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Kinetics and mechanism of the reaction between maleic anhydride and fatty acid esters and the structure of the products

Ştefănoiu, Florina and Candy, Laure and Vaca-Garcia, Carlos and Borredon, Marie-Elisabeth Kinetics and mechanism of the reaction between maleic anhydride and fatty acid esters and the structure of the products. (2008) European Journal of Lipid Science and Technology, 110 (5). 441-447. ISSN 1438-7697

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Official URL: https://doi.org/10.1002/ejlt.200700181

Abstract

Alkenyl succinic anhydrides (ASA) were obtained by reaction between maleic anhydride and high‐oleic sunflower oil (HOSO) esters. A kinetics study of the maleinization of alkyl esters indicated that the maleinization reaction was second order overall and first order with respect to the individual reactants, and the activation energy was 77.2 ± 3.3 kJ/mol in the investigated temperature range (185–225 °C). These results showed that the cis configuration and the central position of the double bond in HOSO esters facilitate the maleinization of the latter. On the contrary, the length of the linear ester moiety had no influence on the course of the maleinization reaction. Moreover, new evidence demonstrates that there are two different reaction mechanisms: ene‐reaction and addition in allylic position with a 2 : 1 ratio, respectively. This ratio was constant throughout the reaction, thus indicating that these mechanisms are independent.

Item Type:Article
HAL Id:hal-02067406
Audience (journal):International peer-reviewed journal
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Institution:Université de Toulouse > Institut National Polytechnique de Toulouse - Toulouse INP (FRANCE)
French research institutions > Institut National de la Recherche Agronomique - INRA (FRANCE)
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Deposited On:14 Mar 2019 10:23

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