Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides

Gogoi, Prasanta; Hazarika, Sukanya; Barman, Pranjit

doi:10.1039/c5ra04573h

Cited by 7 publications

(2 citation statements)

References 24 publications

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“…Given their selective sulfoxidation activity in solution, many studies have explored systems containing bromine (Br y ) and nitrogen oxide (NO x ) species. [21][22][23][24] More recently, this type of system was proven effective for sulfoxidation of the HD simulant, 2-chloroethyl ethyl sulfide (CEES), in acetonitrile. [25][26][27] However, despite promising results, (a) solid formulations of these oxidation catalysts to enable practical applications are unknown, (b) fundamental aspects of the complicated mechanism have eluded researchers, and (c) live agent (HD) studies are lacking.…”

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confidence: 99%

A solvent-free solid catalyst for the selective and color-indicating ambient-air removal of sulfur mustard

et al. 2021

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Bis(2-chloroethyl) sulfide or sulfur mustard (HD) is one of the highest-tonnage chemical warfare agents and one that is highly persistent in the environment. For decontamination, selective oxidation of HD to the substantially less toxic sulfoxide is crucial. We report here a solvent-free, solid, robust catalyst comprising hydrophobic salts of tribromide and nitrate, copper(II) nitrate hydrate, and a solid acid (NafionTM) for selective sulfoxidation using only ambient air at room temperature. This system rapidly removes HD as a neat liquid or a vapor. The mechanisms of these aerobic decontamination reactions are complex, and studies confirm reversible formation of a key intermediate, the bromosulfonium ion, and the role of Cu(II). The latter increases the rate four-fold by increasing the equilibrium concentration of bromosulfonium during turnover. Cu(II) also provides a colorimetric detection capability. Without HD, the solid is green, and with HD, it is brown. Bromine K-edge XANES and EXAFS studies confirm regeneration of tribromide under catalytic conditions. Diffuse reflectance infrared Fourier transform spectroscopy shows absorption of HD vapor and selective conversion to the desired sulfoxide, HDO, at the gas–solid interface.

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confidence: 99%

A solvent-free solid catalyst for the selective and color-indicating ambient-air removal of sulfur mustard

et al. 2021

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“…[1][2][3][4][5][6] In addition, they are also used as efficient catalysts for the oxidation of some organic substrates such as alcohols, 7 aldehydes, 8 and sulfides, 9,10 trimethylsilylation 11,12 or tetrahydropyranylation 13 of alcohols, α-thiocyanation 14 or thioacetalization 15 of ketones, and the synthesis of heterocyclic rings. 16 Typical organic tribromides include tetrabutylammonium tribromide (TBATB), 2,9 pyridinium hydrotribromide (PyHTB), [4][5][6]14 benzyltrimethylammonium tribromide (BTMATB), 7 2-carboxyethyltriphenylphosphonium tribromide (CTPTB) 11 and benzyltriphenylphosphonium tribromide. 13,15 These reagents have attracted considerable attention in organic synthesis and have proven to be leaders over liquid bromine such as N-bromosuccinimide (NBS), Br 2 /HBr and other conventional bromination reagents due to their ease of use, mildness, efficiency and selectivity.…”

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confidence: 99%

Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Tabari

Pourali

Zare

2022

ACSi

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In this research, a novel magnetic nanocatalyst based on iron oxide nanoparticles linked with pyridinium hydrotribromide (Fe3O4@PyHBr3) was synthesized in three steps. In the first step, 3-(aminopropyl)triethoxysilane (APTES) was reacted with 4-(bromomethyl)pyridine hydrobromide. In the second step, the product obtained in the first step was reacted with iron oxide nanoparticles. In the last step, a grinding reaction was carried out with KBr and HIO4 in a mortar. The Fe3O4@PyHBr3 nanocatalyst was characterized by FT-IR, CHN, XRD, SEM, TGA and VSM analysis. The magnetic nanocatalyst was used as a catalyst for the selective oxidation of alcohols to aldehydes and ketones using 30% H2O2 as oxidant in a short time and with high yields. Moreover, no overoxidation of the alcohols was observed. The nanocatalyst was efficiently recycled in five consecutive cycles without significant loss of its catalytic activity. Moreover, trimethylsilylation and tetrahydropyranylation of alcohols were carried out in the presence of this nanocatalyst.

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Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds

Sharghi

Aboonajmi

Mozaffari

et al. 2017

Applied Organom Chemis

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Iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one‐pot synthesis of heterocyclic compounds including bis‐spiro piperidines, piperidines, dihydro‐2‐oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X‐ray diffraction (XRD), inductively coupled plasma (ICP) and FT‐IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT‐IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.

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Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides

Abstract: We report here tetrabutylammonium tribromide supported on MCM-48 as a highly efficient heterogeneous catalyst for the selective oxidation of sulfides, in ethanolic medium using hydrogen peroxide as an oxidant.

Cited by 7 publications

References 24 publications

A solvent-free solid catalyst for the selective and color-indicating ambient-air removal of sulfur mustard

A solvent-free solid catalyst for the selective and color-indicating ambient-air removal of sulfur mustard

Magnetic Nanoparticles Linked to Pyridinium Hydrotribromide Groups as Catalysts for Selective Oxidation of Alcohols and Protection of Alcohols

Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds

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