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Citation: WANG Tao, LIN Zheng-Guo, HU Chang-Wen. Preparation of Benzamide by Hydration of Benzonitrile with Palladium Acetate and Phenylarsonic Acid as Synergistic Catalyst[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(9): 1619-1622. doi: 10.11862/CJIC.2019.181 shu

Preparation of Benzamide by Hydration of Benzonitrile with Palladium Acetate and Phenylarsonic Acid as Synergistic Catalyst

School of Chemistry and Chemical Engineering, Key Laboratory of Cluster Science, Ministry of Education, Beijing Institute of Technology, Beijing 102488, China

Corresponding author: HU Chang-Wen, cwhu@bit.edu.cn
Received Date: 30 April 2019
Revised Date: 17 May 2019

Figures(4)

A new catalytic method for benzonitrile hydration in the absence of solvent was developed by using palladium acetate and phenylarsonic acid (molar ratio n_Pd:n_As=3:2) as catalyst, which exhibited high catalytic activity (space-time yield (STY)=186 mol·kg^-1·h^-1) and recyclability. Moreover, the product can be isolated as pure crystals and filtered from the reaction mixture after the reaction system cooling to low temperature (0℃), and the product was characterized by ¹H NMR, ¹³C NMR and FT-IR.
- benzonitrile,
- hydration,
- amide,
- homogeneous catalysis
1. [1]
  Bernges F, Bürkle A, Küpper J H, et al. Carcinogenesis, 1997, 18(4):663-668 doi: 10.1093/carcin/18.4.663
2. [2]
  Mascharak P K. Coord. Chem. Rev., 2002, 225:201-214 doi: 10.1016/S0010-8545(01)00413-1
3. [3]
  Gangarajula Y, Gopal B. Appl. Catal. A, 2014, 475:211-217 doi: 10.1016/j.apcata.2014.01.036
4. [4]
  Kumar S, Sharma S, Das P. Adv. Synth. Catal., 2016, 358(18):2889-2894 doi: 10.1002/adsc.201600199
5. [5]
  Ramon R S, Marion N, Nolan S P. Chem. Eur. J., 2009, 15(35):8695-8697 doi: 10.1002/chem.200901231
6. [6]
  Hirano T, Uehara K, Kamata K, et al. J. Am. Chem. Soc., 2012, 134(14):6425-6433 doi: 10.1021/ja3006012
7. [7]
  Kesavan L, Tiruvalam R, Rahim M H A, et al. Science, 2011, 331:195-199 doi: 10.1126/science.1198458
8. [8]
  HAN Wang-Kang, TIAN Lei, XU Zong-Li, et al. Chinese J. Inorg. Chem., 2017, 33(4):550-559
9. [9]
  Yamaguchi K, Matsushita M, Mizuno N. Angew. Chem. Int. Ed., 2004, 116(12):1602-1606 doi: 10.1002/ange.200353461
10. [10]
  Shimizu K, Takahiro K, Satsuma A, et al. ACS Catal., 2012, 2(12):2467-2474 doi: 10.1021/cs3006154
11. [11]
  Zhang S C, Xu H S, Lou C L, et al. Eur. J. Org. Chem., 2017, 2017(14):1870-1875 doi: 10.1002/ejoc.201601495
12. [12]
  Yang P, Li H, Ma T, et al. Chem. Eur. J., 2018, 24(10):2466-2478 doi: 10.1002/chem.201705303
13. [13]
  Enache D I, Edwards J K, Landon P, et al. Science, 2006, 311:362-365 doi: 10.1126/science.1120560
1. [1]
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2. [2]
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3. [3]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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