Study on the Epoxidation of α,β-Unsaturated Ketones Catalyzed by MCM-41 Supported Schiff Base

doi:10.6023/A1111283

Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (11): 1289-1294.DOI: 10.6023/A1111283 Previous Articles Next Articles

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MCM-41 负载席夫碱催化α,β-不饱和酮的环氧化反应研究

周广鹏, 余蕾, 惠永海, 解正峰

新疆大学石油天然气精细化工教育部重点实验室乌鲁木齐 830046

投稿日期:2011-11-28 修回日期:2012-04-11 发布日期:2012-04-11
通讯作者: 解正峰 E-mail:xiezhf72@yahoo.com.cn
基金资助:
国家自然科学基金(Nos. 20962018, 20862015, 20562011)资助项目.

Study on the Epoxidation of α,β-Unsaturated Ketones Catalyzed by MCM-41 Supported Schiff Base

Zhou Guangpeng, Yu Lei, Hui Yonghai, Xie Zhengfeng

Key Laboratory of Oil & Gas Fine Chemicals Ministry of Education, Xinjiang University, Urumqi 830046

Received:2011-11-28 Revised:2012-04-11 Published:2012-04-11
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20962018, 20862015, 20562011).

The novel mesoporous molecular sieves MCM-41 supported Schiff base was prepared by MCM-41 and Schiff base, which was synthesized by 3-chloropropyltriethoxysilane, 1,2-cyclohexanediamine with 2-phenyl-2H-1,2,3-triazole-4-carbaldehyde. The catalyst was characterized by methods of Fourier transform infrared spectroscopy (FTIR) and X-ray diffraction (XRD). The epoxidation of α,β-unsaturated ketones catalyzed by MCM-41 supported Schiff base was studied in the presence of H₂O₂. The reaction conditions such as metal salts, different solvents, reaction temperature, the catalyst amount, and reaction time were investigated. It was found that the epoxidation of α,β-unsaturated ketones was easily obtained in excellent yields (up to 99%) using acetonitrile as the solvent at room temperature in short time. Especially, the heterogeneous catalyst can be reused four times without significant loss of its catalytic activity.

Key words: α,β-unsaturated ketone, epoxidation, MCM-41, Schiff base, catalysis

Cite this article

Zhou Guangpeng, Yu Lei, Hui Yonghai, Xie Zhengfeng. Study on the Epoxidation of α,β-Unsaturated Ketones Catalyzed by MCM-41 Supported Schiff Base[J]. Acta Chimica Sinica, 2012, 70(11): 1289-1294.

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References

1 Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 1215.

2 Kinoshita, T.; Okada, S.; Park, S. R.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2003, 42, 4680.

3 Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559.

4 Prasad, M. R.; Hamdy, M. S.; Mul, G.; Bouwman, E.; Drent, E. J. Catal. 2008, 260, 288.

5 Nemoto, T.; Ohshima, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2725.

6 Sun, L.; Du, C.-P.; Qin, J.; You, J.-S.; Yang, M.; Yu, X.-Q. J. Mol. Catal. A: Chem. 2005, 234, 29.

7 Yang, S. G.; Hwang, J. P.; Park, M. Y.; Lee, K.; Kim, Y. H. Tetrahedron 2007, 63, 5184.

8 Cui, H.-F.; Li, Y.-W.; Zheng, C.-W.; Zhao, G.; Zhu, S.-Z. J. Fluorine Chem. 2008, 129, 45.

9 Li, N.-N.; Liu, Y.-M.; Wu, H.-H.; Li, X.-H.; Xie, W.; Zhao, Z.-L.; Wu, P.; He, M.-Y. Chin. J. Catal. 2008, 29, 102.

10 Vega-Pérez, J. M.; Holm, M. V.; Martínez, M. L.; Blanco, E.; Iglesias-Guerra, F. Eur. J. Org. Chem. 2009, 6009.

11 Choudary, B. M.; Kantam, M. L.; Ranganath, K. V. S.; Mahendar, K.; Sreedhar, B. J. Am. Chem. Soc. 2004, 126,3396.

12 Lu, X.-J.; Liu, Y.; Sun, B.-F.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134.

13 Bentley, P. A.; Flood, R. W.; Roberts, S. M.; Skidmore, J.; Smith, C. B.; Smith, J. A. Chem. Commun. 2001, 1616.

14 Berkessel, A.; Gasch, N.; Glaubitz, K.; Koch, C. Org. Lett.2001, 3, 3839.

15 Adam, W.; Rao, P. B.; Degen, H. G.; Levai, A.; Patonay, T.; Saha-M?ller, C. R. J. Org. Chem. 2002, 67, 259.

16 Ye, J.-X.; Wang, Y.-C.; Liu, R.-H.; Zhang, G.-F.; Zhang, Q.; Chen, J.-P.; Liang, X.-M. Chem. Commun. 2003, 2714.

17 Wang, B.; Yang, L.-M.; Suo, J.-S. Acta Chim. Sinica 2003,61, 285 (in Chinese). (王波, 杨立明, 索继栓, 化学学报, 2003, 61, 285.)

18 Ooi, T.; Ohara, D.; Tamura, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 6844.

19 Jew, S. S.; Lee, J. H.; Jeong, B. S.; Yoo, M. S.; Kim, M. J.; Lee, Y. J.; Lee, J.; Choi, S. H.; Lee, K.; Lah, M. S.; Park, H. G. Angew. Chem., Int. Ed. 2005, 44, 1383.

20 Lv, J.; Wang, X.; Liu, J.-Y.; Zhang, L.-P.; Wang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 330.

21 Zhang, Y.-Q.; Shen, Z.-X.; Zhang, Y.-W. Chin. J. Appl. Chem. 2006, 23, 1233 (in Chinese). (张永强, 沈宗旋, 张雅文, 应用化学, 2006, 23, 1233.)

22 Kakei, H.; Tsuji, R.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 8962.

23 Wang, H.-M.; Wang, Z.; Ding, K.-L. Tetrahedron Lett.2009, 50, 2200.

24 Gago, S.; Balula, S. S.; Figueiredo, S.; Lopes, A. D.; Valente, A. A.; Pillinger, M.; Gon?alves, I. S. Appl. Catal. A: General 2010, 372, 67.

25 Lattanzi, A. Org. Lett. 2005, 7, 2579.

26 Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413.

27 Li, Y.-W.; Liu, X.-Y.; Yang, Y.-Q.; Zhao, G. J. Org. Chem.2007, 72, 288.

28 Liu, W.-M.; Liu, X.-Y.; He, W.; Liu, P.; Zhang, S.-Y. J. Mol. Catal. 2007, 21, 255 (in Chinese). (柳文敏, 刘雪英, 何炜, 刘鹏, 张生勇, 分子催化, 2007,21, 255.)

29 Cui, H.-F.; Li, Y.-W.; Zheng, C.-W.; Zhao, G.; Zhu, S.-Z. J. Fluorine Chem 2008, 129, 45.

30 Wang, Q.-F.; Chen, H.; Liu, P.; Wang, Q.-J.; Wang, X.-G.; Zhang, Y.-S. Chin. J. Org. Chem. 2009, 29, 1617 (in Chinese). (王巧峰, 陈惠, 刘鹏, 王全军, 王绪国, 张生勇, 有机化学, 2009, 29, 1617.)

31 Nagano, M.; Doi, M.; Kurihara, M.; Suemune, H.; Tanaka, M. Org. Lett. 2010, 12, 3564.

32 Yi, H.; Zou, G.; Li, Q.; Chen, Q.; Tang, J.; He, M.-Y. Tetrahedron Lett. 2005, 46, 5665.

33 Yang, F.; He, L. M.; Yi, H.; Zou, G.; Tang, T.; He, M.-Y. J. Mol. Catal. A: Chem. 2007, 273, 1.

34 Kureshy, R. I.; Ahmad, I.; Khan, N. H.; Abdi, S. H. R.; Pathak, K.; Jasra, R. V. J. Catal. 2006, 238, 134.

35 Wang, C.-W.; Fu, X.-K.; Huang, J. Acta Chim. Sinica 2011,69, 1681 (in Chinese). (王长炜, 傅相锴, 黄静, 化学学报, 2011, 69, 1681.)

36 Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2000, 65, 6897.

37 Honma, T.; Nakajo, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2002, 43, 6229.

38 Jayaprakash, D.; Kobayashi, Y.; Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. J. Mol. Catal. A: Chem. 2003, 196,145.

39 Li, Z.-G.; Wang, Q.-M.; Huang, J.-M. Preparation of Organic Intermediates, 2nd ed., Chemical Industry press, Beijing,1996, p. 51 (in Chinese). (李在国, 汪清民, 黄君珉, 有机中间体制备, 第2 版, 化学工业出版社, 北京, 1996, p. 51.)

40 Oliveira, P.; Machado, A.; Ramos, A. M.; Fonseca, I.; Fernandes, F. M. B.; Botelho do Rego, A. M.; Vital, J. Microporous Mesoporous Mater. 2009, 120, 432.

41 Liu, F.-M.; Shao, L.; Zhang, Z.-F.; Wang, B.-L.; Guo, Q.-S.; Kiyyum, A. Chin. J. Org. Chem. 2003, 23, 813 (in Chinese). (刘方明, 邵玲, 张正方, 王宝雷, 郭群胜, 阿布拉江·克依木, 有机化学, 2003, 23, 813.)

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MCM-41 负载席夫碱催化α,β-不饱和酮的环氧化反应研究

Study on the Epoxidation of α,β-Unsaturated Ketones Catalyzed by MCM-41 Supported Schiff Base

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