Palladium nanoparticles supported on carbon nanoglobules as efficient catalysts for obtaining benzocaine via selective hydrogenation of ethyl 4-nitrobenzoate

Mironenko, Roman M.; Belskaya, O. B.; Gulyaeva, T. I.; Тренихин, М. В.; Лихолобов, В. А.

doi:10.1016/j.catcom.2018.06.002

Cited by 16 publications

(4 citation statements)

References 26 publications

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“…Catalyst supports, namely, multi-walled carbon nanotubes (MWCNTs) and nanoglobular carbons (carbon blacks) P278-E and T900, were characterized in previous works [45,46] and used in the present study for the preparation of Pd/C catalysts. The MWCNT support (S BET = 213 m 2 g −1 ) exhibited a fiber-like morphology, and according to FTIR spectroscopy, its surface was depleted of oxygen functional groups.…”

Section: Characterization Of Catalystsmentioning

confidence: 99%

“…For catalyst preparation, we used Baytubes ® C 150 HP MWCNTs (Bayer Material Science AG, Leverkusen, Germany) characterized earlier [45,46], as well as furnace and thermal kinds of nanoglobular carbon (carbon blacks) P278-E and T900 (Department of Experimental Technologies, Center of New Chemical Technologies BIC). Palladium(II) chloride (>98%, Aurat, Moscow, Russia) was used for catalyst preparation without any purification.…”

Section: Materials and Reagentsmentioning

confidence: 99%

“…The catalysts denoted as Pd-CCs/C (C = MWCNTs, P278-E, T900) were prepared by incipient wetness impregnation of the carbon supports with aqueous solutions of palladium CCs formed by dissolving PdCl 2 in water containing an equimolar amount of HCl. After deposition of Pd CCs on the supports, the samples were dried in air at room temperature and then at 393 K. Before the experiments, the catalysts were reduced in flowing hydrogen at 573 K for 2 h. Another procedure for catalyst preparation includes the adsorption of Pd PHCs onto carbon supports, as described in detail elsewhere [44,46]. A further reduction of supported Pd PHCs was performed in sodium formate solution at 363 K for 0.5 h. The catalysts obtained by this method were denoted as Pd-PHCs/C.…”

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

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Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Mironenko¹,

Saybulina²,

Степанова³

et al. 2021

Catalysts

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The hydrogenation of unsaturated double bonds with molecular hydrogen is an efficient atom-economic approach to the production of a wide range of fine chemicals. In contrast to a number of reducing reagents typically involved in organic synthesis, hydrogenation with H2 is much more sustainable since it does not produce wastes (i.e., reducing reagent residues). However, its full sustainable potential may be achieved only in the case of easily separable catalysts and high reaction selectivity. In this work, various Pd/C catalysts were used for the liquid-phase hydrogenation of O-, S-, and N-vinyl derivatives with molecular hydrogen under mild reaction conditions (room temperature, pressure of 1 MPa). Complete conversion and high hydrogenation selectivity (>99%) were achieved by adjusting the type of Pd/C catalyst. Thus, the proposed procedure can be used as a sustainable method for vinyl group transformation by hydrogenation reactions. The discovery of the stability of active vinyl functional groups conjugated with heteroatoms (O, S, and N) under hydrogenation conditions over Pd/C catalysts opens the way for many useful transformations.

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Section: Characterization Of Catalystsmentioning

confidence: 99%

Section: Materials and Reagentsmentioning

confidence: 99%

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

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Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Mironenko¹,

Saybulina²,

Степанова³

et al. 2021

Catalysts

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“…The issue is complicated in the case when hydrogenation of functional groups includes several reaction stages. Reduction of nitro‐groups is the most common example of such situation [27b,44] . Formation of several compounds, especially reactive ones, can give rise to increase of the quantity of products in geometric progression.…”

Section: Quality Control Of the Hydrogenation Catalystsmentioning

confidence: 99%

Advances and Challenges in Development of Transition Metal Catalysts for Heterogeneous Hydrogenation of Organic Compounds

Ivanytsya,

Subotin,

Gavrilenko

et al. 2023

The Chemical Record

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Actual problems of development of catalysts for hydrogenation of heterocyclic compounds by hydrogen are summarized and discussed. The scope of review covers composites of nanoparticles of platinum group metals and 3d metals for heterogeneous catalytic processes. Such problems include increase of catalyst activity, which is important for reduction of precious metals content; development of new catalytic systems which do not contain metals of platinum group or contain cheaper analogues of Pd; control of factors which make influence on the selectivity of the catalysts; achievement of high reproducibility of the catalyst‘s performance and quality control of the catalysts. Own results of the authors are also summarized and described. The catalysts were prepared by decomposition of Pd0 and Ni0 complexes, pyrolysis of Ni2+ and Co2+ complexes deposited on aerosil and reduction of Ni2+ in pores of porous support in situ. The developed catalysts were used for hydrogenation of multigram batches of heterocyclic compounds.

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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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Palladium nanoparticles supported on carbon nanoglobules as efficient catalysts for obtaining benzocaine via selective hydrogenation of ethyl 4-nitrobenzoate

Cited by 16 publications

References 26 publications

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Advances and Challenges in Development of Transition Metal Catalysts for Heterogeneous Hydrogenation of Organic Compounds

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

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