ARS | Publication request: The acrylation of glycerol over solid base catalysts: A precursor to functionalized lipids

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: May 4, 2011
Publication Date: May 4, 2011
Citation: Jackson, M.A., Blackburn, J.A., Rheiner, S.N. 2011. The acrylation of glycerol over solid base catalysts: A precursor to functionalized lipids [abstract]. American Oil Chemists' Society. p. 77.

Technical Abstract: Transesterification of lipids using lipases is a common strategy used to incorporate novel acids into triacylglycerides. This approach, however, is limited to acids with pKa’s similar to common fatty acids. To overcome this limitation, we have used heterogeneous basic catalysts for the synthesis of didecanoylacryloylglycerol from decanoic and acrylic acids and glycerol. This reaction was carried out in hexane in a closed stainless steel reactor at 200°C for 5h in the presence of K2O, Cs2O, and BaO both as free bases or immobilized on the silicas SBA-15 and HMS as catalysts. 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 Heck reaction products. It was reacted with bromobenzene in the presence of tris(o-tolyl)phosphine and PdCl2 to yield didecanoylcinnamoylglycerol in high yield.