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Comparative Reactivity of Cyclocarbonate Groups of Oligomeric Triglycerides Based on Soybean Oil and Model Compounds in the Reactions of Nonisocyanate Urethane Formation

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Abstract

A comparative study of kinetic patterns has been carried out for the reaction of cyclocarbonate groups of oligomers and model compounds with n-butylamine in dimethylsulfoxide. The objects of study were ethylene carbonate, monofunctional 4-(2-ethylhexyloxymethyl) cyclocarbonate, trifunctional tricyclocarbonate of polyoxypropylene triol, and an oligomer based on soybean oil triglycerides with an average functionality of ~4.5. The most active compound is ethylene carbonate, whereas cyclocarbonate groups of the oligomer based on soybean oil triglycerides exhibit the lowest reactivity. All the reactions studied proceed via two parallel reaction pathways involving one and two amine molecules, respectively, and the second pathway contributes more to the observed rate of urethane formation. The dependence of the activation energy of aminolysis on the inductive effect of substituents in the model 4,5-substituted 1,3-dioxolane-2-ones has been established by DFT quantum chemical calculations.

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Authors and Affiliations

  1. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Moscow, 119991, Russia

    M. A. Levina, M. V. Zabalov, V. G. Krasheninnikov & R. P. Tiger

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  1. M. A. Levina
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  2. M. V. Zabalov
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  3. V. G. Krasheninnikov
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  4. R. P. Tiger
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Correspondence to M. A. Levina.

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Original Russian Text © M.A. Levina, M.V. Zabalov, V.G. Krasheninnikov, R.P. Tiger, 2018, published in Vysokomolekulyarnye Soedineniya, Seriya B, 2018, Vol. 60, No. 5, pp. 372–379.

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Levina, M.A., Zabalov, M.V., Krasheninnikov, V.G. et al. Comparative Reactivity of Cyclocarbonate Groups of Oligomeric Triglycerides Based on Soybean Oil and Model Compounds in the Reactions of Nonisocyanate Urethane Formation. Polym. Sci. Ser. B 60, 563–570 (2018). https://doi.org/10.1134/S1560090418050081

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  • DOI: https://doi.org/10.1134/S1560090418050081

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