Design of silica supported task-specific ionic liquid catalyst system for oxidation of cyclohexene to adipic acid with 30% H2O2

Vafaeezadeh, Majid; Hashemi, Mohammed M.; Shakourian‐Fard, Mehdi

doi:10.1016/j.catcom.2012.04.031

Cited by 60 publications

(27 citation statements)

References 27 publications

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“…The imidazolium based ILs [C 4 mim][BF 4 ], [C 4 mim][Tf 2 N], and [C 4 mim][Cl] were supplied by Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences. [C 4 mim][OAc] was prepared by following the procedures described in the literature . The protic ILs [DBUH][TFE], [DBUH][MIm], [DBUH][OAc], and [DBUH][Im] were prepared through the neutralization of the corresponding bases and proton donors according to the reported procedures, and the experimental details are provided in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates

Qiu¹,

Zhang²,

Li³

et al. 2016

ChemSusChem

107

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The efficient conversion of CO into value-added chemicals under metal-free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the synthesis of α-alkylidene cyclic carbonates. The protic IL 1,8-diazabicyclo-[5.4.0]-7-undecenium 2-methylimidazolide ([DBUH][MIm]) was prepared by simple neutralization of the superbase with a weak proton donor and could efficiently promote the reactions in high yields. After the reactions, the IL was separated from the reaction mixtures by simply adding water, and then reused after drying without an observable decrease in the catalytic activity and selectivity. NMR spectroscopy and detailed density functional theory analysis were used to propose a reaction mechanism. Both the cation and anion of the IL played a key synergistic role in promoting the reaction. These findings may be useful for the rational design of novel metal-free and recyclable routes for the reaction between CO and propargylic alcohols.

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Section: Methodsmentioning

confidence: 99%

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates

Qiu¹,

Zhang²,

Li³

et al. 2016

ChemSusChem

107

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“…2. The FT-IR spectrum displayed peaks at 3152 cm −1 attributed to the presence of the N-H bond stretching frequency of sulphonamide groups, which has been overlapped with O-H stretching frequency of silanol group or the adsorbed water molecules [57]. The corresponding C=O stretching and bending frequency of N-H were observed at 1717 and 1575 cm −1 , respectively.…”

Section: Characterization Of the Catalystmentioning

confidence: 97%

Silica Bonded N-(Propylcarbamoyl)sulfamic acid (SBPCSA) Mediated Expeditious Approach to C–C Bond Formation: An Innovative Pathway for Acrylonitrile Derivatives

et al. 2016

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A new silica bonded N-(propylcarbamoyl)sulfamic acid (SBPCSA) catalyst has been prepared for the highly efficient synthesis of a series of acrylonitrile derivatives via solvent-free facile Knoevenagel condensation between differently substituted heterocyclic/aromatic aldehydes 1 (a-o) and 2-thiopheneacetonitrile (2). The catalyst was characterized by FT-IR, SEM-EDX and XRD techniques. The thermal stability of the catalyst was evaluated with TGA and DT analysis. The remarkable features of the present protocol are solvent free synthesis, recyclability of the catalyst, mild reaction conditions, shorter reaction profile, excellent yield of products with applicability to broader substrate scope (electron rich and electron deficient) and exclusive formation of E-isomer of the product. DFT calculations also revealed that E-isomer of compound 3f is stabilized by 12.53 kcal mol −1 more than the Z-isomer. Graphical AbstractEfficient and economical synthesis of acrylonitrile derivatives. H O Ar S CN Solvent-free Stirring/ 80 o C Examples:15 Yield: 92-98%

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“…Ionic liquids (IL) are indeed a very attractive class of solvents due to their unique properties including low vapor pressure, good thermal stability, electrical conductivity, and many pharmaceutical applications . The term ‘task‐specific’ IL refers to the non‐solvent applications of ILs such as catalysis and gas separation …”

Section: Total Energies (In Atomic Unit) Of Il and Il@silica; Interacmentioning

confidence: 99%

“…In this approach, ILs are mainly stabilized via hydrogen bonds (H bonds) between their anions and the surface free silanol groups . However, these types of catalyst mainly suffer from significant leaching of ILs from the surface of the solid support . The leaching phenomena lead to observe notable reduction of the catalytic activity, especially in the case of recovered catalyst.…”

Section: Total Energies (In Atomic Unit) Of Il and Il@silica; Interacmentioning

confidence: 99%

Interaction of ionic liquids with the surface of silica gel using nanocluster approach: a combined density functional theory and experimental study

Vafaeezadeh

Fattahi

2013

J. Phys. Org. Chem.

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Silica gel‐confined ionic liquid (IL) is a class of heterogeneous catalysts with broad catalytic applications. Leaching of the IL from the surface of the support is the major drawback of these catalysts, which reduce the catalyst efficiency during the chemical reactions. To investigate the effect of the hydrogen bonding on the leaching phenomena, the interaction between the 1‐ethyl‐3‐methylimidazolium‐based IL with various anions (Cl−, Br−, HSO4−, NO3−, BF4−, and PF6−) and the surface of the silica gel were studied using density functional theory. Hence, a hydroxylated cage‐like cluster of silica gel, Si4O6(OH), was selected to mimic the surface. The values of ΔEinteraction show that ILs with halogen counter ions have stronger interactions than that of the IL with BF4− and PF6− counter ions. We also carried out stirring–filtration method for some prepared samples of IL@silica to experimentally explore the leaching phenomena. The results show good agreement with computational achievements. Copyright © 2013 John Wiley & Sons, Ltd.

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Design of silica supported task-specific ionic liquid catalyst system for oxidation of cyclohexene to adipic acid with 30% H2O2

Cited by 60 publications

References 27 publications

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates

Silica Bonded N-(Propylcarbamoyl)sulfamic acid (SBPCSA) Mediated Expeditious Approach to C–C Bond Formation: An Innovative Pathway for Acrylonitrile Derivatives

Interaction of ionic liquids with the surface of silica gel using nanocluster approach: a combined density functional theory and experimental study

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Design of silica supported task-specific ionic liquid catalyst system for oxidation of cyclohexene to adipic acid with 30% H2O2

Cited by 60 publications

References 27 publications

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates

Silica Bonded N-(Propylcarbamoyl)sulfamic acid (SBPCSA) Mediated Expeditious Approach to C–C Bond Formation: An Innovative Pathway for Acrylonitrile Derivatives

Interaction of ionic liquids with the surface of silica gel using nanocluster approach: a combined density functional theory and experimental study

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Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates

Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO₂ into α‐Alkylidene Cyclic Carbonates