Solvent-Free Acid-Catalyzed Ring-Opening of Epoxidized Oleochemicals Using Stearates/Stearic Acid, and Its Applications
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- 作者：Byung-Jun Kollbe Ahn ; Stefan Kraft ; Xiuzhi Susan Sun
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2012
- 出版时间：March 7, 2012
- 年：2012
- 卷：60
- 期：9
- 页码：2179-2189
- 全文大小：561K
- 年卷期：v.60,no.9(March 7, 2012)
- ISSN：1520-5118
文摘
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 掳C, 12 h) superior to other fatty acid derivatives such as a Lewis acid (lithium and sodium stearate) and Br酶nsted 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路s at 25 掳C when ESO:Mg-stearate increased from 1:1 equiv to 1:2, then behaved like thermoplastics (Tg = 鈭?7 掳C, Tm = 90 掳C) with 1:4.