Chemical Epoxidation of Oleic Acid to Produce Ab Type Monomer for Fatty-Acid-Based Polyester Synthesis

Abstract

Epoxides from vegetable oils are currently gaining more attention to replace petroleum-based monomers for polymer synthesis. As one of unsaturated fatty acids derived from vegetable oil, Oleic acid can be converted into epoxidized oleic acid by chemical epoxidation. Epoxidized oleic acid is a bifunctional monomer that has the potential to be used as raw material for fatty-acid-based polyester synthesis. This paper proposes the Taguchi-based optimization technique for in-situ epoxidation of oleic acid. The combining factors affecting the maximum yield were also determined to obtain a higher quality of epoxidized oleic acid in a relatively short time. Epoxidized oleic acid was characterized and tested for degradation. The characterization result showed the possibility of the polymerization reaction, and the kinetic study showed that the rate of epoxide degradation at room temperature follows second order with a reaction rate constant of2.7235 gr.mmol-1.day-1.

Preparing epoxidized vegetable oil from waste generated by the kapok fiber industry and assessing its thermal stabilization effect as a co-stabilizer for polyvinyl chloride

“…The presence of double bonds is indicated by the absorption peak of C C–H stretching vibration at 3007 cm −1 . The success of epoxidation can be observed through the disappearance of the absorption band of the double bond at 3007 cm −1 and the emergence of a new epoxide band in the EKSO spectrum ranging from 844 to 824 cm −1 , which is indicative of the formation of the epoxide [ 38 , 56 , 57 ].

Fig.

…”

Self-Polymerization Reaction of Epoxidized Oleic Acid: Kinetic and Product Characterization

“…Miao et al [6] explained that epoxidized oleic acid produced through enzymatic epoxidation could be converted into polyester. Furthermore, our preliminary research shows that the same type of polymer can also be synthesized via the chemical epoxidation route [20]. Using oleic acid from crude palm oil, Bahadi et al [21] synthesized epoxidized oleic acid via a chemical epoxidation route to produce palm oil-based polyester.…”

“…EOA was prepared from oleic acid via insitu chemical epoxidation using formic acid as an oxygen carrier and n-hexane as a solvent under optimized reaction conditions [20]. First, oleic acid (50 g), formic acid (20 mL), and solvent (50 g) were transferred to a three-neck flask equipped with a stirrer, heater, thermometer, and reflux system.…”

“…Considering that EOA obtained from the epoxidation reaction does not reach 100% yield [20], it can be said that more carboxylate groups are available for the polymerization reaction than the oxirane groups. Figures 4 show the differences between the initial values for the acid number and the oxirane for each temperature.…”