Skip to main content
SpringerLink
Log in

Metathesis Polymerization in Ionic Media

  • Published:
Polymer Science, Series C Aims and scope Submit manuscript

Abstract

The article summarizes the literature data on polymer synthesis by olefin and acetylene metathesis in ionic liquid media—salts in the liquid state—at room temperature or close to it. The features and methods of optimization of polymerization process in ionic media, including those using ionic catalysts are discussed. The possibility of multiple use of ionic solvents and catalysts dissolved in them is demonstrated. Data on the polymerization of ionic monomers and the prospects for using ionic polymers obtained by metathesis polymerization are presented.

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.

Similar content being viewed by others

REFERENCES

  1. Ionic Liquids in Synthesis, Ed. by P. Wasserscheid and T. Welton (Wiley, Weinheim, 2007).

    Google Scholar 

  2. J. P. Hallett and T. Welton, Chem. Rev. 111, 3508 (2011).

    Article  CAS  PubMed  Google Scholar 

  3. S. A. Forsyth, J. M. Pringle, and D. R. MacFarlane, Aust. J. Chem. 57, 113 (2004).

    Article  CAS  Google Scholar 

  4. Ya. S. Vygodskii, E. I. Lozinskaya, and A. S. Shaplov, Polym. Sci., Ser. C 43, 236 (2001).

    Google Scholar 

  5. R. Sheldon, Chem. Commun. 2001, 2399 (2001).

    Article  CAS  Google Scholar 

  6. K. R. Seddon, J. Chem. Technol. Biotechnol. 68, 351 (1997).

    Article  CAS  Google Scholar 

  7. J. D. Holbrey and K. R. Seddon, Clean Technol. Environ. Policy 1, 223 (1999).

    Article  Google Scholar 

  8. T. Welton, Chem. Rev. 99, 2071 (1999).

    Article  CAS  PubMed  Google Scholar 

  9. P. Sledz, M. Mauduit, and K. Grela, Chem. Soc. Rev. 37, 2433 (2008).

    Article  CAS  PubMed  Google Scholar 

  10. P. A. Thomas and B. B. Marvey, Molecules 21, 184 (2016).

    Article  CAS  PubMed Central  Google Scholar 

  11. M. Xie, H. Han, L. Ding, and J. Shi, Polym. Rev. 49, 315 (2009).

    Article  CAS  Google Scholar 

  12. Yu. P. Yampolskii, L. E. Starannikiva, N. A. Belov, M. V. Bermeshev, M. L. Gringolts, and E. Sh. Finkelshtein, J. Membr. Sci. 453, 532 (2014).

    Article  CAS  Google Scholar 

  13. P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, N. A. Belov, V. E. Ryzhikh, V. P. Shantarovich, V. G. Lakhtin, N. N. Gavrilova, Yu. P. Yampolskii, and E. Sh. Finkelshtein, Macromolecules 48, 8055 (2015).

    Article  CAS  Google Scholar 

  14. E. Sh. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Yu. V. Rogan, T. G. Golenko, L. E. Starannikova, Yu. P. Yampolskii, V. P. Shantarovich, and T. Suzuki, Macromolecules 39, 7022 (2006).

    Article  CAS  Google Scholar 

  15. M. L. Gringolts, M. V. Bermeshev, Yu. P. Yampolskii, L. E. Starannikiva, V. P. Shantarovich, and E. Sh. Finkelshtein, Macromolecules 43, 7165 (2010).

    Article  CAS  Google Scholar 

  16. D. A. Alentiev, D. M. Dzhaparidze, N. N. Gavrilova, V. P. Shantarovich, E. V. Kiseleva, M. A. Topchiy, A. F. Asachenko, P. S. Gribanov, M. S. Nechaev, S. A. Legkov, G. N. Bondarenko, and M. V. Bermeshev, Polymers 10, 1382 (2018).

    Article  CAS  PubMed Central  Google Scholar 

  17. M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).

    Article  CAS  Google Scholar 

  18. W. L. Truett, D. R. Johnson, I. M. Robinson, and B. A. Montague, J. Am. Chem. Soc. 82, 2337 (1960).

    Article  CAS  Google Scholar 

  19. R. R. Schrock, J. Feldman, L. F. Cannizzo, and R. H. Grubbs, Macromolecules 20, 1169 (1987).

    Article  CAS  Google Scholar 

  20. R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, M. DiMare, and M. O’Regan, J. Am. Chem. Soc. 112, 3875 (1990).

    Article  CAS  Google Scholar 

  21. M. R. Buchmeiser, Chem. Rev. 100, 1565 (2000).

    Article  CAS  PubMed  Google Scholar 

  22. P. Schwab, M. B. France, J. W. Ziller, and R. H. Grubbs, Angew. Chem., Int. Ed. 34, 2039 (1995).

    Article  CAS  Google Scholar 

  23. S. T. Nguyen, R. H. Grubbs, and J. W. Ziller, J. Am. Chem. Soc. 115, 9858 (1993).

    Article  CAS  Google Scholar 

  24. Handbook of Metathesis: Catalyst Development, Ed. by R. H. Grubbs (Wiley, Weinheim, 2003).

    Google Scholar 

  25. J. A. Love, J. P. Morgan, T. M. Trnka, and R. H. Grubbs, Angew. Chem., Int. Ed. Engl. 41, 4035 (2002).

    Article  CAS  Google Scholar 

  26. S. B. Garber, J. S. Kingsbury, B. L. Gray, and A. H. Hoveyda, J. Am. Chem. Soc. 122, 8168 (2000).

    Article  CAS  Google Scholar 

  27. Y. S. Vygodskii, A. S. Shaplov, E. I. Lozinskaya, K. A. Lysenko, D. G. Golovanov, I. A. Malyshkina, N. D. Gavrilova, and M. R. Buchmeiser, Macromol. Chem. Phys. 209, 40 (2008).

    Article  CAS  Google Scholar 

  28. H. Han, F. Chen, J. Yu, J. Dang, Z. Ma, Y. Zhang, and M. Xie, J. Polym. Sci., Part A: Polym. Chem. 45, 3986 (2007).

    Article  CAS  Google Scholar 

  29. M. Xie, Y. Kong, H. Han, J. Shi, L. Ding, C. Song, and Y. Zhang, React. Funct. Polym. 68, 1601 (2008).

    Article  CAS  Google Scholar 

  30. Q. Yao and M. Sheets, J. Organomet. Chem. 690, 3577 (2005).

    Article  CAS  Google Scholar 

  31. H. Clavier, N. Audic, J.-C. Guillemin, and M. Mauduit, J. Organomet. Chem. 690, 3585 (2005).

    Article  CAS  Google Scholar 

  32. N. Audic, H. Clavier, M. Mauduit, and J.-C. Guillemin, J. Am. Chem. Soc. 125, 9248 (2003).

    Article  CAS  PubMed  Google Scholar 

  33. C. Thurier, C. Fischmeister, C. Bruneau, H. Olivier-Bourbigou, and P. H. Dixneuf, J. Mol. Catal. A: Chem. 268, 127 (2007).

    Article  CAS  Google Scholar 

  34. T. E. Schmid, A. Dumas, S. Colombel-Rouen, C. Crevisy, O. Basle, and M. Mauduit, Synlett 28, 773 (2017).

    Article  CAS  Google Scholar 

  35. N. Clousier, A. Filippi, E. Borr, E. Guibal, C. Crevisy, F. Caijo, M. Mauduit, I. Dez, and A.-C. Gaumont, ChemSusChem 7, 1040 (2014).

    Article  CAS  PubMed  Google Scholar 

  36. A. Keraani, M. Rabiller-Baudry, C. Fischmeister, and C. Bruneau, Catal. Today 156, 268 (2010).

    Article  CAS  Google Scholar 

  37. C. S. Consorti, G. L. P. Aydos, and J. Dupont, Chem. Commun. 46, 9058 (2010).

    Article  CAS  Google Scholar 

  38. C. S. Consorti, G. L. P. Aydos, G. Ebeling, and J. Dupont, Organometallics 28, 4527 (2009).

    Article  CAS  Google Scholar 

  39. S.-W. Chen, J. H. Kim, K. Y. Ryu, W.-W. Lee, and J. Hong, Tetrahedron 65, 3397 (2009).

    Article  CAS  Google Scholar 

  40. J. H. Kim, B. Y. Park, S.-W. Chen, and S. Lee, Eur. J. Org. Chem. 2009, 2239 (2009).

    Article  CAS  Google Scholar 

  41. H. Wakamatsu, Y. Saito, M. Masubuchi, and R. Fujita, Synlett 2008, 1805 (2008).

    Article  CAS  Google Scholar 

  42. H. Clavier, S. P. Nolan, and M. Mauduit, Organometallics 27, 2287 (2008).

    Article  CAS  Google Scholar 

  43. J. Suriboot, H. S. Bazzi, and D. E. Bergbreiter, Polymers 8, 140 (2016).

    Article  CAS  PubMed Central  Google Scholar 

  44. M. Koy, H. J. Altmann, B. Autenrieth, W. Frey, and M. R. Buchmeiser, Beilstein J. Org. Chem. 11, 1632 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. B. Autenrieth, W. Frey, and M. R. Buchmeiser, Chem.- Eur. J. 18, 14069 (2012).

    Article  CAS  PubMed  Google Scholar 

  46. J. Zhao, D. Wang, B. Autenrieth, and M. R. Buchmeiser, Macromol. Rapid Commun. 36, 190 (2015).

    Article  CAS  PubMed  Google Scholar 

  47. “Olefin Metathesis,” in Metal Catalysed Reactions in Ionic Liquids, Ed. by P. J. Dyson and G. J. Tilmann (Springer, Dordrecht, 2005), Chap. 7, p. 155.

    Google Scholar 

  48. Q. Yao and Y. Zhang, Angew. Chem., Int. Ed. 42, 3395 (2003).

    Article  CAS  Google Scholar 

  49. N. Audic, H. Clavier, M. Mauduit, and J.-C. Guillemin, J. Am. Chem. Soc. 125, 9248 (2003).

    Article  CAS  PubMed  Google Scholar 

  50. H. Clavier, N. Audic, M. Mauduit, and J.-C. Guillemin, Chem. Commun. 2004, 2282 (2004).

    Article  Google Scholar 

  51. W. Song, H. Han, X. Liao, R. Sun, J. Wu, and M. Xie, Macromolecules 47, 6181 (2014).

    Article  CAS  Google Scholar 

  52. M.-R. Xie, Z. Ma, H.-J. Han, J.-X. Shi, W.-Z. Wang, J.-X. Li, and Y.-Q. Zhang, Chem. J. Chin. Univ. 30, 396 (2009).

    CAS  Google Scholar 

  53. H. Han, J. Liu, W. Huang, C. Song, Y. Zhang, and M. Xie, Acta Polym. Sin., No. 5, 492 (2008).

  54. Y. S. Vygodskii, A. S. Shaplov, E. I. Lozinskaya, O. A. Filippov, E. S. Shubina, R. Bandari, and M. R. Buchmeiser, Macromolecules 39, 7821 (2006).

    Article  CAS  Google Scholar 

  55. C. Simocko, T. C. Young, and K. B. Wagener, Macromolecules 48, 5470 (2015).

    Article  CAS  Google Scholar 

  56. Ya. S. Vygodskii, A. S. Shaplov, E. I. Lozinskaya, P. S. Vlasov, I. A. Malyshkina, N. D. Gavrilova, P. S. Kumar, and M. R. Buchmeiser, Macromolecules 41, 1919 (2008).

    Article  CAS  Google Scholar 

  57. C. Simocko, Y. Yang, T. M. Swager, and K. B. Wagener, ACS Macro Lett. 2, 1061 (2013).

    Article  CAS  Google Scholar 

  58. C. Daguenet and P. J. Dyson, Organometallics 23, 6080 (2004).

    Article  CAS  Google Scholar 

  59. S. Csihony, C. Fischmeister, C. Bruneau, I. T. Horvath, and P. H. Dixneu, New J. Chem. 26, 1667 (2002).

    Article  CAS  Google Scholar 

  60. C. P. Ferraz, B. Autenrieth, W. Frey, and M. R. Buchmeiser, ChemCatChem 6, 191 (2014).

    Article  CAS  Google Scholar 

  61. M. M. Gallagher, A. D. Rooney, and J. J. Rooney, J. Mol. Catal. A: Chem. 303, 78 (2009).

    Article  CAS  Google Scholar 

  62. X. Ding, X. Lv, B. Hui, Z. Chen, M. Xiao, B. Guo, W. Tang, Tetrahedron Lett. 47, 2921 (2006).

    Article  CAS  Google Scholar 

  63. T. S. Halbach, J. O. Krause, O. Nuyken, and M. R. Buchmaiser, Macromol. Rapid Commun. 26, 784 (2005).

    Article  CAS  Google Scholar 

  64. S. Naumov and M. R. Buchmaiser, Organometallics 31, 847 (2012).

    Article  CAS  Google Scholar 

  65. A. S. Shaplov, D. O. Ponkratov, and Y. S. Vygodskii, Polym. Sci., Ser. B 58, 73 (2016).

    Article  CAS  Google Scholar 

  66. J. Wang, X. He, H. Zhu, and D. Chen, RSC Adv. 5, 43581 (2015).

  67. X. He, Z. Wang, W. Zhou, X. Jiang, Z. Han, and D. Chen, J. Appl. Polym. Sci. 134, 44884 (2017).

    Google Scholar 

  68. Q. Ye, T. Gao, F. Wan, B. Yu, X. Pei, F. Zhou, and Q. Xue, J. Mater. Chem. 22, 13123 (2012).

    Article  CAS  Google Scholar 

  69. I. Njoroge, M. W. Matson, and G. K. K. Jennings, J. Phys. Chem. C 121, 20323 (2017).

    Article  CAS  Google Scholar 

  70. I. Njoroge, B. W. Bout, M. W. Matson, P. E. Laibinis, and G. K. Jennings, ACS Omega 3, 16158 (2018).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. E. F. Wiesenauer, J. P. Edwards, V. F. Scalfani, T. S. Bailey, and D. L. Gin, Macromolecules 44, 5075 (2011).

    Article  CAS  Google Scholar 

  72. E. F. Wiesenauer, P. T. Nguyen, B. S. Newell, T. S. Bailey, R. D. Noble, and D. L. Gin, Soft Matter 9, 7923 (2013).

    Article  CAS  Google Scholar 

  73. T. Suga, M. Sakata, K. Aoki, and H. Nishide, ACS Macro Lett. 3, 703 (2014).

    Article  CAS  Google Scholar 

  74. J. Cui, F.-M. Nie, J.-X. Yang, L. Pan, Z. Ma, and Y.‑S. Lia, J. Mater. Chem. A 5, 25220 (2017).

    Article  CAS  Google Scholar 

  75. R. R. Maddikeri, S. Colak, S. P. Gido, and G. N. Tew, Biomacromolecules 12, 3412 (2011).

    Article  CAS  PubMed  Google Scholar 

  76. M. Xie, H. Han, W. Wang, X. He, and Y. Zhang, Macromol. Chem. Phys. 209, 544 (2008).

    Article  CAS  Google Scholar 

  77. W. You, K. M. Hugar, and G. W. Coates, Macromolecules 51, 3212 (2018).

    Article  CAS  Google Scholar 

  78. B. L. Langsdorf, X. Zhou, D. H. Adler, and M. C. Lonergan, Macromolecules 32, 2796 (1999).

    Article  CAS  Google Scholar 

  79. D. H. Johnston, L. Gao, and M. C. Lonergan, Macromolecules 43, 2676 (2010).

    Article  CAS  Google Scholar 

  80. H. Li, J. Wang, H. Han, J. Wu, and M. Xie, React. Funct. Polym. 127, 20 (2018).

    Article  CAS  Google Scholar 

  81. Y.-S. Gal, W.-C. Lee, J.-H. Lee, and S.-K. Choi, Bull. Korean Chem. Soc. 18, 22 (1997).

    Google Scholar 

  82. K.-L. Kang, S.-H. Kim, H.-N. Cho, K.-Y. Choi, and S.-K. Choi, Macromolecules 26, 4539 (1993).

    Article  CAS  Google Scholar 

  83. S.-H. Kim, S-J. Choi, J.-W. Park, H.-N. Cho, and S.‑K. Choi, Macromolecules 27, 2339 (1994).

    Article  CAS  Google Scholar 

  84. D.-C. Choi, S.-H. Kim, J.-H. Lee, H.-N. Cho, and S.‑K. Choi, Macromolecules 30, 176 (1997).

    Article  CAS  Google Scholar 

  85. N. Zhang, R. Wu, Q. Li, K. Pakbaz, C. O. Yoon, and F. Wudl, Chem. Mater. 5, 1598 (1993).

    Article  CAS  Google Scholar 

Download references

Funding

This study was supported by the Russian Foundation for Basic Research (project no. 18-33-20108).

Author information

Authors and Affiliations

  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 , Moscow, Russia

    D. O. Ponkratov, A. S. Shaplov & Ya. S. Vygodskii

  2. Luxembourg Institute of Science and Technology, L-4362, Esch-sur-Alzette, Luxembourg

    A. S. Shaplov

Authors
  1. D. O. Ponkratov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Shaplov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya. S. Vygodskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. O. Ponkratov.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ponkratov, D.O., Shaplov, A.S. & Vygodskii, Y.S. Metathesis Polymerization in Ionic Media. Polym. Sci. Ser. C 61, 2–16 (2019). https://doi.org/10.1134/S1811238219010144

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1811238219010144

Search

Navigation