Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

Sakai, Takashi; Tsutsumi, Yoshihiro; Ema, Tadashi

doi:10.1039/b718321f

Cited by 172 publications

(79 citation statements)

References 35 publications

(19 reference statements)

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“…In most reported cases, the heterocycle/CO 2 coupling product can be recovered quantitatively from the reaction mixture by simple distillation. To address catalyst stability/recyclability issues, efforts have been made to develop heterogeneous IL-based catalysts including silica-supported, 72 improved activity, mainly due to more efficient epoxide activation through H-bonding interactions (Scheme 5), and subsequently have been developed in their heterogeneous form.…”

Section: Catalysis By Organic Salts and Ionic Liquidsmentioning

confidence: 99%

Sustainable conversion of carbon dioxide: the advent of organocatalysis

2015

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The conversion of carbon dioxide (CO 2 ), an abundant renewable carbon reagent, into chemicals of academic and industrial interest is of imminent importance to create a higher degree of sustainability in chemical processing and production. Recent progress in this field is characterised by a plethora of organic molecules able to mediate the conversion of suitable substrates in the presence of CO 2 into a variety of value-added commodities with advantageous features combining cost-effectiveness, metalfree transformations and general substrate activation profiles. In this review, the latest developments are discussed in the field of CO 2 catalysis with a focus on organo-mediated conversions and their increasing importance as to serve as practicable alternatives for metal-based processes. Also a critical assessment of the state-of-the-art is presented with attention on those features that need further attention to lift the usefulness of organocatalysis in the production of organic molecules of potential commercial interest.

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Section: Catalysis By Organic Salts and Ionic Liquidsmentioning

confidence: 99%

Sustainable conversion of carbon dioxide: the advent of organocatalysis

2015

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“…The activities of ILs could be greatly improved by adding metal salts or complexes for the synthesis of cyclic carbonates. Furthermore, synergistic effects on promoting the cycloaddition reactions of epoxides have been reported [31,[34][35][36][37][38][39][40][42][43][44][45][46][47][48][49][50][51][52].…”

Section: Metal-based Ionic Liquidsmentioning

confidence: 99%

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Cheng

Wang

et al. 2013

Catalysts

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This review presents the synergistic effect in the catalytic system of ionic liquids (ILs) for the synthesis of cyclic carbonate from carbon dioxide and epoxide. The emphasis of this review is on three aspects: the catalytic system of metal-based ionic liquids, the catalytic system of hydrogen bond-promoted ionic liquids and supported ionic liquids. Metal and ionic liquids show a synergistic effect on the cycloaddition reactions of epoxides. The cations and anions of ionic liquids show a synergistic effect on the cycloaddition reactions. The functional groups in cations or supports combined with the anions have a synergistic effect on the cycloaddition reactions. Synergistic catalytic effects of ILs play an important role of promoting the cycloaddition reactions of epoxides. The design of catalytic system of ionic liquids will be possible if the synergistic effect on a molecular level is understood.

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“…[15][16][17][18][19] Recently, the heterogenization of organic bases has become an interesting subject owing to a variety of basic compounds showing unusual performance for different catalytic reactions. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] For example, amino-functionalized mesoporous materials have attracted much attention for their wide applications in Knoevenagel condensation, aldol reaction, nitroaldol reaction, Michael additions, and epoxide ring-opening reactions. [27][28][29][30][31][32][33] Notably, it was reported that some amino-functionalized materials were efficient catalysts for the transesterification reactions of esters (i.e., ethylene carbonate, diethylmalonate and β-ketoester) with alcohols.…”

mentioning

confidence: 99%

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Liu¹,

Zhao²,

Zhu³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de materiais híbridos mesoporos MCM-41, contendo diferentes grupos amino (como 3-aminopropila (AP-), (2-aminoetilamino)propila (AAP-), ou [2-(2-aminoetilamino) etilamino]propila (AEP-)) foi preparada pelo método de pós-enxertia e caracterizada por difração de raio X de pó (XRD), adsorção de N 2 , espectroscopia de infravermelho com transformada de Fourier (FT-IR) e dessorção de CO 2 com temperatura controlada (CO 2 -TPD). As propriedades catalíticas destes materiais híbridos para a reação de transesterificação de dimetil oxalato com fenol foram investigadas. Verificou-se que todos são ativos, particularmente o AEP-MCM-41, que apresentou a maior atividade dentre eles. Apenas um pequeno decréscimo na atividade foi observado após vários ensaios catalíticos sucessivos utilizando o mesmo catalisador, indicando uma boa reciclabilidade do mesmo. Notavelmente, a atividade do catalisador pode ser regenerado por simples tratamento com base, sob condições brandas. Além disso, os efeitos da densidade e da força básica dos grupos amino sobre as propriedades catalíticas foram exploradas na proposição do mecanismo de reação, incluindo a provável rota que leva à formação do subproduto anisol.A series of hybrid mesoporous MCM-41 materials containing different amino groups (such as 3-aminopropyl (AP-), (2-aminoethylamino)propyl (AAP-), or [2-(2-aminoethylamino)ethylamino] propyl (AEP-) group) were prepared by a post-grafting method, and characterized by means of X-ray powder diffraction (XRD), N 2 adsorption, Fourier transform-infrared spectroscopy (FT-IR) and temperature-programmed desorption of CO 2 (CO 2 -TPD). The catalytic properties of these hybrid materials were investigated for the transesterification of dimethyl oxalate with phenol. All the samples were active for the transesterification. Among them, the sample AEP-MCM-41 exhibited the highest activity under test conditions. And only a slight decrease in activity could be observed after few runs, indicating the good recyclability of this catalyst. Notably, the activity of the used catalyst could be regenerated by simple treatment with diluted basic agents under mild conditions. Moreover, effects of the density and the basic strength of the amino groups on the catalytic properties were taken into consideration for understanding the reaction mechanism and the possible formation route of the by-product anisole.Keywords: amino-functionalized, MCM-41, dimethyl oxalate, transesterification, recyclability IntroductionDiphenyl carbonate (DPC) is an industrially important intermediate for the production of several organic chemicals, especially as the precursor for the synthesis of polycarbonates (PCs), which have been used in many fields due to excellent mechanical, optical, electrical and heatresistance properties. 1,2 So far, various approaches for DPC synthesis have been reported, including phosgene route, oxidative carbonylation of phenol and transesterification reaction. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Among them, transesterification...

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Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides

Cited by 172 publications

References 35 publications

Sustainable conversion of carbon dioxide: the advent of organocatalysis

Sustainable conversion of carbon dioxide: the advent of organocatalysis

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

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