Citation: Chen Fushan, Yang Tao, Zhao Songlin, Jiang Taotao, Yu Lu, Xiong Houfeng, Guo Chuankun, Rao Yufang, Liu Yan, Liu Liu, Zhou Jian, Tu Pengxiang, Ni Jun, Zhang Qunfeng, Li Xiaonian. Highly selective oxidation of amines to imines by Mn₂O₃ catalyst under eco-friendly conditions[J]. Chinese Chemical Letters, ;2019, 30(12): 2282-2286. doi: 10.1016/j.cclet.2019.09.007 shu

Highly selective oxidation of amines to imines by Mn₂O₃ catalyst under eco-friendly conditions

Chen Fushan ^a,b ,
Yang Tao ^b ,
Zhao Songlin ^a,c ,
Jiang Taotao ^a ,
Yu Lu ^a ,
Xiong Houfeng ^b ,
Guo Chuankun ^b ,
Rao Yufang ^b ,
Liu Yan ^b ,
Liu Liu ^a ,
Zhou Jian ^a ,
Tu Pengxiang ^a ,
Ni Jun ^a ,
Zhang Qunfeng ^a,*, ,
Li Xiaonian ^a

a.
Industrial Catalysis Institute of Zhejiang University of Technology, Hangzhou, China
b.
Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang University, Jiujiang, China, br, c School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, China
c.
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, China

zhangqf@zjut.edu.cn

Received Date: 23 June 2019
Revised Date: 30 August 2019
Accepted Date: 5 September 2019
Available Online: 5 December 2019

Figures(4)

Enhancing the selectivity of imines for the oxidative self-coupling of primary amines was found to be challenging in the heterogeneous catalysis. Three different manganese oxides (M-3, M-4, M-5) were synthesized by controlling the calcination temperature using a simple template-free oxalate route. The prepared manganese oxides were systematically characterized using XRD, N₂ sorption, SEM, TEM, XPS, H₂-TPR techniques. M-4 gave 96.2% selectivity of imine at 100% conversion of benzylamine, which was far more superior than other existing protocols. Mn³⁺/Mn⁴⁺ ratio was found to affect the selectivity of the imines. The probable reaction pathway for amines oxidation catalyzed by manganese oxides was proposed for the first time.
- Oxalate route,
- Mn₂O₃,
- Self-coupling of amines,
- Heterogeneous catalysis,
- Aerobic oxidation
1. [1]
  B. Chen, L. Wang, S. Gao, ACS Catal. 5 (2015) 5851-5876. doi: 10.1021/acscatal.5b01479
2. [2]
  B. Dutta, S. March, L. Achola, et al., Green Chem. 20 (2018) 3180-3185. doi: 10.1039/C8GC00862K
3. [3]
  M.T. Schümperli, C. Hammond, I. Hermans, ACS Catal. 2 (2012) 1108-1117. doi: 10.1021/cs300212q
4. [4]
  H. Naeimi, F. Salimi, K. Rabiei, J. Mol. Catal. A Chem. 260 (2006) 100-104. doi: 10.1016/j.molcata.2006.06.055
5. [5]
  K.C. Nicolaou, C.J.N. Mathison, T. Montagnon, Angew. Chem. Int. Ed. 42 (2003) 4077-4082. doi: 10.1002/anie.200352076
6. [6]
  W. He, L. Wang, C. Sun, et al., Chem. -Eur. J. 17 (2011) 13308-13317. doi: 10.1002/chem.201101725
7. [7]
  L. Zhang, W. Wang, A. Wang, et al., Green Chem. 15 (2013) 2680-2684. doi: 10.1039/c3gc41117f
8. [8]
  G. Yuan, M. Gopiraman, H.J. Cha, et al., J. Ind. Eng. Chem. 46 (2017) 279-288. doi: 10.1016/j.jiec.2016.10.040
9. [9]
  B. Zhu, M. Lazar, B.G. Trewyn, et al., J. Catal. 260 (2008) 1-6. doi: 10.1016/j.jcat.2008.08.012
10. [10]
  G. Chu, C. Li, Org. Biomol. Chem. 8 (2010) 4716-4719. doi: 10.1039/c0ob00043d
11. [11]
  L. Al-Hmoud, C.W. Jones, J. Catal. 301 (2013) 116-124. doi: 10.1016/j.jcat.2013.01.027
12. [12]
  A. Santiago-Portillo, J.F. Blandez, S. Navalon, et al., Catal. Sci. Technol. 7 (2017) 1351-1362. doi: 10.1039/C6CY02577C
13. [13]
  H. Huang, J. Huang, Y.M. Liu, et al., Green Chem. 14 (2012) 930-934. doi: 10.1039/c2gc16681j
14. [14]
  C. Xu, H. Liu, D. Li, et al., Chem. Sci. 9 (2018) 3152-3158. doi: 10.1039/C7SC05296K
15. [15]
  Y. Xu, Y. Chen, W.-F. Fu, Appl. Catal. B:Environ. 236 (2018) 176-183. doi: 10.1016/j.apcatb.2018.03.098
16. [16]
  S. Biswas, A.S. Poyraz, Y. Meng, et al., Appl. Catal. B 165 (2015) 731-741. doi: 10.1016/j.apcatb.2014.10.055
17. [17]
  B. Dutta, V. Sharma, N. Sassu, et al., Green Chem. 19 (2017) 5350-5355. doi: 10.1039/C7GC01919J
18. [18]
  D. Biswanath, B. Sourav, S. Vinit, et al., Angew. Chem. Int. Ed. 128 (2016) 2211-2215. doi: 10.1002/ange.201508223
19. [19]
  S. Biswas, B. Dutta, K. Mullick, et al., ACS Catal. 5 (2015) 4394-4403. doi: 10.1021/acscatal.5b00325
20. [20]
  K. Mullick, S. Biswas, C. Kim, et al., Inorg. Chem. 56 (2017) 10290-10297. doi: 10.1021/acs.inorgchem.7b01177
21. [21]
  K. Mullick, S. Biswas, A.M. Angeles-Boza, et al., Chem. Commun. 53 (2017) 2256-2259. doi: 10.1039/C6CC09095H
22. [22]
  S. Biswas, K. Mullick, S.Y. Chen, et al., ACS Catal. 6 (2016) 5069-5080. doi: 10.1021/acscatal.6b00717
23. [23]
  P. Venkataswamy, K.N. Rao, D. Jampaiah, et al., Appl. Catal. B:Environ. 162 (2015) 122-132. doi: 10.1016/j.apcatb.2014.06.038
24. [24]
  C.H. Kuo, I.M. Mosa, A.S. Poyraz, et al., ACS Catal. 5 (2015) 1693-1699. doi: 10.1021/cs501739e
25. [25]
  S.L. Suib, J. Mater. Chem. 18 (2008) 1623-1631. doi: 10.1039/b714966m
26. [26]
  Z. Zhang, F. Wang, M. Wang, et al., Green Chem. 16 (2014) 2523-2527. doi: 10.1039/C3GC42312C
27. [27]
  P. Sudarsanam, B. Hillary, M.H. Amin, et al., Appl. Catal. B:Environ. 185 (2016) 213-224. doi: 10.1016/j.apcatb.2015.12.026
28. [28]
  F. Chen, S. Zhao, T. Yang, et al., Acta Phys. Chim. Sin. 35 (2019) 775-786.
29. [29]
  W. Tang, X. Wu, D. Li, et al., J. Mater. Chem. A 2 (2014) 2544-2554. doi: 10.1039/C3TA13847J
30. [30]
  L.V. Stebounova, N.I. Gonzalez-Pech, T.M. Peters, et al., Environ. Sci. Nano 5 (2018) 696-707. doi: 10.1039/C7EN01046J
31. [31]
  Y. Wu, R. Feng, C. Song, et al., Catal. Today 281 (2017) 500-506. doi: 10.1016/j.cattod.2016.05.024
32. [32]
  X.B. Huang, L.P. Liu, H.Y. Gao, et al., Green Chem. 19 (2017) 769-777. doi: 10.1039/C6GC02065H
33. [33]
  G. Liu, L. Sun, J. Liu, et al., Mol. Catal. 440 (2017) 148-157. doi: 10.1016/j.mcat.2017.07.017
34. [34]
  A.S. Poyraz, W. Song, D. Kriz, et al., ACS Appl. Mater. Interface 6 (2014) 10986-10991. doi: 10.1021/am502846e
35. [35]
  V.D. Makwana, Y.C. Son, A.R. Howell, et al., J. Catal. 210 (2002) 46-52. doi: 10.1006/jcat.2002.3680
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Highly selective oxidation of amines to imines by Mn2O3 catalyst under eco-friendly conditions

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通讯作者: 陈斌, bchen63@163.com

Highly selective oxidation of amines to imines by Mn₂O₃ catalyst under eco-friendly conditions