Polymer supported Nickel nanoparticles as recyclable catalyst for the reduction of nitroarenes to anilines in aqueous medium

Romanazzi, Giuseppe; Fiore, Ambra Maria; Mali, Matilda; Rizzuti, Antonino; Leonelli, Cristina; Nacci, Angelo; Mastrorilli, Piero; Dell’Anna, Maria Michela

doi:10.1016/j.mcat.2017.12.015

Cited by 64 publications

(26 citation statements)

References 87 publications

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“…The catalytic hydrogenation of nitroarenes (-NO 2 ) is one of the most important organic reactions for the preparation of amines (-NH 2 ), since they are used as intermediates or precursors in the synthesis of drugs, agrochemicals, dyes and other organic compounds [1][2][3][4][5]. The traditional methods for preparing these compounds involve the use of dangerous reducing agents and/or contaminants, such as N 2 H 4 , Na 2 S, silyl hydrides, in situ H 2 generation, among others [2,6].…”

Section: Introductionmentioning

confidence: 99%

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

et al. 2020

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In this work, Au nanoparticles, supported in Al2O3 nanowires (ANW) modified with (3-aminopropyl)trimethoxysilane were synthetized, for their use as catalysts in the hydrogenation reaction of 4-(2-fluoro-4-nitrophenyl)-morpholine and 4-(4-nitrophenyl)morpholin-3-one. ANW was obtained by hydrothermal techniques and the metal was incorporated by the reduction of the precursor with NaBH4 posterior to superficial modification. The catalysts were prepared at different metal loadings and were characterized by different techniques. The characterization revealed structured materials in the form of nanowires and a successful superficial modification. All catalysts show that Au is in a reduced state and the shape of the nanoparticles is spherical, with high metal dispersion and size distributions from 3.7 to 4.6 nm. The different systems supported in modified-ANW were active and selective in the hydrogenation reaction of both substrates, finding for all catalytic systems a selectivity of almost 100% to the aromatic amine. Catalytic data showed pseudo first-order kinetics with respect to the substrate for all experimental conditions used in this work. The solvent plays an important role in the activity and selectivity of the catalyst, where the highest efficiency and operational stability was achieved when ethanol was used as the solvent.

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Section: Introductionmentioning

confidence: 99%

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

et al. 2020

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“…For instance, it has been reported as a successful catalyst for promoting the steam reforming of ethanol [11], partial oxidation of methane to syngas [12], or urea electro-oxidation [13]. This is surprising because recent trends in research regarding the catalytic reaction with transition metals has focused on nickel [14][15][16][17][18]. It is an attractive metal for catalysis since it can adopt a flexible number of oxidation states, Ni(−I), Ni(0), Ni(I), Ni(II), Ni(III), Ni(IV), offering unique reactivity pathways [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Nickel Nanowires: Synthesis, Characterization and Application as Effective Catalysts for the Reduction of Nitroarenes

et al. 2018

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We have demonstrated a convenient method of synthesizing nickel nanowires (NiNWs), which could be easily tuned to produce materials with a carefully defined nanostructure. By varying the concentration of the Ni precursor, pH of the medium or reaction temperature, we directly affected the diameter of the formed product as well as the yield of the process. The obtained material consisted of straight bundles of NiNWs, which revealed powerful catalytic action for the reduction of nitroarenes to appropriate amine derivatives. A selection of substrates were employed and all of them were successfully converted into the corresponding aromatic amine despite the presence of different substituents on the aromatic ring with high yields, even in large scale reactions. The results showed that NiNW-based catalysts could constitute efficient catalytic systems for the synthesis of aryl amines at industrial levels.

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“…Therefore, many synthetic methods have been developed to achieve heterogeneous catalysts in which metal nanoparticles are loaded on various kinds of solid supports such as silica, organic polymers, zeolite, alumina, graphite oxide and magnetic nanoparticles. Moreover, appropriate pore size and relatively high surface area of such supports maintain their competitive advantages over others . Hydroxyapatite, with high surface area, adsorption capacity, ionic substitution ability, thermal and chemical stability and environment‐friendly nature, is a useful inorganic mesoporous solid material for engineering new functionalized heterogeneous catalysts .…”

Section: Introductionmentioning

confidence: 99%

Engineered mesoporous ionic‐modified γ‐Fe₂O₃@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water

Pashaei

Mehdipour

Azaroon

2018

Applied Organom Chemis

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A new mesoporous organic-inorganic nanocomposite was formulated and then used as stabilizer and support for the preparation of palladium nanoparticles (Pd NPs). The properties and structure of Pd NPs immobilized on prepared 1,4-diazabicyclo[2.2.2]octane (DABCO) chemically tagged on mesoporous γ-Fe 2 O 3 @hydroxyapatite (ionic modified (IM)-MHA) were investigated using various techniques. The synergistic effects of the combined properties of MHA, DABCO and Pd NPs, and catalytic activity of γ-Fe 2 O 3 @hydroxyapatite-DABCO-Pd (IM-MHA-Pd) were investigated for the Heck cross-coupling reaction in aqueous media. The appropriate surface area and pore size of mesoporous IM-MHA nanocomposite can provide a favourable hard template for immobilization of Pd NPs. The loading level of Pd in the nanocatalyst was 0.51 mmol g −1 . DABCO bonded to the MHA surface acts as a Pd NP stabilizer and can also lead to colloidal stability of the nanocomposite in aqueous solution. The results reveal that IM-MHA-Pd is highly efficient for coupling reactions of a wide range of aryl halides with olefins under green conditions. The superparamagnetic nature of the nanocomposite means that the catalyst to be easily separated from solution through magnetic decantation, and the catalytic activity of the recycled IM-MHA-Pd showed almost no appreciable loss even after six consecutive runs.KEYWORDS aqueous media, Heck coupling reaction, mesoporous ionic-modified γ-Fe 2 O 3 @hydroxyapatite, palladium nanoparticle, sustainable organometallic platform

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Polymer supported Nickel nanoparticles as recyclable catalyst for the reduction of nitroarenes to anilines in aqueous medium

Cited by 64 publications

References 87 publications

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Nickel Nanowires: Synthesis, Characterization and Application as Effective Catalysts for the Reduction of Nitroarenes

Engineered mesoporous ionic‐modified γ‐Fe₂O₃@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water

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Polymer supported Nickel nanoparticles as recyclable catalyst for the reduction of nitroarenes to anilines in aqueous medium

Cited by 64 publications

References 87 publications

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Nickel Nanowires: Synthesis, Characterization and Application as Effective Catalysts for the Reduction of Nitroarenes

Engineered mesoporous ionic‐modified γ‐Fe2O3@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water

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Engineered mesoporous ionic‐modified γ‐Fe₂O₃@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water