Reactivity of New Monomers of the Polyurethanes Green Chemistry, the Reaction Mechanism, and the Medium Effect

M. V. Zabalov; Забалов М. В.; M. A. Levina; Левина М. А.; V. G. Krasheninnikov; Крашенинников В. Г.; R. P. Tiger; Тигер Р. П.

doi:10.31857/S2308113923700511

Reactivity of New Monomers of the Polyurethanes Green Chemistry, the Reaction Mechanism, and the Medium Effect

Authors: Zabalov M.V.¹, Levina M.A.¹, Krasheninnikov V.G.¹, Tiger R.P.¹
Affiliations:
1. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences
Issue: Vol 65, No 4 (2023)
Pages: 286-294
Section: ХИМИЧЕСКИЕ ПРЕВРАЩЕНИЯ
URL: https://ruspoj.com/2308-1139/article/view/650882
DOI: https://doi.org/10.31857/S2308113923700511
EDN: https://elibrary.ru/QORWFU
ID: 650882

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Abstract

The influence of the substituents inductive effect and the proton-donor OH group in the substituted cyclocarbonates differing in the alkyl chain length on the activation barrier of their aminolysis reaction, which underlies the process of urethane formation without the participation of isocyanates, has been studied. Account for the solvent molecules has allowed quantitative interpretation of the process regularities. Kinetics of the model aminolysis reaction of a series of monomers in DMSO has been investigated.

References

Saunders J.H., Frisch K.C. Polyurethanes – Chemistry and Technology. New York; London: Interscience Publ., 1962. V. 16. Part I.
Tiger R.P. // Polymer Science B. 2004. V. 46. № 5–6. P. 142.
Guan J., Song Y., Lin Y., Yin X., Zuo M., Zhao Y., Tao X., Zheng Q. // Ind. Eng. Chem. Res. 2011. V. 50. № 11. P. 6517.
Figovsky O., Shapovalov L., Leykin A., Birukova O., Po-tashnikova R. // PU Magazine. 2013. V. 10. № 4. P. 1.
Nohra B., Candy L., Blanco J.-F., Guerin C., Raoul Y., Mouloungui Z. // Macromolecules. 2013. V. 46. № 10. P. 3771.
Blattmann H., Fleischer M., Bahr M., Mulhaupt R. // Macromol. Rapid Comm. 2014. V. 35. № 14. P. 1238.
Rokicki G., Parzuchowski P.G., Mazurek M. // Polym. Adv. Technol. 2015. V. 26. № 7. P. 707.
Maisonneuve L., Lamarzelle O., Rix E., Grau E., Cramail H. // Chem. Rev. 2015. V. 115. P. 12407.
Cornille A., Auvergne R., Figovsky O., Boutevin B., Caillol S. // Eur. Polym. J. 2017. V. 87. P. 535.
Błażek K., Datta J. // Crit. Rev. Environ. Sci. Technol. 2019. V. 49. № 3. P. 173.
Carre C., Ecochard Y., Caillol S., Averous L. // ChemSusChem. 2019. V. 12. № 15. P. 3410.
Ecochard Y., Caillol S. // Eur. Polym. J. 2020. V. 137. 109915.
Lambeth R.H. // Polym. Int. 2020. V. 70. P. 696.
Tiger R.P., Zabalov M.V., Levina M.A. // Polymer Science C. 2021. V. 63. № 2. P. 113.
Gomez-Lopez A., Elizalde F., Calvo I., Sardon H. // Chem. Comm. 2021. V. 57. № 92. P. 12254.
Brzeska J., Piotrowska-Kirschling A.A. // Processes. 2021. V. 9. P. 1929.
Bizet B., Grau E., Asua J.M., Cramail H. // Macromol. Chem. Phys. 2022. V. 223. № 13. 2100437.
Kaur R., Singh P., Tanwar S., Varshney G., Yadav S. // Macromolecules. 2022. V. 2. № 3. P. 284.
Figovsky O.L., Bol’shakov O.I., Vikhareva I.N. Nonisocyanate Polyurethanes: Green Solutions. Chelyabinsk: SUSU Publ., 2023.
Catalá J., Guerra I., García-Vargas J.M., Ramos M.J., García M.T., Rodríguez J.F. // Polymers. 2023. V. 15. № 6. P. 1589.
Levina M.A., Zabalov M.V., Krasheninnikov V.G., Tiger R.P. // Polymer Science B. 2018. V. 60. № 5. P. 563.
Zabalov M.V., Levina M.A., Krasheninnikov V.G., Tiger R.P. // Russ. Chem. Bull., Int. Ed. 2014. V. 63. № 8. P. 1740.
Levina M.A., Krasheninnikov V.G., Zabalov M.V., Tiger R.P. // Polymer Science B. 2014. V. 56. № 2. P. 139.
Levina M.A., Zabalov M.V., Krasheninnikov V.G., Tiger R.P. // Polymer Science B. 2017. V. 59. № 5. P. 497.
Zabalov M.V., Levina M.A., Tiger R.P. // Kinet. Catal. 2020. V. 61. № 5. P. 721.
Zabalov M.V., Levina M.A., Krasheninnikov V.G., Tiger R.P. // Reac. Kinet. Mech. Cat. 2020. V. 129. № 1. P. 65.
Zabalov M.V., Levina M.A., Tiger R.P. // Polymer Science B. 2020. V. 62. № 5. P. 457.
Zabalov M.V., Tiger R.P. // Theor. Chem. Acc. 2017. V. 136. P. 95.
Quienne B., Poli R., Pinaud J., Caillol S. // Green Chem. 2021. V. 23. № 4. P. 1678.
Perdew J.P., Burke K., Ernzerhof M. // Phys. Rev. Lett. 1996. V. 77. № 18. P. 3865.
Ernzerhof M., Scuseria G.E. // J. Chem. Phys. 1999. V. 110. № 11. P. 5029.
Laikov D.N. // Chem. Phys. Lett. 1997. V. 281. № 1–3. P. 151.
Laikov D.N., Ustynyuk Y.A. // Russ. Chem. Bull., Int. Ed. 2005. V. 54. № 3. P. 820.
Zabalov M.V., Tiger R.P. // Russ. Chem. Bull. Int. Ed. 2016. V. 65. № 3. P. 631.
Caldeweyher E., Bannwarth C., Grimme S. // J. Chem. Phys. 2017. V. 147. № 3. 034112.
Caldeweyher E., Ehlert S., Hansen A., Neugebauer H., Spicher S., Bannwarth C., Grimme S. // J. Chem Phys. 2019. V. 150. № 15. 154122.
Caldeweyher E., Mewes J.-M., Ehlert S., Grimme S. // Phys. Chem. Chem. Phys. 2020. V. 22. № 16. P. 8499.
Zabalov M.V., Tiger R.P., Berlin A.A. // Dokl. Chem. 2011. V. 441. Pt 2. P. 355.
Zabalov M.V., Tiger R.P., Berlin A.A. // Russ. Chem. Bull., Int. Ed. 2012. V. 61. P. 518.
Alves M., Mereau R., Grignard B., Detrembleur C., Jerome C., Tassaing T. // RSC Adv. 2017. V. 7. № 31. P. 18993.
Levina M.A., Zabalov M.V., Gorshkov A.V., Shashkova V.T., Krasheninnikov V.L., Tiger R.P., Miloslavskii D.G., Pridatchenko M.L. // Polymer Science B. 2019. V. 61. № 5. P. 540.
Mizuno K., Imafuji S., Ochi T., Ohta T., Maeda S. // J. Phys. Chem. B. 2000. V. 104. № 47. P. 11001.
Li Q., Wu G., Yu Z. // J. Am. Chem. Soc. 2006. V. 128. № 5. P. 1438.
Li Q., An X., Gong B., Cheng J. // Spectrochim. Acta A. 2008. V. 69. № 1. P. 211.
Li Q., An X., Gong B., Cheng J. // Vib. Spectrosc. 2008. V. 46. № 1. P. 28.
Zhang L., Wang Y., Xu Z., Li H. // J. Phys. Chem. B. 2009. V. 113. № 17. P. 5978.
Noack K., Kiefer J., Leipertz A. // ChemPhysChem. 2010. V. 11. № 3. P. 630.
Venkataramanan N.S., Suvitha A. // J. Mol. Graph. Model. 2018. V. 81. P. 50.
Mrázková E., Hobza P. // J. Phys. Chem. A. 2003. V. 107. № 7. P. 1032.
Venkataramanan N.S. // Int. J. Quant. Chem. 2012. V. 112. № 13. P. 2599.
Venkataramanan N.S. // J. Mol. Model. 2016. V. 22. № 7. Art. 151.
Venkataramanan N.S., Suvitha A., Kawazoe Y. // J. Mol. Liq. 2018. V. 249. P. 454.
Li X., Liu L., Schlegel H.B. // J. Am. Chem. Soc. 2002. V. 124. № 32. P. 9639.
Joseph J., Jemmis E.D. // J. Am. Chem. Soc. 2007. V. 129. № 15. P. 4620.
Mo Y., Wang C., Guan L., Braïda B., Hiberty P.C., Wu W. // Chem. Eur. J. 2014. V. 20. № 27. P. 8444.