Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

Hosseini, Seyed Hossein; Tavakolizadeh, Maryam; Zohreh, Nasrin; Soleyman, Rouhollah

doi:10.1002/aoc.3953

Cited by 12 publications

(5 citation statements)

References 63 publications

(30 reference statements)

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“…Likewise, uniform distribution of the O, C, N, and W in the CQDs@DDA-IL/W mapping images can be seen (Figure S2B). ,,− Finally, the results of these two analyses are in close overlap with each other and with FT-IR, NMR, and XPS observations.…”

Section: Resultssupporting

confidence: 63%

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Mohammadi

Rezaei

Khazaei

et al. 2019

ACS Appl. Mater. Interfaces

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Achieving green and sustainable chemical processes by replacing organic solvents with water has always been one of the green chemistry goals and a challenging topic for chemists. However, the poor solubility of organic materials is a major limitation to achieving this goal, especially in alcohol oxidation. In this contribution, the development and design of amphiphilic catalysts via abundant, safe, cheaper, and more biocompatible sources have received notable attention. To this purpose, herein, our group successfully synthesized a new multifunctional amphiphilic carbon quantum dot (CQD) composed of 1-aminopropyl-3-methyl-imidazolium chloride ([APMim][Cl]), dodecylamine (DDA), and citric acid (CA) (denoted as CQDs@DDA-IL/Cl) using a one-pot hydrothermal route. The CQDs@DDA-IL/Cl was then utilized as an amphiphilic stabilizer for anchoring tungsten ions using an anion-exchange method (marked as CQDs@DDA-IL/W). The CQDs@DDA-IL/W as a reusable catalyst selectivity mediated the oxidation of alcoholic substrates with stoichiometric H2O2 in water solvent. The extraordinary performance of our catalyst was attributable to the coexistence of ionic liquid (IL) and DDA upon the surface of the CQDs@DDA-IL/W, which plays a main duty in the hydrophobic/hydrophilic balance, and significantly increase the catalyst compatibility in the aqueous medium with the purpose of removing organic solvents. As a result, the great mass transfer occurs in the two-phase medium using this amphiphilic nanocatalyst without any phase transfer catalyst (PTC) or other additives. The 100% selectivity, excellent turnover number (TON) and turnover frequency (TOF), high yield, almost complete and fast conversion of alcohol to the desired aldehydes and ketones without more oxidation, and easy and no-trouble isolation of product and catalyst are outstanding features of this catalytic system.

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Section: Resultssupporting

confidence: 63%

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Mohammadi

Rezaei

Khazaei

et al. 2019

ACS Appl. Mater. Interfaces

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“…Unfortunately, these reagents not only are toxic and expensive, but they also generate a high volume of reduced residues of heavy metals . From an economic and environmental standpoint, these restrictions encourage chemists to replace them with green oxidants such as molecular oxygen (O 2 ) and hydrogen peroxide (H 2 O 2 ), because these oxidants are available, inexpensive, atom-efficient, safe, and produce water as the only byproduct. , Based on the above considerations, the use of H 2 O 2 as a green oxidant along with immobilization (heterogenization) of catalytically active species onto the solid supports, is an effective method for alleviating the aforementioned problems in the oxidation reactions. − Among catalytically active species, tungsten-based ones, because of their excellent performance for activation of H 2 O 2 and among the various supports used for immobilization of WO 4 2– species, ionic-liquid-functionalized or modified ones have been considerably interested in various oxidation reactions. − The successful and high loading of anions on the support surface through electrostatic interactions, increase the thermal stability of a catalyst and minimizing the leaching of tungsten ions to the reaction vessels or goal product structure are the highlight features of this technique. , Despite all these advantages, the design of environmentally benign catalysts through simple and one-step synthetic methods, using inexpensive, available, and Earth-abundant sources for oxidation of alcohols is still a challenging issue for researchers.…”

Section: Introductionmentioning

confidence: 99%

Ionic-Liquid-Modified Carbon Quantum Dots as a Support for the Immobilization of Tungstate Ions (WO₄^2–): Heterogeneous Nanocatalysts for the Oxidation of Alcohols in Water

Mohammadi

Khazaei

Rezaei

et al. 2019

ACS Sustainable Chem. Eng.

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An effective heterogeneous nanocatalyst was successfully designed by immobilization of tungstate ions (WO 4 2− ) onto the modified surface of carbon quantum dots (CQDs) with the 1-aminopropyl-3-methyl-imidazolium chloride ([APMim][Cl]). In this work, for the first time, the synthesized CQDs@IL/Cl − , via a facile one-step hydrothermal method, was used as an adsorbent and stabilizing support for tungstate ions. Characterization of the synthesized nanoparticles (NPs) by various physicochemical techniques illustrated that tungstate ions have been immobilized on the surface of IL-modified CQDs. With this novel nanocatalyst, a variety of primary, secondary alcohols, and other alcohol substrates have been efficiently oxidized to their corresponding aldehydes and ketones in yields of ≥88% with high selectivity (100%). In the presence of CQDs@IL/WO 4 2− as a recyclable nanocatalyst, all alcohol substrates without overoxidation to carboxylic acid were oxidized within 2 h, under a temperature of 70 °C with H 2 O 2 as the oxidant. The above catalyst can be readily recycled using a simple extraction and reused consecutive runs under the described reaction conditions without a considerable decrease in the activity and selectivity. In conclusion, this Article offers a novel application for CQD chemistry.

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“…Reusability of the catalyst PVPyPSPMo 10 V 2 is an important advantage when it is introduced for practical application in catalytic processes. It was found that the catalyst could be SCHEME 6 | Preparation of MNP@TA-IL/W and catalytic oxidation of sulfides to sulfoxides (Hosseini et al, 2018). reusable at least four times, and the yield of 98% for the first run to 90% for the fourth run was observed.…”

Section: Zhou Et Al Prepared a New Class Of Il-stabilizedmentioning

confidence: 99%

“…Hosseini et al reported the selective oxidation of sulfides with H 2 O 2 as an oxidant catalyzed by magnetic-supported triazine-based ionic liquid MNP@TA-IL/W at room temperature. Various sulfides could be smoothly converted into the corresponding sulfoxides with high conversions (83–99%) and excellent yields (95–99%) in 1–3 h ( Hosseini et al, 2018 ). The magnetic-supported triazine-based ionic liquid was prepared by a five-step reaction.…”

Section: Oxidation Of Sulfides To Sulfones or Sulfoxidesmentioning

confidence: 99%

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Recent Advances in Catalytic Oxidation of Organic Sulfides: Applications of Metal–Ionic Liquid Catalytic Systems

Liu

Tan

et al. 2022

Front. Chem.

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Catalytic oxidation of organic sulfides is of considerable significance in industrial chemistry and fuel industry. Therefore, numerous methods have been developed for the oxidation. Metal-containing ionic liquid-based catalysts can catalyze the selective oxidation reactions and are highly used in chemical processes, which have also been used as effective solvents, reaction media, extractants, and catalysts for the oxidation of organic sulfides including oxidative desulfurization of fuel oil. Recently, much attention is being drawn to the preparation of heterogenous catalysts based on the immobilization of metal- or nonmetal-containing ILs on diverse solid supports, which can be easily separated after the completion reaction and recycled. Therefore, there is still an increasing interest in developing new and efficient catalytic procedures for the oxidation of organic sulfides. In this review, we have outlined the recent advances in catalytic oxidation of organic sulfides including oxidative desulfurization of fuel oil. The versatilities and adaptabilities of metal–ionic liquid catalytic systems in the selective oxidation of sulfides are considered a powerful research field in these transformations.

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Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

Cited by 12 publications

References 63 publications

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Ionic-Liquid-Modified Carbon Quantum Dots as a Support for the Immobilization of Tungstate Ions (WO₄^2–): Heterogeneous Nanocatalysts for the Oxidation of Alcohols in Water

Recent Advances in Catalytic Oxidation of Organic Sulfides: Applications of Metal–Ionic Liquid Catalytic Systems

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Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

Cited by 12 publications

References 63 publications

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Targeted Development of Sustainable Green Catalysts for Oxidation of Alcohols via Tungstate-Decorated Multifunctional Amphiphilic Carbon Quantum Dots

Ionic-Liquid-Modified Carbon Quantum Dots as a Support for the Immobilization of Tungstate Ions (WO42–): Heterogeneous Nanocatalysts for the Oxidation of Alcohols in Water

Recent Advances in Catalytic Oxidation of Organic Sulfides: Applications of Metal–Ionic Liquid Catalytic Systems

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Ionic-Liquid-Modified Carbon Quantum Dots as a Support for the Immobilization of Tungstate Ions (WO₄^2–): Heterogeneous Nanocatalysts for the Oxidation of Alcohols in Water