Skip to main content
Log in

Ring-opening polymerization by N-heterocyclic carbenes as catalysts: Characteristics and kinetics

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

In this work catalytic ring-opening polymerization of cyclic esters in THF in the presence of benzyl alcohol is described. The polymerization is catalyzed by 1,3-bis(4-methoxyphenyl)imidazolium carbene, N-heterocyclic carbene (NHC). The ability of two different monomers, ɛ-caprolactone and L-lactide, to enter into the polymerization via ring-opening polymerization with NHCs as catalysts was evaluated. The plot of ln([M]0/[M]t) versus reaction time yielded a straight line indicating that the kinetics of polymerization of ɛ-caprolactone and L-lactide was first-order in monomer concentration. Moreover, a direct relation between the rate of ring-opening polymerization of ɛ-caprolactone and the catalyst concentration suggested a first-order dependence of the rate of polymerization on the catalyst concentration.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Yasuda, H., Aludin, M.S., Kitamura, N., Tanabe, M., and Sirahama, H., Macromolecules, 1999, vol. 32, no. 19, p. 6047.

    Article  CAS  Google Scholar 

  2. Jerome, C. and Lecomte, P., Adv. Drug Delivery Rev., 2008, vol. 60, no. 9, p. 1056.

    Article  CAS  Google Scholar 

  3. Penczek, S., Cypryk, M., Duda, A., Kubisa, P., and Slomkowski, S., Prog. Polym. Sci., 2007, vol. 32, no. 2, p. 247.

    Article  CAS  Google Scholar 

  4. Albertsson, A.C. and Varma, I.K., Biomacromolecules, 2003, vol. 4, no. 6, p. 1466.

    Article  CAS  Google Scholar 

  5. Chiellini, E. and Solaro, R., Adv. Mater., 1996, vol. 8, no. 4, p. 305.

    Article  CAS  Google Scholar 

  6. Ghosh, S., J. Chem. Res., 2004, no. 4, p. 241.

    Google Scholar 

  7. Dechy-Cabaret, O., Martin-Vaca, B., and Bourissou, D., Chem. Rev., 2004, vol. 104, no. 12, p. 6147.

    Article  CAS  Google Scholar 

  8. Kricheldorf, H.R., Berl, M., and Scharnagl, N., Macromolecules, 1988, vol. 21, no. 2, p. 286.

    Article  CAS  Google Scholar 

  9. Duda, A. and Penczek, S., Macromolecules, 1995, vol. 28, no. 18, p. 5981.

    Article  CAS  Google Scholar 

  10. Biela, T., Kowalski, A., Libiszowski, J., Duda, A., and Penczek, S., Macromol. Symp., 2006, vol. 240, no. 1, p. 47.

    Article  CAS  Google Scholar 

  11. Duda, A., Kowalski, A., Libiszowski, J., and Penczek, S., Macromol. Symp., 2005, vol. 224, no. 1, p. 71.

    Article  CAS  Google Scholar 

  12. Chisholm, M.H. and Delbridge, E.E., New J. Chem., 2003, vol. 27, no. 8, p. 1167.

    Article  CAS  Google Scholar 

  13. Chamberlain, B.M., Cheng, M., Moore, D.R., Ovitt, T.M., Lobkovsky, E.B., and Coates, G.W., J. Am. Chem. Soc., 2001, vol. 123, no. 14, p. 3229.

    Article  CAS  Google Scholar 

  14. Zamfir, M., Patrickios, C.S., Montagne, F., Abetz, C., Abetz, V., Oss-Ronen, L., and Talmon, Y., J. Polym. Sci., Part A: Polym. Chem., 2012, vol. 50, no. 8, p. 1636.

    Article  CAS  Google Scholar 

  15. Hamou, A.S.H. and Djadoun, S., Macromol. Symp., 2011, vol. 303, no. 1, p. 114.

    Article  Google Scholar 

  16. Nomura, N., Akita, A., Ishii, R., and Mizuno, M., J. Am. Chem. Soc., 2010, vol. 132, no. 6, p. 1750.

    Article  CAS  Google Scholar 

  17. Kamber, N.E., Jeong, W., Gonzalez, S., Hedrick, J.L., and Waymouth, R.M., Macromolecules, 2009, vol. 42, no. 5, p. 1634.

    Article  CAS  Google Scholar 

  18. Dove, A.P., Pratt, R.C., Lohmeijer, B.G.G., Culkin, D.A., Hgberg, E.C., Nyce, G.W., Waymouth, R.M., and Hedrick, J.L., Polymer, 2006, vol. 47, no. 11, p. 4018.

    Article  CAS  Google Scholar 

  19. Coulembier, O., Mespouille, L., Hedrick, J.L., Waymouth, R.M., and Dubois, P., Macromolecules, 2006, vol. 39, no. 12, p. 4001.

    Article  CAS  Google Scholar 

  20. Kamber, N.E., Jeong, W., Gonzalez, S., Hedrick, J.L., and Waymouth, R.M., Macromolecules, 2009, vol. 42, no. 5, p. 1634.

    Article  CAS  Google Scholar 

  21. Connor, E.F., Nyce, G.W., Myers, M., Mock, A., and Hedrick, J.L., J. Am. Chem. Soc., 2002, vol. 124, no. 6, p. 914.

    Article  CAS  Google Scholar 

  22. Trollsas, M., Claesson, H., and Atthoff, B., Angew. Chem., Int. Ed. Engl., 1998, vol. 37, no. 22, p. 3132.

    Article  CAS  Google Scholar 

  23. Arduengo, A.J., Rasika Dias, H.V., Harlow, R.L., and Kline, M., J. Am. Chem. Soc., 1992, vol. 114, no. 14, p. 5530.

    Article  CAS  Google Scholar 

  24. Arduengo, A.J., Krafczyk, R., and Schmutzler, R., Tetrahedron, 1999, vol. 55, no. 51, p. 14523.

    Article  CAS  Google Scholar 

  25. Kuhn, N. and Kratz, T., Synthesis, 1993, no. 6, p. 561.

    Google Scholar 

  26. Gross, R.A., Kumar, A., and Kalra, B., Chem. Rev., 2001, vol. 101, no. 7, p. 2097.

    Article  CAS  Google Scholar 

  27. Spivey, A.C. and Arseniyadis, S., Angew. Chem., Int. Ed. Engl., 2004, vol. 43, no. 41, p. 5436.

    Article  CAS  Google Scholar 

  28. Movassaghi, M. and Schmidt, M.A., Org. Lett., 2005, vol. 7, no. 12, p. 2453.

    Article  CAS  Google Scholar 

  29. Lai, C.L., Lee, H.M., and Hu, C.H., Tetrahedron Lett., 2005, vol. 46, no. 37, p. 6265.

    Article  CAS  Google Scholar 

  30. Lee, J.W., Oh, D.K., Yelamaggad, C.V., Nagamani, S.A., and Jing, J., J. Mater. Chem., 2002, vol. 12, no. 8, p. 2225.

    Article  CAS  Google Scholar 

  31. Raynaud, J., Gnanou, Y., and Taton, D., Macromolecules, 2009, vol. 42, no. 16, p. 5996.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. Zhang.

Additional information

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, Y., Li, N., Zhang, L. et al. Ring-opening polymerization by N-heterocyclic carbenes as catalysts: Characteristics and kinetics. Kinet Catal 55, 416–421 (2014). https://doi.org/10.1134/S0023158414040168

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158414040168

Keywords

Navigation