Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition

Mansoor Kazemimoghadam

doi:doi:10.11648/j.ajpc.20170605.12

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Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition

Mansoor Kazemimoghadam

Published in American Journal of Physical Chemistry (Volume 6, Issue 5)

Received: 2 October 2017 Accepted: 20 October 2017 Published: 27 November 2017

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Abstract

The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403°K, 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.

Published in	American Journal of Physical Chemistry (Volume 6, Issue 5)
DOI	10.11648/j.ajpc.20170605.12
Page(s)	88-96
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

Liquid-Phase Hydrogenation, Ni Catalysts, Dimethyl-Nitrobenzene, Dimethyl-Aniline, Operation Condition

References

[1]	J. Maria, C. Barrera, Naphthalene hydrogenation over Mg-doped Pt/Al₂O₃, Catalysis Today, 296 (2017) 197-204.
[2]	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.
[3]	Y. Liu, X. Deng, CO hydrogenation to higher alcohols over Cu Zn Al catalysts without promoters: Effect of pH value in catalyst preparation, Fuel Processing Technology, 167(2017) 575-581.
[4]	I. Maizatul, S. Shaharun, Carbon nanofiber-based copper/zirconia catalyst for hydrogenation of CO₂ to methanol, Journal of CO₂ Utilization, 21 (2017) 145-155.
[5]	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.
[6]	S. Lee, Z. Yu, Acetophenone hydrogenation on Rh/Al₂O₃ catalyst: Intrinsic reaction kinetics and effects of internal diffusion, Chemical Engineering Journal, 288 (2016) 711-723.
[7]	A. jeli, M. Grilc, Catalytic hydrogenation and hydrodeoxygenation of lignin-derived model compound eugenol over Ru/C: Intrinsic microkinetics and transport phenomena, Chemical Engineering Journal, 333 (2018) 240-259.
[8]	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.
[9]	D. Perz, C. Fuentes, Study of the selective hydrogenation of 1, 3-butadiene in three types of industrial reactors, Fuel, 149 (2015) 34-45.
[10]	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.
[11]	M. Walesa, L. Joos, Composite catalytic tubular membranes for selective hydrogenation in three-phase systems, Catalysis Today, 268 (2016) 12–18.
[12]	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.
[13]	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.
[14]	M. Li, D. Wang, Surfactant-assisted hydrothermally synthesized MoS₂ samples with controllable morphologies and structures for anthracene hydrogenation, Chinese Journal of Catalysis, (2017) 597-606.
[15]	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.
[16]	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.
[17]	R. Soeiro, S. Richard, Influence of noble metals (Pd, Pt) on the performance of Ru/Al₂O₃ based catalysts for toluene hydrogenation in liquid phase, Applied Catalysis A: General, 525 (2016) 41-49.
[18]	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.
[19]	F. Lali, G. Bottcher, Preparation and characterization of Pd/Al₂O₃ catalysts on aluminum foam supports for multiphase hydrogenation reactions in rotating foam reactors, Chemical Engineering Research and Design, 94 (2015) 365-374.

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APA Style

Mansoor Kazemimoghadam. (2017). Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. American Journal of Physical Chemistry, 6(5), 88-96. https://doi.org/10.11648/j.ajpc.20170605.12

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ACS Style

Mansoor Kazemimoghadam. Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. Am. J. Phys. Chem. 2017, 6(5), 88-96. doi: 10.11648/j.ajpc.20170605.12

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AMA Style

Mansoor Kazemimoghadam. Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. Am J Phys Chem. 2017;6(5):88-96. doi: 10.11648/j.ajpc.20170605.12

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@article{10.11648/j.ajpc.20170605.12,
  author = {Mansoor Kazemimoghadam},
  title = {Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition},
  journal = {American Journal of Physical Chemistry},
  volume = {6},
  number = {5},
  pages = {88-96},
  doi = {10.11648/j.ajpc.20170605.12},
  url = {https://doi.org/10.11648/j.ajpc.20170605.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajpc.20170605.12},
  abstract = {The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403°K, 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.},
 year = {2017}
}

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TY  - JOUR
T1  - Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition
AU  - Mansoor Kazemimoghadam
Y1  - 2017/11/27
PY  - 2017
N1  - https://doi.org/10.11648/j.ajpc.20170605.12
DO  - 10.11648/j.ajpc.20170605.12
T2  - American Journal of Physical Chemistry
JF  - American Journal of Physical Chemistry
JO  - American Journal of Physical Chemistry
SP  - 88
EP  - 96
PB  - Science Publishing Group
SN  - 2327-2449
UR  - https://doi.org/10.11648/j.ajpc.20170605.12
AB  - The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403°K, 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.
VL  - 6
IS  - 5
ER  -

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Author Information

Mansoor Kazemimoghadam

Faculty of Chemical and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran

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Plain Text BibTeX RIS

APA Style

Mansoor Kazemimoghadam. (2017). Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. American Journal of Physical Chemistry, 6(5), 88-96. https://doi.org/10.11648/j.ajpc.20170605.12

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ACS Style

Mansoor Kazemimoghadam. Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. Am. J. Phys. Chem. 2017, 6(5), 88-96. doi: 10.11648/j.ajpc.20170605.12

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AMA Style

Mansoor Kazemimoghadam. Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition. Am J Phys Chem. 2017;6(5):88-96. doi: 10.11648/j.ajpc.20170605.12

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@article{10.11648/j.ajpc.20170605.12,
  author = {Mansoor Kazemimoghadam},
  title = {Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition},
  journal = {American Journal of Physical Chemistry},
  volume = {6},
  number = {5},
  pages = {88-96},
  doi = {10.11648/j.ajpc.20170605.12},
  url = {https://doi.org/10.11648/j.ajpc.20170605.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajpc.20170605.12},
  abstract = {The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403°K, 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.},
 year = {2017}
}

Copy | Download

TY  - JOUR
T1  - Catalytic Hydrogenation of Dimethyl-Nitrobenzene to Dimethyl-Aniline in a Three-Phase Reactor: Reaction Kinetics and Operation Condition
AU  - Mansoor Kazemimoghadam
Y1  - 2017/11/27
PY  - 2017
N1  - https://doi.org/10.11648/j.ajpc.20170605.12
DO  - 10.11648/j.ajpc.20170605.12
T2  - American Journal of Physical Chemistry
JF  - American Journal of Physical Chemistry
JO  - American Journal of Physical Chemistry
SP  - 88
EP  - 96
PB  - Science Publishing Group
SN  - 2327-2449
UR  - https://doi.org/10.11648/j.ajpc.20170605.12
AB  - The catalytic transfer hydrogenation of dimethyl-nitrobenzene (DN) to Dimethyl-aniline (DA) was studied in the temperature range 343–403°K, 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.
VL  - 6
IS  - 5
ER  -

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