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Amino-Functional Imidazolium Ionic Liquids for CO2 Activation and Conversion to Form Cyclic Carbonate

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Abstract

A series of amino-functional imidazolium ionic liquids have been prepared and used as catalysts for cycloaddition of CO2 with epoxide. The reactions generated the cyclic carbonate even at room temperature under atmospheric pressure. Under the optimal reaction conditions, the propylene carbonate was yield to 98.0 % in the presence of [APbim]I, and the ionic liquids could be reused at least nine times without noticeable decrease in activity and selectivity. Besides, the reaction mechanism was proposed.

Graphical Abstract

Cycloaddition of CO2 with epoxides catalyzed by amino-functionalized imidazolium ionic liquid can achieve CO2 activation and conversion directly. The reactions generated the corresponding products even at room temperature under atmospheric pressure. Amino-functionalized imidazolium ionic liquid has showed excellent catalytic activity, reusability and general applicability.

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References

  1. Behr A (1988) Angew Chem Int Ed 27:661–678

    Article  Google Scholar 

  2. Mikkelsen M, Jorgensen M, Krebs FC (2010) Energy Environ Sci 3:43–81

    Article  CAS  Google Scholar 

  3. Kuwahara Y, Yamashita H (2013) J CO2 Util 1:50–59

  4. Omae I (2012) Coord Chem Rev 256:1384–1405

    Article  CAS  Google Scholar 

  5. Razali NAM, Lee KT, Bhatia S (2012) Renew Sustain Energy Rev 16:4951–4964

    Article  CAS  Google Scholar 

  6. Shaikh AAG (1996) Chem Rev 96:951–976

    Article  CAS  Google Scholar 

  7. Zhang LF, Fu XL, Gao GH (2011) ChemCatChem 3:1359–1364

    Article  CAS  Google Scholar 

  8. Gao GH, Zhang LF, Wang BS (2013) Chin J Catal 34:1187–1191

    Article  CAS  Google Scholar 

  9. Kihara N, Hara N, Endo T (1993) J Org Chem 58:6198–6202

    Article  CAS  Google Scholar 

  10. Huang JW, Shi M (2003) J Org Chem 68:6705–6709

    Article  CAS  Google Scholar 

  11. Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda K (1999) J Am Chem Soc 121:4526–4527

    Article  CAS  Google Scholar 

  12. Xie ZZ, Zhu MQ, Nambo A, Jasinski JB, Carreon MA (2013) Dalton Trans 42:6732–6735

    Article  CAS  Google Scholar 

  13. Castro-Gomez F, Salassa G, Kleij AW, Bo C (2013) Chem Eur J 19:6289–6298

    Article  CAS  Google Scholar 

  14. Yan P, Jing HW (2009) Adv Synth Catal 351:1325–1332

    Article  CAS  Google Scholar 

  15. Li FW, Xia CG, Xu LW, Sun W, Chen GX (2003) Chem Commun 2003:2042–2043

    Article  Google Scholar 

  16. Huang ZJ, Li FB, Chen BF, Lu T, Yuan Y, Yuan GQ (2013) Appl Catal A Gen 136–137:269–277

    Article  Google Scholar 

  17. Saunders LN, Ikpo N, Petten CF, Das UK, Dawe LN, Kozak CM, Kerton FM (2012) Catal Commun 18:165–167

    Article  CAS  Google Scholar 

  18. Bai DS, Duan SH, Hai L, Jing HW (2012) ChemCatChem 4:1752–1758

    Article  CAS  Google Scholar 

  19. Wu ZL, Xie HB, Yu X, Liu EH (2013) ChemCatChem 5:1328–1333

    Article  CAS  Google Scholar 

  20. Kumar S, Jain SL, Sain B (2012) Catal Lett 142:615–618

    Article  CAS  Google Scholar 

  21. Zhou H, Wang YM, Zhang WZ, Qu JP, Lu XB (2011) Green Chem 13:644–650

    Article  CAS  Google Scholar 

  22. Xie Y, Wang TT, Liu XH, Zou K, Deng WQ (2013) Nat Commun 4:1960

    Article  Google Scholar 

  23. Zalomaeva OV, Chibiryaev AM, Kovalenko KA, Kholdeeva OA, Balzhinimaev BS, Fedin VP (2013) J Catal 298:179–185

    Article  CAS  Google Scholar 

  24. Lescouet T, Chizallet C, Farrusseng D (2012) ChemCatChem 4:1725–1728

    Article  CAS  Google Scholar 

  25. Gao WY, Wojtas L, Ma SQ (2014) Chem Commun. doi:10.1039/c3cc47542e

    Google Scholar 

  26. Huang XQ, Chen YF, Lin ZG, Ren XQ, Song YN, Xu ZZ, Dong XM, Li XG, Hu CW, Wang B (2014) Chem Commun. doi:10.1039/c3cc49187k

    Google Scholar 

  27. Caló V, Nacci A, Monopoli A, Fanizzi A (2002) Org Lett 4:2561–2563

    Article  Google Scholar 

  28. Zhang YY, Chen L, Yin SF, Luo SL, Au CT (2012) Catal Lett 142:1376–1381

    Article  CAS  Google Scholar 

  29. Tharun J, Kim DW, Roshan R, Hwang Y, Park DW (2013) Catal Commun 31:62–65

    Article  CAS  Google Scholar 

  30. Zhou X, Zhang Y, Yang XG, Zhao LZ, Wang GY (2012) J Mol Catal A Chem 362:12–16

    Article  Google Scholar 

  31. Wang JQ, Dong K, ChenG WG, Sun J, Zhang SJ (2012) Catal Sci Technol 2:1480–1484

    Article  Google Scholar 

  32. Shi F, Zhang Q, Ma Y, He Y, Deng Y (2005) J Am Chem Soc 127:4182–4183

    Article  CAS  Google Scholar 

  33. Xiong YB, Wang H, Wang RM, Yan YF, Zheng B, Wang YP (2010) Chem Commun 46:3399–3401

    Article  CAS  Google Scholar 

  34. Peng JJ, Deng Y (2001) New J Chem 25:639–641

    Article  CAS  Google Scholar 

  35. Xiao LF, Lv DW, Wu W (2011) Catal Lett 141:1838–1844

    Article  CAS  Google Scholar 

  36. Ghazali-Esfahani S, Song HB, Paunescu E, Bobbink FD, Liu HZ, Fei ZF, Laurenczy G, Bagherzadeh M, Yan N, Dyson PJ (2013) Green Chem 15:1584–1589

    Article  CAS  Google Scholar 

  37. Choi HJ, Selvaraj M, Park D (2013) Chem Eng Sci 100:242–248

    Article  CAS  Google Scholar 

  38. Cheng WG, Chen X, Sun J, Wang JQ, Zhang S (2013) Catal Today 200:117–124

    Article  CAS  Google Scholar 

  39. Li FW, Xiao LF, Xia CG, Hu B (2004) Tetrahedron Lett 45:8307–8310

    Article  CAS  Google Scholar 

  40. Xiao LF, Li FW, Peng JJ, Xia CG (2006) J Mol Catal A Chem 253:265–269

    Article  CAS  Google Scholar 

  41. Dai WL, Jin B, Luo SL, Luo XB, Tu XM, Au CT (2014) Appl Catal A Gen 470:183–188

    Article  CAS  Google Scholar 

  42. Agrigento P, Al-Amsyar SM, Sorée B, Taherimehr M, Gruttadauria M, Aprile C, Pescarmona PP (2014) Catal Sci Technol. doi:10.1039/C3CY01000G

    Google Scholar 

  43. Sun JM, Fujita SI, Arai M (2005) J Organomet Chem 690:3490–3497

    Article  CAS  Google Scholar 

  44. Handy ST (ed) (2011) Ionic liquids—classes and properties, chap. 12. INTECH, Rijeka, pp 273–310

  45. He Q, O’Brien JW, Kitselman KA, Tompkins LE, Curtisa GCT, Kerton FM (2014) Catal Sci Technol. doi:10.1039/C3CY00998

    Google Scholar 

  46. Sakakura T, Kohno K (2009) Chem Commun 1312–1330

  47. Zhou Y, Hu S, Ma X, Liang S, Jiang T, Han B (2008) J Mol Catal A Chem 284:52–57

    Article  CAS  Google Scholar 

  48. Sun J, Zhang SJ, Cheng WG, Ren JY (2008) Tetrahedron Lett 49:3588–3591

    Article  CAS  Google Scholar 

  49. Han LN, Choi SJ, Park MS, Lee SM, Kim YJ, Kim MT, Liu BY, Park DW (2012) React Kinet Mech Catal 106:25–35

    Article  CAS  Google Scholar 

  50. Srivastava R, Srinivas D, Ratnasamy P (2006) Microporous Mesoporous Mater 90:314–326

    Article  CAS  Google Scholar 

  51. Zhang XH, Zhao N, Wei W, Sun YH (2006) Catal Today 115:102–106

    Article  CAS  Google Scholar 

  52. Shiels RA, Jones CW (2007) J Mol Catal A Chem 261:160–166

    Article  CAS  Google Scholar 

  53. Lu JN, Toy PH (2011) Synlett 2011:659–662

    Article  Google Scholar 

  54. Jagtap SR, Raje VP, Samant SD, Bhanage BM (2007) J Mol Catal A Chem 266:69–74

    Article  CAS  Google Scholar 

  55. Dai WL, Jin B, Luo SL, Luo XB, Tu XM, Au CT (2013) J Mol Catal A Chem 378:326–332

    Article  CAS  Google Scholar 

  56. Yu KMK, Curcic I, Gabriel J, Morganstewart H, Tsang SC (2010) J Phys Chem A 114:3863–3872

    Article  CAS  Google Scholar 

  57. Bates ED, Mayton RD, Ntai I, Davis JH Jr (2002) J Am Chem Soc 124:926–927

    Article  CAS  Google Scholar 

  58. Xue ZM, Zhang ZF, Han J, Chen Y, Mu TC (2011) Int J Greenh Gas Control 5:628–633

    Article  CAS  Google Scholar 

  59. Chen JJ, Li WW, Li XL, Yu HQ (2012) Phys Chem Chem Phys 14:4589–4596

    Article  CAS  Google Scholar 

  60. Peng H, Zhou YL, Liu J, Zhang HB, Xia CL, Zhou XH (2013) RSC Adv 3:6859–6864

    Article  CAS  Google Scholar 

  61. Sharma P, Park SD, Park KT, Nam SC, Jeong SK, Yoon Y, Baek H (2012) Chem Eng J 193–194:267–275

    Article  Google Scholar 

  62. Han LN, Choi HJ, Choi SJ, Liu BY, Park DW (2011) Green Chem 13:1023–1028

    Article  CAS  Google Scholar 

  63. Gurkan BE, de la Fuente JC, Mindrup EM, Ficke LE, Goodrich BF, Price EA, Schneider WF, Brennecke JF (2010) J Am Chem Soc 132:2116–2117

    Article  CAS  Google Scholar 

  64. Han LN, Li HQ, Choi SJ, Park MS, Lee SM, Kim YJ, Park DW (2012) Appl Catal A Gen 429–430:67–72

    Article  Google Scholar 

  65. Yang ZZ, Zhao YN, He LN (2011) RSC Adv 1:545–567

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the Chinese National Sciences Foundation (21006021) and the Foundation for Youth Science and Technology Innovation Talents of Harbin of China (RC2013LX018002) for financial support.

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Correspondence to Wei Wu or Linfei Xiao.

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Yue, C., Su, D., Zhang, X. et al. Amino-Functional Imidazolium Ionic Liquids for CO2 Activation and Conversion to Form Cyclic Carbonate. Catal Lett 144, 1313–1321 (2014). https://doi.org/10.1007/s10562-014-1241-5

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  • DOI: https://doi.org/10.1007/s10562-014-1241-5

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