Fixation of CO<sub>2</sub>into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach

Xu, Bo; Wang, Jinquan; Sun, Jian; Zhang, Shuai; Zhang, Junping; Zhang, Xiangping; Zhang, Suojiang

doi:10.1039/c4gc01754d

Cited by 386 publications

(190 citation statements)

References 164 publications

(88 reference statements)

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“…[5] Many highly active and selective metal-based catalysts containing Lewis acid sites have been reported, such as metal complexes [10] and metal-organic frameworks (MOFs). [1,12] Several metal-free organic catalysts have also been investigated, such as ammonium halides, [1,[13][14][15] phosphonium halides, [3,16] and imidazolium-basedi onic liquids, [17][18][19] in which the halidesa re the catalytic speciesa cting as nucleophiles. [1,12] Several metal-free organic catalysts have also been investigated, such as ammonium halides, [1,[13][14][15] phosphonium halides, [3,16] and imidazolium-basedi onic liquids, [17][18][19] in which the halidesa re the catalytic speciesa cting as nucleophiles.…”

Section: Introductionmentioning

confidence: 99%

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

Alassmy

Pescarmona

2019

ChemSusChem

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The role of water as highly effective hydrogen‐bond donor (HBD) for promoting the coupling reaction of CO2 with a variety of epoxides was demonstrated under very mild conditions (25–60 °C, 2–10 bar CO2). Water led to a dramatic increase in the cyclic carbonate yield when employed in combination with tetrabutylammonium iodide (Bu4NI) whereas it had a detrimental effect with the corresponding bromide and chloride salts. The efficiency of water in promoting the activity of the organic halide was compared with three state‐of‐the‐art hydrogen bond donors, that is, phenol, gallic acid and ascorbic acid. Although water required higher molar loadings compared to these organic hydrogen‐bond donors to achieve a similar degree of conversion of CO2 and styrene oxide into the corresponding cyclic carbonate under the same, mild reaction conditions, its environmental friendliness and much lower cost make it a very attractive alternative as hydrogen‐bond donor. The effect of different parameters such as the amount of water, CO2 pressure, reaction temperature, and nature of the organic halide used as catalyst was investigated by using a high‐throughput reactor unit. The highest catalytic activity was achieved with either Bu4NI or bis(triphenylphosphine)iminium iodide (PPNI): with both systems, the cyclic carbonate yield at 45 °C with different epoxide substrates could be increased by a factor of two or more by adding water as a promoter, retaining high selectivity. Water was an effective hydrogen‐bond donor even at room temperature, allowing to reach 85 % conversion of propylene oxide with full selectivity towards propylene carbonate in combination with Bu4NI (3 mol %). For the conversion of epoxides in which PPNI is poorly soluble, the addition of a cyclic carbonate as solvent allowed the formation of a homogeneous solution, leading to enhanced product yield.

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Section: Introductionmentioning

confidence: 99%

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

Alassmy

Pescarmona

2019

ChemSusChem

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“…6 To date, various valuable chemicals including methanol, 7 formic acid, 8 amides, 9 carbonates, 10 and aryl aldehydes 11 have been produced using CO 2 as a C1 feedstock. Synthesis of organosulfur compounds via the construction of C−S bonds using CO 2 as a C1 feedstock is very interesting.…”

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confidence: 99%

Ionic Liquid-Catalyzed C–S Bond Construction using CO₂ as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

et al. 2015

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The construction of the C−S bond using CO 2 as a C1 feedstock can be considered as a green route for the synthesis of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO 2 and hydrosilane under mild conditions (e.g., 60°C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO 2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO 2 as a C1 building block under metalfree and mild conditions.

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“…In this work, three metal complexes based on 2,6-bis[1-(phenylimino)ethyl] pyridine ( L ), namely [Cu L Cl 2 ] ( 1 ), [Cr L Cl 3 ] ( 2 ), and [Mn L Cl 2 ]·0.5(CH 3 CN) ( 3 ) were constructed, and were investigated in terms of their activity in catalyzing the cycloaddition reaction between propylene oxide and carbon dioxide (Scheme 1) [26,27,28], in the presence of co-catalyst. Furthermore, the relationship between the molecular structures and catalysis performance was analyzed based on experiment and density functional theory (DFT) calculation, and a reaction mechanism is proposed.…”

Section: Introductionmentioning

confidence: 99%

New Coordination Complexes Based on the 2,6-bis[1-(Phenylimino)ethyl] Pyridine Ligand: Effective Catalysts for the Synthesis of Propylene Carbonates from Carbon Dioxide and Epoxides

Wang

Liu

et al. 2018

Molecules

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We aimed to develop new effective catalysts for the synthesis of propylene carbonate from propylene oxide and carbon dioxide. A kind of Mx+LClx coordination complex was fabricated based on the chelating tridentate ligand 2,6-bis[1-(phenylimino)ethyl] pyridine (L). The obtained products were characterized by elemental analysis, infrared spectroscopy, ultraviolet spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction. It was found that the catalytic activity of the complexes with different metal ions, the same ligand differed and co-catalyst, where the order of greatest to least catalytic activity was 2 > 3 > 1. The catalytic system composed of complex 2 and DMAP proved to have the better catalytic performance. The yields for complex 2 systems was 86.7% under the reaction conditions of 100 °C, 2.5 MPa, and 4 h. The TOF was 1026 h−1 under the reaction conditions of 200 °C, 2.5 MPa, and 1 h. We also explored the influence of time, pressure, temperature, and reaction substrate concentration on the catalytic reactions. A hypothetical catalytic reaction mechanism is proposed based on density functional theory (DFT) calculations and the catalytic reaction results.

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Fixation of CO₂into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach

Abstract: The fixation of CO2into cyclic carbonates using the emerging ionic liquid (IL) technology is reviewed from a multi-scale viewpoint.

Cited by 386 publications

References 164 publications

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

Ionic Liquid-Catalyzed C–S Bond Construction using CO₂ as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

New Coordination Complexes Based on the 2,6-bis[1-(Phenylimino)ethyl] Pyridine Ligand: Effective Catalysts for the Synthesis of Propylene Carbonates from Carbon Dioxide and Epoxides

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Fixation of CO2into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach

Abstract: The fixation of CO2into cyclic carbonates using the emerging ionic liquid (IL) technology is reviewed from a multi-scale viewpoint.

Cited by 386 publications

References 164 publications

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO2 into Cyclic Carbonates under Mild Conditions

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO2 into Cyclic Carbonates under Mild Conditions

Ionic Liquid-Catalyzed C–S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

New Coordination Complexes Based on the 2,6-bis[1-(Phenylimino)ethyl] Pyridine Ligand: Effective Catalysts for the Synthesis of Propylene Carbonates from Carbon Dioxide and Epoxides

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Fixation of CO₂into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

The Role of Water Revisited and Enhanced: A Sustainable Catalytic System for the Conversion of CO₂ into Cyclic Carbonates under Mild Conditions

Ionic Liquid-Catalyzed C–S Bond Construction using CO₂ as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles