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Updated: May 25, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Solvent-free acid-catalyzed ring-opening of epoxidized oleochemicals using stearates/stearic acid, and its
Byung-Jun Kollbe Ahn1, Stefan Kraft, Xiuzhi Susan Sun
1Department of Grain Science and Industry, Kansas State University, Manhattan, Kansas 66506, United States.
Abstract:
Toxic solvent and strong acid catalysts causing environmental issues have been mainly used for ring-opening of epoxidized oleochemicals. Here, we demonstrated that magnesium stearate (Mg-stearate) was a high efficient catalyst for solvent-free ring-opening of epoxidized methyl oleate, a model compound of midchain epoxide. Mg-stearate resulted in the highest yield (95%) and conversion rate (99%) toward midchain alkoxyesters under the same conditions (160 °C, 12 h) superior to other fatty acid derivatives such as a Lewis acid (lithium and sodium stearate) and Brønsted acid (stearic acid). Based on this chemical study, we synthesized biogrease and thermoplastic using epoxidized soybean oil (ESO) and Mg-stearate via one-pot, solvent-free, and purification-free process. Mg-stearate played a significant role as a reactant for epoxide ring-opening and as a thickener when excess loading rate was used; viscosity increased from 1800 to 4500 Pa·s at 25 °C when ESO:Mg-stearate increased from 1:1 equiv to 1:2, then behaved like thermoplastics (T(g) = -27 °C, T(m) = 90 °C) with 1:4.
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