Cycloaddition of carbon dioxide for commercially-imperative cyclic carbonates using ionic liquid-functionalized porous amorphous silica

Udayakumar, Seshachalam; Vedarajan, Raman; Shim, Hye-Lim; Park, Dae‐Won

doi:10.1016/j.apcata.2009.08.015

Cited by 56 publications

(27 citation statements)

References 55 publications

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“…5) of the pristine GO showed four intensive peaks at 1720, 1612, 1228, and 1072 cm −1 , indexed as the stretching vibration of C=O, C=C, C-O, and C-O groups of GO 43 , respectively. Additionally, a sharp peak located at 1126 cm −1 , and two tiny yet pronounced peaks at 2941 and 2883 cm −1 5 emerged in the case of GO-[SmIm]I, which corresponded to imidazole motifs, and symmetric and asymmetric vibrations of CH 2 of the alkyl chains 22,46 , respectively. After the immobilization of [SmIm]I, the bands about the C=O and C=C groups have been well retained, whereas the intensity of the peaks corresponding to C-OH and C-O chemical functions decreased noticeably.…”

Section: Resultsmentioning

confidence: 99%

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

et al. 2015

RSC Adv.

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Functionalized imidazolium-based ionic liquids (ILs) with different halides (Cl, Br, and I) were successfully immobilized on the surface of graphene oxide materials by one step through covalent condensation between alcoholic hydroxyl groups of GO and alkoxyl groups of functionalized ILs. Several characterization including TG, Raman, AFM, FT-IR, and XPS techniques have been applied to 10 characterize the physicochemical properties of the synthesized GO-[SmIm]X materials. In the solventfree cycloaddition reactions of CO 2 to propylene oxide, GO-[SmIm]I showed remarkably catalytic activity, affording a maximum yield of propylene carbonate as ca. 96%. The heterogeneous catalyst could be reused for at least four runs without any significant loss in activity, and demonstrated versatile catalysis for a wide range of substrates. A possible catalytic mechanism has been proposed, wherein 15 epoxides were activated by the oxygen-containing groups of GO and the halide anions of the grafted ILs acted as key active species for the catalytic cycloaddition reactions. 75 Graphical AbstractGraphene oxides were grafted with functionalized ionic liquid and showed high catalytic activity in cycloaddition of CO 2 with propylene oxide to propylene carbonate.

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Section: Resultsmentioning

confidence: 99%

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

et al. 2015

RSC Adv.

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“…However, the use of zinc halides as co-catalysts (e.g., ZnCl 2 , ZnBr 2 ) is required in this approach. Recently, Udayakumar et al [42][43][44][45][46] and Zhang et al [47] reported some ionic liquid (without hydroxyl groups) functionalized catalysts via immobilization of imidazolium or quaternary ammonium salts onto MCM-41 or SiO 2 . However, their catalytic activities were not satisfactory.…”

Section: Introductionmentioning

confidence: 98%

3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides

et al. 2010

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3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO 2 by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO 2 and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120°C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction.

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“…[15][16][17][18][19] Considering the separation and reusability of the catalysts, heterogeneous catalysts based on ILs were developed by supporting on silica, MCM-41 and crosslinked polymer. [20][21][22][23][24] The solvent-free and metal-free reactions proceeded successfully under mild conditions, and the heterogeneous catalysts could be separated easily and reused. The combination of ILs as versatile reaction media with suitable catalyst, such as acid, base, nanostructures, or metal complex, may result in a more diverse and flexible platform to establish a highly effective and easily separable catalytic system.…”

Section: Introductionmentioning

confidence: 99%

Novel one‐step synthesis to cross‐linked polymeric nanoparticles as highly active and selective catalysts for cycloaddition of CO₂ to epoxides

Xiong

Wang

et al. 2011

J of Applied Polymer Sci

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Highly cross-linked polymeric nanoparticles were prepared via novel one-step synthesis by copolymerizing ethylene glycol dimethacrylate (EGDMA) and the ionic liquid, 1-vinyl-3-(2-methoxy-2-oxyl ethyl) imidazolium chloride ([VMIm]Cl). The results indicated that nanoparticles with the average size of about 350 nm could be obtained conveniently through the cross-linking copolymerization. The nanoparticles were characterized using scanning electron microscopy, atomic force microscopy, Fourier transform Infrared, thermo gravimetric analysis, element analysis, and X-ray diffraction techniques. Moreover, the cross-linked polymeric nanoparticles were highly active and selective catalysts for the cycloaddition reaction of carbon dioxide to epoxides. The influences of reaction time, reaction temperature, CO 2 pressure, and amount of catalyst on yield of the products were investigated. The results revealed that cyclic carbonates with high yield (98.4%) and selectivity (100%) could be produced on the condition of 0.1 g catalyst, 5 MPa CO 2 , 160 C and 12 h. In addition, the nanocatalysts could be easily recovered by filtration, and reused several times with only slight loss of catalytic activity.

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Cycloaddition of carbon dioxide for commercially-imperative cyclic carbonates using ionic liquid-functionalized porous amorphous silica

Cited by 56 publications

References 55 publications

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides

Novel one‐step synthesis to cross‐linked polymeric nanoparticles as highly active and selective catalysts for cycloaddition of CO₂ to epoxides

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Cycloaddition of carbon dioxide for commercially-imperative cyclic carbonates using ionic liquid-functionalized porous amorphous silica

Cited by 56 publications

References 55 publications

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO2to propylene carbonate

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO2to propylene carbonate

3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides

Novel one‐step synthesis to cross‐linked polymeric nanoparticles as highly active and selective catalysts for cycloaddition of CO2 to epoxides

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Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

Graphene oxide immobilized with ionic liquids: facile preparation and efficient catalysis for solvent-free cycloaddition of CO₂to propylene carbonate

Novel one‐step synthesis to cross‐linked polymeric nanoparticles as highly active and selective catalysts for cycloaddition of CO₂ to epoxides