Skip to main content
SpringerLink
Log in

Synthesizing cyclic carbonates from olefin oxides and carbon dioxide. I: Catalysis with ionic liquids

  • Catalysis in Chemical and Petrochemical Industry
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

A review of catalytic systems based on ionic liquids used for promoting reactions between olefin oxides and carbon dioxide is presented. It is shown that ionic liquids based on imidazoles, pyridines, quaternary ammonium salts, and other compounds exhibit high activity in these processes and can serve as alternatives to conventional catalysts of cyclocarboxylation of olefin oxides under certain conditions. Specific features of the reactions between oxiranes and carbon dioxide in the presence of ionic liquids are considered, including reactions with the use of promoting additions based on metal salts. Mechanisms of the catalytic action of ionic liquids in syntheses of cyclocarbonates are described. Other works are critically analyzed to develop new lines in the catalysis of cyclocarboxylations of olefin oxides with ionic liquids.

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

Similar content being viewed by others

References

  1. Krylov, O.V. and Mamedov, A.Kh., Russ. Chem. Rev., 1995, vol. 64, no. 9, pp. 877–900.

    Article  Google Scholar 

  2. Shaikh, A.-A.G. and Sivaram, S., Chem. Rev., 1996, vol. 96, no. 3, pp. 951–976.

    Article  CAS  Google Scholar 

  3. Zabalov, M.V., Abstracts of Papers, Trudy nauchnoi konferentsii s mezhdunarodnym uchastiem “Khimiya elementoorganicheskikh soedinenii i polimerov” (Proc. of Scientific Conference with International Participation “Chemistry of Organoelemental Compounds and Polymers”), Moscow, 2014, p. 121.

    Google Scholar 

  4. Plate, N.A. and Slivinskii, E.V., Osnovy khimii i tekhnologii monomerov (Fundamentals of Chemistry and Technology of Monomers), Moscow: Nauka, 2002.

    Google Scholar 

  5. Mikheev, V.V., Neizotsionatnye uretany: monografiya (Non-Isocyanate Urethanes: Monograph), Kazan: Izd. KNITU, 2011.

    Google Scholar 

  6. Stroganov, V.F., Savchenko, V.N., and Omel’chenko, S.I., Tsiklokarbonaty i ikh primenenie dlya sinteza polimerov (Cyclocarbonates and Their Application for the Synthesis of Polymers), Moscow: NIITEKhIM, 1984.

    Google Scholar 

  7. Koren’kova, O.P., Khim. Prom-st’, 1961, no. 9, pp. 33–38.

    Google Scholar 

  8. North, M., Pasquale, R., and Young, C., Green Chem., 2010, vol. 12, no. 9, pp. 1514–1539.

    Article  CAS  Google Scholar 

  9. Peng, J. and Deng, Y., New J. Chem., 2001, vol. 25, no. 4, pp. 639–641.

    Article  CAS  Google Scholar 

  10. Kawanami, H., Sasaki, A., Matsui, K., and Ikushima, Y., Chem. Commun., 2003, no. 7, pp. 896–897.

    Article  Google Scholar 

  11. Yamaguchi, K., Ebitani, K., Yoshida, T., Yoshida, H., and Kaneda, K., J. Am. Chem. Soc., 1999, vol. 121, no. 18, pp. 4526–4527.

    Article  CAS  Google Scholar 

  12. Yano, T., Matsui, H., Koike, T., Ishiguro, H., Fujihara, H., Yoshihara, M., and Maeshima, T., Chem. Commun., 1997, no. 12, pp. 1129–1130.

    Article  Google Scholar 

  13. Paddock, R.L. and Nguyen, S.T., J. Am. Chem. Soc., 2001, vol. 123, no. 46, pp. 11498–11499.

    Article  CAS  Google Scholar 

  14. Shen, Y.-M., Duan, W.-L., and Shi, M., J. Org. Chem., 2003, vol. 68, no. 4, pp. 1559–1562.

    Article  CAS  Google Scholar 

  15. Caló, V., Nacci, A., Monopoli, A., and Fanizzi, A., Org. Lett., 2002, vol. 4, no. 15, pp. 2561–2563.

    Article  Google Scholar 

  16. Kossev, K., Koseva, N., and Troev, K., J. Mol. Catal. A: Chem., 2003, vol. 194, nos. 1–2, pp. 29–37.

    Article  CAS  Google Scholar 

  17. Yu, K.M.K., Curcic, I., Gabriel, J., Morganstewart, H., and Tsang, S.C., J. Phys. Chem. A, 2010, vol. 114, no. 11, pp. 3863–3872.

    Article  CAS  Google Scholar 

  18. Shiels, R.A. and Jones, C.W., J. Mol. Catal. A: Chem., 2007, vol. 261, no. 2, pp. 160–166.

    Article  CAS  Google Scholar 

  19. Freemantle, M., An Introduction to Ionic Liquids, Cambridge: RSC Publishing, 2009.

    Google Scholar 

  20. Hallett, J.P. and Welton, T., Chem. Rev., 2011, vol. 111, no. 5, pp. 3508–3576.

    Article  CAS  Google Scholar 

  21. Seki, T., Grunwaldt, J.-D., and Baiker, A., J. Phys. Chem. B, 2009, vol. 113, no. 1, pp. 114–122.

    Article  CAS  Google Scholar 

  22. Sun, J., Zhang, S., Cheng, W., and Ren, J., Tetrahedron Lett., 2008, vol. 49, no. 22, pp. 3588–3591.

    Article  CAS  Google Scholar 

  23. Wang, L., Jin, X., Li, P., Zhang, J., He, H., and Zhang, S., Ind. Eng. Chem. Res., 2014, vol. 53, no. 20, pp. 8426–8435.

    Article  CAS  Google Scholar 

  24. Zhou, Y., Hu, S., Ma, X., Liang, S., Jiang, T., and Han, B., J. Mol. Catal. A: Chem., 2008, vol. 284, nos. 1–2, pp. 52–57.

    Article  CAS  Google Scholar 

  25. Sun, J., Ren, J., Zhang, S., and Chenget, W., Tetrahedron Lett., 2009, vol. 50, no. 4, pp. 423–426.

    Article  CAS  Google Scholar 

  26. Ma, J., Liu, J., Zhang, Z., and Han, B., Green Chem., 2012, vol. 14, no. 9, pp. 2410–2420.

    Article  CAS  Google Scholar 

  27. Ion, A., Parvulescu, V., Jacobs, P., and de Vos, D., Appl. Catal., A, 2009, vol. 363, nos. 1–2, pp. 40–44.

    Article  CAS  Google Scholar 

  28. Kim, H.S., Kim, J.J., Lee, B.G., Jung, O.S., Jang, H.G., and Kang, S.O., Angew. Chem., Int. Ed., 2000, vol. 39, no. 22, pp. 4096–4098.

    Article  CAS  Google Scholar 

  29. Ramin, M., Grunwaldt, J.-D., and Baiker, A., J. Catal., 2005, vol. 234, no. 2, pp. 256–267.

    Article  CAS  Google Scholar 

  30. Kim, H.S., Kim, J.J., Kim, H., and Jang, H.G., J. Catal., 2003, vol. 220, no. 1, pp. 44–46.

    Article  CAS  Google Scholar 

  31. Palgunadi, J., Kwon, O.-S., Lee, H., Bae, J.Y., Ahn, B.S., Min, N.-Y., and Kim, H.S., Catal. Today, 2004, vol. 98, no. 4, pp. 511–514.

    Article  CAS  Google Scholar 

  32. Fujita, S.-I., Nishiura, M., and Arai, M., Catal. Lett., 2010, vol. 135, no. 3, pp. 263–268.

    Article  CAS  Google Scholar 

  33. Sun, J., Fujita, S.-I., Zhao, F., and Arai, M., Green Chem., 2004, vol. 6, no. 12, pp. 613–616.

    Article  CAS  Google Scholar 

  34. Sun, J., Fujita, S.-I., Zhao, F., and Arai, M., Appl. Catal., A, 2005, vol. 287, no. 2, pp. 221–226.

    Article  CAS  Google Scholar 

  35. Ramin, M., Grunwaldt, J.-D., and Baiker, A., Appl. Catal., A, 2006, vol. 305, no. 1, pp. 46–53.

    Article  CAS  Google Scholar 

  36. Yu, J.-I., Ju, H.Y., Kim, K.-H., and Park, D.-W., Korean J. Chem. Eng., 2010, vol. 27, no. 2, pp. 446–451.

    Article  CAS  Google Scholar 

  37. Li, F., Xiao, L., Xia, C., and Hu, B., Tetrahedron Lett., 2004, vol. 45, no. 45, pp. 8307–8310.

    Article  CAS  Google Scholar 

  38. He, Q., O’Brien, J.W., Kitselman, K.A., Tompkins, L.E., Curtis, G.C.T., and Kerton, F.M., Catal. Sci. Technol., 2014, vol. 4, no. 6, pp. 1513–1528.

    Article  CAS  Google Scholar 

  39. Wang, J.-Q., Kong, D.-L., Chen, J.-Y., Cai, F., and He, L.-N., J. Mol. Catal. A: Chem., 2006, vol. 249, nos. 1–2, pp. 143–148.

    Article  CAS  Google Scholar 

  40. Wang, J.-Q., Yue, X.-D., Cai, F., and He, L.-N., Catal. Commun., 2007, vol. 8, no. 2, pp. 167–172.

    Article  CAS  Google Scholar 

  41. Zhu, A., Jiang, T., Han, B., Zhang, J., Xie, Y., and Ma, X., Green Chem., 2007, vol. 9, no. 2, pp. 169–172.

    Article  CAS  Google Scholar 

  42. Takahashi, T., Watahiki, T., Kitazume, S., Yasuda, H., and Sakakura, T., Chem. Commun., 2006, no. 15, pp. 1664–1666.

    Article  Google Scholar 

  43. Sakai, T., Tsutsumi, Y., and Ema, T., Green Chem., 2008, vol. 10, no. 3, pp. 337–341.

    Article  CAS  Google Scholar 

  44. Han, L., Park, S.-W., and Park, D.-W., Energy Environ. Sci., 2009, vol. 2, no. 12, pp. 1286–1292.

    Article  CAS  Google Scholar 

  45. Han, L., Choi, H.-J., Choi, S.-J., Liu, B., and Park, D.-W., Green Chem., 2011, vol. 13, no. 4, pp. 1023–1028.

    Article  CAS  Google Scholar 

  46. Xie, Y., Ding, K., Liu, Z., Li, J., An, G., Tao, R., Sun, Z., and Yang, Z., Chem.-Eur. J., 2010, vol. 16, no. 22, pp. 6687–6692.

    Article  CAS  Google Scholar 

  47. Xie, Y., Zhang, Z., Jiang, T., He, J., Han, B., Wu, T., and Ding, K., Angew. Chem., Int. Ed., 2007, vol. 46, no. 38, pp. 7255–7258.

    Article  CAS  Google Scholar 

  48. Qiao, K., Ono, F., Bao, Q., Tomida, D., and Yokoyama, C., J. Mol. Catal. A: Chem., 2009, vol. 303, nos. 1–2, pp. 30–34.

    Article  CAS  Google Scholar 

  49. Han, L., Li, H., Choi, S.-J., Park, M.-S., Lee, S.-M., Kim, Y.-J., and Park, D.-W., Appl. Catal., A, 2012, vols. 429–430, pp. 67–72.

    Article  Google Scholar 

  50. Zheng, X., Luo, S., Zhang, L., and Cheng, J.-P., Green Chem., 2009, vol. 11, no. 4, pp. 455–458.

    Article  CAS  Google Scholar 

  51. Shim, H.-L., Udayakumar, S., Yu, J.-I., Kim, I., and Park, D.-W., Catal. Today, 2009, vol. 148, nos. 3–4, pp. 350–354.

    Article  CAS  Google Scholar 

  52. Udayakumar, S., Raman, V., Shim, H.-L., and Park, D.-W., Appl. Catal., A, 2009, vol. 368, nos. 1–2, pp. 97–104.

    Article  CAS  Google Scholar 

  53. Xiao, L.-F., Li, F.-W., Peng, J.-J., and Xia, C.-G., J. Mol. Catal. A: Chem., 2006, vol. 253, nos. 1–2, pp. 265–269.

    Article  CAS  Google Scholar 

  54. Zhang, X., Wang, D., Zhao, N., Al-Arifi, A.S.N., Aouak, T., Al-Othman, Z.A., Wei, W., and Sun, Y., Catal. Commun., 2009, vol. 11, no. 1, pp. 43–46.

    Article  Google Scholar 

  55. Udayakumar, S., Lee, M.-K., Shim, H.-L., and Park, D.-W., Appl. Catal., A, 2009, vol. 365, no. 1, pp. 88–95.

    Article  CAS  Google Scholar 

  56. Udayakumar, S., Park, S.-W., Park, D.-W., and Choi, B.-S., Catal. Commun., 2008, vol. 9, no. 7, pp. 1563–1570.

    Article  CAS  Google Scholar 

  57. Zhao, Y., Tian, J.-S., Qi, X.-H., Han, Z.-N., Zhuang, Y.-Y., and He, L.-N., J. Mol. Catal. A: Chem., 2007, vol. 271, nos. 1–2, pp. 284–289.

    Article  CAS  Google Scholar 

  58. Dai, W.-L., Chen, L., Yin, S.-F., Luo, S.-L., and Au, C.-T., Catal. Lett., 2010, vol. 135, no. 3, pp. 295–304.

    Article  CAS  Google Scholar 

  59. Xu, L.-W., Yang, M.-S., Jiang, J.-X., Qiu, H.-Y., and Lai, G.-Q., Cent. Eur. J. Chem., 2007, vol. 5, no. 4, pp. 1073–1083.

    CAS  Google Scholar 

  60. Jutz, F., Andanson, J.-M., and Baiker, A., Chem. Rev., 2011, vol. 111, no. 2, pp. 322–353.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Nizhny Novgorod State Technical University, Nizhny Novgorod, 603155, Russia

    A. V. Sulimov, A. V. Ovcharova, A. A. Ovcharov, T. A. Ryabova, G. M. Kravchenko & S. A. Lysanov

Authors
  1. A. V. Sulimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Ovcharova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Ovcharov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. A. Ryabova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. M. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. A. Lysanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Sulimov.

Additional information

Original Russian Text © A.V. Sulimov, A.V. Ovcharova, A.A. Ovcharov, T.A. Ryabova, G.M. Kravchenko, S.A. Lysanov, 2016, published in Kataliz v Promyshlennosti.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sulimov, A.V., Ovcharova, A.V., Ovcharov, A.A. et al. Synthesizing cyclic carbonates from olefin oxides and carbon dioxide. I: Catalysis with ionic liquids. Catal. Ind. 8, 300–309 (2016). https://doi.org/10.1134/S2070050416040103

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050416040103

Keywords

Search

Navigation