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Effect of water and lipophilic alcohols or amines on the 4-dodecylbenzenesulfonic acid-catalyzed esterifications, trans- esterifications, and amidations

Abstract : 4‐Dodecylbenzenesulfonic acid (DBSA) was employed in the esterification of oleic acid (OA) and the trans‐esterification of oleic oil (OO) with 1‐butanol as alcohol in the presence of various degrees of excess water. Under these conditions DBSA was found to be a highly active esterification catalyst regardless of excess water content, but was found to be a less effective for trans‐esterification reactions. Lipophilic alcohols of differing straight and branched C3‐6 chains were also tested on mixtures of OA/water (1:1) in DBSA‐catalyzed esterifications; OO/water (1:1) in trans‐esterifications; and OA/OO/water (1:1:1) in simultaneous esterifications and trans‐esterifications. While longer straight chain alcohols generally gave a two‐fold increase in yield of their corresponding alkyl oleates to 80%+, we observed a doubling from 30–50% to 60–95% of alkyl oleate yield for the OO/OA/water mixture. DBSA‐catalyzed amidations of OO and methyl oleate emulsions in water were conducted with 1‐butyl and 1‐heptyl amine where it was found that the more lipophilic the ester moiety the higher the yield of alkyl amide.
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Submitted on : Wednesday, November 27, 2019 - 3:13:01 PM
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Christopher D. Wallis, Muriel Cerny, Eric Lacroux, Zéphirin Mouloungui. Effect of water and lipophilic alcohols or amines on the 4-dodecylbenzenesulfonic acid-catalyzed esterifications, trans- esterifications, and amidations. European Journal of Lipid Science and Technology, Wiley-VCH Verlag, 2017, 119 (9), pp.1600483. ⟨10.1002/ejlt.201600483⟩. ⟨hal-02383045⟩

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