Citation: YANG Zhi-Wang, CHEN Li-Na, HONG Wei, KANG Rui-Xue, WANG Jia, JIA Na, ZHAO Lei, MA Heng-Chang. Baeyer-Villiger Oxidation and Acetalization of Cyclic Ketones on SO₄^2-/SnO₂-Fe₂O₃ Solid Acid Catalysts[J]. Acta Physico-Chimica Sinica doi: 10.3866/PKU.WHXB201206121 shu

Baeyer-Villiger Oxidation and Acetalization of Cyclic Ketones on SO₄^2-/SnO₂-Fe₂O₃ Solid Acid Catalysts

1.
Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China

Received Date: 26 March 2012
Available Online: 12 June 2012
Fund Project: 国家自然科学基金(21163016, 21174114) (21163016, 21174114) 甘肃省自然科学基金(1010RJZA024) (1010RJZA024)(NWNU-KJCXGC-03-63)资助 (NWNU-KJCXGC-03-63)

Fe-doped SO₄^2-/SnO₂ (STF) solid acid catalysts with different amounts of iron were prepared via co-condensation, followed by sulfation and calcination. These materials were characterized by Fourier transform infrared (FTIR) spectroscopy, X-ray powder diffraction (XRD), N₂ adsorption-desorption analysis (BET), thermogravimetric (TG) analysis, and scanning electron microscopy (SEM). The Fe-doped catalysts exhibited more activity than undoped catalysts in acetalization reactions of 4-tert-butylcyclohexanone and diols. The catalytic acetalization of several ketones and 1,2-diols with the SO₄^2-/SnO₂-Fe₂O₃ catalysts (with the Fe/Sn molar ratio of 0.5) were studied. The influence of the reaction time and the amount of the catalysts on the acetalization were also investigated. In addition, the high performance of this Fe-modified catalyst was demonstrated in the Baeyer-Villiger oxidation of cyclic ketones. The catalyst can be recycled several times without any significant loss in catalytic activity.
- Solid acid,
- Acetalization,
- Baeyer-Villiger oxidation,
- Fe₂O₃-doping,
- Sulfated tin oxide
1. [1]
  
  (1) Ma, H. Z.; Xiao, J.;Wang, B. J. Hazard. Mater. 2009, 166, 860.doi: 10.1016/j.jhazmat.2008.11.096
2. [2]
  (2) Reddy, B. M.; Sreekanth, P. M.; Reddy, V. R. J. Mol. Catal. A: Chem. 2005, 225, 71. doi: 10.1016/j.molcata.2004.09.003
3. [3]
  (3) Mao,W.; Ma, H. Z.;Wang, B. J. Hazard. Mater. 2010, 176, 361.doi: 10.1016/j.jhazmat.2009.11.036
4. [4]
  (4) Reddy, B. M.; Sreekanth, P. M.; Yamada, Y.; Xu, Q.; Kobayashi,T. Appl. Catal. A: Gen. 2002, 228, 229.
5. [5]
  (5) Furuta, S.; Matsuhashi, H.; Arata, K. Appl. Catal. A: Gen. 2004,269, 187. doi: 10.1016/j.apcata.2004.04.017
6. [6]
  (6) Yoshida, K.; Shiju, N. R.; Brown, D. R.; Boyes, E. D.; Gai, P. L.J. Phys.: Conf. Ser. 2010, 241, 012035. doi: 10.1088/1742-6596/241/1/012035
7. [7]
  (7) Xia, J. J.; Yu, D. H.; Hu, Y.; Zou, B.; Sun, P.; Li, H.; Huang, H.Catal. Commun. 2011, 12, 544. doi: 10.1016/j.catcom.2010.12.002
8. [8]
  (8) Cui, X.; Ma, H. Z.;Wang, B.; Chen, H.W. J. Hazard. Mater.2007, 147, 800. doi: 10.1016/j.jhazmat.2007.01.118
9. [9]
  (9) Chen, H.W.;Wang, B.; Ma, H. Z.; Cui, X. J. Hazard. Mater.2008, 150, 300. doi: 10.1016/j.jhazmat.2007.04.101
10. [10]
  (10) Zhao, H. Y.; Bennici, S.; Cai, J. X.; Shen, J. Y.; Auroux, A.J. Catal. 2010, 274, 259. doi: 10.1016/j.jcat.2010.07.011
11. [11]
  (11) Khder, A. S.; Ahmed, A. I. Appl. Catal. A: Gen. 2009, 354, 153.doi: 10.1016/j.apcata.2008.11.030
12. [12]
  (12) Chen, L.; Ding, L. X.; Cui, L. Y. Chin. J. Chem. Phys. 1997, 10,85. [陈里, 丁来, 崔立燕. 化学物理学报, 1997, 10, 85.]
13. [13]
  (13) Wang, J.; Fan, M. Q.; Yang, P. P.; Yu,W.; Jing, X. Y.; Zhang, M.L.; Liu, T. F.; Duan, X. Acta Phys. -Chim. Sin. 2007, 23, 595.[王君, 范美青, 杨飘萍, 于微, 景晓燕, 张密林, 刘天孚,段雪. 物理化学学报, 2007, 23, 595.] doi: 10.3866/PKU.WHXB20070428
14. [14]
  (14) Yang, J.; Zang, J.; Chen, T. T.; Sun, D. M.; Li, J.;Wu, F. X.Chin. Chem. Lett. 2011, 22, 1391. doi: 10.1016/j.cclet.2011.06.006
15. [15]
  (15) Wang, X. Y.; Shi, L.; Chen, C. L.; Xu, N. P. Chin. J. Catal.2006, 27, 60. [汪显阳, 时连, 陈长林, 徐南平. 催化学报,2006, 27, 60.]
16. [16]
  (16) Reddy, B. M.; Patil, M. K. Chem. Rev. 2009, 109, 2185. doi: 10.1021/cr900008m
17. [17]
  (17) Chen, T. Y.; Chu, X. F.; Hu, K. L. Chin. J. Chem. Phys. 2009,22, 322. doi: 10.1088/1674-0068/22/03/322-326
18. [18]
  (18) Du, C. H.; Qin, Y. N.; He,Y. F.; Ma, Z.;Wu, S. X. Chin. J. Chem. Phys. 2003, 16, 504. [杜长海, 秦永宁, 贺岩峰,马智, 吴树新. 化学物理学报, 2003, 16, 504.]
19. [19]
  (19) Zhu, Q.; Liang, L. P.; Jia, Z. Q.; Gao, C. G.; Zhao, Y. X. Acta Phys. -Chim. Sin. 2011, 27, 491. [朱晴, 梁丽萍, 贾志奇, 高春光, 赵永祥. 物理化学学报, 2011, 27, 491.] doi: 10.3866/PKU.WHXB20110212
20. [20]
  (20) Dias, A. S.; Lima, S.; Pillinger, M.; Valente, A. A. Catal. Lett.2007, 114, 151. doi: 10.1007/s10562-007-9052-6
21. [21]
  (21) Wang, Z. C.; Sun, K.; Liu, J. L. J. Mol. Catal. (China) 2007, 21,38. [王知彩, 孙康, 刘九玲. 分子催化, 2007, 21, 38.]
22. [22]
  (22) Guo, H. F.; Yan, P.; Hao, X. Y.;Wang, Z. Z. Mater. Chem. Phys.2008, 112, 1065. doi: 10.1016/j.matchemphys.2008.07.001
23. [23]
  (23) Khder, A. S.; El-Sharkawy, E. A.; El-Hakam, S. A.; Ahmed, A. I.Catal. Commun. 2008, 9, 769. doi: 10.1016/j.catcom.2007.08.022
24. [24]
  (24) Yu, H. G.; Fang, H. J.; Zhang, H. L.; Li, B. J.; Deng, F. Catal. Commun. 2009, 10, 920. doi: 10.1016/j.catcom.2008.12.023
25. [25]
  (25) Zhou, L. N.; Xu, B. J.; Hua,W. M.; Yue, Y. H.; Gao, Z. Catal. Commun. 2008, 9, 2274. doi: 10.1016/j.catcom.2008.05.018
26. [26]
  (26) Lam, M. K.; Lee, K. T.; Mohamed, A. R. Appl. Catal. B: Environ. 2009, 93, 134. doi: 10.1016/j.apcatb.2009.09.022
27. [27]
  (27) Matsuhashi, H.; Miyazaki, H.; Kawamura, Y.; Nakamura, H.;Arata, K. Chem. Mater. 2001, 13, 3038. doi: 10.1021/cm0104553
28. [28]
  (28) Zhai, D.W.; Nie, Y. Y.; Yue, Y. H.; He, H. Y.; Hua,W. M.; Gao,Z. Catal. Commun. 2011, 12, 593. doi: 10.1016/j.catcom.2010.12.020
29. [29]
  (29) Suzuki, T.; Yokoi, T.; Otomo, R.; Kondo, J. N.; Tatsumi, T. Appl. Catal. A: Gen. 2011, 408, 117. doi: 10.1016/j.apcata.2011.09.009
30. [30]
  (30) Zhai, D.W.; Yue, Y. H.; Hua,W. M.; Gao, Z. Acta Phys. -Chim. Sin. 2010, 26, 1867. [翟德伟, 乐英红, 华伟明, 高滋. 物理化学学报, 2010, 26, 1867.] doi: 10.3866/PKU.WHXB20100709
31. [31]
  (31) Arata, K.; Matsuhashi, H.; Hino, M.; Nakamura, H. Catal. Today 2003, 81, 17. doi: 10.1016/S0920-5861(03)00098-1
32. [32]
  (32) Arata, K. Appl. Catal. A: Gen. 1996, 146, 3. doi: 10.1016/0926-860X(96)00046-4
33. [33]
  (33) Li, Y.; Suo, Y. H.;Wang, Y. J. J. Mol. Catal. (China) 2011, 25,476. [李言, 所艳华, 汪颖军. 分子催化, 2011, 25, 476.]
34. [34]
  (34) Guierrez-Baez, R.; Toledo-Antonio, J. A.; Cortes-Jacome, M.A.; Sebastian, P. J.; Vazquez, A. Langmuir 2004, 20, 4265. doi: 10.1021/la036364x
35. [35]
  (35) Ponde, D.; Borate, H. B.; Sudalai, A.; Ravindranathan, T.;Deshpande, V. H. Tetrahedron Lett. 1992, 33, 825. doi: 10.1016/S0040-4039(00)77725-2
36. [36]
  (36) Li, T. S.; Lin, L. J.; Lu, B.; Yang, F. J. Chem. Soc. Perkin Trans.1998, 1, 3561.
37. [37]
  (37) Shihagahi, M.; Takahashi, K.; Kuno, H.; Matsushita, H. Bull. Chem. Soc. Jpn. 1990, 63, 1258. doi: 10.1246/bcsj.63.1258
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沈阳化工大学材料科学与工程学院沈阳 110142

Baeyer-Villiger Oxidation and Acetalization of Cyclic Ketones on SO42-/SnO2-Fe2O3 Solid Acid Catalysts

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通讯作者: 陈斌, bchen63@163.com

Baeyer-Villiger Oxidation and Acetalization of Cyclic Ketones on SO₄^2-/SnO₂-Fe₂O₃ Solid Acid Catalysts