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Derivatization of castor oil based estolide esters: Preparation of epoxides and cyclic carbonates
- Kenneth M. Doll, Steven C. Cermak, James A. Kenar, Erin L. Walter, Terry A. Isbell
- Industrial crops and products 2017 v.104 pp. 269-277
- carbon dioxide, carbonates, castor oil, derivatization, epoxides, estolides, hydrogen peroxide, industrial applications, oleic acid, oxidation, temperature, tetrabutylammonium compounds, viscosity
- Estolides that are based on castor oil and oleic acid are versatile starting points for the production of industrial fluids with new properties. A variety of unsaturated estolides were derivatized by epoxidation with hydrogen peroxide. The epoxidized estolides were further modified using supercritical carbon dioxide and tetrabutylammonium bromide to chemically incorporate carbon dioxide into the material yielding a 5-membered cyclic carbonate structure. These new epoxides and cyclic carbonates exhibited higher pour points, oxidation onset temperatures, and viscosities, compared to the corresponding unsaturated precursors. One derivative had a dynamic viscosity of ∼9000mPa s at 40°C, demonstrating potential for use in industrial applications.