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Ruthenium Catalyzed Oxidative Cleavage of High Oleic Sunflower Oil: Considerations Regarding the Synthesis of a Fully Biobased Triacid

Santos Correa, Luis 1,2; Meier, Michael A. R. 1,2
1 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


Tricarboxylic acids are molecules of interest for the synthesis of highly cross-linked polymers, for instance, for the curing of epoxy resins. Herein, a synthesis route to a novel high oleic sunflower oil based triacid is described by applying a ruthenium catalyzed oxidative cleavage of its double bonds. A statistical concept is devised for the prediction of the yields of mono-, di-, and trifunctional derivatives that can be formed from high oleic sunflower oil, depending on the overall conversion of double bonds into this functional group and the overall oleic acid content of the used oil. This concept proved to be highly useful for the explanation of seemingly moderate triacid yields, which are inherently dependent on the unsaturated fatty acid content of the used oil. All obtained sunflower oil based polyacids are fully analyzed by attenuated total reflection infrared spectroscopy (ATR-IR), electrospray ionization mass spectrometry (ESI-MS), $^1$H, $^{13}$C, and quantitative $^{31}$P nuclear magnetic resonance (NMR) spectroscopy. In addition, a more sustainable purification procedure is developed to obtain a polymerizable mixture of polyacids containing more than 2.0 carboxylic acids per molecule in average.
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Verlagsausgabe §
DOI: 10.5445/IR/1000154484
Veröffentlicht am 13.01.2023
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 05.2023
Sprache Englisch
Identifikator ISSN: 1438-7697, 0015-038X, 0367-2107, 0367-3278, 0931-5985, 1438-9312, 1521-4133
KITopen-ID: 1000154484
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in European Journal of Lipid Science and Technology
Verlag John Wiley and Sons
Band 125
Heft 5
Seiten Art.-Nr.: 2200171
Vorab online veröffentlicht am 04.12.2022
Schlagwörter catalysis, fatty acids, green chemistry, oils, oxidative cleavage, triacid
Nachgewiesen in Scopus
Web of Science
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