: Applications of chemical and enzymatic methods of esterification have been limited by low selectivity of chemical catalysts and low productivity and high cost of enzymes. The objective of this study was to produce eugenol esters with high productivity and selectivity using a microwave technique without adding any catalyst or solvent. Specific focus was given to reaction temperature and molar ratio to establish the kinetics and mechanism of eugenol auto‐catalytic acylation using microwave radiation. RESULTS: Reaction conversion was observed to increase in response to higher temperatures. The optimum molar ratio of eugenyl/acetic anhydride was 1:6, while the optimum molar ratio of eugenyl/butyric anhydride was 1:4.5. A high degree of selectivity (of over 97%) occurred under all conditions of the reaction. Based on modelling studies, it can be concluded that the intended reaction follows second‐order kinetics for both eugenyl acetate and eugenyl butyrate. Microwave heating at 70 °C led to an increase of rate constant by 3.71‐ and 3.83‐fold for eugenyl acetate and eugenyl butyrate, respectively, as compared to the conventional method. This was associated with a decrease in the activation energy (4.38% for eugenyl acetate and 3.11% for eugenyl butyrate) and an increase in the frequency factor (42.31% for eugenyl acetate and 49.84% for eugenyl butyrate) and entropy (4.71% for eugenyl acetate and 5.22% for eugenyl butyrate) as a result of using microwave radiation. CONCLUSIONS: The microwave technique can be considered as a green, low‐cost and quick process for auto‐catalytic production of eugenol esters. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/596793/7/596793.pdf text Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1002/jctb.6583 10.1002/jctb.6583 info:eu-repo/semantics/altIdentifier/doi/10.1002/jctb.6583 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1002/jctb.6583 |
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Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 |
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Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 Keramat, Malihe Golmakani, Mohammad-Taghi Durand, Erwann Villeneuve, Pierre Hashem Hosseini, Seyed Mohammad Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
description |
BACKGROUND: Applications of chemical and enzymatic methods of esterification have been limited by low selectivity of chemical catalysts and low productivity and high cost of enzymes. The objective of this study was to produce eugenol esters with high productivity and selectivity using a microwave technique without adding any catalyst or solvent. Specific focus was given to reaction temperature and molar ratio to establish the kinetics and mechanism of eugenol auto‐catalytic acylation using microwave radiation. RESULTS: Reaction conversion was observed to increase in response to higher temperatures. The optimum molar ratio of eugenyl/acetic anhydride was 1:6, while the optimum molar ratio of eugenyl/butyric anhydride was 1:4.5. A high degree of selectivity (of over 97%) occurred under all conditions of the reaction. Based on modelling studies, it can be concluded that the intended reaction follows second‐order kinetics for both eugenyl acetate and eugenyl butyrate. Microwave heating at 70 °C led to an increase of rate constant by 3.71‐ and 3.83‐fold for eugenyl acetate and eugenyl butyrate, respectively, as compared to the conventional method. This was associated with a decrease in the activation energy (4.38% for eugenyl acetate and 3.11% for eugenyl butyrate) and an increase in the frequency factor (42.31% for eugenyl acetate and 49.84% for eugenyl butyrate) and entropy (4.71% for eugenyl acetate and 5.22% for eugenyl butyrate) as a result of using microwave radiation. CONCLUSIONS: The microwave technique can be considered as a green, low‐cost and quick process for auto‐catalytic production of eugenol esters. |
format |
article |
topic_facet |
Q02 - Traitement et conservation des produits alimentaires Q04 - Composition des produits alimentaires F60 - Physiologie et biochimie végétale micro-ondes butyrate butyrate (ester) acétate (ester) Activité catalytique http://aims.fao.org/aos/agrovoc/c_4815 http://aims.fao.org/aos/agrovoc/c_1167 http://aims.fao.org/aos/agrovoc/c_32023 http://aims.fao.org/aos/agrovoc/c_32018 http://aims.fao.org/aos/agrovoc/c_1382 |
author |
Keramat, Malihe Golmakani, Mohammad-Taghi Durand, Erwann Villeneuve, Pierre Hashem Hosseini, Seyed Mohammad |
author_facet |
Keramat, Malihe Golmakani, Mohammad-Taghi Durand, Erwann Villeneuve, Pierre Hashem Hosseini, Seyed Mohammad |
author_sort |
Keramat, Malihe |
title |
Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
title_short |
Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
title_full |
Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
title_fullStr |
Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
title_full_unstemmed |
Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach |
title_sort |
auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: a kinetic and mechanism-related approach |
url |
http://agritrop.cirad.fr/596793/ http://agritrop.cirad.fr/596793/7/596793.pdf |
work_keys_str_mv |
AT keramatmalihe autocatalyticproductionofeugenylacetateandeugenylbutyrateusingmicrowaveradiationakineticandmechanismrelatedapproach AT golmakanimohammadtaghi autocatalyticproductionofeugenylacetateandeugenylbutyrateusingmicrowaveradiationakineticandmechanismrelatedapproach AT duranderwann autocatalyticproductionofeugenylacetateandeugenylbutyrateusingmicrowaveradiationakineticandmechanismrelatedapproach AT villeneuvepierre autocatalyticproductionofeugenylacetateandeugenylbutyrateusingmicrowaveradiationakineticandmechanismrelatedapproach AT hashemhosseiniseyedmohammad autocatalyticproductionofeugenylacetateandeugenylbutyrateusingmicrowaveradiationakineticandmechanismrelatedapproach |
_version_ |
1792500044073533440 |