Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids

Sun, Jianmin; Fujita, Shin‐ichiro; Arai, Masahiko

doi:10.1016/j.jorganchem.2005.02.011

Cited by 366 publications

(153 citation statements)

References 69 publications

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“…This could be assigned to the non-nucleophilic natures of the Tf 2 N -and BF 4 − anions. 27 When [bmim][Cl] is used as catalyst, probably the attack of the epoxide is performed by the Cl − in the less hindered carbon atom, in the first step of the reaction, see Scheme 1b.…”

Section: Resultsmentioning

confidence: 99%

A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

Aquino¹,

Bernard²,

Vieira³

et al. 2014

Journal of the Brazilian Chemical Society

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Embora tecnologias de captura e armazenamento de carbono (CCS) estejam recebendo grande atenção para a mitigação do efeito estufa, ainda existem muitas desvantagens, tais como o aumento dos custos e gastos de energia associados à sua implementação. No entanto, o uso de CO 2 como bloco de construção C1 em síntese orgânica pode ser muito atraente para o desenho de processos ecológicos. Neste trabalho, foram estudados a sorção de CO 2 e atividades catalíticas de alguns líquidos iônicos (ILs) base imidazólio para síntese de carbonato cíclico. O trabalho demonstra que a presença de um grupo nucleófilo no sistema catalítico pode melhorar seu desempenho, através da utilização de um IL com ânion halogenado ou por mistura de co-catalisador halogenado com ILs. A última abordagem permitiu a obtenção de um sistema de captura de CO 2 eficaz, constituída por IL fluorado mais ZnBr 2 que realiza a síntese de carbonato cíclico com 90% de rendimento e 82% de seletividade.Although the carbon capture and storage (CCS) technologies are receiving great attention for mitigation of greenhouse gas effect, the increasing costs and energy penalties associated to its implementation are still major drawbacks. However, the use of CO 2 as a C1 building block in organic synthesis can be very attractive for the design of environmentally friendly processes. In this work, we have studied both the CO 2 sorption and catalytic activities of some imidazolium based ionic liquids (ILs) for cyclic carbonate synthesis. The work demonstrates that the presence of a nucleophilic group in the catalytic system can enhance its performance by the use of an IL with a halide anion or by mixing a halide co-catalyst with ILs. The latter approach allowed to obtain an effective system for CO 2 capture constituted by a fluorinated IL plus ZnBr 2 that performs cyclic carbonate synthesis with 90% yield and 82% of selectivity.

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Section: Resultsmentioning

confidence: 99%

A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

Aquino¹,

Bernard²,

Vieira³

et al. 2014

Journal of the Brazilian Chemical Society

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“…One reaction attracting significant attention in this respect is the 100 % atom-economical synthesis of cyclic carbonates by the insertion of carbon dioxide into an epoxide (Scheme 1), though most current catalysts for this process require the use of high reaction temperatures and/or high pressures of carbon dioxide. [1,2] We recently reported the development of bimetallic aluminum(salen) complex 1, which when used in conjunction with tetrabutylammonium bromide constitutes the only catalyst system capable of catalyzing the insertion of carbon dioxide into terminal epoxides at 1 atm (760 mm Hg) and at ambient temperature. [3] These extremely mild reaction conditions have allowed us to carry out the first mechanistic study of this important reaction, revealing a previously unanticipated role for the tetrabutylammonium bromide in the catalytic cycle.…”

mentioning

confidence: 99%

“…By working under conditions where carbon dioxide is present in large excess, and noting that the concentrations of catalysts 1 and tetrabutylammonium bromide will be effectively constant during the reaction, this can be simplified to Equation (2). In the event, the reactions followed first-order kinetics, [4] and by varying the concentrations of carbon dioxide, catalyst 1, and tetrabutylammonium bromide, we could determine the rate equation as Equation (3).…”

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confidence: 99%

Mechanism of Cyclic Carbonate Synthesis from Epoxides and CO₂

2009

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Drei verknüpfte Katalysezyklen spielen bei der durch einen Di(aluminium(salen))‐Komplex und Bu4NBr katalysierten Titelreaktion eine Rolle. Im ersten aktiviert Bu4NBr als Nucleophil das Epoxid. Im zweiten wird CO2 durch das in situ gebildete Bu3N aktiviert. Im dritten bringt der Aluminium(salen)‐Komplex die beiden aktivierten Spezies zusammen, sodass die entscheidenden Bindungen intramolekular gebildet werden können.

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“…avoiding the usage of phosgene and having only water as by-product). A large number of catalysts for the cycloaddition of CO 2 to epoxides have been proposed, ranging from heterogeneous catalysts (such as alkali metal salts 11,12 , organo-phosphorus compounds 13 , metal oxides 14,15 , covalent organic framework (COF) functionalized with triazine 16 ) to homogeneous catalysts (such as chromium complex in dichloromethane, isolated zinc complexes 17,18 and ionic liquids in scCO 2 [19][20][21] . Despite their high efficiency, homogeneous catalysts present the known disadvantages of difficult product separation and catalyst recycling.…”

Section: Introductionmentioning

confidence: 99%

Design of high surface area poly(ionic liquid)s to convert carbon dioxide into ethylene carbonate

et al. 2015

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A series of porous poly(ionic liquid)s (PILs) were synthesized using an innovative method which involves the synthesis of a non-ionic co-polymer of divinylbenzene and vinylimidazole, followed by an alkylation step to introduce the Io nic Liquid functionality in the polymeric matrix. This synthetic strategy allowed to obtain tuneable imidazolium type PILs having simultaneously high surface area and exposed ionic moieties. A set of PILs was obtained changing systematically the alkyl chains, the anions and the cross-link degree. This approach allowed to elucidate the effect of each synthetic variable on the catalytic performances of PILs towards carbon dioxide cycloaddition reaction in very mild conditions (room temperature and low pressure). Finally, in-situ FTIR spectroscopy allowed to establish a relation between structure of PILs and their catalytic properties.

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Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids

Cited by 366 publications

References 69 publications

A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

Mechanism of Cyclic Carbonate Synthesis from Epoxides and CO₂

Design of high surface area poly(ionic liquid)s to convert carbon dioxide into ethylene carbonate

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Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids

Cited by 366 publications

References 69 publications

A New Approach to CO2Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

A New Approach to CO2Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

Mechanism of Cyclic Carbonate Synthesis from Epoxides and CO2

Design of high surface area poly(ionic liquid)s to convert carbon dioxide into ethylene carbonate

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Product

Resources

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A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

A New Approach to CO₂Capture and Conversion Using Imidazolium Based-Ionic Liquids as Sorbent and Catalyst

Mechanism of Cyclic Carbonate Synthesis from Epoxides and CO₂