Various Reactivity of Cyclocarbonate-Containing Chains of Vegetable Oil Triglycerides as the Cause of the Abnormal Kinetics of Urethane Formation with Their Participation

The comparative reactivity of oleic, linoleic, and linolenic fragments of vegetable oil triglyceride chains in the processes of their conversion to the corresponding hydroxyurethanes is studied. According to DFT quantum-chemical calculations, the linolenic fragments of triglyceride chains are the mo...

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Bibliographic Details
Published inPolymer science. Series B Vol. 62; no. 5; pp. 457 - 464
Main Authors Zabalov, M. V., Levina, M. A., Tiger, R. P.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.09.2020
Springer Nature B.V
Subjects
Chains
Chemistry
Chemistry and Materials Science
Conversion
Fragments
Polymer Sciences
Quantum chemistry
Synthesis
Triglycerides
Vegetable oils
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Summary:The comparative reactivity of oleic, linoleic, and linolenic fragments of vegetable oil triglyceride chains in the processes of their conversion to the corresponding hydroxyurethanes is studied. According to DFT quantum-chemical calculations, the linolenic fragments of triglyceride chains are the most reactive. The activation barriers of reactions involving the second cyclocarbonate group of the linoleic fragment and the second and third cyclocarbonate groups of the linolenic fragment are lower than the conversion barriers of first cyclocarbonate groups of the corresponding models, which is explained by the catalytic assistance of the OH groups of hydroxyurethanes, which are formed at the first stage of aminolysis, to the proton transfer act.
ISSN:1560-0904
1555-6123
DOI:10.1134/S1560090420050152