Oxidation of Aniline to Nitrobenzene Catalysed by 1-Butyl-3-methyl imidazolium phosphotungstate Hybrid Material Using m-chloroperbenzoic Acid as an Oxidant

Meenakshi, R.; Shakeela, K.; Rani, S. Kutti; Rao, G. Ranga

doi:10.1007/s10562-017-2214-2

Cited by 26 publications

(29 citation statements)

References 44 publications

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“…From the results in Table 3 and Figure 10a–c, phenylhydroxylamine (as the main and chemoselective product), nitrobenzene, azoxybenzene, nitrosoaniline, and azobenzene are the most well‐defined products by GC/MS. [ 27–30 ] This shows that the oxidation reaction will not yield the desired product in the absence of the oxidant.…”

Section: Resultsmentioning

confidence: 99%

“…Products synthesized by selective aniline oxidation have gained much attention as pivotal industrial intermediates in the organic synthesis (e.g., nitrobenzene, nitrosobenzene, azobenzene, phenylhydroxylamine, and azoxybenzene). [ 29 ] Such organic reactions are catalyzed by alternative catalysts, such as heterogeneous metal oxides, [ 29,30 ] widely, and homogeneous inorganic‐organocatalysts, rarely. [ 31 ] Due to the low selectivity of the catalytic aniline oxidation, the chemoselective product could be determined according to the reaction conditions and the type of the catalyst and solvent used.…”

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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“…Ranga Rao et al used methyl imidazolium phosphotungstate as a catalyst for selective oxidation of aniline to nitrobenzene using m -MCPBA as an oxidant. 21 These catalysts have a drawback in terms of either poor selectivity or the cost of the catalysts used. The use of a greener and safer oxidant like H 2 O 2 or oxygen is an advantage.…”

Section: Introductionmentioning

confidence: 99%

Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid

2019

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Development of novel and greener methods for the selective oxidation of various organic compounds is a challenging task. Herein, a novel protocol for the selective oxidation of aromatic amines to nitroaromatics at room temperature is developed. The oxidation reaction was carried out using a mixture of formic acid and aqueous hydrogen peroxide, which resulted in the in situ formation of performic acid. Further, improvement of selectivity was studied using different surfactants, of which cetyltrimethylammonium bromide (CTAB) gave the highest selectivity (85%) toward nitrobenzene. The role of CTAB in achieving higher selectivity is discussed. Under optimized reaction conditions, various substituted amines were successfully oxidized to corresponding nitro compounds. It is worth mentioning that this is the first report on oxidation of amines to nitro compounds in an aqueous medium with high selectivity.

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“…Inorganic‐organic hybrid materials containing polyoxometalates (POMs) have been explored for various applications including heterogeneous catalysis, photocatalysis, sensing and electrochemistry . Ferrocene is an iron containing metallocene Fe(C 5 H 5 ) 2 that shows excellent redox activity due to Fe 2+ /Fe 3+ redox couple .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photocatalytic Study of Ferrocenium Ion Incorporated Lacunary Keggin Hybrid Material

Guru

Rao

2019

ChemistrySelect

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Oxidation of Aniline to Nitrobenzene Catalysed by 1-Butyl-3-methyl imidazolium phosphotungstate Hybrid Material Using m-chloroperbenzoic Acid as an Oxidant

Cited by 26 publications

References 44 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

Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid

Synthesis and Photocatalytic Study of Ferrocenium Ion Incorporated Lacunary Keggin Hybrid Material

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Oxidation of Aniline to Nitrobenzene Catalysed by 1-Butyl-3-methyl imidazolium phosphotungstate Hybrid Material Using m-chloroperbenzoic Acid as an Oxidant

Cited by 26 publications

References 44 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

Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid

Synthesis and Photocatalytic Study of Ferrocenium Ion Incorporated Lacunary Keggin Hybrid Material

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Product

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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

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