Journal
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
Volume 114, Issue 1, Pages 49-54Publisher
WILEY
DOI: 10.1002/ejlt.201100136
Keywords
Calendula oil; Diels-Alder reaction; Plasticizers; Tricarboxylic acid tri esters; Tung oil
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Funding
- German Federal Ministry of Food, Agriculture, and Consumer Protection [FKZ 2026905]
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Some plant oil derived cyclohexane tricarboxylic acid triesters were synthesized and suggested as potential plasticizers based mainly on renewable feedstock. Methyl calendulate 1 and a-eleostearate 2 obtained from calendula oil and tung oil, respectively, as well as methyl oleate 3 were used as starting material. Reactions with maleic anhydride gave the corresponding DielsAlder adducts 4 and 5 and ene adduct 6, which were converted by ring-opening reactions with various alcohols to the respective tricarboxylic acid triesters. Especially the cyclohexane tricarboxylic trimethyl triester 9 derived from DielsAlder adduct 5 showed excellent absorption properties by PVC, superior to bis(2-ethylhexyl)phthalate (DEHP). Moreover, the commercially available DielsAlder adduct of CLA 7 (Admergin acid (R)) was ring-opened with methanol showing an absorption by PVC that was still higher compared to triester 9 although the viscosity was significantly higher.
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