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Consecutive reactions in an oleic acid and acetic anhydride reaction medium

Peydecastaing, Jérôme and Vaca-Garcia, Carlos and Borredon, Marie-Elisabeth Consecutive reactions in an oleic acid and acetic anhydride reaction medium. (2009) European Journal of Lipid Science and Technology, 111 (7). 723-729. ISSN 1438-7697

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Official URL: https://doi.org/10.1002/ejlt.200800189


When mixing acetic anhydride and oleic acid, two consecutive reactions take place. The first one yields acetic‐oleic anhydride (AOA) and acetic acid. In the second one, oleic acid reacts with AOA to form oleic anhydride at 5% in a mixture when the initial molar ratio is 1:1. Therefore, at equilibrium, the global reaction yields a mixture of AOA, acetic anhydride, oleic acid, acetic acid and oleic anhydride. Based on a new HPLC protocol, all the species of the reaction medium could be separated and quantified. This permitted for the first time to study the kinetics and thermodynamics of the reaction. In the 30–70 °C range, reactions were of order 2 with partial orders of 1 for each reactant. Equilibrium constants were determined for both reactions. Enthalpy, entropy and activation energies were calculated for the main reaction. The influence of molar ratio on the composition at equilibrium was also investigated. The synthesis of AOA could thus be understood and new data were obtained for this singular molecule scarcely cited in the CAS database.

Item Type:Article
HAL Id:hal-02072202
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:19 Mar 2019 07:34

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