Title: The Acrylation of Glycerol: a Precursor to Functionalized Lipids Authors
Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 30, 2011
Publication Date: October 28, 2011
Citation: Jackson, M.A., Appell, M.D., Blackburn, J.A., Rheiner, S.N., Berhow, M.A. 2011. The acrylation of glycerol: A precursor to functionalized lipids. Journal of the American Oil Chemists' Society. 89(4):713-719. DOI: 10.1007/s11746-011-1950-5. Interpretive Summary: We have prepared a series of modified oils that could lead to new uses and markets for seed oils. Some modifications to oils are not possible through the usual chemistry. We set out to prepare those compounds that are otherwise not possible and found an alternative method. The resulting oils have potential uses in cosmetics, lubricants, oil metabolism studies, and even food additives. Having these oils available will be a benefit to manufacturers of these products or to scientists who study oils in the diet.
Technical Abstract: Didecanoylacryloylglycerol was synthesized from decanoic and acrylic acids and glycerol using K2O as catalyst. This reaction was carried out in hexane in a closed stainless steel reactor at 200°C for 5h. The reactants were added in a 1:3:4 glycerol:decanoic acid:acrylic acid molar ratio. The resulting product which was isolated at about 40% yield, was then converted to functionalized lipids by addition of thiols and using the Heck reaction. The Michael addition of thiophenol and 4-bromothiophenol yielded the corresponding linear thioethers whereas and Heck reaction products from bromobenzene and bromoanisole yielded TAGs containing trans cinnamic acid and trans-(4-methoxy)cinnamic acid, respectively.