Preview

Proceedings of the National Academy of Sciences of Belarus, Chemical Series

Advanced search

Synthesis of new imides and imidoamides of citraconopimaric acid

https://doi.org/10.29235/1561-8331-2023-59-1-35-41

Abstract

For the first time, a method has been developed for the synthesis of aromatic imides of citraconopimaric acid by the interaction of primary aromatic amines (aniline, p-toluidine) and citraconopimaric acid in p-xylene at reflux. New aliphatic imides have been synthesized by the reaction of citraconopimaric acid and primary aliphatic amines (octyl-, octadecylamine) in a melt at 125–150°C. For the first time, the synthesis of citraconopimaric acid imidoamides was developed by treating citraconopimaric acid N-octylimide with thionyl chloride and subsequent reaction of the resulting acid chloride with primary aromatic amines (aniline, p-bromoaniline). A method has been developed for the synthesis of aliphatic imides of the rosin-citraconic adduct (in the form of technical products) by its interaction with primary aliphatic amines (octyl- and octadecylamine) at 180–200°C for 8–12 hours.

Together with Belarusian state technological university, the relationship between the structure of imides of rosin-citraconic adducts as modifiers of unfilled and filled industrial rubber compounds was studied, and the obtained additives were found to improve the technological properties of compositions while maintaining, and in some cases improving physical and mechanical parameters (increasing the resistance of compositions to thermal aging, bond strength of the cord with rubber, etc.).

About the Authors

M. P. Bei
Institute of Chemistry of New Materials of the National Academy of Science of Belarus
Belarus

Bei Maksim P.– Ph. D. (Chemistry), Leading Researcher

36, F. Skoriny str., 220141, Minsk



A. P. Yuvchenko
Institute of Chemistry of New Materials of the National Academy of Science of Belarus
Belarus

Yuvchenko Anatolij P. – Ph. D. (Chemistry), Senior Researcher

36, F. Skoriny str., 220141, Minsk



References

1. Bei M. P., Yuvchenko A. P. The method for preparation of citraconopimaric acid. Patent Republic of Belarus, no. 13646. Publ. date 30.10.2010 (in Russian).

2. Bei M. P., Baranovskii A. V., Yuvchenko A. P. Structure of rosin and itaconic acid adduct by two-dimensional NMR spectroscopy. Journal of Applied Spectroscopy, 2009, vol. 76, no. 4, pp. 603–606. https://doi.org/10.1007/s10812-009-9240-9

3. Bei M. P., Puchkova N. V., Yuvchenko A. P., Baranovskii A. V. New adducts of turpentine and rosin with citraconic anhydride and itaconic acid. Vestsi Natsyyanal'nai akademii navuk Belarusi. Seryya khimichnyh navuk = Proceedings of the National Academy of Science of Belarus. Chemical series, 2018, vol. 54, no. 4, pp. 434–441 (in Russian). https://doi.org/10.29235/1561-8331-2018-54-4-434-441

4. Langlois N., Gastambide B. Action de l’acide p-nitroperbenzoique sur composes d’addition de Diels-Alder en serie diterpenique. Ouverture cis d’une fonction epoxyde. Numerotation des diterpenes pontes. Bull. Soc. Chim. France, 1965, no. 10, pp. 2966−2971 (in French).

5. Gastambide B., Langlois N. Etudes stereochimiques VII. Syntheses dieniques en serie resinique; action des peroxoacides et des hydrures doubles. Helvetica Chimica Acta, 1968, vol. 51, no. 8, pp. 2048–2057. https://doi.org/10.1002/hlca.19680510824

6. Bei M. P., Azarko V. A., Yuvchenko A. P. Synthesis, film-forming, and light-sensitivity properties of allyl and propargyl maleopimarates and cytraconopimarates. Russian Journal of General Chemistry, 2010, vol. 80, no. 5, pp. 940–943. https://doi.org/10.1134/S1070363210050130

7. Koroleva E. V., Gusak K. N., Ignatovich Zh. V., Ermolinskaya A. L., Bei M. P., Yuvchenko A. P. Synthesis of maleopimaric and citraconopimaric acids N-[3-(pyrimidin-2-yl)aryl]amides. Russian Journal of General Chemistry, 2012, vol. 48, no. 8, pp. 1121–1125. https://doi.org/10.1134/S1070428012080143

8. Bei M. P., Yuvchenko A. P., Sokol O. V. Synthesis and properties of new derivatives of maleopimaric and citraconopimaric acids. Vestsi Natsyyanal'nai akademii navuk Belarusi. Seryya khimichnyh navuk = Proceedings of the National Academy of Science of Belarus. Chemical series, 2017, no. 2, pp. 111–125.

9. Bei M. P., Muravskii Al. An., Muravskii An. Al., Chepeleva D. S., Puchkova N. V., Yuvchenko A. P. Synthesis of mal eo- and citraconopimaric acid derivatives with mesogenic groups as chiral dopants to LC-compositions. Vestsi Natsyyanal'nai akademii navuk Belarusi. Seryya khimichnyh navuk = Proceedings of the National Academy of Science of Belarus. Chemical series, 2020, vol. 56, no. 3, pp. 293–300 (in Russian). https://doi.org/10.29235/1561-8331-2020-56-3-293-300

10. Bei M. P., Yuvchenko A. P., Baranovskii A. V. Formation of N-Alkylimides in Reaction of Maleopimaric and Citraconopimaric Acids with Secondary Amines. Vestsi Natsyyanal'nai akademii navuk Belarusi. Seryya khimichnyh navuk = Proceedings of the National Academy of Science of Belarus. Chemical series, 2013, no. 4, pp. 104–108 (in Russian).

11. Wendlandt W. Thermal methods of analysis. Moscow: Mir Publ., 1978. 526 p. (in Russian).

12. Bei M. P., Yuvchenko A. P. Synthesis and Properties of Maleopimaric N-(n-alkyl)imides. Russian Journal of General Chemistry, 2010, vol. 80, no. 2, pp. 253–257. https://doi.org/10.1134/ S107036321002012X

13. Prokopchuk N. R., Vishnevskii K. V., Krut’ko E. T., Prokopovich Y. M., Bei M. P., Yuvchenko A. P. Rubber compound. Patent Republic of Belarus, no. 23018. Publ. date 30.06.2020 (in Russian).

14. Prokopchuk N. R., Vishnevskii K. V., Krut'ko E. T., Bei M. P., Yuvchenko A. P., Piakarski N. S. The effect of diene adducts of rosin and their nitrogen-containing derivatives on the properties of elastomeric compositions. Polymer materials and technologies, 2018, vol. 4, no. 3, pp. 66–71 (in Russian). https://doi.org/10.32864/polymmattech-2018-4-3-66-71


Review

Views: 274


Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.


ISSN 1561-8331 (Print)
ISSN 2524-2342 (Online)