TY  - JOUR
A1  - Biermann, Ursula
A1  - Meier, Michael A. R.
A1  - Butte, Werner
A1  - Metzger, Jürgen O.
T1  - Cross-metathesis of unsaturated triglycerides with methyl acrylate  synthesis of a dimeric metathesis product
JF  - European journal of lipid science and technology
N2  - 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.
KW  - Highly functionalized dimeric triglycerides
KW  - Olefin self- and cross-metathesis
KW  - Renewable resources
Y1  - 2011
U6  - https://doi.org/10.1002/ejlt.201000109
SN  - 1438-7697
VL  - 113
IS  - 1
SP  - 39
EP  - 45
PB  - Wiley-VCH
CY  - Weinheim
ER  -