Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Preparation of Copper Nanoparticles and Catalytic Properties for the Reduction of Aromatic Nitro Compounds

  • Duan, Zhongyu (Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, School of Chemical Engineering & Technology, Hebei University of Technology) ;
  • Ma, Guoli (Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, School of Chemical Engineering & Technology, Hebei University of Technology) ;
  • Zhang, Wenjun (Hebei Provincial Key Lab of Green Chemical Technology & High Efficient Energy Saving, School of Chemical Engineering & Technology, Hebei University of Technology)
  • Received : 2012.08.02
  • Accepted : 2012.09.11
  • Published : 2012.12.20
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Abstract

A novel copper nanoparticles were synthesized from cupric sulfate using hydrazine as reducing reagents. A series of aromatic nitro compounds were reacted with sodium borohydride in the presence of the copper nanoparticles catalysts to afford the aromatic amino compounds in high yields. Additionally, the catalysts system can be recycled and maintain a high catalytic effect in the reduction of aromatic nitro compounds.

Keywords

References

  1. Joseph, T.; Kumar, K. V.; Ramaswamy, A. V.; Halligudi, S. B. Catal. Commun. 2007, 8, 629. https://doi.org/10.1016/j.catcom.2006.03.004
  2. Khan, F. A.; Dash, J.; Sudheer, C.; Gupta, R. K. Tetrahedron Lett. 2003, 44, 7783. https://doi.org/10.1016/j.tetlet.2003.08.080
  3. Rai, G.; Jeong, J. M.; Lee, Y. S.; Kim, H. W.; Lee, D. S.; Chung, J. K.; Leea, M. C. Tetrahedron Lett. 2005, 46, 3987. https://doi.org/10.1016/j.tetlet.2005.04.035
  4. Figueras, F.; Coq, B. J. Mol. Catal. A: Chem. 2001, 173, 223. https://doi.org/10.1016/S1381-1169(01)00151-0
  5. Tan, X. Y.; Zhang, Z. X.; Xiao, Z. H.; Xu, Q.; Liang, C. H.; Wang, X. H. Catal. Lett. 2012, 142, 788. https://doi.org/10.1007/s10562-012-0821-5
  6. Zheng, Y. F.; Ma, K.; Wang, H. L.; Sun, X.; Jiang, J.; Wang, C. F.; Li, R.; Ma, J. T. Catal. Lett. 2008, 124, 268. https://doi.org/10.1007/s10562-008-9452-2
  7. Lagrost, C.; Preda, L.; Volanschi, E.; Hapiot, P. J. Electroanal. Chem. 2005, 585, 1. https://doi.org/10.1016/j.jelechem.2005.06.013
  8. Magdalene, R. M.; Leelamani, E. G.; Nanje, G. N. M. J. Mol.Catal A: Chem. 2004, 223, 17. https://doi.org/10.1016/j.molcata.2003.12.041
  9. Cardenas-Lizana, F.; Gomez-Quero, S.; Keane, M. A. Catal. Commun. 2008, 9, 475. https://doi.org/10.1016/j.catcom.2007.07.032
  10. Vilella, I. M. J.; Miguel, S. R.; Scelza, O. A. Chem. Eng. J. 2005, 114, 33. https://doi.org/10.1016/j.cej.2005.08.011
  11. Kuroda, K.; Ishida, T.; Haruta, M. J. Mol. Catal A: Chem. 2009, 298, 7. https://doi.org/10.1016/j.molcata.2008.09.009
  12. Swathi, T.; Buvaneswari, G. Materials Lett. 2008, 62, 3900. https://doi.org/10.1016/j.matlet.2008.05.028
  13. Kumar, P. S.; Rai, K. L. Chemical Papers 2012, 66, 772. https://doi.org/10.2478/s11696-012-0195-6
  14. Gowda, S.; Gowda, D. C. Tetrahedron. 2002, 58, 2211. https://doi.org/10.1016/S0040-4020(02)00093-5
  15. Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400. https://doi.org/10.1002/anie.200300594
  16. Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359. https://doi.org/10.1021/cr078346g
  17. Qiu, G. M.; Wang, C. J.; Zhang, Y. J.; Huang, S.; Liu, X. L.; Zhang, B. J.; Zhou, X. L. Bull. Korean Chem. Soc. 2012, 33, 2603. https://doi.org/10.5012/bkcs.2012.33.8.2603
  18. Lu, L.; Sui, M. L.; Lu, K. Science 2000, 287, 1463. https://doi.org/10.1126/science.287.5457.1463
  19. Safaei-Ghomi, J.; Ziarati, A.; Teymuri, R. Bull. Korean Chem. Soc. 2012, 33, 2679. https://doi.org/10.5012/bkcs.2012.33.8.2679
  20. Ranjit, S.; Duan, Z.; Zhang, P.; Liu, X. Org. Lett. 2010, 12, 4134. https://doi.org/10.1021/ol101729k
  21. Khan, F. A.; Dash, J.; Sudheer, C.; Gupta, R. K. Tetrahedron Lett. 2003, 44, 7783. https://doi.org/10.1016/j.tetlet.2003.08.080
  22. Chaubal, N. S.; Sawant, M. R. J. Mol. Catal A: Chem. 2007, 261, 232. https://doi.org/10.1016/j.molcata.2006.06.033

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