Efficient and Convenient Synthesis of Ionic Liquid Supported SBA-15 Mesoporous Srganosilica and Its Beneficial Applications in Henry Reaction

doi:10.6023/cjoc201212031

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1791-1797.DOI: 10.6023/cjoc201212031 Previous Articles Next Articles

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新型固载碱性功能化离子液体的制备、表征及其在Henry反应中的应用

赵东旺^a,b, 吴悦彤^a, 陈婷婷^a, 戴立益^a, 王媛媛^a

a 华东师范大学化学系上海 200241;
b 郑州师范学院化学系郑州 450044

收稿日期:2012-12-20 修回日期:2013-02-09 发布日期:2013-04-07
通讯作者: 戴立益, 王媛媛 E-mail:yywang@chem.ecnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21073064/B030302, 21003049/B030301)资助项目.

Efficient and Convenient Synthesis of Ionic Liquid Supported SBA-15 Mesoporous Srganosilica and Its Beneficial Applications in Henry Reaction

Zhao Dongwang^a,b, Wu Yuetong^a, Chen Tingting^a, Dai Liyi^a, Wang Yuanyuan^a

a Department of Chemistry, East China Normal University, Shanghai 200241;
b Department of Chemistry, Zhengzhou Normal University, Zhengzhou 450044

Received:2012-12-20 Revised:2013-02-09 Published:2013-04-07
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21073064/B030302, 21003049/B030301).

Compared with post-grafting method, a novel and controllable strategy is applied to introduce highly dispersed ionic liquid species into mesoporous SBA-15 silica, providing simpler synthesis steps, more uniform surface coverage and higher loading of ionic liquid, with fewer raw materials. Basic task-specific ionic liquids are synthesized and characterized by X-ray diffraction, N₂ adsorption-desorption, thermogravimetry and fourier transform infrared spectroscopy. The results showed that the catalysts, prepared by co-condensation method, have better ordered mesostructure and higher loading of ionic liquid than those by post-grafting approach. Meanwhile, the catalysts exhibit much higher activity than those by post-grafting approach in Knoevenagel condensation. Furthermore, these supported catalysts are also proven to be efficient and reusable in Henry reaction under solvent-free conditions.

Key words: supported catalyst, ionic liquid, SBA-15, Knoevenagel condensation, Henry reaction

Cite this article

Zhao Dongwang, Wu Yuetong, Chen Tingting, Dai Liyi, Wang Yuanyuan. Efficient and Convenient Synthesis of Ionic Liquid Supported SBA-15 Mesoporous Srganosilica and Its Beneficial Applications in Henry Reaction[J]. Chin. J. Org. Chem., 2013, 33(08): 1791-1797.

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[1] Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508.
[2] Wassercheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 9, 3772.
[3] Davis, J. H. Jr.; Fox, P. A. Chem. Commun. 2003, 1209.
[4] Gong, X.-X.; Wang, Y.-Y.; Wang, Y.; Dai, L.-Y. Chin. J. Chem. 2011, 22, 968.
[5] Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H. Jr. J. Am. Chem Soc. 2002, 124, 926.
[6] Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H. Jr.; Rogers, R. D. Chem. Commun. 2001, 135.
[7] Wang, Y.-Y.; Wu, Y.-T.; Wang, Y.; Dai, L.-Y. Chin. J. Chem. 2012, 30, 1709.
[8] Wasserscheid, P.; Driessen-Hoelscher, B.; Steffens, H.; Zimmer-mann, C. J. Chem. Commun. 2003, 2038.
[9] (a) Mehnert, C. P. Chem. Eur. J. 2005, 11, 50.
(b) Riisager, A.; Fehrmann, R.; Haumann, M.; Wasserscheid, P. Top. Catal. 2006, 40, 91.
(c) Gu, Y.; Li, G. Adv. Synth. Catal. 2009, 351, 817.
[10] (a) Zhao, H.; Yu, N.; Wang, J.; Zhuang, D.; Ding, Y.; Tan, R.; Yin, D. Microporous Mesoporous Mater. 2009, 122, 240.
(b) Kumar, P.; Vermeiren, W.; Dath, J. P.; Höderich, W. F. Appl. Catal. 2006, 304, 131.
(c) Sasaki, T.; Zhong, C.; Tada, M.; Iwasawa, Y. Chem. Commun. 2005, 2506.
(d) Abelló, S.; Medina, F.; Rodríguez, X.; Cesteros, Y.; Salagre, P.; Sueiras, J. E.; Tichit, D.; Coq, B. Chem. Commun. 2004, 1096.
[11] Guli, M.-N.; Chen, Y.; Li, X.-T.; Yao, J.-X. Acta Chim. Sinica 2011, 69, 2827 (in Chinese).
(古丽米娜, 陈悦, 李晓天, 姚建曦, 化学学报, 2011, 69, 2827.)
[12] Jiang, L.; Wei, L.; Yao, J.-L.; Chen, B.; Gu, R.-A. Acta Chim. Sinica 2011, 69, 2368 (in Chinese).
(蒋丽, 刘伟, 姚建林, 陈彪, 顾仁敖, 化学学报, 2011, 69, 2368.)
[13] Du, M.-X.; Xu, M.-Z.; Shao, X.; Pu, X.-P.; Li, W.-Z. Acta Chim. Sinica 2011, 69, 2746 (in Chinese).
(杜明霞, 徐茂震, 邵鑫, 蒲锡鹏, 李文智, 化学学报, 2011, 69, 2746.)
[14] Luo, X.-J.; Yang, C.; Chen, Y. Acta Chim. Sinica 2011, 69, 1 (in Chinese).
(罗秀娟, 杨春, 陈煜, 化学学报, 2011, 69, 1.)
[15] Zhao, D. Y.; Huo, Q. S.; Feng, J. L.; Chmelka, B. F.; Stucky, G. D. J. Am. Chem. Soc. 1998, 120, 6024.
[16] Zhao, D. Y.; Sun, J. Y.; Li, Q. Z.; Stucky, G. D. Chem. Mater. 2000, 12, 275.
[17] Galarneau, A.; Cambon, N.; Renzo, F. D.; Ryoo, R.; Choi, M.; Fajula, F. New J. Chem. 2003, 27, 73.
[18] Kruk, M.; Asefa, T.; Jaroniec, M.; Ozin, G. A. J. Am. Chem. Soc. 2002, 124, 6383.
[19] (a) Wan, Y.; Zhao, D. Chem. Rev. 2007, 107, 2821.
(b) Li, C.; Zhang, H.; Jiang, D.; Yang, Q. Chem. Commun. 2007, 547.
[20] Zhao, H. H.; Yu, N. Y.; Ding, Y.; Tan, R.; Liu, C.; Yin, D. H.; Qiu, H. Y.; Yin, D. L. Microporous Mesoporous Mater. 2010, 136, 10.

新型固载碱性功能化离子液体的制备、表征及其在Henry反应中的应用

Efficient and Convenient Synthesis of Ionic Liquid Supported SBA-15 Mesoporous Srganosilica and Its Beneficial Applications in Henry Reaction

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