Direct Cyclic Carbonate Synthesis from CO<sub>2</sub> and Diol over Carboxylation/Hydration Cascade Catalyst of CeO<sub>2</sub> with 2-Cyanopyridine

Honda, Masayoshi; Tamura, Masazumi; Nakao, Kenji; Suzuki, Kimihito; Nakagawa, Yoshinao; Tomishige, Keiichi

doi:10.1021/cs500301d

Cited by 177 publications

(133 citation statements)

References 48 publications

(31 reference statements)

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“…Scheme shows the results of the synthesis of cyclic carbonate from CO 2 +diols+2‐cyanopyridine. Various vicinal diols reacted with CO 2 to give corresponding five‐membered ring carbonates in high yield . In the case of the synthesis of five‐membered ring carbonates, although the reactivity of secondary‐secondary vicinal OH groups is not high, the target products were obtained in high yield.…”

Section: Synthesis Of Organic Carbonates From Co2+alcohols Over Ceo2 supporting

confidence: 80%

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine

Tomishige

Tamura

Nakagawa

2018

The Chemical Record

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Recent progress on the CeO2 catalyzed synthesis of organic carbonates, ureas, and carbamates from CO2+alcohols, CO2+amines, and CO2+alcohols+amines, respectively, is reviewed. The reactions of CO2 with alcohols and amines are reversible ones and the degree of the equilibrium limitation of the synthesis reactions is strongly dependent on the properties of alcohols and amines as the substrates. When the equilibrium limitation of the reaction is serious, the equilibrium conversion of the substrate and the yield of the target product is very low, therefore, the shift of the equilibrium reaction to the product side by the removal of H2O is essential in order to get the target product in high yield. One of the effective method of the H2O removal from the related reaction systems is the combination with the hydration of 2‐cyanopyridine to 2‐picolinamide, which is also catalyzed by CeO2.

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Section: Synthesis Of Organic Carbonates From Co2+alcohols Over Ceo2 supporting

confidence: 80%

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine

Tomishige

Tamura

Nakagawa

2018

The Chemical Record

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“…As a main‐group element with low cost, nontoxicity, and stability in air, magnesium oxide is efficient for the highly selective synthesis of PC from PG and CO 2 without any organic solvents or additives in 100% selectivity, which is more environmentally friendly than the Sn complex 68. Recently, the cooperative catalyst system CeO 2 /2‐cyanopyridine was first applied to direct synthesis of PC from CO 2 and 1,2‐propanediol by Tomishige and co‐workers, and excellent yields of cyclic carbonates, including six‐membered ring carbonates, were obtained due to the high activity of CeO 2 for both carboxylation of diols and hydration of 2‐cyanopyridine 69. Using dibromomethane as the solvent, alcohol activator, and [Bmim][PF 6 ] to increase the solubility of CO 2 , transition‐metal‐free synthesis of cyclic carbonates was realized recently in the presence of organic base, 1,8‐diaza‐bicyclo[5.4.0]undec‐7‐ene (DBU) 70…”

Section: Carboxylation Of 12‐diol With Co2 To Cyclic Carbonatesmentioning

confidence: 99%

Green Catalytic Process for Cyclic Carbonate Synthesis from Carbon Dioxide under Mild Conditions

Lang

2016

The Chemical Record

100

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As a renewable and abundant C1 resource possessing multiple attractive characteristics, such as low cost, nontoxicity, non-flammability, and easy accessibility, CO2 conversion into value-added chemicals and fuels can contribute to green chemistry and sustainable development. Since CO2 is a thermodynamically inert molecule, the activation of CO2 is pivotal for its effective conversion. In this regard, the formation of a transition-metal CO2 complex through direct coordination is one of the most powerful ways to induce the inert CO2 molecule to undergo chemical reactions. To date, numerous processes have been developed for efficient synthesis of cyclic carbonates from CO2 . On the basis of mechanistic understanding, we have developed efficient metal catalysts and green processes, including heterogeneous catalysis, and metal-free systems, such as ionic liquids, for cyclic carbonate synthesis. The big challenge is to develop catalysts that promote the reaction under low pressure (preferably at 1 bar). In this context, bifunctional catalysis is capable of synergistic activation of both the substrate and CO2 molecule, and thus, could render CO2 conversion smoothly under mild conditions. Alternatively, converting CO2 derivatives, that is, the captured CO2 as an activated species, would more easily take place at low pressure in comparison with gaseous CO2 . The aim of this Personal Account is to summarize versatile catalytic processes for cyclic carbonate synthesis from CO2 , including epoxide/CO2 coupling reaction, carboxylation of 1,2-diol with CO2 , oxidative cyclization of olefins with CO2 , condensation of vicinal halohydrin with CO2 , carboxylative cyclization of propargyl alcohols with CO2 , and conversion of the CO2 derivatives.

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“…The conversion of CO 2 into value added chemicals has been widely investigated in an attempt to reduce the atmospheric levels of CO 2 . Recently, CO 2 has attracted great interests as an environmentally benign building block in the chemical industry due to its non-toxic, non-flammable and recyclable properties [1][2][3][4]. However, CO 2 is a very stable compound as the carbon atom is in the most oxidized form and thermodynamically stable [5] and therefore large energy input is required to transform CO 2 .…”

Section: Introductionmentioning

confidence: 99%

Greener synthesis of dimethyl carbonate using a novel ceria–zirconia oxide/graphene nanocomposite catalyst

Saada

Kellici

Heil³

et al. 2015

Applied Catalysis B: Environmental

123

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Direct Cyclic Carbonate Synthesis from CO₂ and Diol over Carboxylation/Hydration Cascade Catalyst of CeO₂ with 2-Cyanopyridine

Cited by 177 publications

References 48 publications

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine

Green Catalytic Process for Cyclic Carbonate Synthesis from Carbon Dioxide under Mild Conditions

Greener synthesis of dimethyl carbonate using a novel ceria–zirconia oxide/graphene nanocomposite catalyst

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Direct Cyclic Carbonate Synthesis from CO2 and Diol over Carboxylation/Hydration Cascade Catalyst of CeO2 with 2-Cyanopyridine

Cited by 177 publications

References 48 publications

CO2 Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO2 Catalyst in the Presence and Absence of 2‐Cyanopyridine

CO2 Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO2 Catalyst in the Presence and Absence of 2‐Cyanopyridine

Green Catalytic Process for Cyclic Carbonate Synthesis from Carbon Dioxide under Mild Conditions

Greener synthesis of dimethyl carbonate using a novel ceria–zirconia oxide/graphene nanocomposite catalyst

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Product

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Direct Cyclic Carbonate Synthesis from CO₂ and Diol over Carboxylation/Hydration Cascade Catalyst of CeO₂ with 2-Cyanopyridine

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine

CO₂ Conversion with Alcohols and Amines into Carbonates, Ureas, and Carbamates over CeO₂ Catalyst in the Presence and Absence of 2‐Cyanopyridine