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Synthesis of organic cyclic carbonates assisted by macroporous polystyrene-based catalyst

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Abstract

An easy-to-prepare recyclable catalyst of quaternary ammonium nature and based on commercially available and inexpensive macroporous polymeric sorbent Purolite A103 resin has been devised for the carbon dioxide addition to epoxides. The catalyst can be easily separated due to its 0.6–0.85 mm bead size and recycled at least seven times. The catalyst makes it possible to carry out the reaction under solvent-free conditions. It is insensitive to the steric and electronic effects of various epoxy substrates.

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References

  1. S. Dabral, T. Schaub, Adv. Synth. Catal., 2019, 361, 223.

    Article  CAS  Google Scholar 

  2. W. J. Peppel, Ind. Eng. Chem., 1958, 50, 767.

    Article  CAS  Google Scholar 

  3. C. Calabrese, F. Giacalone, C. Aprile, Catalysts, 2019, 9, 325.

    Article  Google Scholar 

  4. K. Xu, Chem. Rev., 2004, 104, 4303.

    Article  CAS  Google Scholar 

  5. B. Schaffner, F. Schaffner, S. P. Verevkin, A. Borner, Chem. Rev., 2010, 110, 4554.

    Article  CAS  Google Scholar 

  6. A. A. G. Shaikh, S. Sivaram, Chem. Rev., 1996, 96, 951.

    Article  CAS  Google Scholar 

  7. L. Zhang, X. Fu, G. Gao, Chem. Cat. Chem., 2011, 3, 1359.

    CAS  Google Scholar 

  8. M. Liu, K. Gao, L. Liang, J. Sun, L. Sheng, M. Arai, Catal. Sci. Technol., 2016, 16, 6406.

    Article  Google Scholar 

  9. B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai, Appl. Catal. A-Gen., 2001, 219, 259.

    Article  CAS  Google Scholar 

  10. W. N. Sit, S. M. Ng, K. Y. Kwong, C. P. Lau, J. Org. Chem., 2005, 70, 8583.

    Article  CAS  Google Scholar 

  11. J. Peng, Y. Deng, New. J. Chem., 2001, 25, 639.

    Article  CAS  Google Scholar 

  12. J. Qin, V. A. Larionov, K. Harms, E. Meggers, Chem. Sus. Chem., 2019, 12, 320.

    Article  CAS  Google Scholar 

  13. H. Bettner, J. Steinbauer, T. Werner, Chem. Sus. Chem., 2015, 8, 2655.

    Article  Google Scholar 

  14. C. J. Whiteoak, A. Nova, F. Maseras, A. W. Kley, Chem. Sus. Chem., 2012, 5, 2032.

    Article  CAS  Google Scholar 

  15. P. A. Carvalho, J. W. Comerford, K. J. Lamb, M. North, P. S. Reiss, Adv. Synth. Catal., 2019, 361, 345.

    Article  CAS  Google Scholar 

  16. M. Nourian, F. Zadehahmadi, R. Kardanpour, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, M. Bahadori, Catal. Commun., 2017, 94, 42.

    Article  CAS  Google Scholar 

  17. L. Han, H. Li, S. J. Choi, M. S. Park, S. M. Lee, Y. J. Kim, D. W. Park, Appl. Catal. A Gen., 2012, 429–430, 67.

    Article  Google Scholar 

  18. F. D. Bobbink, A. P. Van Muyden, A. Gopakumar, Z. Fei, P. J. Dyson, Chem. Sus. Chem., 2017, 82, 144.

    CAS  Google Scholar 

  19. L. Tan, B. Tan, Chem. Soc. Rev., 2017, 46, 3322.

    Article  CAS  Google Scholar 

  20. S. N. Sidorov, I. V. Volkov, V. A. Davankov, M. P. Tsyurupa, P. M. Valetsky, L. M. Bronstein, R. Karlinsey, J. W. Zwanziger, V. G. Matveeva, E.M. Sulman, N. V. Lakina, E. A. Wilder, R. J. Spontak, J. Am. Chem. Soc., 2001, 123, 10502.

    Article  CAS  Google Scholar 

  21. E. Sulman, V. Matveeva, L. Bronstein, A. Sidorov, N. Lakina, S. Sidorov, P. Valetsky, Green. Chem., 2003, 5, 205.

    Article  CAS  Google Scholar 

  22. E. Sulman, V. Doluda, S. Dzwigaj, E. Marceau, L. Kustov, O. Tkachenko, A. Bykov, V. Matveeva, M. Sulman, N. Lakina, J. Mol. Catal. A: Chem., 2007, 278, 112.

    Article  CAS  Google Scholar 

  23. E. M. Sulman, V. G. Matveeva, L. M. Bronstein, M. G. Sulman, V. D. Doluda, A. V. Tokarev, E. V. Murzina, D. Yu. Murzin, Stud. Surf. Sci. Catal., 2006, 162, 119.

    Article  CAS  Google Scholar 

  24. E. M. Sulman, A. A. Ivanov, V. S. Chernyavsky, M. G. Sulman, A. I. Bykova, A. I. Sidorov, V. Yu. Doluda, V. G. Matveeva, L. M. Bronstein, B. D. Stein, A. S. Kharitonov, Chem. Eng. J., 2011, 176–177, 33.

    Article  Google Scholar 

  25. S. E. Lyubimov, M. V. Sokolovskaya, A. A. Korlyukov, O. P. Parenago, V. A. Davankov, J. Iran. Chem. Soc., 2020, 17, 1283.

    Article  CAS  Google Scholar 

  26. S. E. Lyubimov, A. A. Vasil’ev, A. A. Korlyukov, M. M. Ilyin, S. A. Pisarev, V. V. Matveev, A. E. Chalykh, S. G. Zlotin, V. A. Davankov, React. Funct. Polym., 2009, 69, 755.

    Article  CAS  Google Scholar 

  27. S. E. Lyubimov, E. A. Rastorguev, K. I. Lubentsova, A. A. Korlyukov, V. A. Davankov, Tetrahedron Lett., 2013, 54, 1116.

    Article  CAS  Google Scholar 

  28. M. North, R. Pasquale, C. Young, Green. Chem., 2010, 12, 1514.

    Article  CAS  Google Scholar 

  29. A. S. Nair, S. Cherian, N. Balachandran, U. G. Panicker, S. K. K. Sankaranarayanan, ACS Omega, 2019, 4, 13042.

    Article  Google Scholar 

  30. J.-Z. Hwang, S.-C. Wang, P.-C. Chen, C.-Y. Huang, J.-T. Yeh, K.-N. Chen, J. Polym. Res., 2012, 19, 9900.

    Article  Google Scholar 

  31. J. Nanclares, Z. S. Petrovic, I. Javni, M. Ionescu, F. Jaramillo, J. Appl. Polym. Sci., 2015, 132, 42492.

    Article  Google Scholar 

  32. J. Jindrich, H. Dvorakova, A. Holy, Collect. Czech. Chem. Commun., 1992, 57, 1466.

    Article  CAS  Google Scholar 

  33. N. Roques, US Pat. 0147789, 2004; https://patents.google.com/patent/US20040147789A1/en.

  34. F. Chen, T. Dong, T. Xu, X. Li, C. Hu, Green Chem., 2011, 13, 2518.

    Article  CAS  Google Scholar 

  35. J. Blankenburg, M. Wagner, H. Frey, Macromolecules, 2017, 50, 8885.

    Article  CAS  Google Scholar 

  36. S. T. K. Kumar, L. Kumar, V. L. Sharma, A. Jain, R. K. Jain, J. P. Maikhuri, M. Kumar, P. K. Shukla, G. Gupta, Eur. J. Med. Chem., 2008, 43, 2247.

    Article  Google Scholar 

  37. S. E. Lyubimov, M. V. Sokolovskaya, B. Chowdhury, A. V. Arzumanyan, R. Sh. Tukhvatshin, L. F. Ibragimova, A. A. Tyutyunov, V. A. Davankov, A. M. Muzafarov, Russ. Chem. Bull. (Int. Ed.), 2019, 68, 1866.

    Article  CAS  Google Scholar 

  38. Z. Zhao, J. Qin, C. Zhang, Y. Wang, D. Yuan, Y. Yao, Inorg. Chem., 2017, 56, 4568.

    Article  Google Scholar 

  39. Y. Tsutsumi, K. Yamakawa, M. Yoshida, T. Ema, T. Sakai, Org. Lett., 2010, 12, 5728.

    Article  CAS  Google Scholar 

  40. V. Legros, G. Taing, P. Buisson, M. Schuler, S. Bostyn, J. Rousseau, C. Sinturel, A. Tatibouet, Eur. J. Org. Chem., 2017, 5032.

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Correspondence to S. E. Lyubimov.

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This study was financially supported by the Russian Science Foundation (Project No. 19-43-02031).

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Lyubimov, S.E., Zvinchuk, A.A., Tyutyunov, A.A. et al. Synthesis of organic cyclic carbonates assisted by macroporous polystyrene-based catalyst. Russ Chem Bull 69, 2345–2348 (2020). https://doi.org/10.1007/s11172-020-3032-z

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  • DOI: https://doi.org/10.1007/s11172-020-3032-z

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