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The Acrylation of Glycerol: A Precursor to Functionalized Lipids
Author(s) -
Jackson Michael A.,
Appell Michael,
Berhow Mark A.,
Blackburn Judith A.,
Rheiner Steven N.
Publication year - 2012
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-011-1950-5
Subject(s) - glycerol , acrylic acid , chemistry , decanoic acid , catalysis , yield (engineering) , cinnamic acid , organic chemistry , nuclear chemistry , polymer chemistry , copolymer , materials science , metallurgy , polymer
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 K 2 O 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 K 2 O 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.