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Cross‐metathesis of unsaturated triglycerides with methyl acrylate: Synthesis of a dimeric metathesis product
Author(s) -
Biermann Ursula,
Meier Michael A. R.,
Butte Werner,
Metzger Jürgen O.
Publication year - 2011
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201000109
Subject(s) - metathesis , chemistry , salt metathesis reaction , methyl acrylate , glycerol , triglyceride , acyclic diene metathesis , dimer , polymerization , organic chemistry , ring opening metathesis polymerisation , catalysis , acrylate , copolymer , polymer , biochemistry , cholesterol
Highly functionalized dimeric triglycerides, such as compound 2 , are obtained as minor products besides branched macromolecules from the acyclic triene metathesis (ATMET) polymerization of unsaturated triglycerides such as glyceryl triundec‐10‐enoate 1 and methyl acrylate (MA) in the presence of the second generation Hoveyda–Grubbs catalyst. The formed amount of interesting products of lower molecular weight during the ATMET reaction depends on the ratio of MA and triglyceride, reaction time, and temperature. We isolated the dimeric metathesis product 2 and synthesized the respective partially hydrogenated dimer 3 regioselectivly in a seven step reaction sequence starting from 10‐undecenoic acid 7 and glycerol. Product 3 was unambiguously characterized by 13 C and 1 H NMR and MS as well as the further intermediate products of the seven step reaction including 10,11 bromo‐undecanoic acid 8 , the respective brominated 1,3‐diglyceride 9 , the brominated 1,3‐triglyceride 6 , and the self‐metathesis products 4 and 5 which were isolated and purified.