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
1. [1]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202309002
2. [2]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230459
3. [3]
  Siyu HOU , Weiyao LI , Jiadong LIU , Fei WANG , Wensi LIU , Jing YANG , Ying ZHANG . Preparation and catalytic performance of magnetic nano iron oxide by oxidation co-precipitation method. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230469
4. [4]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202408015
5. [5]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230369
6. [6]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202309037
7. [7]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, doi: 10.3866/PKU.DXHX202310074
8. [8]
  Tong Zhou , Jun Li , Zitian Wen , Yitian Chen , Hailing Li , Zhonghong Gao , Wenyun Wang , Fang Liu , Qing Feng , Zhen Li , Jinyi Yang , Min Liu , Wei Qi . Experiment Improvement of “Redox Reaction and Electrode Potential” Based on the New Medical Concept. University Chemistry, doi: 10.3866/PKU.DXHX202401005
9. [9]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, doi: 10.3866/PKU.DXHX202401031
10. [10]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202308032
11. [11]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, doi: 10.3866/PKU.DXHX202309095
12. [12]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202403009
13. [13]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20240256
14. [14]
  Peng XU , Shasha WANG , Nannan CHEN , Ao WANG , Dongmei YU . Preparation of three-layer magnetic composite Fe₃O₄@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230239
15. [15]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, doi: 10.3866/PKU.WHXB202402006
16. [16]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230350
17. [17]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20240210
18. [18]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230346
19. [19]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20240149
20. [20]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, doi: 10.11862/CJIC.20230421

Get Citation

PDF

XML

Metrics

PDF Downloads(1034)
Abstract views(2009)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
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

Metrics

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