Skip to main content
SpringerLink
Log in

Hydrolysis of Hydroxypropyl Methylcellulose by Trifluoromethanesulfonic Acid and Subsequent Determination of Chemical Structure by 13C NMR Spectroscopy

  • NATURAL POLYMERS
  • Published:
Polymer Science, Series B Aims and scope Submit manuscript

Abstract

The hydrolysis of three hydroxypropyl methylcellulose samples with varying degrees of polymerization by aqueous solutions of trifluoromethanesulfonic acid with a concentration of 1, 2, 3, and 4% at a temperature of 80, 90, 100, and 110°C in a microwave reactor is studied. The completeness of hydrolysis is estimated by 13C NMR spectroscopy of the disappearance of the signal the acetal carbon atom. It is shown that the concentration of acid has the greatest influence on the hydrolysis rate, the effect of temperature increase is not so strong, and the effect of reaction time is even smaller. Using 13C NMR spectroscopy, substitution parameters at the second, third, and sixth positions (DSC-2, DSC-3, and DSC-6) are determined, the amount of methyl (DSMe) and hydroxypropyl groups (DSHP) is estimated, and the total degree of substitution (DStotal) is calculated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. V. N. Kryazhev and V. A. Shirokov, Khim. Rastit. Syr’ya, No. 3, 7 (2005).

    Google Scholar 

  2. W. Kaialy and M. Al Shafiee, Adv. Colloid Interface Sci. 228, 71 (2016).

    Article  CAS  Google Scholar 

  3. N. Jedinger, J. Khinast, and E. Roblegg, Eur. J. Pharm. Biopharm. 87, 217 (2014).

    Article  CAS  Google Scholar 

  4. E. T. Cole, D. Cadé, and H. Benameur, Adv. Drug Delivery Rev. 60, 747 (2008).

    Article  CAS  Google Scholar 

  5. P. Del Gaudio, P. Russo, R. R. Dorado, F. Sansone, T. Mencherini, F. Gasparri, an R. P. Aquino, Carbohydr. Polym. 165, 22 (2017).

    Article  CAS  Google Scholar 

  6. M. Cespi, G. Bonacucina, G. Mencarelli, L. Casettari, and G. F. Palmieri, Eur. J. Pharm. Biopharm. 79, 458 (2011).

    Article  CAS  Google Scholar 

  7. P. Mischnick and D. Momcilovic, Adv.Carbohydr.Chem. Biochem. 64, 117 (2010).

    Article  CAS  Google Scholar 

  8. G. Wypych, HPMC Hydroxypropyl Methylcellulose. Handbook of Polymers (ChemTec Publ., Toronto, 2016), p. 166.

    Google Scholar 

  9. E. Kaal, S. Koning, S. Brudin, and H.-G. Janssen, J. Chromatogr. A 1201, 169 (2008).

    Article  CAS  Google Scholar 

  10. R. Adden, R. Müller, and P. Mischnick, Cellulose 13, 459 (2006).

    Article  CAS  Google Scholar 

  11. Y. Li, H. Shen, J. W. Lyons, R. L. Sammler, M. Brackhagen, and D. M. Meunier, Carbohydr. Polym. 138, 290 (2016).

    Article  CAS  Google Scholar 

  12. R. Chen, Int. J. Polym. Anal. Charact. 14, 617 (2009).

    Article  CAS  Google Scholar 

  13. B. Deshmukh, R. G. Harfmann, J. Conklin, M. Turowski, and S. Lync, Food Chem. 104 (2), 852 (2007).

    Article  CAS  Google Scholar 

  14. J. A. Cuers, M. B. Rinken, R. C. Adden, and P. Mischnick, Anal. Bioanal. Chem. 405, 9021 (2013).

    Article  CAS  Google Scholar 

  15. R. Adden, W. Niedner, R. Müller, and P. Mischnick, Anal. Chem. 78, 1146 (2006).

    Article  CAS  Google Scholar 

  16. A. Parfondry and A. S. Perlin, Carbohydr. Res. 57, 39 (1977).

    Article  CAS  Google Scholar 

  17. I. Nehls, W. Wagenknecht, B. Philipp, and D. Stscherbina, Prog. Polym. Sci. 19, 29 (1994).

    Article  CAS  Google Scholar 

  18. N. N. D. Sachinvala, D. L. Winsor, W. P. Niemczura, K. Maskos, T. L. Vigo, and N. R. Bertoniere, ACS Symp. Ser. 834, 306 (2002).

    Article  Google Scholar 

  19. J. Kunze, A. Ebert, and H. P. Fink, Cellul. Chem. Technol. 34, 21 (2000).

    CAS  Google Scholar 

  20. M. Brogly, A. Fahs, and S. Bistac, ARPN J. Eng. Appl. Sci. 11, 7188 (2016).

    CAS  Google Scholar 

  21. S. V. Araslankin, S. G. Kostryukov, and P. S. Petrov, Vestn. Permsk. Univ., Ser. Khim. 8, 54 (2018).

    Google Scholar 

  22. S. V. Araslankin, V. A. Kalyazin, S. G. Kostryukov, and P. S. Petrov, Khim. Rastit. Syr’ya, No. 1, 51 (2019).

    Google Scholar 

  23. A. Martínez-Richa, Carbohydr. Polym. 87, 2129 (2012).

    Article  Google Scholar 

  24. B. Saake, S. Horner, J. Puls, T. Heinze, and W. Koch, Cellulose 8 (1), 59 (2001).

    Article  CAS  Google Scholar 

  25. A. Karrasch, C. Jäger, B. Saake, A. Potthast, and T. Rosenau, Cellulose 16, 1159 (2009).

    Article  CAS  Google Scholar 

  26. S. G. Kostryukov, S. V. Araslankin, and P. S. Petrov, Khim. Rastit. Syr’ya, No. 4, 31 (2017).

    Google Scholar 

  27. M. Pisklak, M. Zielińska-Pisklak, Ł. Szeleszczuk, and I. Wawer, J. Pharm. Biomed. Anal. 122, 81 (2016).

    Article  CAS  Google Scholar 

  28. S. G. Kostryukov, S. V. Araslankin, P. S. Petrov, V. A. Kalyazin, and A. A. I. Al’-Rubaie, Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol. 62, 102 (2019).

    Google Scholar 

  29. A. Trummal, L. Lipping, I. Kaljurand, I. A. Koppel, and I. Leito, J. Phys. Chem. A 120, 3663 (2016).

    Article  CAS  Google Scholar 

  30. Hallo from Phyl Toukach. https://toukach.ru/files/biopsel.zip. Cited 2020.

  31. F. V. Toukach and V. P. Ananikov, Chem. Soc. Rev. 42, 8376 (2013).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Mordovian National Research State University, 430005, Saransk, Russia

    S. G. Kostryukov, P. S. Petrov, V. A. Kalyazin, A. A. Burtasov, M. K. Pryanichnikova, A. A. Odnopolov, E. V. Krainov & V. S. Tezikova

Authors
  1. S. G. Kostryukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. S. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Kalyazin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Burtasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. K. Pryanichnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. A. Odnopolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. V. Krainov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. S. Tezikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. G. Kostryukov.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kostryukov, S.G., Petrov, P.S., Kalyazin, V.A. et al. Hydrolysis of Hydroxypropyl Methylcellulose by Trifluoromethanesulfonic Acid and Subsequent Determination of Chemical Structure by 13C NMR Spectroscopy. Polym. Sci. Ser. B 62, 279–289 (2020). https://doi.org/10.1134/S1560090420030082

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1560090420030082

Search

Navigation