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3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides

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Abstract

3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO2 by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO2 and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction.

Graphical Abstract

3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO2 to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action.

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References

  1. Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107:2365 and review references therein

    Article  CAS  Google Scholar 

  2. Dai WL, Luo SL, Yin SF, Au CT (2009) Appl Catal A: Gen 366:2 and review references therein

    Article  CAS  Google Scholar 

  3. Kasuga K, Kabata N (1997) Inorg Chim Acta 257:277

    Article  CAS  Google Scholar 

  4. Sako T, Fukai T, Sahashi R (2002) Ind Eng Chem Res 41:5353

    Article  Google Scholar 

  5. Nomura R, Kimura M, Teshima S, Ninagawa A, Matsuda H (1982) Bull Chem Soc Jpn 55:3200

    Article  CAS  Google Scholar 

  6. Baba A, Nozaki T, Matsuda H (1987) Bull Chem Soc Jpn 60:1552

    Article  CAS  Google Scholar 

  7. Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) Chem Commun 39:896

    Article  CAS  Google Scholar 

  8. Wang JQ, Yue XD, Cai F, He LN (2007) Catal Commun 8:167

    Article  CAS  Google Scholar 

  9. Zhao Y, Tian JS, Qi XH, Han ZN, Zhuang YY, He LN (2007) J Mol Catal A: Chem 271:284

    Article  CAS  Google Scholar 

  10. Lu XB, He R, Bai CX (2002) J Mol Catal A: Chem 186:1

    Article  CAS  Google Scholar 

  11. Kim HS, Kim JJ, Kim H, Jang HG (2003) J Catal 220:44

    Article  CAS  Google Scholar 

  12. Li FW, Xiao LF, Xia CG, Hu B (2004) Tetrahedron Lett 45:8307

    Article  CAS  Google Scholar 

  13. Sun JM, Fujita S, Zhao FY, Arai M (2004) Green Chem 6:613

    Article  CAS  Google Scholar 

  14. Sun JM, Fujita SI, Zhao FY, Arai M (2005) Appl Catal A: Gen 287:221

    Article  CAS  Google Scholar 

  15. Xiao LF, Li FW, Peng JJ, Xia CG (2006) J Mol Catal A: Chem 253:265

    Article  CAS  Google Scholar 

  16. Sun J, Wang L, Zhang SJ, Li ZX, Zhang XP, Dai WB, Mori R (2006) J Mol Catal A: Chem 256:295

    Article  CAS  Google Scholar 

  17. Ono F, Qiao K, Tomida D, Yokoyama C (2007) J Mol Catal A: Chem 263:223

    Article  CAS  Google Scholar 

  18. Kim YJ, Varma RS (2005) J Org Chem 70:7882

    Article  CAS  Google Scholar 

  19. Sun J, Zhang SJ, Cheng WG, Ren JY (2008) Tetrahedron Lett 49:3588

    Article  CAS  Google Scholar 

  20. Sun J, Ren JY, Zhang SJ, Cheng WG (2009) Tetrahedron Lett 50:423

    Article  CAS  Google Scholar 

  21. Jiang JL, Gao FX, Hao RM, Qiu XQ (2005) J Org Chem 70:381

    Article  CAS  Google Scholar 

  22. Lu XB, Xiu JH, He R, Jin K, Luo LM, Feng XJ (2004) Appl Catal A: Gen 275:73

    Article  CAS  Google Scholar 

  23. Kim HS, Kim JJ, Kwon HN, Chung MJ, Lee BG, Jang HG (2002) J Catal 205:226

    Article  CAS  Google Scholar 

  24. Kim HS, Kim JJ, Lee SD, Lah MS, Moon D, Jang HG (2003) Chem Eur J 9:678

    Article  CAS  Google Scholar 

  25. Kim HS, Bae JY, Lee JS, Kwon O, Jelliarko P, Lee SD, Lee SH (2005) J Catal 232:80

    Article  CAS  Google Scholar 

  26. Ramin M, Grunwaldt JD, Baiker A (2005) J Catal 234:256

    Article  CAS  Google Scholar 

  27. Jutz F, Grunwaldt JD, Baiker A (2008) J Mol Catal A: Chem 279:94

    Article  CAS  Google Scholar 

  28. Melendez J, North M, Pasquale R (2007) Eur J Inorg Chem 2007:3323

    Article  CAS  Google Scholar 

  29. Jing SH, Chang T, Jin L, Wu M, Qiu W (2007) Catal Commun 8:1630

    Article  CAS  Google Scholar 

  30. Sibaouih A, Ryan P, Leskela M, Rieger B, Repo T (2009) Appl Catal A: Gen 365:194

    Article  CAS  Google Scholar 

  31. Sibaouih A, Ryan P, Axenov KV, Sunderg MR, Leskela M, Repo T (2009) J Mol Catal A: Chem 312:87

    Article  CAS  Google Scholar 

  32. Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda K (1999) J Am Chem Soc 121:4526

    Article  CAS  Google Scholar 

  33. Yasuda H, He LN, Takahashi T, Sakakura T (2006) Appl Catal A: Gen 298:177

    Article  CAS  Google Scholar 

  34. Ramin M, van Vegten N, Grunwaldt J, Baiker A (2006) J Mol Catal A: Chem 258:165

    Article  CAS  Google Scholar 

  35. Tu M, Davis RJ (2001) J Catal 199:85

    Article  CAS  Google Scholar 

  36. Doskocil EJ (2004) Micropor Mesopor Mater 76:177

    Article  CAS  Google Scholar 

  37. Fujita S, Bhanage BM, Ikushima Y, Shirai M, Torii K, Arai M (2002) Catal Lett 79:95

    Article  CAS  Google Scholar 

  38. Bhanage BM, Fujita S, Ikushima Y, Arai M (2003) Green Chem 5:71

    Article  CAS  Google Scholar 

  39. Sankar M, Tarte NH, Manikandan P (2004) Appl Catal A: Gen 276:217

    Article  CAS  Google Scholar 

  40. Yasuda H, He LN, Sakakura T, Hu C (2005) J Catal 233:119

    Article  CAS  Google Scholar 

  41. Xie Y, Zhang ZF, Jiang T, He JL, Han BX, Wu TB, Ding KL (2007) Angew Chem Int Ed 46:7255

    Article  CAS  Google Scholar 

  42. Udayakumar S, Son YS, Lee MK, Park SW, Park DW (2008) Appl Catal A: Gen 347:192

    Article  CAS  Google Scholar 

  43. Udayakumar S, Park SW, Park DW, Choi BS (2008) Catal Commun 9:1563

    Article  CAS  Google Scholar 

  44. Udayakumar S, Lee MK, Shim HL, Park SW, Park DW (2009) Catal Commun 10:659

    Article  CAS  Google Scholar 

  45. Udayakumar S, Raman V, Shim HL, Park DW (2009) Appl Catal A: Gen 368:97

    Article  CAS  Google Scholar 

  46. Udayakumar S, Lee MK, Shim HL, Park DW (2009) Appl Catal A: Gen 365:88

    Article  CAS  Google Scholar 

  47. Zhang XL, Wang DF, Zhao N, Al-Arifi ASN, Aouak T, Al-Othman ZA, Wei W, Sun YH (2009) Catal Commun 11:43

    Article  CAS  Google Scholar 

  48. Yin SF, Dai WL, Li WS, Zhou XP, Shimada S (2006) J Mol Catal (China) 21:264

    Google Scholar 

  49. Wu SS, Zhang XW, Dai WL, Yin SF, Li WS, Ren YQ, Au CT (2008) Appl Catal A: Gen 341:106

    Article  CAS  Google Scholar 

  50. Yin SF, Maruyama J, Yamashita T, Shimada S (2008) Angew Chem Int Ed 47:6590

    Article  CAS  Google Scholar 

  51. Zhao DY, Huo QS, Feng JL, Chmelka BF, Stucky GD, Am J (1998) Chem Soc 120:6024

    Article  CAS  Google Scholar 

  52. Srivastava R, Srinivas D, Ratnasamy P (2006) Microporous Mesoporous Mater 90:314

    Article  CAS  Google Scholar 

  53. Hiyoshi N, Yogo K, Yashima T (2005) Microporous Mesoporous Mater 84:357

    Article  CAS  Google Scholar 

  54. Valkenberg MH, deCastro C, Hölderich WF (2002) Green Chem 4:88

    Article  CAS  Google Scholar 

  55. The IR spectrum of imidazole is available from SDBSWeb: http://riodb01.ibase.aist.go.jp/sdbs/

  56. Wang JQ, Kong DL, Chen JY, Cai F, He LN (2006) J Mol Catal A: Chem 249:143

    Article  CAS  Google Scholar 

  57. Takahashi T, Watahiki T, Kitazume S, Yasuda H, Sakakura T (2006) Chem Commun 42:1664

    Article  CAS  Google Scholar 

  58. Sakai T, Tsutsumi Y, Ema T (2008) Green Chem 10:337

    Article  CAS  Google Scholar 

  59. Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155

    Article  CAS  Google Scholar 

  60. De CY, Lu B, Lv H, Yu YY, Bai Y, Cai QH (2009) Catal Lett 128:459

    Article  CAS  Google Scholar 

  61. Ratzenhofer M, Kisch H (1980) Angew Chem Int Ed Engl 19:317

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by National 863 Program of China (2009AA05Z319), National Natural Science Foundation of China (Grant Nos 20873038 and 20507005), and the Outstanding Young Research Award of National Natural Science Foundation of China (Grant No E50725825). CTA thanks the Hunan University for an adjunct professorship and the Hong Kong Baptist University for financial support (FRG/08-09/II-09). The spectral database for organic compounds SDBS (http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, date of access)) is gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Hunan University, 410082, Changsha, Hunan, China

    Wei-Li Dai, Lang Chen, Shuang-Feng Yin, Sheng-Lian Luo & Chak-Tong Au

  2. Department of Chemistry, Center for Surface Analysis and Research, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China

    Chak-Tong Au

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  1. Wei-Li Dai
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  2. Lang Chen
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  3. Shuang-Feng Yin
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  5. Chak-Tong Au
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Correspondence to Shuang-Feng Yin or Sheng-Lian Luo.

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Dai, WL., Chen, L., Yin, SF. et al. 3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides. Catal Lett 135, 295–304 (2010). https://doi.org/10.1007/s10562-010-0285-4

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