Preparation Of Fatty Acids Esters Derived From Epoxidized Soybean Oil

As the mineral oil reserves drastically reduced and people’s awareness of environmental protection, the development and utilization of sustainable energy is a matter of great urgency. Sustainable energy must be necessary to meet the large reserves or productive, but also instead of petroleum as renewable industrial raw materials to some extent, in addition, their use can’t pollute the environment. Plant oil as the product of nature may be in full compliance with the requirements of sustainable energy. In this paper, we take soybean oil as raw material and explored its epoxide. In recent years, plant oil-base epoxidized products in green materials, lubricants, plasticizers and other fields has been used widely. In this paper, we take cheap and readily available soybean oil as raw material, the products and its ethylene derivatives were studied.Firstly, take a trans-treatment of soybean oil to make it contains trans- fatty acids. Epoxidized the soybean oil containing trans- fatty acids using chemical catalysis. The experiments on the amount of catalyst, reaction temperature, reaction time, the amount of formic acid, the amount of hydrogen peroxide were compared on the influence of epoxidation reaction, respectively. The results indicated that the epoxy oxygen group content(EOC) of soybean oil containing trans- fatty acids was 6.1% under the conditions of Soybean oil 10 g, sulfuric acid 33.3?L, formic acid 3mL, hydrogen peroxide 13.3mL, 60℃, 2.5h. It was also found that under this reaction condition, soybean oil containing trans-fatty acids and soybean oil in nature reached the same maximum, was 6.1%. Finally, evaluated the oxidative stability of epoxy oil with as well as without trans- fatty acids by oil accelerated oxidation method(Rancimat method). Experimental results show that epoxy oil with trans-fats has better oxidative stability than that without trans-fats.Secondly, alcoholysis of the epoxidized soybean oil to prepare epoxy methyl esters catalyzed by Novozym435. The effects of reaction time, amount of catalyst and substrate molar ratio, reaction temperature on the alcoholysis of epoxidized oil and its epoxy value was explored. The optimal conditions of epoxidized soybean oil’s alcoholysis by Single factor optimization experiments are as follows, the reaction temperature is 45 ℃, Novozym435 enzyme dosage to 5% by weight of epoxide oil, methanol to oil molar ratio of 5:1, reaction time is 14 hours. Under this condition, the alcoholysis yield of epoxy oil is 94.5%, and the epoxy value of the materials will not change significantly with changing the reaction conditions. We also prepared epoxy ethyl esters through alcoholysis of the epoxidized soybean oil and ethyl alcohol under the same conditions.Finally, we made the transesterification of epoxy soybean oil fatty acid methyl ester and hydroxyethyl acrylate catalyzed by Novozym435 enzyme to produce allyl epoxy fatty acid ester with carbon-carbon double bond. The optimum reaction conditions of the transesterification is as follows, the reaction temperature is 50℃, Novozym435 enzyme dosage is 5% by weight of the substrate, the molar ratio(hydroxylethyl acrylate and epoxy fatty acid methyl ester) is 4:1, the reaction time is 24 hours. The yield of transesterification in this condation is 83.69%, and the experiments show that using Novozym435 enzyme as the catalyst hardly causes a ring-opening reaction of epoxy groups. The final products were analysis by 1H NMR, it proved that the obtained product is indeed the propylene-based epoxy methyl esters. The carbon-carbon double chain was then polymerized to an epoxy polymer catalyzed by AIBN, which proved that propylene-based epoxy soybean oil fatty acid esters can be easily polymerized to achieve polymer containing epoxy groups and provides a new reference for the development of vegetable oil-based polymer.