Title: Influence of solid supports on acyl migration in 2-Monoacylglycerols: Purification of 2-MAG via flash chromatography Authors
Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 10, 2013
Publication Date: August 23, 2013
Citation: Compton, D.L., Laszlo, J.A., Evans, K.O. 2013. Influence of solid supports on acyl migration in 2-Monoacylglycerols: Purification of 2-MAG via flash chromatography. Journal of the American Oil Chemists' Society. 90(9):1397-1403. Interpretive Summary: This research describes a superior method for purifying bio-based, eco-friendly chemical intermediates made from vegetable oils. Our mission is to develop new, value added uses for commodity crops and crop oils by developing bio-based chemicals and products that replace those made from petroleum. Much of today’s health and nutritional research investigates how the body uses and processes fats from food. This research has led to the development of naturally-derived synthetic fats, for example synthetic fats that mimic human milk fat. The manufacturing of these biomimetic fats depends on a particularly unstable intermediate called a 2-monoacylglycerol (2-MAG). Our research demonstrates a superior method called flash chromatography for purifying these 2-MAG intermediates. Our method can be applied to a wider variety of 2-MAG intermediates compared to conventional purification methods. This demonstrated application of a new analytical method will be of use to other scientists and researchers trying to design new, healthier, and more nutritious synthetic fats.
Technical Abstract: Soybean oil 2-MAG was synthesized via the Novozym 435 catalyzed ethanolysis of TAG and purified by conventional liquid-liquid extraction. The 2-MAG was subjected to incubation at 20 and 40 °C in the presence of five solid commercial support materials, Lewatit, Silica Gel 60, Alumina-Neutral Brockman Activity 1, Amberlyst-15, and SBA-15, to determine their effect on acyl migration rates. Lewatit and SBA-15 did not catalyze acyl migration rates after 144 h, while silica gel slightly increased migration rates. The more polar alumina and the cationic Amberlyst 15 significantly increased migration rates. Flash chromatography purification of 2-MAG using silica gel as the immobile phase developed with an acetone/hexane binary gradient proved to be a comparable purification method to liquid-liquid extraction, resulting in 60% 2-MAG yield, no residual triacylglycerol, diacylglycerol, or glycerol co-products, and a 95 mol% 2-MAG purity vs. 1-MAG, demonstrating that flash chromatography did not catalyze acyl migration.