Hydrogenation of Aromatic Nitro Compounds to Amines on Nickel and Iron-Containing Catalysts

Sassykova, L.R.; Sassykova, A.R.; Kubekova, Sh. N.; Batyrbayeva, A.А.; Azhigulova, R. N.; Zhaxibayeva, Zh. M.; Kozhaisakova, M. A.; Zhusupova, L. A.; Sendilvelan, S.; Ponomarenko, O.I.

doi:10.31788/rjc.2021.1426124

Cited by 7 publications

(7 citation statements)

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“…X-ray photoelectron spectroscopy (XPS) measurements were carried out on Thermo Fisher ESCALAB 250Xi with an Al Kα source. 1 H and 13 C NMR spectra of TANP and TAP 3HCl•H 2 O were collected on a Bruker Ascend 600 MHz spectrometer. H 2 -TPR measurements were performed on a Micrometrics Autochem 2920 chemisorption instrument equipped with a thermal conductivity detector.…”

Section: Methodsmentioning

confidence: 99%

“…TAP•3HCl• H 2 O was purified by a recrystallization process in concentrated hydrochloric acid. The obtained products were determined to be of high purity by the 1 H and 13 C NMR spectra (Figures S3 and S4). The chromatographic column was ZORBAX SB-C18 and the volume ratio of methanol to water (0.04 mol L −1 NH 4 H 2 PO 4 and 0.08 mol L −1 tetrabutylammonium bromide) in the mobile phase was set to 40:60.…”

Section: Methodsmentioning

confidence: 99%

“…Selective hydrogenations of nitro compounds achieved by supported metal catalysts are widely used in the synthesis of amines as intermediates for fine chemicals and building blocks for high-performance polymers. − An important instance is the selective hydrogenation of nitroarenes to anilines, − which has been extensively studied in the past decades focusing on improving formations of target anilines over supported catalysts. − Although progress has been made in the hydrogenation of nitroarenes, investigations on the heterogeneous catalysts for the hydrogenation of nitropyridine to aminopyridine are rarely reported, which is significant for producing high-performance polymers. For example, Pd-catalyzed selective hydrogenation of 2,6-diamino-3,5-dinitropyridine (DADNP) is an important route for the production of 2,3,5,6-tetraaminopyridine (TAP), an essential monomer of poly(pyridobisimidazole) (PIPD) with excellent thermal and mechanical properties. − Designing advanced catalysts for the selective hydrogenation of DADNP is highly desirable for the production of PIPD, which necessitates a mechanistic understanding of the structure–performance relationships, yet it has not attracted attention so far.…”

Section: Introductionmentioning

confidence: 99%

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Size Dependence of Pd-Catalyzed Hydrogenation of 2,6-Diamino-3,5-dinitropyridine

Chen

Cao

et al. 2022

Ind. Eng. Chem. Res.

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An in-depth understanding of the effects of metal particle sizes on reactions is crucial for tailoring and designing catalysts. Herein, the Pd/CNT catalysts with different Pd particle sizes were prepared and employed to explore the size effects on the Pdcatalyzed hydrogenation of 2,6-diamino-3,5-dinitropyridine (DADNP). The apparent turnover frequencies for DADNP conversion and target 2,3,5,6-tetraaminopyridine (TAP) formation are found to exhibit strong dependence on the Pd particle sizes, indicating that the hydrogenation of DADNP to TAP is typically structure-sensitive. The size-insensitive activation energies extracted from the kinetics studies for DADNP conversion on ≥2.6 nmsized Pd catalysts with similar electronic properties suggest the presence of only one type of active site mainly dominating the reaction. Further combining model calculations based on the cuboctahedron shape for Pd nanoparticles characterized by electron microscopy, the (111) sites are demonstrated as the dominant active sites for DADNP conversion on the ≥2.6 nm-sized Pd catalysts. However, for the Pd catalyst size <2.6 nm, the reaction is shown to be mainly dominated by the Pd electronic properties.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Size Dependence of Pd-Catalyzed Hydrogenation of 2,6-Diamino-3,5-dinitropyridine

Chen

Cao

et al. 2022

Ind. Eng. Chem. Res.

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“…Magnetite-based nanomaterials are widely used as part of composite systems in medicine, biotechnology and engineering. In particular, catalysts based on nanosized magnetite have fast adsorption-desorption kinetics and high chemical activity [32][33][34][35]37,38,[47][48][49][50][51][52][56][57][58][59][60][61]. Due to its excellent physicochemical properties, iron oxide (Fe 3 O 4 ) has attracted much attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

Catalysts Based on Iron Oxides for Wastewater Purification from Phenolic Compounds: Synthesis, Physicochemical Analysis, Determination of Catalytic Activity

Dossumova,

Sassykova,

Shakiyeva

et al. 2024

ChemEngineering

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In this work, the synthesis of magnetite nanoparticles and catalysts based on it stabilized with silicon and aluminum oxides was carried out. It is revealed that the stabilization of the magnetite surface by using aluminum and silicon oxides leads to a decrease in the size of magnetite nanocrystals in nanocomposites (particle diameter less than ~10 nm). The catalytic activity of the obtained catalysts was evaluated during the oxidation reaction of phenol, pyrocatechin and cresol with oxygen. It is well known that phenolic compounds are among the most dangerous water pollutants. The effect of phenol concentration and the effect of temperature (303–333 K) on the rate of oxidation of phenol to Fe3O4/SiO2 has been studied. It has been determined that the dependence of the oxidation rate of phenol on the initial concentration of phenol in solution is described by a first-order equation. At temperatures of 303–313 K, incomplete absorption of the calculated amount of oxygen is observed, and the analysis data indicate the non-selective oxidation of phenol. Intermediate products, such as catechin, hydroquinone, formic acid, oxidation products, were found. The results of UV and IR spectroscopy showed that catalysts based on magnetite Fe3O4 are effective in the oxidation of phenol with oxygen. In the UV spectrum of the product in the wavelength range 190–1100 nm, there is an absorption band at a wavelength of 240–245 nm and a weak band at 430 nm, which is characteristic of benzoquinone. In the IR spectrum of the product, absorption bands were detected in the region of 1644 cm−1, which is characteristic of the oscillations of the C=O bonds of the carbonyl group of benzoquinone. The peaks also found at 1353 cm−1 and 1229 cm−1 may be due to vibrations of the C-H and C-C bonds of the quinone ring. It was found that among the synthesized catalysts, the Fe3O4/SiO2 catalyst demonstrated the greatest activity in the reaction of liquid-phase oxidation of phenol.

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“…This is due to the fact that iron is characterized by low cost, is widely distributed in soils, iron is non-toxic and has unique magnetic properties. Among the oxides of variable metals, iron oxides and their composites are used with great success [33][34][35][36][37][38][39][40]. They are used not only in the field of electronics, medicine, protection and purification of the environment from various pollutants such as phenol and its derivatives, but also due to their cheapness, good thermal stability, high specific surface area as heterogeneous catalysts in complete and partial oxidation reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Magnetic Composites and Testing of Their Activity in Liquid-phase Oxidation of Phenol with Oxygen

Dossumova¹,

Shakiyeva²,

Muktaly³

et al. 2022

Preprint

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The development and improvement of methods for the synthesis of environmentally friendly catalysts based on base metals is currently an urgent and promising task of modern catalysis. Catalysts based on nanoscale magnetite and maghemite have fast adsorption-desorption kinetics and high chemical activity. The purpose of this work was to obtain magnetic composites, determine their physicochemical characteristics and verify their activity in the process of liquid-phase oxidation of phenol with oxygen. Magnetic nanocomposites were obtained by chemical co-deposition of salts of ferrous and trivalent iron. The synthesized magnetic composites were studied by X-ray diffractometry, energy dispersive X-ray fluorescence and Mössbauer spectroscopy, IR-Fourier spectroscopy, elemental analysis. To increase the catalytic activity in oxidative processes, the magnetite surfaces were modified using cobalt nitrate salt. Further, CoFe2O4 was stabilized by adding polyethylenimine (PEI) as a surfactant. Preliminary studies of the oxidation of phenol with oxygen, as the most typical environmental pollutant were carried out on the obtained Fe3O4, CuFe2O4, CoFe2O4/PEI catalysts. The spectrum of the reaction product shows the presence of CH in the aromatic ring and double C=C bonds, stretching vibrations of the C=O groups of carbonyl compounds; the band at 3059 cm–1 corresponds to the presence of double C=C bonds, the band at 3424 cm–1 hydroquinone compounds. The band at 1678 cm–1 and the intense band at 1646 cm–1 refer to vibrations of the С=О bonds of the carbonyl group of benzoquinone. Peaks at 1366 cm–1 and 1310 cm–1 can be related to the vibrations of C–H and C–C bonds of the quinone ring. Thus it was demonstrated that produced magnetic composites based on iron oxide are quite effective in the oxidation of phenol with oxygen.

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Hydrogenation of Aromatic Nitro Compounds to Amines on Nickel and Iron-Containing Catalysts

Cited by 7 publications

References 0 publications

Size Dependence of Pd-Catalyzed Hydrogenation of 2,6-Diamino-3,5-dinitropyridine

Size Dependence of Pd-Catalyzed Hydrogenation of 2,6-Diamino-3,5-dinitropyridine

Catalysts Based on Iron Oxides for Wastewater Purification from Phenolic Compounds: Synthesis, Physicochemical Analysis, Determination of Catalytic Activity

Synthesis, Characterization of Magnetic Composites and Testing of Their Activity in Liquid-phase Oxidation of Phenol with Oxygen

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