Low-temperature catalytic oxidation of aniline to azoxybenzene over an Ag/Fe2O3 nanoparticle catalyst using H2O2 as an oxidant

Paul, Bappi; Sharma, Sachin Kumar; Adak, Shubhadeep; Khatun, Rubina; Singh, Gurmeet; Das, Dipak K.; Joshi, Vedant; Bhandari, Sahil; Dhar, Siddhartha Sankar; Bal, Rajaram

doi:10.1039/c9nj01085h

Cited by 18 publications

(7 citation statements)

References 36 publications

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“…The miscibility and solubility of the reaction components are the substantial factors that promote the oxidation systems. [ 32,34,69 ] The poor solubility of the reactant (aniline) in water (high polar solvent) could inhibit the catalytic potential of CuLAn 2 using either H 2 O 2 or t BuOOH.…”

Section: Resultsmentioning

confidence: 99%

“…[ 33 ] The most effective and selective oxidant for aniline oxidation was aqueous hydrogen peroxide, a highly eco‐friendly oxidizing agent. [ 34 ] Till now, the catalytic oxidation of aminopyridines has not been reported in literature, which may be because of their high toxicity. Only one attempt was made electrochemically by Goyal and Kumar.…”

Section: Introductionmentioning

confidence: 99%

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Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Adam

Al‐Omair

2020

Applied Organom Chemis

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Bis‐imino Cu(II) complex (CuLAn2), in which the imine ligand (HLAn) acts as a bidentate chelating ligand, was synthesized. The catalytic potential of the inorganic‐organocatalyst was studied homogeneously and heterogeneously in the oxidation of aniline and 2‐aminopyridine by H2O2 or tBuOOH. Two heterogeneous inorganic‐organocatalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were synthesized by the successful immobilization of CuLAn2 on the Fe3O4 surface and the composited Fe3O4 with SiO2, respectively. The heterogeneous structure of those inorganic‐organocatalysts was confirmed using Fourier‐transform infrared, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, X‐ray diffraction, transmission electron microscopy, and magnetic properties. The adsorption–desorption isotherms revealed respectable adsorption parameters (SBET, Vp, and rp). All catalysts exhibited high potential in the oxidation of aniline (with phenylhydroxylamine as the main product) and good potential in the oxidation of 2‐aminopyridine, in the first attempt (with 2‐nitropyridine‐N‐oxide and 2‐nitrosopyridine‐N‐oxide as main products), at room temperature. Acetonitrile was found to be the best solvent compared to ethanol, dimethyl sulfoxide, chloroform, and water. The homogeneous catalyst exhibited reusability for three times. The heterogeneous catalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were active for five and seven times, respectively. A mechanism was proposed within electron and oxygen transfer processes.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Adam

Al‐Omair

2020

Applied Organom Chemis

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“…It is noteworthy that the conversion was completed with a considerable turnover of ~592 (Scheme 12). [38] Azoxybenzene was eventually synthesised from phenylamine and nitrobenzene. Notably, in both cycles, catalyst regeneration was observed (Scheme 13).…”

Section: Nanoparticle Mediated Synthesis Of Symmetrical Azoxybenzenesmentioning

confidence: 99%

Sustainable Synthesis of N−N Bond Bearing Organic Frameworks by Advanced Heterogeneous Metal Catalysis

Panjacharam,

Rajasekhara Reddy

2023

Eur J Org Chem

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The most significant task in synthetic organic chemistry is developing organic reactions from a green and sustainable perspective. In these ways, heterogeneous catalysts are essential in many organic reactions. Thus, this study focuses on the synthesis of N−N bond bearing organic frameworks, particularly aromatic azo compounds and indazoles, using a heterogeneous metal catalyst. Organic molecules containing nitrogen‐nitrogen bonds are greatly sought after in the synthesis of dyes, photochemical switches, food additives, and bioactive chemicals due to industry and human requirements. Finally, this review provides an overview of synthetic routes for the formation of N−N bonds by using various heterogeneous metal catalytic systems.

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“…Since the past few years, our group has been dedicated to the selective catalytic oxidation of aniline to azoxybenzene using several nanostructured catalysts, – but all the reports dealt with H 2 O 2 as an oxidant. The use of H 2 O 2 or TBHP, stoichiometric reagents, or the need of strong oxidants is concerned with high cost, corrosion, and environmental issues.…”

Section: Introductionmentioning

confidence: 99%

SiO₂-Encapsulated Ag/WO₃ Nano-architectures for Azoxybenzene Production via Simultaneous Activation of Aniline and Molecular O₂

Ghosh,

Sharma,

Rana

et al. 2023

ACS Appl. Nano Mater.

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Nanocomposites Ag/WO3 intercalated within the channels of the silica network have been developed using a surfactant-assisted hydrothermal process. Structural and morphological studies indicated that the material exhibited two-dimensional type enchiladas-like nanoarchitectures. Higher-resolution electron microscopy results demonstrated that twinned Ag nanoparticles supported on WO3 units were embedded within the stacked layers of silica without agglomerating. This unique morphology led to higher dispersion of the Ag/WO3 framework that compelled the availability of more exposed surface-active Ag(111) sites, which triggered the activation of molecular O2 in furnishing a high yield of azoxybenzene, and this phenomenon has been explained in the light of DFT.

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Low-temperature catalytic oxidation of aniline to azoxybenzene over an Ag/Fe₂O₃ nanoparticle catalyst using H₂O₂ as an oxidant

Abstract: Highly dispersed Ag-supported α-Fe2O3 is found to be a recyclable and efficient catalyst for one-pot conversion of aniline to azoxybenzene.

Cited by 18 publications

References 36 publications

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Sustainable Synthesis of N−N Bond Bearing Organic Frameworks by Advanced Heterogeneous Metal Catalysis

SiO₂-Encapsulated Ag/WO₃ Nano-architectures for Azoxybenzene Production via Simultaneous Activation of Aniline and Molecular O₂

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Low-temperature catalytic oxidation of aniline to azoxybenzene over an Ag/Fe2O3 nanoparticle catalyst using H2O2 as an oxidant

Abstract: Highly dispersed Ag-supported α-Fe2O3 is found to be a recyclable and efficient catalyst for one-pot conversion of aniline to azoxybenzene.

Cited by 18 publications

References 36 publications

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO2‐ and Fe3O4 nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO2‐ and Fe3O4 nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Sustainable Synthesis of N−N Bond Bearing Organic Frameworks by Advanced Heterogeneous Metal Catalysis

SiO2-Encapsulated Ag/WO3 Nano-architectures for Azoxybenzene Production via Simultaneous Activation of Aniline and Molecular O2

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Low-temperature catalytic oxidation of aniline to azoxybenzene over an Ag/Fe₂O₃ nanoparticle catalyst using H₂O₂ as an oxidant

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

SiO₂-Encapsulated Ag/WO₃ Nano-architectures for Azoxybenzene Production via Simultaneous Activation of Aniline and Molecular O₂