Cited by 203biodegradable polymer synthesis and propertiesAdvanced Polymer Synthesis and CharacterizationPolymer crystallization and properties

Long-Chain Linear C 19 and C 23 Monomers and Polycondensates from Unsaturated Fatty Acid Esters

Stempfle, Florian, Quinzler, Dorothee, Heckler, Ilona, Mecking, Stefan·2011·Macromolecules

Abstract

Isomerizing alkoxycarbonylation of methyl oleate and ethyl erucate, respectively, yielded dimethyl 1,19-nonadecanedioate and diethyl 1,23-tricosanedioate in >99% purity. With [κ 2 -(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 H 2, 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] T m 92, T c 75 °C. Thermal properties of novel long-chain polyamides are reported.

Integrity signals

Registry

Crossref · 10.1021/ma200627e

Cites

25 of 25 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • Isomerizing alkoxycarbonylation of methyl oleate catalyzed by a palladium catalyst bearing phosphorus ligands can convert the internal double bond deep in the hydrocarbon chain to a terminal ester group with high yield and selectivity.

    “In one example, they showed that isomerizing alkoxycarbonylation of methyl oleate catalyzed by a palladium catalyst bearing phosphorus ligands can convert the internal double bond deep in the hydrocarbon chain to a terminal ester group with high yield and selectivity.100”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [100]

Cites

Flagged first, then by citations

Cited by

Sorted by citations

Authors
Stempfle, F., Quinzler, D., Heckler, I., & Mecking, S.
Affiliations
University of Konstanz (DE)
Corresponding author
Mecking, Stefan
Venue
Macromolecules
Published
2011-05-09
Volume
44
Issue
11
Pages
4159-4166
ISSN
  • 0024-9297 (ISSN-L)
  • 1520-5835
OpenAlex
W2028984848
Cited by
203
References
25
Citations by year
2026: 6 · 2025: 9 · 2024: 19 · 2023: 10 · 2022: 6 · 2021: 15 · 2020: 5 · 2019: 11 · 2018: 10 · 2017: 28 · 2016: 10 · 2015: 20 · 2014: 19 · 2013: 16 · 2012: 17
FWCI
7.07
Type
journal article
Language
en
Open access
closed
Locations
  • Macromolecules (publishedVersion)
  • KOPS (University of Konstanz) (submittedVersion)
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
Keywords
long-chain dicarboxylic acids, unsaturated fatty acid esters, methyl oleate, alkoxycarbonylation, palladium catalysts, saponification, hydrogenation, polyesters, polyamide, thermal properties, crystallization

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review