The Acrylation of Glycerol: A Precursor to Functionalized Lipids |
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Authors: | Michael A. Jackson Michael Appell Mark A. Berhow Judith A. Blackburn Steven N. Rheiner |
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Affiliation: | (1) Renewable Product Technology Unit, United States Department of Agriculture, National Center for Agricultural Utilization Research, Agricultural Research Service, 1815 N. University St, Peoria, IL 61604, USA;(2) Bacterial Foodborne Pathogens and Mycology, United States Department of Agriculture, National Center for Agricultural Utilization Research, Agricultural Research Service, 1815 N. University St, Peoria, IL 61604, USA;(3) Functional Foods Research Unit, United States Department of Agriculture, National Center for Agricultural Utilization Research, Agricultural Research Service, 1815 N. University St, Peoria, IL 61604, USA |
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Abstract: | With the objective of expanding the number of functionalized lipids available, the reactive vinyl group of acrylic acid was introduced to triacylglycerol by esterification of glycerol. Didecanoylacryloylglycerol was synthesized from decanoic and acrylic acids and glycerol using K2O as catalyst. 2 g (21.7 mmol) glycerol, 11.3 g (65.4 mmol) decanoic acid, 6.2 g (86.1 mmol) acrylic acid, 60 ml hexane, and 400 mg K2O were added to 300-ml closed stainless steel reactor and maintained at 200 °C for 5 h. The resulting product, designated DDA, was isolated at about 40% yield based on the acylglycerol products. The other products included tridecanoylglycerol, diacryloyldecanoylglycerol, and the diacylglycerols of these acids. DDA was then converted to functionalized lipids by the Michael addition and 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 triacylglycerols containing trans-cinnamic acid and trans-(4-methoxy)cinnamic acid, respectively. |
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