Kinetics and mechanism of the hydrogenation of m-dinitrobenzene to m-phenylenediamine

Rojas, Hugo; Borda, Gloria; Brijaldo, María H.; Reyes, Patricio; Valencia, Jesús

doi:10.1007/s11144-011-0380-6

Cited by 18 publications

(14 citation statements)

References 36 publications

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“…During the conversion of the nitro groups (electron‐withdrawing groups) of polynitroaromatics to amine groups (electron‐donating groups), the electronic deficiency of the aromatic ring decreases, which hinders the reduction of the second nitro group. Therefore, the reduction of the first nitro group is generally much faster than that of the remaining nitro groups . The activation energy for the partial and complete reduction of DNB was 31 and 40.5 kJ mol −1 , respectively.…”

Section: Resultsmentioning

confidence: 97%

Nickel/USY Catalyst Derived from a Layered Double Hydroxide/Zeolite Hybrid Structure with a High Hydrogenation Efficiency

Wang

Guan

et al. 2017

ChemCatChem

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It is important and challenging in heterogeneous catalysis to prepare catalysts with highly dispersed metal nanoparticles that have a high activity. Herein, a new Ni/USY catalyst derived from a core–shell NiAl‐LDHs/USY hybrid material has been prepared by the in situ growth of a layered double hydroxides (LDHs) precursor on the surface of USY zeolite crystals. Under the appropriate conditions, the adscititious Ni source interacted chemoselectively with Al species dissolved from the zeolite framework to form a LDHs structure anchored robustly on the surface of zeolite crystals. The dealumination of the low‐silica zeolite and the immobilization of Ni metal species were realized simultaneously in this one‐pot synthesis to afford hierarchical NiAl‐LDHs/USY hybrid composites. The NiII species in these hybrid composites were reduced readily at much lower temperatures than that of bulk NiAl‐LDH, which gave rise to highly dispersed Ni nanoparticles. Meanwhile, the resultant material possessed an excellent mesoporous structure and a high surface area inherited from the USY structure, which led to an excellent hydrogenation rate and activity for the conversion of m‐nitroaniline to m‐phenylenediamine. This unique method could be a promising and general strategy to fabricate desirable hybrid materials for redox catalysis in particular for supported transition metals with similar characteristics to Ni.

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Section: Resultsmentioning

confidence: 97%

Nickel/USY Catalyst Derived from a Layered Double Hydroxide/Zeolite Hybrid Structure with a High Hydrogenation Efficiency

Wang

Guan

et al. 2017

ChemCatChem

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“…Selectivity to m-PDM was favoured at increasing conversion. Consecutive formation of m-NAN and m-PDM has been reported for batch liquid reaction over Pt/TiO 2 [75] and carbon supported Ni [26] and Ni-Pt [26]. Distinct differences in selectivity are in evidence for the two metals at higher conversions where a preferential formation of m-NAN was observed over Ag/AC.…”

Section: Catalyst Selectivitymentioning

confidence: 79%

“…Enhanced activity for Au/AC extended over the 463-573 K range as demonstrated by the Arrhenius plots in Fig. 7(II) with an apparent activation energy of 110 kJ mol −1 for m-DNB → m-NAN (Scheme 1) that is somewhat higher than the range of values (33-74 kJ mol −1 ) reported for batch liquid phase hydrogenation of substituted nitroarenes (dinitrobenzene [75], dinitrotoluene [76], chloronitrobenzene [77] and nitrophenol [78]) over supported Pt [75,78], Ni [77] and Pd [76].…”

Section: Catalyst Activitymentioning

confidence: 82%

Carbon supported gold and silver: Application in the gas phase hydrogenation of m -dinitrobenzene

Cárdenas‐Lizana

Pedro

Gómez‐Quero

et al. 2015

Journal of Molecular Catalysis A: Chemical

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“…(2014) [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] www.deswater.com doi: 10.1080/19443994.2014.990932 excellent chemical and temperature stability, and fast cure. The demand for m-PDA is growing rapidly with increase in application of engineering materials, especially aromatic polyamide fibers and polyurethane [6].…”

Section: Desalination and Water Treatmentmentioning

confidence: 99%

“…The demand for m-PDA is growing rapidly with increase in application of engineering materials, especially aromatic polyamide fibers and polyurethane [6]. If released to water, m-PDA is expected to be adsorbed by hazardous sediment and suspended solids in the acidic environment [7,8].…”

Section: Desalination and Water Treatmentmentioning

confidence: 99%

Removal of m-phenylene diamine by adsorption onto activated carbon: kinetics, equilibrium and process design

Patel

Rathod

Mody

et al. 2016

Desalination and Water Treatment

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A B S T R A C TThe adsorption behavior of m-phenylene diamine (m-PDA) from aqueous solution onto activated carbon was investigated under various experimental conditions, such as contact time, adsorbate concentration, and temperature. Maximum adsorption capacity for m-PDA was found to be 33.17 mg g −1 at pH 7.0 and temperature 303 K. The adsorption kinetics data were best described by the pseudo-second-order rate equation and the equilibrium was achieved after 120 min. The m-PDA adsorption was governed by film diffusion process. Besides, equilibrium data were very well represented by the Redlich-Peterson model. A model for prediction of the dose of adsorbent required to achieve a range of m-PDA removals for a given number of adsorption-desorption cycles has been developed and validated based on the Langmuir isotherm. Thermodynamic parameters indicated the spontaneous, endothermic, and increased random nature of m-PDA adsorption. The amide, carboxylic acid, and nitro groups of the activated carbon were involved in chemical interaction with the m-PDA molecules. Results suggested that the activated carbon has good potential for remediation of m-PDA contaminated waters.

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Kinetics and mechanism of the hydrogenation of m-dinitrobenzene to m-phenylenediamine

Cited by 18 publications

References 36 publications

Nickel/USY Catalyst Derived from a Layered Double Hydroxide/Zeolite Hybrid Structure with a High Hydrogenation Efficiency

Nickel/USY Catalyst Derived from a Layered Double Hydroxide/Zeolite Hybrid Structure with a High Hydrogenation Efficiency

Carbon supported gold and silver: Application in the gas phase hydrogenation of m -dinitrobenzene

Removal of m-phenylene diamine by adsorption onto activated carbon: kinetics, equilibrium and process design

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