Reduction of Nitroarenes to Aromatic Amines with Sodium Borohydride in the Presence of Selenium and Actived Carbon

*Ke Ying Cai  -  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou, Jiangsu 221111,, China
Ying Mei Zhou  -  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou, Jiangsu 221111,, China
Received: 3 May 2015; Published: 30 Dec 2015.
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Abstract

A selenium and actived carbon (AC) catalyst has been applied for the selective reduction of nitroarenes to their corresponding amines respectively using sodium borohydride (NaBH4) as a reducing source un-der mild conditions. Under the optimized conditions, efficient and selective reduction of nitroarenes into the corresponding aromatic amines occurred over a recyclable selenium catalyst. The catalyst can be easily recovered after catalytic reaction and readily reused for 4 cycles with consistent activity hence reduces the cost of the catalyst. © 2015 BCREC UNDIP. All rights reserved.

Received: 3rd May 2015; Revised: 5th October 2015; Accepted: 5th October 2015

How to Cite: Cai, K.Y., Zhou, Y.M. (2015). Reduction of Nitroarenes to Aromatic Amines with Sodium Borohydride in the Presence of Selenium and Actived Carbon. Bulletin of Chemical Reaction Engineering & Catalysis, 10 (3): 275-280. (doi:10.9767/bcrec.10.3.8512.275-280)

Permalink/DOI: http://dx.doi.org/10.9767/bcrec.10.3.8512.275-280

Keywords: Sodium Borohydride; Reduction; Nitroarenes; Selenium; Amines; Activated Carbon
Funding: Xuzhou Institute of Technology

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Article Info
Section: Original Research Articles
Language: EN
In 2015: BCREC Volume 10 Issue 3 Year 2015 (SCOPUS Indexed, December 2015)
Statistics: 1835 1949
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  9. Pogorelić, I., Filipan-Litivić, M., Merkaš, S., Ljubić, G., Capanec, I., Litivić, M. (2007). Rapid, Efficient and Selective Reduction of Aromatic Nitro Compounds with Sodium Borohydride and Raney Nickel. J. Mol. Catal. A-Chem. 274: 202-207
  10. Nandanwar, S. U., Chakraborty, M. (2012). Synthesis of Colloidal Cu/γ-Al2O3 by Microemulsion and Catalytic Reduction of Aromatic Nitro Compounds. Chin. J. Catal. 33(9): 1532-1541
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  16. Liu, X.Z., Lu, S.W. (2001). Selective Formation of Aromatic Amines by Selenium-Catalyzed Reduction of Aromatic Nitro Compounds with CO/H2O under Atmosspheric Pressure. J. Mol. Catal. A-Chem. 212: 127-130
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