Type of Publication: | Journal article |
URI (citable link): | http://nbn-resolving.de/urn:nbn:de:bsz:352-192646 |
Author: | Stempfle, Florian; Quinzler, Dorothee; Heckler, Ilona; Mecking, Stefan |
Year of publication: | 2011 |
Published in: | Macromolecules ; 44 (2011), 11. - pp. 4159-4166. - ISSN 0024-9297 |
DOI (citable link): | https://dx.doi.org/10.1021/ma200627e |
Summary: |
Isomerizing alkoxycarbonylation of methyl oleate and ethyl erucate, respectively, yielded dimethyl 1,19-nonadecanedioate and diethyl 1,23-tricosanedioate in >99% purity. With [κ2-(P̂ P)Pd(OTf)][OTf] as a defined catalyst precursor (P̂P = 1,2-bis[(di-tert-butylphosphino)methyl]benzene) the reaction can be carried out without the need for additional added diphosphine. Saponification of the diesters yielded 1,19-nonadecanedicarboxylic acid and 1,23-tricosanedicarboxylic acid in >99% purity. By ruthenium-catalyzed reduction of the diesters with H2, 1,19-nonadecanediole and 1,23-tricosanediole were formed in high yield and purity (>99%). From the latter, 1,19-nonadecanediamine and 1,23-tricosanediamine were generated. Polyesters with commercially available shorter-chain petrochemical or renewable diols exhibit high melting points due to the crystallizable long-chain methylene segments from the dicarboxylic acid component, e.g., poly[1,6-hexadiyl-1,23-tricosanedioate] Tm 92, Tc 75 °C. Thermal properties of novel long-chain polyamides are reported.
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Subject (DDC): | 540 Chemistry |
Link to License: | In Copyright |
Bibliography of Konstanz: | Yes |
STEMPFLE, Florian, Dorothee QUINZLER, Ilona HECKLER, Stefan MECKING, 2011. Long-chain linear C19 and C23 Monomers and Polycondensates from unsaturated fatty acid esters. In: Macromolecules. 44(11), pp. 4159-4166. ISSN 0024-9297. Available under: doi: 10.1021/ma200627e
@article{Stempfle2011Longc-19264, title={Long-chain linear C19 and C23 Monomers and Polycondensates from unsaturated fatty acid esters}, year={2011}, doi={10.1021/ma200627e}, number={11}, volume={44}, issn={0024-9297}, journal={Macromolecules}, pages={4159--4166}, author={Stempfle, Florian and Quinzler, Dorothee and Heckler, Ilona and Mecking, Stefan} }
mecking.pdf | 1492 |