TY  - JOUR
A1  - Kreye, Oliver
A1  - Toth, Tommy
A1  - Meier, Michael A. R.
T1  - Poly-alpha,beta-unsaturated aldehydes derived from castor oil via ADMET polymerization
JF  - European journal of lipid science and technology
N2  - 10-Undecenal, derived by pyrolysis and reduction from castor oil, was almost quantitatively transformed into the corresponding aldol condensation product under basic conditions. This alpha,omega-diene monomer was polymerized using acyclic diene metathesis (ADMET) polymerization. In a catalyst screening, four of nine different ruthenium-based metathesis catalysts showed good reactivity under neat conditions at 80 degrees C in the presence of 1,4-benzoquinone and polymers with molecular weights up to 11 kDa were formed. Furthermore, the (1)H NMR spectra showed that the metathesis catalysts tolerate the alpha,beta-unsaturated aldehyde function and due to the addition of benzoquinone, the degree of double bond isomerization was low. Further experiments investigating reduced catalyst amounts (down to 0.2 mol%) and the temperature dependence of these ADMET polymerizations gave also satisfying results for the formation of poly-alpha,beta-unsaturated aldehydes. Moreover, ADMET polymerizations with different amounts of methyl 10-undecenoate as chain-stopper were performed and the integrals of the corresponding (1)H NMR spectra allowed the determination of an absolute degree of polymerization. Finally, a reduction of a poly-alpha,beta-unsaturated aldehyde with sodium borohydride was accomplished. The resulting poly-(allyl alcohol) could be a useful compound in the generation of polymer networks like polyesters, polyurethanes, and polycarbonates and thus be of high interest in materials research.
KW  - ADMET
KW  - Aldol condensation
KW  - Castor oil
KW  - Poly(allyl alcohol)s
KW  - Poly-alpha,beta-unsaturated aldehydes
Y1  - 2011
U6  - https://doi.org/10.1002/ejlt.201000108
SN  - 1438-7697
VL  - 113
IS  - 1
SP  - 31
EP  - 38
PB  - Wiley-VCH
CY  - Weinheim
ER  -