Open Access Open Access  Restricted Access Subscription or Fee Access

Catalytic hydrogenation of dimethyl-nitrobenzene to dimethyl-aniline over Ni catalysts

Mansoor Kazemimoghadam

Abstract


The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403 , pressure range of 4–10 bar H2 and ethanol as solvent using Ni on alumina-silicate as catalyst above agitation speed 800 rpm. The substrate feed concentration was varied in the range from 0.124 to 0.745 kmol/m3 while catalyst loading was in the range 4–12% (w/w) of dimethyl-nitrobenzene. Dimethyl-aniline was the only reaction product, generated through the hydrogenation of the Nitro group of dimethyl-nitrobenzene. The effects of hydrogen partial pressure, catalyst loading, dimethyl-nitrobenzene concentration and temperature on the reaction conversion have been reported. Near first-order dependence on dimethyl-nitrobenzene concentration and hydrogen pressure were observed for the initial rate of dimethyl-nitrobenzene hydrogenation over the Ni catalyst. Furthermore, an increase in the catalytic activity as the reaction temperature, pressure and weight of catalysts was observed. Conventional Arrhenius behavior was exhibited by catalyst, Ni showed activation energies of 808 J/mol.

Keywords: Liquid-phase hydrogenation; Ni catalysts; dimethyl-nitrobenzene; dimethyl-aniline; operation condition

Full Text:

PDF

References


P. Reyes, H. Rojas, J.L.G. Fierro, Kinetic study of liquid-phase hydrogenation of citral over Ir/TiO2 catalysts, Applied Catalysis A: General 248 (2003) 59–65.

P. Haldar, V.V. Mahajani, Catalytic transfer hydrogenation: o-nitro anisole to o-anisidine, some process development aspects, Chemical Engineering Journal 104 (2004) 27–33.

Dilip R.Patel, R.N. Ram, Hydrogenation of nitrobenzene using polymer anchored Pd (II) complexes, Journal of Molecular Catalysis A: Chemical 130 (1998) 57-64.

Volker Holler, Dagmar Wegricht, Igor Yuranov, Lioubov Kiwi-Minsker, and Albert Renken, Three-Phase Nitrobenzene Hydrogenation over Supported Glass Fiber Catalysts: Reaction Kinetics Study, Chem. Eng. Technol. 23 (2000) 3.

Nivedita S. Chaubal, Manohar R. Sawant, Nitro compounds reduction via hydride transfer using mesoporous mixed oxide catalyst, Journal of Molecular Catalysis A: Chemical 261 (2006) 232–241

Shao-Pai Lee, Yu-Wen Chen, Nitrobenzene hydrogenation on Ni–P, Ni–B and Ni–P–B ultrafine materials, Journal of Molecular Catalysis A: Chemical 152 _2000. 213–223.

Sunil P. Bawane, Sudhirprakash B. Sawant, Hydrogenation of p-nitrophenol to metol using Raney nickel catalyst: Reaction kinetics, Applied Catalysis A: General 293 (2005) 162–170.

Sunil K. Maity, Narayan C. Pradhan, Anand V. Patwardhan, Kinetics of the reduction of nitrotoluenes by aqueous ammonium sulfide under liquid–liquid phase transfer catalysis, Applied Catalysis A: General 301 (2006) 251–258

Prakash D. Vaidya, Vijaykumar V. Mahajani, Kinetics of liquid-phase hydrogenation of n-valeraldehyde to n-amyl alcohol over a Ru/Al2O3 catalyst, Chemical Engineering Science 60 (2005) 1881 – 1887.

T. Swathi, G. Buvaneswari, Application of NiCo2O4 as a catalyst in the conversion of p-nitrophenol to p-aminophenol, Materials Letters 62 (2008) 3900–3902.

Leanne McLaughlin, Ekaterina Novakova, Robbie Burch, Christopher Hardacre, Hydrogenation/hydrogenolysis of disulfides using sulfided Ni/Mo catalysts, Applied Catalysis A: General 340 (2008) 162–168.

Sachin U. Sonavane, Manoj B. Gawande, Sameer S. Deshpande, A. Venkataraman, Radha V. Jayaram, Chemo selective transfer hydrogenation reactions over nanosized c-Fe2O3 catalyst prepared by novel combustion route, Catalysis Communications 8 (2007) 1803–1806

Jia-Huei Shen, Yu-Wen Chen, Catalytic properties of bimetallic NiCoB nanoalloy catalysts for hydrogenation of p-chloronitrobenzene, Journal of Molecular Catalysis A: Chemical 273 (2007) 265–276.

Tatiana Tehila Bovkun, Michael Grayevsky, Yoel Sasson, Jochanan Blum, Liquid phase hydrogenation and hydrodenitrogenation of aromatic nitrogen-containing environmental pollutants, Journal of Molecular Catalysis A: Chemical 270 (2007) 171–176

Ekaterina K. Novakova, Leanne McLaughlin, Robbie Burch, Paul Crawford, Ken Griffin, Christopher Hardacre, Peijun Hu, David W. Rooney, Palladium-catalyzed liquid-phase hydrogenation/hydrogenolysis of disulfides, Journal of Catalysis 249 (2007) 93–101.

Yu-Zhi Haoa, Zuo-Xi Li, Jin-Lei Tian, Synthesis, characteristics and catalytic activity of water-soluble [Pd(lysine·HCl)(Cl)2] complex as hydrogenation catalyst, Journal of Molecular catalysis A: Chemical 265 (2007) 258–267.

Christopher M. Vogels, Andreas Decken and Stephen A. Westcott, Catalyzed hydroboration of nitrostyrenes and 4-vinylaniline: a mild and selective route to aniline derivatives containing boronate esters, Tetrahedron Letters 47 (2006) 2419–2422.

Qiong Xua, Xin-Mei Liu, Jun-Ru Chen, Rui-Xiang Li, Xian-Jun Li, Modification mechanism of Sn4+ for hydrogenation of p-chloronitrobenzene over PVP-Pd/Al2O3, Journal of Molecular Catalysis A: Chemical 260 (2006) 299–305

Atsushi Akao, Kimihiko Sato, Nobuaki Nonoyama, Toshiaki Masea and Nobuyoshi Yasud, Highly chemo selective reduction using an Rh/C–Fe (OAc) 2 system: practical synthesis of functionalized indoles, Tetrahedron Letters 47 (2006) 969–972.




DOI: https://doi.org/10.37628/jcep.v3i2.420

Refbacks

  • There are currently no refbacks.