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One-Pot Synthesis of Styrene Carbonate from Styrene and CO2 Over the Nanogold-Ionic Liquid Catalyst

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Abstract

A catalyst system for the efficient two-step coupling of CO2 and styrene to styrene carbonate was developed. Gold nanoparticles immobilized on multi-walled carbon nanotubes (Au/CNT) of 6 nm in diameter were used as a catalyst for the epoxidation step. The process was carried out at 80 °C for 4 h in the presence of anhydrous tert-butyl hydroperoxide as an oxidant. The reaction of the resulting epoxide and CO2 was catalyzed by the 1-butyl-3-methylimidazolium bromide [bmim]Br-ZnBr2 system under the CO2 pressure (1.2 MPa) at 120 °C. A high styrene carbonate yield of 60 % was achieved. After the reaction, Au/CNT could be easily separated and reused without any significant loss of activity.

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References

  1. Aresta M, Dibenedetto A, Angelini A (2014) Chem Rev 114:1709

    Article  CAS  Google Scholar 

  2. Sakakura T, Choi J-C, Yasuda H (2007) Chem Rev 107:2365

    Article  CAS  Google Scholar 

  3. Song C (2006) Catal Today 115:2

    Article  CAS  Google Scholar 

  4. North M, Pasquale R, Young C (2010) Green Chem 12:1514

    Article  CAS  Google Scholar 

  5. Hargrove GL, Maruvada S (2014) US Patent 2014/0331727 A1

  6. Gan H, Takeuchi ES (1998) US Patent 5753389 A

  7. Sun J, Yao X, Cheng W, Zhang S (2014) Green Chem 16:3297

    Article  CAS  Google Scholar 

  8. Lombardo VM, Dhulst EA, Leitsch EK, Wilmot N, Heath WH, Gies AP, Miller MD, Torkelson JM, Scheidt KA (2015) Eur J Org Chem 2015:2791

    Article  CAS  Google Scholar 

  9. Sun J, Liang L, Sun J, Jiang Y, Lin K, Xu X, Wang R (2011) Catal Surv Asia 15:49

    Article  CAS  Google Scholar 

  10. Aresta M, Dibenedetto A (2002) J Mol Catal Chem 182–183:399

    Article  Google Scholar 

  11. Sun J, Fujita S, Bhanage BM, Arai M (2004) Catal Today 93–95:383

    Article  Google Scholar 

  12. Bai D, Jing H (2010) Green Chem 12:39

    Article  CAS  Google Scholar 

  13. Eghbali N, Li C-J (2007) Green Chem 9:213

    Article  CAS  Google Scholar 

  14. Wang J-L, Wang J-Q, He L-N, Dou X-Y, Wu F (2008) Green Chem 10:1218

    Article  CAS  Google Scholar 

  15. Xiang D, Liu X, Sun J, Xiao F-S, Sun J (2009) Catal Today 148:383

    Article  CAS  Google Scholar 

  16. Chen F, Dong T, Xu T, Li X, Hu C (2011) Green Chem 13:2518

    Article  CAS  Google Scholar 

  17. Ono F, Qiao K, Tomida D, Yokoyama C (2007) Appl Catal A Gen 333:107

    Article  CAS  Google Scholar 

  18. Carvalho Rocha C, Onfroy T, Launay F (2015) CR Chimie 18:270

    Article  CAS  Google Scholar 

  19. Peng L, Zhang J, Yang S, Han B, Sang X, Liu C, Ma X, Yang G (2015) Chem Commun 51:4398

    Article  CAS  Google Scholar 

  20. Jin Y, Zhuang D, Yu N, Zhao H, Ding Y, Qin L, Liu J, Yin D, Qiu H, Fu Z, Yin D (2009) Microporous Mesoporous Mater 126:159

    Article  CAS  Google Scholar 

  21. Jin Y, Wang P, Yin D, Liu J, Qiu H, Yu N (2008) Microporous Mesoporous Mater 111:569

    Article  CAS  Google Scholar 

  22. Wang F, Liu C, Liu G, Liu J (2015) J Porous Mater 22:1423

    Article  CAS  Google Scholar 

  23. Liu J, Wang F, Xu T, Gu Z (2010) Catal Lett 134:51

    Article  CAS  Google Scholar 

  24. Sun J, Fujita S, Zhao F, Hasegawa M, Arai M (2005) J Catal 230:398

    Article  CAS  Google Scholar 

  25. Wang Y, Sun J, Xiang D, Wang L, Sun J, Xiao F-S (2009) Catal Lett 129:437

    Article  CAS  Google Scholar 

  26. Lancaster NL, Salter PA, Welton T, Young GB (2002) J Org Chem 67:8855

    Article  CAS  Google Scholar 

  27. Liu HR, Yu HW, Zhou EP, Zhang XH, Zhang XC (2013) Asian J Chem 25:8266

    Article  CAS  Google Scholar 

  28. Peng X, Chen J, Misewich JA, Wong SS (2009) Chem Soc Rev 38:1076

    Article  CAS  Google Scholar 

  29. Li B, He P, Yi G, Lin H, Yuan Y (2009) Catal Lett 133:33

    Article  CAS  Google Scholar 

  30. Haruta M (1997) Catal Today 36:153

    Article  CAS  Google Scholar 

  31. He Q, O’Brien JW, Kitselman KA, Tompkins LE, Curtis GCT, Kerton FM (2014) Catal Sci Technol 4:1513

    Article  CAS  Google Scholar 

  32. Shim J-J, Kim D, Ra CS (2006) Bull Korean Chem Soc 27:744

    Article  CAS  Google Scholar 

  33. Li F, Xiao L, Xia C, Hu B (2004) Tetrahedron Lett 45:8307

    Article  CAS  Google Scholar 

  34. Bawaked S, Dummer NF, Bethell D, Knight DW, Hutchings GJ (2011) Green Chem 13:127

    Article  CAS  Google Scholar 

  35. Paul S, Zhu Y, Romain C, Brooks R, Saini PK, Williams CK (2015) Chem Commun 51:6459

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Polish National Science Centre (NCN); Decision No.: 2011/03/B/ST8/06178. Co-author of this paper, Katarzyna Jasiak, is a scholar under the project “DoktoRIS—Scholarship Programme for Innovative Silesia” co-financed by the European Union under the European Social Fund.

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Correspondence to Tomasz Krawczyk.

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Jasiak, K., Krawczyk, T., Pawlyta, M. et al. One-Pot Synthesis of Styrene Carbonate from Styrene and CO2 Over the Nanogold-Ionic Liquid Catalyst. Catal Lett 146, 893–901 (2016). https://doi.org/10.1007/s10562-016-1703-z

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  • DOI: https://doi.org/10.1007/s10562-016-1703-z

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