Liquid phase hydrogenation of nitrobenzene

Turáková, Mária; Salmi, Tapio; Eränen, Kari; Wärnå, Johan; Murzin, Dmitry Yu.; Králik, Milan

doi:10.1016/j.apcata.2015.04.002

Cited by 80 publications

(65 citation statements)

References 43 publications

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“…44,45 According to the Balandin-type volcano plots, the moderate adsorption on metals is demanded for efficient catalytic conversion because a weak adsorption cannot effectively activate substrates and a strong adsorption precludes product desorption. 7b) would promote the adsorption of polar -N δ+ -O δbonds in NB, 42,46,47 as compared with the neutral Au on Ta 2 O 5 , which presents optimized activity and selectivity (Scheme 2). XPS in Fig.…”

Section: Nitrobenzene Hydrogenationmentioning

confidence: 99%

“…46,47 Negatively charged Au δover TaON resulting from electronic metal-support interactions 38,39 (c.f. 46 And thus, the reduced activity and AN selectivity are observed. 7b) would promote the adsorption of polar -N δ+ -O δbonds in NB, 42,46,47 as compared with the neutral Au on Ta 2 O 5 , which presents optimized activity and selectivity (Scheme 2).…”

Section: Nitrobenzene Hydrogenationmentioning

confidence: 99%

See 1 more Smart Citation

Controlled nitridation of tantalum (oxy)nitride nanoparticles towards optimized metal-support interactions with gold nanocatalysts

Yang

Shu

et al. 2015

RSC Adv.

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Graphic abstractOptimized metal-support interactions was achieved on ionothermally prepared tantalum (oxy)nitrides with controlled nitridation, and the as-formed Au δspecies promoted by TaON are efficient for nitrobenzene hydrogenation due to its moderated adsorption of substrates.The electron regulation on supports can vary metal-support interactions with loaded metals in heterogeneous catalysis. In this paper, a facile Sr 2+ -mediated ionothermal route was introduced to control the nitridation degree in tantalum (oxy)nitrides, resulting in varied electronic properties and optimized interactions with gold nanocatalysts. A new mechanism was proposed that the formation of SrTa4O11 intermediates facilitated the replacement of O by N in controlled nitridation, and more importantly avoided undesired over-nitridation. As expected, the TaON support with defined nitridation promoted electronic metal-support interactions to generate Au δspecies, which was highly active for the thermal hydrogenation of nitrobenzene due to the moderated adsorption and effective activation on Au δin Au/TaON. This work elucidated the optimized metal-support interactions achieved on controllably nitridated supports, opening up new opportunities for the development of efficient nanocatalysts.

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Section: Nitrobenzene Hydrogenationmentioning

confidence: 99%

Section: Nitrobenzene Hydrogenationmentioning

confidence: 99%

Controlled nitridation of tantalum (oxy)nitride nanoparticles towards optimized metal-support interactions with gold nanocatalysts

Yang

Shu

et al. 2015

RSC Adv.

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“…The catalyst may be present in one of the liquid phases (continuous or dispersed) which becomes the reaction phase. This is sometimes achieved using various chemical methods like use of a complex forming agent as in hydrogenation of benzene [1,2] or adjusting the pH of aqueous phase in the case of hydrogenation of cinnamaldehyde [3,4] . Due to these two characteristics a four phase system becomes sensitive to parameters like reaction conditions, hold up, mass transfer etc.…”

Section: Introductionmentioning

confidence: 99%

“…In four phase systems the desired product or intermediate is absorbed by the secondary phase where it may undergo a separate set of reactions that finally leads to higher selectivity. In some cases, the product is simply isolated in an immiscible solvent where it can be easily separated downstream [1,2,6] .…”

Section: Introductionmentioning

confidence: 99%

Modeling G-L-L-S Reactor: A Case of Hydrogenation of Nitrobenzene

Sharma

Patwardhan

Ranade

2017

Ind. Eng. Chem. Res.

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Gas–liquid–liquid–solid (GLLS) reaction systems are often encountered in manufacturing of fine and specialty chemicals. More often than not, such reaction systems involve multiple reactions, and selectivity toward the desired component always poses challenges. An adequate understanding of various parameters affecting GLLS reactor performance is essential to develop strategies for realizing desired selectivity. In this work, a comprehensive reaction engineering model for simulating four phase hydrogenation reactions has been developed. A generalized mixing cell based framework for a reaction system with four interacting phases (gas [G], aqueous [L], organic [L], and solid catalyst [S]) was developed. The model is written in a general way so as to specify one of the liquid phases as a continuous phase, and the other three phases are dispersed into it. In each cell, vapor space is included. The model includes the possibility of evaporation of solvent and internal condensation (in vapor space). The model can also be applied for a dead end (from a perspective of reacting gas) reactor. Model equations were solved using MATLAB. The equations and solution methodology were verified by comparing numerical solutions with available solutions of various limiting cases. A case of four phase hydrogenation of nitrobenzene to para amino phenol and aniline was considered to illustrate the application of the developed model. Key findings from the model were validated by comparing with laboratory scale experimental data. The model was then used to develop insights and guidelines for enhancing selectivity toward desired product. The developed model and presented results will be useful to develop general guidelines for design and optimization of GLLS reactors.

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“…It is widely accepted that the nitroarene hydrogenation has two possible reaction pathways: one is the direct route, and the other is the condensation route . The direct route assumes that nitrobenzene is reduced to nitrosobenzene, then to phenylhydroxylamine, and finally to aniline.…”

Section: Resultsmentioning

confidence: 99%

Poly(amic acid) salt‐mediated palladium and platinum nanoparticles as highly active and recyclable catalysts for hydrogenation of nitroarenes in water under ambient conditions

Wang

Jin

et al. 2018

Applied Organom Chemis

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Development of highly active and recyclable catalysts for selective hydrogenation of nitroarenes to amines in water at room temperature is always a challenge in chemical industry. This study reports a facile in situ method for synthesis of ultrafine palladium and platinum nanoparticles (NPs) stabilized by poly (amic acid) salt (PAAS) and their potential as catalysts for hydrogenation of nitroarenes with sodium borohydride or molecular hydrogen as reductant in water at room temperature. In the reduction of 4‐nitrophenol to 4‐aminophenol by sodium borohydride, the activity parameters of PdNPs–PAAS and PtNPs–PAAS catalyst is 6.66 × 103 and 5.58 × 103 s−1 M−1 respectively. In the hydrogenation of diverse nitroarenes under atmospheric hydrogen pressure, PdNPs–PAAS shows high activity but poor selectivity toward desired amines in some cases, while PtNPs–PAAS shows both high activity and high selectivity for selective hydrogenation of nitroarenes to corresponding anilines. The high efficiency of nanocatalyst is due to the quasi‐homogeneous dispersion of metal NPs and synergistic effects between metal NPs and PAAS. In addition, nanocatalyst can be easily recovered with pH‐sensibility of PAAS and reused at least six times without significant loss of catalytic activities.

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Liquid phase hydrogenation of nitrobenzene

Cited by 80 publications

References 43 publications

Controlled nitridation of tantalum (oxy)nitride nanoparticles towards optimized metal-support interactions with gold nanocatalysts

Controlled nitridation of tantalum (oxy)nitride nanoparticles towards optimized metal-support interactions with gold nanocatalysts

Modeling G-L-L-S Reactor: A Case of Hydrogenation of Nitrobenzene

Poly(amic acid) salt‐mediated palladium and platinum nanoparticles as highly active and recyclable catalysts for hydrogenation of nitroarenes in water under ambient conditions

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