Citation: Jing-Hui Lyu, Xiao-Bo He, Chun-Shan Lu, Lei Ma, Qun-Feng Zhang, Feng Feng, Xiao-Nian Li, Jian-Guo Wang. The promoting role of minor amount of water in solvent-free hydrogenation of halogenated nitrobenzenes[J]. Chinese Chemical Letters, ;2014, 25(2): 205-208.
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This study shows that minor amount of water plays a very important role in solvent-free hydrogenation of halogenated nitrobenzenes. For dried sponge Pd, the reaction cannot occur in the absence of water. For Pd/C catalyst, minor amount of water reduces the induction time, increases the reaction rate and reaction TOFs. Water might enhance the diffusion, adsorption and dissociation of H2 on Pd catalysts.
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Keywords:
- Halogenated nitrobenzenes,
- Solvent free,
- Water,
- Hydrogenation
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[1]
[1] G.Y. Fan, L. Zhang, H.Y. Fu, et al., Hydrous zirconia supported iridium nanoparticles: an excellent catalyst for the hydrogenation of haloaromatic nitro compounds, Catal. Commun. 11 (2010) 451-455.
-
[2]
[2] X.D. Wang, M.H. Liang, H.Q. Liu, Y. Wang, Selective hydrogenation of bromonitrobenzenes over Pt/gamma-Fe2O3, J. Mol. Catal. A-Chem. 273 (2007) 160-168.
-
[3]
[3] C. Feng, H.Y. Zhang, N.Z. Shang, S.T. Gao, C. Wang, Magnetic graphene nanocomposite as an efficient catalyst for hydrogenation of nitroarenes, Chin. Chem. Lett. 24 (2013) 539-541.
-
[4]
[4] X. Yuan, N. Yan, C.X. Xiao, et al., Highly selective hydrogenation of aromatic chloronitro compounds to aromatic chloroamines with ionic-liquid-like copolymer stabilized platinum nanocatalysts in ionic liquids, Green Chem. 12 (2010) 228-233.
-
[5]
[5] M.H. Liang, X.D. Wang, H.Q. Liu, H.C. Liu, Y. Wang, Excellent catalytic properties over nanocomposite catalysts for selective hydrogenation of halonitrobenzenes, J. Catal. 255 (2008) 335-342.
-
[6]
[6] C.H. Liang, J.G. Han, K.H. Shen, et al., Palladium nanoparticle microemulsions: Formation and use in catalytic hydrogenation of o-chloronitrobenzene, Chem. Eng. J. 165 (2010) 709-713.
-
[7]
[7] H.Q. Liu, M.H. Liang, C. Xiao, et al., An excellent Pd-based nanocomposite catalyst for the selective hydrogenation of para-chloronitrobenzene, J. Mol. Catal. A-Chem. 308 (2009) 79-86.
-
[8]
[8] L.M. Sikhwivhilu, N.J. Coville, B.M. Pulimaddi, J. Venkatreddy, V. Vishwanathan, Selective hydrogenation of o-chloronitrobenzene over palladium supported nanotubular titanium dioxide derived catalysts, Catal. Commun. 8 (2007) 1999-2006.
-
[9]
[9] X.C. Meng, H.Y. Cheng, S. Fujita, et al., Selective hydrogenation of chloronitrobenzene to chloroaniline in supercritical carbon dioxide over Ni/TiO2: significance of molecular interactions, J. Catal. 269 (2010) 131-139.
-
[10]
[10] X.X. Han, H.R. Li, R.M. Zhou, Effect of rare earths on selective hydrogenation of pchloronitrobenzene over PtMOx/CNTs catalysts, Chin. Chem. Lett. 20 (2009) 96-98.
-
[11]
[11] M. Sankar, N. Dimitratos, P.J. Miedziak, et al., Designing bimetallic catalysts for a green and sustainable future, Chem. Soc. Rev. 41 (2012) 8099-8139.
-
[12]
[12] L. Kesavan, R. Tiruvalam, M.H. Ab Rahim, et al., Solvent-free oxidation of primary carbon-hydrogen bonds in toluene using Au-Pd alloy nanoparticles, Science 331 (2011) 195-199.
-
[13]
[13] L. Ma, S. Chen, C.S. Lu, Q.F. Zhang, X.N. Li, Highly selective hydrogenation of 3,4- dichloronitrobenzene over Pd/C catalysts without inhibitors, Catal. Today 173 (2011) 62-67.
-
[14]
[14] C.S. Lu, J.H. Lv, L. Ma, et al., Highly selective hydrogenation of halonitroaromatics to aromatic haloamines by ligand modified Ni-based catalysts, Chin. Chem. Lett. 23 (2012) 545-548.
-
[15]
[15] C. Su, X.N. Li, Q.F. Zhang, et al., Behavior of adsorbed diphenyl-sulfide on the Pd/C catalyst for o-chloronitrobenzene hydrogenation, Chin. Chem. Lett. 24 (2013) 59- 62.
-
[16]
[16] C. Lian, H.Q. Liu, C. Xiao, et al., Solvent-free selective hydrogenation of chloronitrobenzene to chloroaniline over a robust Pt/Fe3O4 catalyst, Chem. Commun. 48 (2012) 3124-3126.
-
[17]
[17] M. Pietrowski, M. Zielinski, M. Wojciechowska, Selective reduction of chloronitrobenzene to chloroaniline on Ru/MgF2 catalysts, Catal. Lett. 128 (2009) 31-35.
-
[18]
[18] J. Ning, J. Xu, J. Liu, et al., A remarkable promoting effect of water addition on selective hydrogenation of p-chloronitrobenzene in ethanol, Catal. Commun. 8 (2007) 1763-1766.
-
[19]
[19] H.Y. Cheng, X.C. Meng, Y.C. Yu, F.Y. Zhao, The effect of water on the hydrogenation of o-chloronitrobenzene in ethanol, n-heptane and compressed carbon dioxide, Appl. Catal. A-Gen. 455 (2013) 8-15.
-
[20]
[20] J.Y. Li, L. Ma, X.N. Li, C.S. Lu, H.Z. Liu, Effect of nitric acid, pretreatment on the properties of activated carbon and supported palladium catalysts, Ind. Eng. Chem. Res. 44 (2005) 5478-5482.
-
[21]
[21] G. Kresse, J. Furthmuller, Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set, Phys. Rev. B 54 (1996) 11169-11186.
-
[22]
[22] H.P. Boehm, Surface oxides on carbon and their analysis: a critical assessment, Carbon 40 (2002) 145-149.
-
[23]
[23] R.H. Bradley, M.W. Smith, A. Andreu, M. Falco, Surface studies of novel hydrophobic active carbons, Appl. Surf. Sci. 257 (2011) 2912-2919.
-
[24]
[24] B. Coq, F. Figueras, Structure-activity relationships in catalysis by metals: some aspects of particle size, bimetallic and supports effects, Coord. Chem. Rev. 178 (1998) 1753-1783.
-
[25]
[25] L.R. Merte, G.W. Peng, R. Bechstein, et al., Water-mediated proton hopping on an iron oxide surface, Science 336 (2012) 889-893.
-
[26]
[26] A. Gross, Ab initio molecular dynamics simulations of the adsorption of H-2 on palladium surfaces, ChemPhysChem 11 (2010) 1374-1381.
-
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