Abstract
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.
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REFERENCES
J. Guan, Y. Song, Y. Lin, X. Yin, M. Zuo, Y. Zhao, X. Tao, and Q. Zheng, Ind. Eng. Chem. Res. 50, 6517 (2011).
O. Figovsky, L. Shapovalov, A. Leykin, O. Birukova, and R. Potashnikova, PU Magaz. 10 (4), 1 (2013).
B. Nohra, L. Candy, J.-F. Blanco, C. Guerin, Y. Raoul, and Z. Mouloungui, Macromolecules 46, 3771 (2013).
H. Blattmann, M. Fleischer, M. Bahr, and R. Mulhaupt, Macromol. Rapid Commun. 35, 1238 (2014).
G. Rokicki, P. G. Parzuchowski, and M. Mazurek, Polym. Adv. Technol. 26, 707 (2015).
L. Maisonneuve, O. Lamarzelle, E. Rix, E. Grau, and H. Cramail, Chem. Rev. 115, 12407 (2015).
A. Cornille, R. Auvergne, O. Figovsky, B. Boutevin, and S. Caillol, Eur. Polym. J. 87, 535 (2017).
K. Błażek and J. Datta, Crit. Rev. Environ. Sci. Technol. 49, 173 (2019).
C. Carre, Y. Ecochard, S. Caillol, and L. Avérous, ChemSusChem 12, 3410 (2019).
M. A. Levina, D. G. Miloslavskii, M. L. Pridatchenko, A. V. Gorshkov, V. T. Shashkova, E. M. Gotlib, and R. P. Tiger, Polym. Sci., Ser. B 57, 584 (2015).
M. A. Levina, D. G. Miloslavskii, M. V. Zabalov, M. L. Pridatchenko, A. V. Gorshkov, V. T. Shashkova, V. L. Krasheninnikov, and R. P. Tiger, Polym. Sci., Ser. B 61, 540 (2019).
M. V. Zabalov, V. L. Krasheninnikov, and R. P. Tiger, Polym. Sci., Ser. B 59, 497 (2017).
M. V. Zabalov, V. L. Krasheninnikov, and R. P. Tiger, Polym. Sci., Ser. B 60, 563 (2018).
M. V. Zabalov, M. A. Levina, and R. P. Tiger, Russ. J. Phys. Chem. B 13, 778 (2019).
M. A. Levina, M. V. Zabalov, V. G. Krasheninnikov, and R. P. Tiger, React. Kinet., Mech. Catal. 129, 65 (2020).
A. Cornille, M. Blain, R. Auvergne, B. Andrioletti, B. Boutevina, and S. Caillol, Polym. Chem. 8, 592 (2017).
M. A. Levina, V. G. Krasheninnikov, M. V. Zabalov, and R. P. Tiger, Polym. Sci., Ser. B 56, 139 (2014).
M. V. Zabalov and R. P. Tiger, Theor. Chem. Acc. 136, Article 95 (2017).
J. P. Perdew, K. Burke, and M. Ernzerhoff, Phys. Rev. Lett. 77, 3865 (1996).
M. Ernzerhoff and G. E. Scuseria, J. Chem. Phys. 110, 5029 (1999).
D. N. Laikov, Chem. Phys. Lett. 281, 151 (1997).
D. N. Laikov and Yu. A. Ustiniuk, Russ. Chem. Bull., Int. Ed. 54, 820 (2005).
R. M. Garipov, V. A. Sysoev, V. V. Mikheev, A. I. Zagidullin, R. Y. Deberdeev, V. I. Irzhak, and A. A. Berlin, Dokl. Phys. Chem. 393, 289 (2003).
O. Lamarzelle, P.-L. Durand, A.-L. Wirotius, G. Chollet, E. Grau, and H. Cramail, Polym. Chem. 7, 1439 (2016).
M. V. Zabalov and R. P. Tiger, Russ. Chem. Bull., Int. Ed. 65, 631 (2016).
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The work was performed as a part of the State Assignment 0082-2019-0003 (no. AAAA-A20-120021090129-9).
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Zabalov, M.V., Levina, M.A. & Tiger, R.P. Various Reactivity of Cyclocarbonate-Containing Chains of Vegetable Oil Triglycerides as the Cause of the Abnormal Kinetics of Urethane Formation with Their Participation. Polym. Sci. Ser. B 62, 457–464 (2020). https://doi.org/10.1134/S1560090420050152
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DOI: https://doi.org/10.1134/S1560090420050152