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Mechanochemical ethoxylation of benzoic acid and its halogene derivatives

https://doi.org/10.34680/2076-8052.2021.4(125).64-67

Abstract

Ethoxylated derivatives of halogen-substituted benzoic acids have been obtained by the method of mechanochemical solid- phase synthesis in a vibrating apparatus. The reaction products have been characterized by IR spectroscopy and acid-base potentiometric titration. It has been shown that, as a result of ethoxylation reactions, changes occur in the IR spectra of the reaction products in comparison with the initial reagents. The absorption bands of vibrations of the carbonyl group of acids during the formation of reaction products are shifted to the high-frequency region. The method of potentiometric titration of solutions of halogen-containing benzoic acids and the products of their interaction with polyethylene glycol has revealed a decrease in the number of carboxyl groups in the ethoxylated sample. According to IR spectroscopy and potentiometric titration data, the interaction of benzoic acids with polyethylene glycol proceeds through the carboxyl group.

About the Authors

S. L. Khil’ko
Институт физико-органической химии и углехими, им. Л.М. Литвиненко
Russian Federation


O. I. Nevecheryа
Институт физико-органической химии и углехими, им. Л.М. Литвиненко
Russian Federation


R. A. Makarova
Институт физико-органической химии и углехими, им. Л.М. Литвиненко
Russian Federation


R. G. Semenova
Институт физико-органической химии и углехими, им. Л.М. Литвиненко
Russian Federation


References

1. Zelenaya khimiya v Rossii [Green chemistry in Russia]. Ed. Lunina V.V., Tundo P., Loktevoy Ye.S. Moscow, MSU Publ., 2004. 230 p.

2. Alferova N.A., Minakova A.M., Averina YU.M., Menshikov V.V. Zelenaya khimiya i tendentsii yeye razvitiya [Green chemistry and trends in its development]. Uspekhi khimii i khim. Tekhnologii — Advances in Chemistry and Chemical Technology, 2017, vol. 31, no. 15, pp. 84-85.

3. Tarasova N.P., Makarova A.S., Shchukina M.YU., et al. Zelenaya khimiya i rossiyskaya promyshlennost [Green chemistry and Russian industry]. Vestnik RAN — Herald of the Russian Academy of Sciences, 2013, vol. 83, no. 12, pp. 1068-1075.

4. Boldyrev V.V. Mehanohimija i mehanohimicheskaja aktivacija tverdyh veshhestv [Mechanochemistry and mechanochemical activation of solids]. Uspehi Himii — Advances in Chemistry, 2006, vol. 75, no. 3, pp. 203-216.

5. James S.L., Friscic T. Mechanochemistry: fundamentals and applications in synthesis. Chem. Commun, 2013, vol. 49, pp. 5349-5365.

6. Achar T.K., Bose A., Mal P. Mechanochemical synthesis of small organic molecules. Beilstein J. Org. Chem, 2017, vol. 13, pp. 1907-1931. doi: https://doi.org/10.3762/bjoc.13.186

7. Guan-Wu Wang. Mechanochemical organic synthesis. Chem. Soc. Rev., 2013, vol. 42, pp. 7668-7700. doi: https://doi.org/10.1039/C3CS35526H

8. Fundamentalnyye osnovy mekhanicheskoy aktivatsii, mekhanosinteza i mekhanokhimicheskikh tekhnologiy [Fundamentals of mechanical activation, mechanosynthesis, and mechanochemical technologies]. Ed. Avakumov Ye.G. Novosibirsk, SB RAS Publ., 2009. 342 p.

9. Barambojm N.K. Mehanohimija vysokomolekuljarnyh soedinenij [Mechanochemistry of high-molecular compounds]. M.: Himija, 1978, 384 p.

10. Baláž P. Hallmarks of Mechanochemistry: From nanoparticles to technology. Chem. Soc. Rev., 2013, vol. 42, pp. 7571-7637.

11. Oprea C., Vasiliu-Oprea C., Dan F. Macromolecular mechanochemistry: Polymer mechanochemistry. Cambridge: Cambridge Int. Science Publishing, 2003, 650 р.

12. Radtsig V.A. Mekhanokhimiya polimerov glazami metoda EPR (obzor) [Mechanochemistry of polymers through the eyes of the EPR method (review)]. Khim. Fizika — Russian Journal of Physical Chemistry B, 2004, vol. 23, no. 10, pp. 70-109.

13. Umbach W., Stein W. Continuous alkoxylation process. J. Am. Oil Chem. Soc., 1971, vol. 48, no. 8, рр. 394-397. doi: https://doi.org/10.1007/BF02637359

14. Sallaya P., Farkas L., Szlovák Z., Fogassy G. Novel General Procedure for the Preparation of Homogeneous Nonionic Surfactants. J. Surfactants Deterg., 2002, vol. 5, no. 4, pp. 353-357.

15. Hreczueh W., Miszkiewicz W., Szymanowski J., Zimoch J., Jerzykiewicz A. High Ethoxylated Alcohols with Narrow Distribution of Homologues. J. Chem. Biotechnol., 1996, vol. 67, pp. 53-60.

16. Agronomov A.Ye. Izbrannyye glavy organicheskoy khimii [Selected Chapters of Organic Chemistry]. M.: Khimiya, 1990, 560 p.

17. Taylor T.J., Seitz E.P., Fox P.S., Fals J.L. Antimikrobnyye kompozitsii, soderzhashchiye aromaticheskiye karbonovyye kisloty i spirtovoy rastvoritel [Antimicrobic compositions of aromatic carboxylic acid and alcoholic solution]. Patent RF, no. 2325203C2, 2008.


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Khil’ko S.L., Nevecheryа O.I., Makarova R.A., Semenova R.G. Mechanochemical ethoxylation of benzoic acid and its halogene derivatives. Title in english. 2021;(4(125)):64-67. (In Russ.) https://doi.org/10.34680/2076-8052.2021.4(125).64-67

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