Palladium Supported on Carbon Nanoglobules as a Promising Catalyst for Selective Hydrogenation of Nitroarenes

Mironenko, Roman M.; Belskaya, O. B.; Степанова, Л. Н.; Gulyaeva, T. I.; Тренихин, М. В.; Likholobov, V. A.

doi:10.1007/s10562-019-02974-6

Cited by 15 publications

(14 citation statements)

References 60 publications

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“…While the Pd/C catalyst yielded the 98.7% conversion after 3 h under the optimized reaction conditions (Figure 2b). To further evaluate their intrinsic catalytic activity, the turnover frequency (TOF) values based on each exposed Pd atom were calculated by the Equations (S1) and (S2) [20]. The TOF value of Pd/CoFe-LDHs is 1706 h −1 , which is 1.8 times higher than that of Pd/C (962 h −1 , Figure 2c).…”

Section: Resultsmentioning

confidence: 99%

Electron-Enriched Pd Nanoparticles for Selective Hydrogenation of Halonitrobenzenes to Haloanilines

Liang

Zhang

et al. 2021

Catalysts

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Selective hydrogenation of halonitrobenzenes into haloanilines represents a green process to replace the environmentally unfriendly non-catalytic chemical reduction process in industry. However, this transformation often suffers from serious dehalogenation due to the easy break of carbon-halogen bonds on metal surfaces. Modulations of the electronic structure of the supported Pd nanoparticles on Lewis-basic layered double hydroxides have been demonstrated to promote catalytic activity and selectivity for hydrogenation of halonitrobenzenes into haloanilines. Mechanism studies suggest that Pd with the enhanced electron density not only improves the capability for hydrogen activation, but also generates the partially negative-charged hydrogen species to suppress the electrophilic attack on the carbon-halogen bond and avoid the dehalogenation.

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Section: Resultsmentioning

confidence: 99%

Electron-Enriched Pd Nanoparticles for Selective Hydrogenation of Halonitrobenzenes to Haloanilines

Liang

Zhang

et al. 2021

Catalysts

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“…Catalytic experiments were performed using a Miniclave drive (Büchi AG) batch‐type reactor (see Figure S1 in Supporting Information) [43] . Initially, the reactor was loaded with reduced catalyst and a solution of vinyl derivative (9‐VC in benzene, BVE and DVS in aqueous ethanol).…”

Section: Methodsmentioning

confidence: 99%

“…TEM images of the fresh and spent catalyst samples were taken by a JEM‐2100 (JEOL) instrument with a lattice resolution of 0.145 nm. The average size of Pd nanoparticles (NPs) was determined by measuring the size of more than 150 NPs, as described elsewhere [39,43] …”

Section: Methodsmentioning

confidence: 99%

“…The conventional approach for testing metal catalyst reusability in liquid‐phase heterogeneous reactions includes catalyst separation (CS) from the reaction mixture using a standard protocol: centrifugation/filtration→washing→drying [20–24] . Then, the used catalyst is utilized again in the next run (cycle) of the catalytic reaction (Figure 1, top).…”

Section: Introductionmentioning

confidence: 99%

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Comparing Separation vs. Fresh Start to Assess Reusability of Pd/C Catalyst in Liquid‐Phase Hydrogenation

Mironenko¹,

Saybulina²,

Тренихин³

et al. 2021

ChemCatChem

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The reusability of metal catalysts is a key issue for the potential application of new catalysts in research and industrial practice. The most common procedure for testing catalyst reusability in liquid‐phase heterogeneous reactions is based on separating a catalyst from a reaction mixture followed by the next run. An alternative procedure called “fresh start” consists of the addition of a new portion of reagents to the reaction mixture without any isolation operation. In this work, we compare both procedures in a model Pd/C‐catalyzed hydrogenation with different heteroatoms, e. g., O‐, S‐, and N‐vinyl derivatives. It was shown that regardless of whether the catalyst is stable or potentially poisoned during the reaction, both procedures lead to comparable results. It appears that a much easier implementation of a fresh start procedure may be an option of choice. The possibilities of using both procedures to rationalize the experimental protocol for assessing Pd/C catalyst reusability in liquid‐phase hydrogenations are discussed.

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“…Catalytic hydrogenation reactions have drawn the attention of many researchers due to their wide applications in the synthesis of chemicals and pharmaceuticals. , Selectively reducing nitro compounds to amines is of great commercial importance, as amines can be the intermediates for the manufacture of pharmaceuticals, fine chemicals, dyes, herbicides, and chelating agents. , Many metal-based catalysts with good activity and durability have been developed to catalyze the hydrogenation of nitroarenes. − Recently, metal-free catalysts attracted great attention in the area of hydrogenation as a cost-effective and environmental-friendly route.…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Chemoselective Hydrogenation of Nitroarenes by N-Doped Carbon Nanotubes via In Situ Polymerization of Pyrrole

Zheng

Wang

et al. 2020

ACS Omega

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Chemoselective hydrogenation of nitroarenes to anilines is of great importance for the manufacture of pharmaceuticals, fine chemicals, and dyes. In this study, a series of metal-free N-doped carbon nanotubes (NCNTs) have been prepared by the carbonization of in situ polymerized pyrrole on CNTs. The concentration of pyrrole, pyrolysis temperature, and the outside diameter of CNTs were investigated to improve the catalytic performance. As characterized by Raman and X-ray photoelectron spectroscopy (XPS), the optimal catalyst (NCNTs-800) possessed a unique structure doped with the same content of pyrrolic N and graphitic N. The activity and selectivity of NCNTs-800 have been evaluated for the selective hydrogenation of substituted nitroarenes. Highly selective hydrogenation of the nitro group of 12 different substrates has been achieved on NCNTs-800, even in the presence of a fragile iodo group. The hydrogenation reaction on N-doped CNTs from polypyrrole involved a mixture of different hydrogen species including nonpolar H radicals. In addition, stability and recyclability of NCNTs-800 have been tested.

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Palladium Supported on Carbon Nanoglobules as a Promising Catalyst for Selective Hydrogenation of Nitroarenes

Cited by 15 publications

References 60 publications

Electron-Enriched Pd Nanoparticles for Selective Hydrogenation of Halonitrobenzenes to Haloanilines

Electron-Enriched Pd Nanoparticles for Selective Hydrogenation of Halonitrobenzenes to Haloanilines

Comparing Separation vs. Fresh Start to Assess Reusability of Pd/C Catalyst in Liquid‐Phase Hydrogenation

Metal-Free Chemoselective Hydrogenation of Nitroarenes by N-Doped Carbon Nanotubes via In Situ Polymerization of Pyrrole

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