Solvent-Free Acid-Catalyzed Ring-Opening of Epoxidized Oleochemicals Using Stearates/Stearic Acid, and Its Applications

• Published in: Journal of agricultural and food chemistry 2012-03, Vol.60 (9), p.2179-2189
• Main Authors: Ahn, Byung-Jun Kollbe, Kraft, Stefan, Sun, Xiuzhi Susan
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; Catalysis; catalysts; Epoxy Compounds - chemistry; Fat industries; Food industries; Fundamental and applied biological sciences. Psychology; lithium; Lubricants - chemical synthesis; magnesium; oleic acid; Oleic Acids - chemistry; Petroleum; soybean oil; Soybean Oil - chemistry; stearic acid; Stearic Acids - chemistry; Thermodynamics; thermoplastics; toxicity; Viscosity
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf204275q

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.