The Acrylation of Glycerol: A Precursor to Functionalized Lipids

• DOI: 10.1007/s11746-011-1950-5
• Publication Date: 2011-10-27T18:59:55Z
• Authors: Michael A. Jackson; Michael Appell; Mark A. Berhow; Judith A. Blackburn; Steven N. Rheiner
• Keywords: Acrylic acid; Decanoic acid; Cinnamic acid

Abstract With the objective of expanding number functionalized lipids available, reactive vinyl group acrylic acid was introduced to triacylglycerol by esterification glycerol. Didecanoylacryloylglycerol synthesized from decanoic and acids glycerol using K 2 O as catalyst. g (21.7 mmol) glycerol, 11.3 (65.4 acid, 6.2 (86.1 60 ml hexane, 400 mg were added 300‐ml closed stainless steel reactor maintained at 200 °C for 5 h. The resulting product, designated DDA, isolated about 40% yield based on acylglycerol products. other products included tridecanoylglycerol, diacryloyldecanoylglycerol, diacylglycerols these acids. DDA then converted Michael addition Heck reaction. thiophenol 4‐bromothiophenol yielded corresponding linear thioethers whereas reaction bromobenzene bromoanisole triacylglycerols containing trans ‐cinnamic ‐(4‐methoxy)cinnamic respectively.