Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 641–645 | Cite as

Effect of Association on Nucleophilic Addition of (Meth)acrylic Aminoamides to Acrylic Acids in Aqueous Solutions

  • О. А. Kazantsev
  • D. S. Baruta
  • D. М. Kamorin
  • K. K. Shirshin
  • А. P. Sivokhin
Article

Abstract

Reactions of nucleophilic addition of N-(3-dimethylaminoalkyl)(meth)acrylamides to acrylic, N-acryloylaminoacetic, and 2-acrylamido-2-methylpropanesulfonic acid with the formation of betaines revealed an unusual dependence of the initial rate and equilibrium conversion on concentration of the reagents. The observed effects were explained by structural features of the reagents and the products.

Keywords

N-(3-dimethylaminoalkyl)metacrylamides acrylic acid N-acryloylaminoacetic acid 2-acrylamido- 2-methylpropanesulfonic acid betaines 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

This work was performed with the financial support from the Ministry of Education and Science (State contract 10.2326.2017/PCh) and the Program of development of R.E. Alekseev Nizhny Novgorod State Technical University.

References

  1. 1.
    Yang, J., Curr. Opinion Colloid Interface Sci., 2002, vol. 7, p. 276. doi 10.1016/S1359-0294(02)00071-7CrossRefGoogle Scholar
  2. 2.
    Gui, Z., Qian, J., An, Q., Xu, H., and Zhao, Q., Eur. Polym. J., 2009, vol. 45, no. 5, p. 1403. doi 10.1016/j.eurpolymj.2009.02.010CrossRefGoogle Scholar
  3. 3.
    Hoover, M.F., J. Macromol. Sci. (A), 1970, vol. 4, no. 6, p. 1327. doi 10.1080/00222337008081733CrossRefGoogle Scholar
  4. 4.
    Sadiku, E., J. Appl. Pol. Sci., 2006, vol. 102, no. 1, p. 166. doi 10.1002/app.23407CrossRefGoogle Scholar
  5. 5.
    Shachat, N., Haggard, R.A., and Lewis, S.N., USA Patent 3689470A, 1972.Google Scholar
  6. 6.
    Kazantsev, O.A., Zil’berman, E.N., Salov, V.N., and Krasnov, V.L., Zh. Prikl. Khim, 1987, vol. 60, no. 9, p. 2142.Google Scholar
  7. 7.
    Kazantsev, O.A., Kazakov, S.A., Shirshin, K.V., Danov, S.M., and Krasnov, V.L., Chem. Heterocycl. Compd., 1998, vol. 370, no. 4, p. 547. doi 10.1002/chin.199841152Google Scholar
  8. 8.
    Kazantsev, O.A., Kazakov, S.A., Shirshin, K.V., and Danov, S.M., Russ. J. Org. Chem., 2000, vol. 36, no. 3, p. 343. doi 10.1002/chin.200051078Google Scholar
  9. 9.
    Shirshin, K.V., Kazantsev, O.A., Kazakov, S.A., and Danov, S.M., J. Appl. Chem., 1999, vol. 72, no. 2, p. 278.Google Scholar
  10. 10.
    Kazantsev, O.A., Baruta, D.S., Shirshin, K.V., Sivokhin, A.P., and Kamorin, D.M., Russ. J. Phys. Chem., 2010, vol. 84, no. 12, p. 2071. doi 10.1134/s0036024410120113CrossRefGoogle Scholar
  11. 11.
    Kazantsev, O.A., Baruta, D.S., Shirshin, K.V., Sivokhin, A.P., and Kamorin, D.M., Russ. J. Phys. Chem., 2011, vol. 85, no. 3, p. 413. doi 10.1134/s0036024411030162CrossRefGoogle Scholar
  12. 12.
    Kazantsev, O.A., Shirshin, K.V., Kazakov, S.A., and Danov, S.M., Zh. Obshch. Khim., 1996, vol. 66, no. 12, p. 2014.Google Scholar
  13. 13.
    Suminov, S.I. and Kost, A.N., Russ. Chem. Rev., 1969, vol. 38, no. 11, p. 1933. doi 10.1070/rc1969v038n11abeh001860CrossRefGoogle Scholar
  14. 14.
    Le Berre, A. and Delacroix, A., Bull. Soc. Chim. Fr., 1973, vols. 7–8, p. 2404.Google Scholar
  15. 15.
    Shirshin, K.V., Kazantsev, O.A., and Sivokhin A.P., Plastmassy, 2009, no. 11, p. 14.Google Scholar
  16. 16.
    Bondarenko S.P., Tiger R.P., and Jentelis, S.G., Zh. Fiz. Khim., 1981, vol. 55, no. 7, p. 1716.Google Scholar
  17. 17.
    Stul’, B.Ya. and Chesnokov, B.B., Kinet. Catal., 2002, vol. 43, no. 5, p. 741. doi 10.1023/a:1020620500591CrossRefGoogle Scholar
  18. 18.
    Kulagina, T.P. and Smirnov, L.P., Doklady Chem., 2009, vol. 427, no. 2, p. 136. doi 10.1134/s0012501609080028CrossRefGoogle Scholar
  19. 19.
    Kabanov, V.A. and Topchiev, D.A., Polimerizatsiya ionizuyushchikhsya monomerov (Polymerization of Ionizing Monomers), Мoscow: Nauka, 1975.Google Scholar
  20. 20.
    Kolomeitseva, O.P. and Kuznetsova, N.N., Zh. Prikl. Khim., 1972, vol. 45, p. 1978.Google Scholar
  21. 21.
    Shirshin, K.V., Kazantsev, O.A., Zil’berman, E.N., Salov, V.N., and Molotkov, V.A., Zh. Prikl. Khim., 1990, vol. 63, no. 12, p. 1978.Google Scholar
  22. 22.
    Galkin, V.I., Cherkasov, A.R., Sayakhov, R.D., and Cherkasov, R.A., Russ. J. Gen. Chem., 1995, vol. 65, no. 3, p. 404.Google Scholar
  23. 23.
    Sayakhov, R.D., Cherkasov, R.A., and Galkin, V.I., Russ. Chem. Rev., 1991, vol. 60, no. 8, p. 815. doi 10.1070/rc1991v060n08abeh001113CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • О. А. Kazantsev
    • 1
  • D. S. Baruta
    • 1
  • D. М. Kamorin
    • 1
  • K. K. Shirshin
    • 1
    • 2
  • А. P. Sivokhin
    • 1
  1. 1.R.E. Alekseev Nizhny Novgorod State Technical UniversityNizhny NovgorodRussia
  2. 2.N.I. Lobachevsky State University of Nizhny NovgorodNizhny NovgorodRussia

Personalised recommendations