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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 solvents

Author
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: 12/22/2023
Citation: Shah, S.N., Liu, Z. 2023. Natural epoxy oil (Euphorbia oil) polymerization in liquid carbon dioxide-green solvents. In: Liu, Z., Kraus, G., editors. Green Chemistry and Green Materials from Plant Oils and Natural Acids. Volume 83. Cambridge, UK:Royal Society of Chemistry Publishing. p. 144-158. https://doi.org/10.1039/9781837671595.
DOI: https://doi.org/10.1039/9781837671595

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. Plant oils with an epoxidized ring have been investigated to overcome this shortcoming. One such plant oil is euphorbia oil (EuO). This chapter discusses the ring-opening polymerization of EuO in a liquid carbon dioxide–green solvent using the boron trifluoride diethyl etherate (BF3·OEt2) catalyst. A variety of analytical techniques have been used to characterize the material, including FTIR, 1H-NMR, 13C-NMR, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and gel permeation chromatography (GPC). Using subcritical carbon dioxide (CO2) and a pressure of 65.5 bar, the ring-opening polymerization of euphorbia oil (RPEuO) was carried out under mild conditions, such as at room temperature. It was found that the cross-linked polymers formed by RPEuO had glass transition temperatures ranging from -15.0 °C to -22.7 °C. RPEuO polymers were thermally stable below 220 °C, and decomposition occurred above 340 °C, according to the TGA results.