Fluoroantimonic acid hexahydrate (HSbF6·6H2O) catalysis: The ring-opening polymerization of epoxidized soybean oil

Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by a super acid, fluoroantimonic acid hexahydrate (HSbF6·6H2O) in ethyl acetate was conducted in an effort to develop useful biodegradable polymers. The resulting polymerized ESO (SA-RPESO) was characterized using infrared (IR) spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), 1H NMR, 13C NMR, solid state 13C NMR, and gel permeation chromatography (GPC). The results indicated that ESO was effectively polymerized by fluoroantimonic acid and formed polymers with relatively high crosslink density. Glass transition temperatures of these polymers ranged from −13 °C to −21 °C. TGA results showed the SA-RPESO polymers were thermally stable at temperatures up to 200 °C. Decomposition of the polymers was found to occur at temperatures greater than 350 °C. GPC results indicated the extracted soluble substances from SA-RPESO polymers were oligomers of ESO. These soybean oil-based polymers will be functionalized to hydrogels and their applications explored in the personal and health care areas.

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► Epoxidized soybean oil was polymerized in ethyl acetate solution at room temperature.
► Fluoroantimonic acid hexahydrate (HSbF6·6H2O) was used as catalyst.
► The formed biodegradable polymers are highly desirable from renewable resources.
► 1H and 13C NMR, solid NMR and GPC were used to characterize the polymers.