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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #400727

Research Project: New High-Value Biobased Materials with Applications Across Industry

Location: Bio-oils Research

Title: Natural epoxy oil (Euphorbia oil) polymerization in liquid carbon dioxide-green solvent

item SHAH, SHAILESH - The University Of Texas At Dallas
item Liu, Zengshe - Kevin

Submitted to: Book Chapter
Publication Type: Book / Chapter
Publication Acceptance Date: 2/10/2023
Publication Date: N/A
Citation: N/A

Interpretive Summary: Materials made out of vegetable oils, which actually perform like their petroleum-based counterparts, have been a research goal for many years. A chemical method where a reactive group called an oxirane is incorporated into the oil is one route that has been well explored, and the resulting oils have been used in coatings, lubricants, and solid plastics for years. However, this chemical route adds expense to the oil and in some cases, the chemical transformation can be incomplete. An oil called euphorbia oil naturally has some of these chemical groups already present in the oil. Similar products can be made using the same types of catalysts that work for chemically modified oils. Further this process can be made to work in liquid carbon dioxide avoiding the need for harmful volatile chemical solvents. This will provide materials that are attractive candidates for use in personal care products, water absorbing gels, and coatings produced from a natural oil.

Technical Abstract: Aside from being renewable, non-toxic, non-polluting, biodegradable, and environmentally friendly, vegetable oils also possess renewable properties. Due to these properties, vegetable oils have been used in a variety of industrial applications, such as plastics, lubricants, adhesives, inks, fuels/biodiesel, coatings, printing inks, varnish solvents, and surfactants. Many researchers have reported the production of polymers from vegetable oils, specifically from epoxidized soybean oil (ESO). However, ESO must be synthesized using conventional synthetic routes, and some of the synthesized epoxide rings can degrade during the process. A plant oil with an epoxidized ring has been investigated by our group to overcome this shortcoming. One such plant oil is Euphorbia Oil (EuO). The current chapter discusses the formation of the ring-opening polymerization of euphorbia oil (RPEuO) in liquid carbon dioxide-green solvent using boron trifluoride diethyl etherate (BF3·OEt2) catalyst. A variety of analytical techniques have been used to characterize the RPEuO materials, including FTIR, 1H-NMR, 13C-NMR, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and gel permeation chromatography (GPC). Using a subcritical carbon dioxide (CO2) pressure of 65.5 bar, the RPEuO occurred under mild conditions, such as at room temperature. It was found that the cross-linked polymers formed by RPEuO had polymers with glass transition temperatures ranging from -15.0 deg. C to -22.7 deg. C. According to TGA results, RPEuO polymers were thermally stable below 220 deg. C. and decomposition occurred above 340 deg. C.