Rh promotional effects on Pt–Rh alloy catalysts for chemoselective hydrogenation of nitrobenzene to p-aminophenol

Yao, Sheng; Liu, Yang; Yin, Yuchen; Zou, Xingli; Ren, Jiaan; Wu, Baoqin; Wang, Xueguang; Lu, Xionggang

doi:10.1016/j.cej.2022.139448

Cited by 25 publications

(23 citation statements)

References 52 publications

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“…The intermediate PHA can be converted into PAP by acid-catalyzed Bamberger rearrangement, − and thus, the influence of acid concentration on the selectivity of PAP was examined. As shown in Figure d, the acid concentration ranged from 0 to 1.13 M under the standard reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported that the supported noble metal (Pt, Pd, Ru, and Au etc.) catalysts have been utilized for selective hydrogenation of NB to PAP. − Among them, Pt/C was widely used for catalytic hydrogenation of NB to PAP in terms of low loading (3–5% Pt), high reaction rate, and PAP selectivity. , The catalysts showed only moderate selectivity to PAP (60–80%) with the formation of a byproduct (AN). , Also, in the process of the hydrogenation reaction, the activated carbon particles could crack due to mechanical stirring, causing trouble for separation and recycles. As the reaction needed always liquid acids as additives to enhance the PAP selectivity, solid acids were sequentially employed in order to reduce the pollution caused by the liquid acids.…”

Section: Introductionmentioning

confidence: 99%

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Selective Hydrogenation of Nitrobenzene to para-Aminophenol on a Zirconium-Phosphate-Supported Platinum Catalyst

Zhang

Jiang

Dai

et al. 2023

Ind. Eng. Chem. Res.

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In this work, zirconium-phosphate-supported platinum catalysts have been prepared by a wetness impregnation method and characterized thoroughly by various methods. The 1% Pt/ZrP catalyst displayed superior catalytic performance for the selective hydrogenation of nitrobenzene. It was found that the formation rate of para-aminophenol was much higher than that of aniline over the catalyst in the presence of inorganic acid and DMSO. A full conversion of nitrobenzene and high selectivity to para-aminophenol (89%) were achieved under mild reaction conditions (80 °C, 0.6 MPa H 2 ). Also, the catalyst can be recycled in 14 consecutive catalytic runs without any obvious decrease in activity and selectivity for the hydrogenation of nitrobenzene. The electron transfer interaction of Pt(0) species with zirconium phosphate accounted for the high dispersion and leaching resistance of the Pt sites, leading to excellent recyclability of the catalysts. The further characterization by in situ DRIFT demonstrated that the nitro functional group was dominantly adsorbed on acid sites of zirconium phosphate and reduced to N-phenylhydroxylamine by spillover hydrogen, followed by rearrangement to afford paraaminophenol.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Nitrobenzene to para-Aminophenol on a Zirconium-Phosphate-Supported Platinum Catalyst

Zhang

Jiang

Dai

et al. 2023

Ind. Eng. Chem. Res.

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“…Contrasting previous work focusing on catalysts for the catalytic hydrogenation and acid-catalyzed Bamberger rearrangement of NB to PAP, − this work uncovers that the dual-shield structure of the thermocatalyst on the nanoscale, with the unique architecture of dual-shield, is vital for the establishment of high-activity nanocatalysts. The exclusive dual-shield and electron-rich surface have a significant influence on the catalyst surface performance, containing hydrophilicity, adsorption capacity, cycling stability, and so forth, which decides the catalytic performance.…”

Section: Resultsmentioning

confidence: 99%

“…p -Aminophenol (PAP) is a remarkable intermediate for the synthesis of paracetamol drugs, dyestuffs, and photographic developer. − Several methods for instance the cyclization–aromatization of enamines, reduction of p -nitrophenol, and Beckmann rearrangement of p -hydroxyacetophenone oxime, have been developed for the preparation of PAP. − However, the synthesis of PAP involves the multireaction coupling of selective catalytic hydrogenation and acid-catalyzed Bamberger rearrangement in an extreme reaction environment, which poses a serious challenge for metal catalysts. Moreover, these multistep processes have some drawbacks: weak process efficiency, the difficulty in the disposing of the pollutant emissions, and low product quality, which could not meet the strategies of green development.…”

Section: Introductionmentioning

confidence: 99%

Shield Effect in Palladium@Graphene with Stability in Strong Acid and Sluggish H-Dissociation for Robust Coupling Hydrogenation–Bamberger Rearrangement of Nitrobenzene

Yin,

Xiang,

Yao

et al. 2023

ACS Catal.

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The inferior stability of noble metal-based thermocatalysts for effective catalytic hydrogenation reaction severely restricts the production of value-added fine chemicals under a strong acid reaction environment. Herein, a shield effect strategy is proposed to establish ultrafine metal NPs with oxidation layers encapsulated in S- and N-doped graphene with stability for robust coupling-efficient catalytic hydrogenation and acid-catalyzed Bamberger rearrangement of nitrobenzene to p-aminophenol. The unconventional structure based on shield effect comprises an oxide layer with dislocation and tensile strain, enabling sluggish dissociation of H2 to H*, coupled with a local electron-enriched S,N-doped graphene shell, restraining the ultrafast hydrogenation rate to form aniline and enhancing the stability of the catalyst. In addition, the experimental characterization and density functional theory simulation further manifest that the oxidizing effect of nitric acid reconstitutes the charge of the graphene shell, rendering it highly specific for phenylhydroxylamine rearrangement to obtain p-aminophenol with high selectivity. The proposed strategy in this work showcases a universal and practicable method for pinpoint modulation of the inherent performance of attainable metal nanoparticles with a programmable graphene shell microenvironment toward highly specific catalysis under the strong acid reaction environment.

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“…Pt–Rh-based materials have attracted a great deal of attention in the last years due to their wide range of catalytic applications, including the preferential oxidation of CO in hydrogen, , the control of NO x and CO emissions from car exhaust, the hydrogen evolution reaction, formic acid oxidation, , and the hydrogenation of organic compounds, , among others. Furthermore, Pt–Rh-based materials have been explored as catalysts for proton exchange membrane fuel cells (PEMFCs), both in the cathode and in the anode, where they have been investigated for the oxidation of methanol , and ethanol − or as CO-tolerant hydrogen oxidation reaction (HOR) catalysts. , …”

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confidence: 99%

Electrochemical Stability of Rhodium–Platinum Core–Shell Nanoparticles: An Identical Location Scanning Transmission Electron Microscopy Study

Vega-Paredes,

Aymerich-Armengol,

Arenas Esteban

et al. 2023

ACS Nano

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Rhodium–platinum core–shell nanoparticles on a carbon support (Rh@Pt/C NPs) are promising candidates as anode catalysts for polymer electrolyte membrane fuel cells. However, their electrochemical stability needs to be further explored for successful application in commercial fuel cells. Here we employ identical location scanning transmission electron microscopy to track the morphological and compositional changes of Rh@Pt/C NPs during potential cycling (10 000 cycles, 0.06–0.8 VRHE, 0.5 H2SO4) down to the atomic level, which are then used for understanding the current evolution occurring during the potential cycles. Our results reveal a high stability of the Rh@Pt/C system and point toward particle detachment from the carbon support as the main degradation mechanism.

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Rh promotional effects on Pt–Rh alloy catalysts for chemoselective hydrogenation of nitrobenzene to p-aminophenol

Cited by 25 publications

References 52 publications

Selective Hydrogenation of Nitrobenzene to para-Aminophenol on a Zirconium-Phosphate-Supported Platinum Catalyst

Selective Hydrogenation of Nitrobenzene to para-Aminophenol on a Zirconium-Phosphate-Supported Platinum Catalyst

Shield Effect in Palladium@Graphene with Stability in Strong Acid and Sluggish H-Dissociation for Robust Coupling Hydrogenation–Bamberger Rearrangement of Nitrobenzene

Electrochemical Stability of Rhodium–Platinum Core–Shell Nanoparticles: An Identical Location Scanning Transmission Electron Microscopy Study

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