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. Auto-catalytic production of eugenyl acetate and eugenyl butyrate using microwave radiation: A kinetic and mechanism-related approach. Journal of Chemical Technology and Biotechnology, 96 (3) : 704-713.

https://doi.org/10.1002/jctb.6583

Article de revue ; Article de recherche ; Article de revue à facteur d'impact

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Quartile : Q2, Sujet : BIOTECHNOLOGY & APPLIED MICROBIOLOGY / Quartile : Q2, Sujet : CHEMISTRY, MULTIDISCIPLINARY / Quartile : Q2, Sujet : ENGINEERING, CHEMICAL / Quartile : Q3, Sujet : ENGINEERING, ENVIRONMENTAL

Résumé : 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.

Mots-clés Agrovoc : micro-ondes, butyrate, butyrate (ester), acétate (ester), Activité catalytique

Mots-clés libres : Auto-catalytic production, Eugenyl acetate, Eugenyl butyrate, Kinetics, Microwave

Classification Agris : Q02 - Traitement et conservation des produits alimentaires
Q04 - Composition des produits alimentaires
F60 - Physiologie et biochimie végétale

Champ stratégique Cirad : CTS 3 (2019-) - Systèmes alimentaires

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