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.
Similar content being viewed by others
References
Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107:2365 and review references therein
Dai WL, Luo SL, Yin SF, Au CT (2009) Appl Catal A: Gen 366:2 and review references therein
Kasuga K, Kabata N (1997) Inorg Chim Acta 257:277
Sako T, Fukai T, Sahashi R (2002) Ind Eng Chem Res 41:5353
Nomura R, Kimura M, Teshima S, Ninagawa A, Matsuda H (1982) Bull Chem Soc Jpn 55:3200
Baba A, Nozaki T, Matsuda H (1987) Bull Chem Soc Jpn 60:1552
Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) Chem Commun 39:896
Wang JQ, Yue XD, Cai F, He LN (2007) Catal Commun 8:167
Zhao Y, Tian JS, Qi XH, Han ZN, Zhuang YY, He LN (2007) J Mol Catal A: Chem 271:284
Lu XB, He R, Bai CX (2002) J Mol Catal A: Chem 186:1
Kim HS, Kim JJ, Kim H, Jang HG (2003) J Catal 220:44
Li FW, Xiao LF, Xia CG, Hu B (2004) Tetrahedron Lett 45:8307
Sun JM, Fujita S, Zhao FY, Arai M (2004) Green Chem 6:613
Sun JM, Fujita SI, Zhao FY, Arai M (2005) Appl Catal A: Gen 287:221
Xiao LF, Li FW, Peng JJ, Xia CG (2006) J Mol Catal A: Chem 253:265
Sun J, Wang L, Zhang SJ, Li ZX, Zhang XP, Dai WB, Mori R (2006) J Mol Catal A: Chem 256:295
Ono F, Qiao K, Tomida D, Yokoyama C (2007) J Mol Catal A: Chem 263:223
Kim YJ, Varma RS (2005) J Org Chem 70:7882
Sun J, Zhang SJ, Cheng WG, Ren JY (2008) Tetrahedron Lett 49:3588
Sun J, Ren JY, Zhang SJ, Cheng WG (2009) Tetrahedron Lett 50:423
Jiang JL, Gao FX, Hao RM, Qiu XQ (2005) J Org Chem 70:381
Lu XB, Xiu JH, He R, Jin K, Luo LM, Feng XJ (2004) Appl Catal A: Gen 275:73
Kim HS, Kim JJ, Kwon HN, Chung MJ, Lee BG, Jang HG (2002) J Catal 205:226
Kim HS, Kim JJ, Lee SD, Lah MS, Moon D, Jang HG (2003) Chem Eur J 9:678
Kim HS, Bae JY, Lee JS, Kwon O, Jelliarko P, Lee SD, Lee SH (2005) J Catal 232:80
Ramin M, Grunwaldt JD, Baiker A (2005) J Catal 234:256
Jutz F, Grunwaldt JD, Baiker A (2008) J Mol Catal A: Chem 279:94
Melendez J, North M, Pasquale R (2007) Eur J Inorg Chem 2007:3323
Jing SH, Chang T, Jin L, Wu M, Qiu W (2007) Catal Commun 8:1630
Sibaouih A, Ryan P, Leskela M, Rieger B, Repo T (2009) Appl Catal A: Gen 365:194
Sibaouih A, Ryan P, Axenov KV, Sunderg MR, Leskela M, Repo T (2009) J Mol Catal A: Chem 312:87
Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda K (1999) J Am Chem Soc 121:4526
Yasuda H, He LN, Takahashi T, Sakakura T (2006) Appl Catal A: Gen 298:177
Ramin M, van Vegten N, Grunwaldt J, Baiker A (2006) J Mol Catal A: Chem 258:165
Tu M, Davis RJ (2001) J Catal 199:85
Doskocil EJ (2004) Micropor Mesopor Mater 76:177
Fujita S, Bhanage BM, Ikushima Y, Shirai M, Torii K, Arai M (2002) Catal Lett 79:95
Bhanage BM, Fujita S, Ikushima Y, Arai M (2003) Green Chem 5:71
Sankar M, Tarte NH, Manikandan P (2004) Appl Catal A: Gen 276:217
Yasuda H, He LN, Sakakura T, Hu C (2005) J Catal 233:119
Xie Y, Zhang ZF, Jiang T, He JL, Han BX, Wu TB, Ding KL (2007) Angew Chem Int Ed 46:7255
Udayakumar S, Son YS, Lee MK, Park SW, Park DW (2008) Appl Catal A: Gen 347:192
Udayakumar S, Park SW, Park DW, Choi BS (2008) Catal Commun 9:1563
Udayakumar S, Lee MK, Shim HL, Park SW, Park DW (2009) Catal Commun 10:659
Udayakumar S, Raman V, Shim HL, Park DW (2009) Appl Catal A: Gen 368:97
Udayakumar S, Lee MK, Shim HL, Park DW (2009) Appl Catal A: Gen 365:88
Zhang XL, Wang DF, Zhao N, Al-Arifi ASN, Aouak T, Al-Othman ZA, Wei W, Sun YH (2009) Catal Commun 11:43
Yin SF, Dai WL, Li WS, Zhou XP, Shimada S (2006) J Mol Catal (China) 21:264
Wu SS, Zhang XW, Dai WL, Yin SF, Li WS, Ren YQ, Au CT (2008) Appl Catal A: Gen 341:106
Yin SF, Maruyama J, Yamashita T, Shimada S (2008) Angew Chem Int Ed 47:6590
Zhao DY, Huo QS, Feng JL, Chmelka BF, Stucky GD, Am J (1998) Chem Soc 120:6024
Srivastava R, Srinivas D, Ratnasamy P (2006) Microporous Mesoporous Mater 90:314
Hiyoshi N, Yogo K, Yashima T (2005) Microporous Mesoporous Mater 84:357
Valkenberg MH, deCastro C, Hölderich WF (2002) Green Chem 4:88
The IR spectrum of imidazole is available from SDBSWeb: http://riodb01.ibase.aist.go.jp/sdbs/
Wang JQ, Kong DL, Chen JY, Cai F, He LN (2006) J Mol Catal A: Chem 249:143
Takahashi T, Watahiki T, Kitazume S, Yasuda H, Sakakura T (2006) Chem Commun 42:1664
Sakai T, Tsutsumi Y, Ema T (2008) Green Chem 10:337
Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155
De CY, Lu B, Lv H, Yu YY, Bai Y, Cai QH (2009) Catal Lett 128:459
Ratzenhofer M, Kisch H (1980) Angew Chem Int Ed Engl 19:317
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.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-010-0285-4