ARS | Publication request: Epoxidation of methyl oleate using heterogeneous catalyst

Submitted to: Chemical Reaction Engineering
Publication Type: Abstract
Publication Acceptance Date: January 24, 2008
Publication Date: June 15, 2008
Citation: Suarez, P.A., Costa, M.S., Sharma, B.K., Doll, K.M., Erhan, S.Z. 2008. Epoxidation of methyl oleate using heterogeneous catalyst [abstract]. Chemical Reaction Engineering. p.19.

Technical Abstract: A variety of synthetic processes have been reported, utilizing epoxidized soybean oil and corresponding epoxy fatty ester systems, as intermediates to obtain industrially significant materials, e.g. bio-based polymers, emollients, chemical solvents, fuel additives, and lubricants. One of the reasons for the use of vegetable oils or its derivatives in these applications is their inherent biodegradability, which reduces their environmental impact. Vegetable oils, especially soybean oil, are relatively inexpensive and their production has been increasing in recent years. At the same time, petroleum prices are high, and not likely to significantly decline in the near future. The use of oleochemicals as lubricants is well known, demonstrated by their superior lubricity compared to petroleum diesel. However, vegetable oils have oxidative stability so low and cold flow properties too poor for their use in lubricant applications. One potential way to change these properties is through chemical derivatization of the olefinic groups of the oleochemical. Hydrogenation, transesterification, epoxidation, metathesis, and alkylation, or a combination of chemistries have all been used in order to synthesize an improved product. We have previously studied epoxidation of unsaturated fatty acid esters using a slight modification of the synthesis of Bunker and Wool. Apart from use as intermediates in various products, the fully epoxidized compounds have also been patented for potential use as fuel and lubricant additives, and is important in the replacement of petrochemicals with biobased alternatives. In this work we studied synthesis of epoxidized methyl oleate from methyl oleate and hydrogen peroxide in the presence of alumina catalysts. The reaction progress was monitored using GC-FID. Experimental conditions involving various catalysts, based on aluminum oxide with different surface area and acidity, were compared. Catalyst amount, peroxide amount, and time were optimized for research quantity.