CO<sub>2</sub> capture by 1,2,3-triazole-based deep eutectic solvents: the unexpected role of hydrogen bonds

Wang, Zonghua; Wu, Congyi; Wang, Ze; Zhang, Shaoze; Yang, Dezhong

doi:10.1039/d2cc02503e

Cited by 20 publications

(19 citation statements)

References 43 publications

(71 reference statements)

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“…Carbon dioxide absorption in DESs has been extensively studied in the past decade. − ,− Previously, we have investigated the capacity of CO 2 absorption and associated mechanism for a series of anion-functionalized protic ILs, i.e., [DBUH][X] . We found that the basicity of comprising anion (X – ) of the IL dictates the maximum absorption capacity as well as kinetic and mechanism.…”

Section: Resultsmentioning

confidence: 99%

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

et al. 2023

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An equilibrium acidity (pK a ) scale that comprises 16 Bronsted organic acids, including phenols, carboxylic acids, azoles, and phenylmalononitriles, was established in a choline chloride/EG-based deep eutectic solvent (DES) ([Ch][Cl]:2EG) by ultraviolet−visible (UV−Vis) spectroscopic methods. The established acidity scale spans about 6 pK units in the DES, which is similar to that for these acids in water. The acidity comparisons and linear correlations between the DES and other solvents show that the solvent property of [Ch][Cl]:2EG is quite different from those of amphiphilic protic and dipolar aprotic molecular solvents. The carbon dioxide absorption capabilities as well as apparent absorption kinetics for a series of anion-functionalized DESs ([Ch][X]:2EG) were measured, and the results show that the basicity of comprising anion [X] of choline salt is essential for the maximum carbon dioxide absorption capacity, i.e., a stronger basicity leads to a greater absorption capacity. The possible absorption mechanisms for carbon dioxide absorption in these DESs were also discussed based on the spectroscopic evidence.

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Section: Resultsmentioning

confidence: 99%

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

et al. 2023

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“…In our previous work, we reported that DESs consisting of solid azolide ionic liquids (ILs) and EG could chemically absorb CO 2 by forming carbonate species, 33 and the chemisorbed CO 2 by the DESs based on tetraethylammonium 1,2,3-triazolide ([Et 4 N][Tz]) can be desorbed even at 30 °C. 34 ■ METHODS AND MATERIALS Materials and Characterizations. DBU (98%) and EG (99.5%) were purchased from J&K Scientific Ltd. and Innochem.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Recently, anion-functionalized DESs have also been investigated for CO 2 capture. In our previous work, we reported that DESs consisting of solid azolide ionic liquids (ILs) and EG could chemically absorb CO 2 by forming carbonate species, and the chemisorbed CO 2 by the DESs based on tetraethylammonium 1,2,3-triazolide ([Et 4 N][Tz]) can be desorbed even at 30 °C . Gurkan et al studied the CO 2 capture by the DESs formed by 1-ethyl-3-methylimidazolium 2-cyanopyrrolide ([Emim][2-CNpyr]) and EG and found that CO 2 can react with the cation of [Emim] + , the anion [2-CNpyr], and EG.…”

Section: Introductionmentioning

confidence: 99%

Effect of Hydrogen Bonds on CO₂ Capture by Functionalized Deep Eutectic Solvents Derived from 4-Fluorophenol

Wang

Chen

et al. 2023

ACS Sustainable Chem. Eng.

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Deep eutectic solvents (DESs) have received a great amount of attention for CO 2 uptake due to their unique properties. Here, deep eutectic solvents (DESs) based on 4-fluorophenol-derived superbase ionic liquid are studied for CO 2 capture. The ionic liquid used is [DBUH][4-F-PhO], formed by 1,8-diazabicyclo[5.4.0]undecane-7-ene (DBU) and 4-fluorophenol (4-F-PhOH). The DESs are obtained by mixing [DBUH][4-F-PhO] with ethylene glycol (EG) or 4-F-PhOH. Surprisingly, [DBUH][4-F-PhO]-EG DESs present a much higher CO 2 capacity (∼1.0 mol CO 2 /mol solvent) than [DBUH][4-F-PhO]-4-F-PhOH (∼0.10 mol CO 2 /mol solvent) at 25 °C and 1.0 atm. However, after EG is added into [DBUH][4-F-PhO]-4-F-PhOH, the ternary solvents [DBUH][4-F-PhO]-4-F-PhOH-EG exhibit an unexpected high capacity, although both EG and [DBUH][4-F-PhO]-4-F-PhOH exhibit a low capacity. Moreover, the capacities of ternary solvents [DBUH][4-F-PhO]-4-F-PhOH-EG decrease with increasing concentration of 4-F-PhOH in the solvents. NMR and Fourier transform infrared (FTIR) results demonstrate that CO 2 reacts with EG in [DBUH][4-F-PhO]-EG or [DBUH][4-F-PhO]-4-F-PhOH-EG by forming a carbonate species, while [DBUH][4-F-PhO]-4-F-PhOH binary mixtures are chemically inert to CO 2 . NMR analysis and theoretical calculations evidence that the strength of hydrogen bonds between [4-F-PhO] − and hydrogen-bond donors (EG and 4-F-PhOH) governs the CO 2 absorption behaviors, and the strength of the hydrogen bond between the anion [4-F-PhO] − and 4-F-PhOH is much stronger than that between [4-F-PhO] −and EG. Moreover, the desorption behaviors of the DESs studied can also be controlled by tuning the strength of the hydrogen bonds in the solvents. This work highlights the important role of hydrogen bonds in CO 2 capture, which may be useful for the rational design of efficient solvents for carbon capture in the future.

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“…[2][3][4][5] A major driver for the recent surge in eutectic solvent research for lowpressure CO 2 separations is their appreciable CO 2 capacities, attainable when functionalized with nucleophilic sites for CO 2 chemisorption. 5,6 Choline-based eutectic solvents, particularly those containing biodegradable choline chloride ([Ch] + [Cl] À ), are readily available and can be derivatized for specific applications. 7 Ethaline is a common example of a eutectic solvent composed of [Ch] + [Cl] À and EG (about 1 : 4 molar ratio).…”

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confidence: 99%

“…8 While ethaline has no CO 2 chemisorption capacity, anion functionalization, such as replacing the [Cl] À anion with prolinate [Pro] À or glycinate [Gly] À , results in the formation of CO 2 reactive eutectic solvents, 5,9 with CO 2 binding to the anion, but not to [Ch] + or EG. These functionalized solvents present appreciable CO 2 capacities at low partial pressures, 6,[9][10][11] which is ideal for CO 2 capture applications, such as direct air capture.…”

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confidence: 99%

Formation of choline salts and dipolar ions for CO₂ reactive eutectic solvents

Dikki,

Cagli,

Penley

et al. 2023

Chem. Commun.

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CO₂ capture by 1,2,3-triazole-based deep eutectic solvents: the unexpected role of hydrogen bonds

Abstract: Hydrogen bonding is found to be a switch for the reaction between CO2 and the 1,2,3-triazole-based deep eutectic solvents.

Cited by 20 publications

References 43 publications

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

Effect of Hydrogen Bonds on CO₂ Capture by Functionalized Deep Eutectic Solvents Derived from 4-Fluorophenol

Formation of choline salts and dipolar ions for CO₂ reactive eutectic solvents

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CO2 capture by 1,2,3-triazole-based deep eutectic solvents: the unexpected role of hydrogen bonds

Abstract: Hydrogen bonding is found to be a switch for the reaction between CO2 and the 1,2,3-triazole-based deep eutectic solvents.

Cited by 20 publications

References 43 publications

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

Effect of Hydrogen Bonds on CO2 Capture by Functionalized Deep Eutectic Solvents Derived from 4-Fluorophenol

Formation of choline salts and dipolar ions for CO2 reactive eutectic solvents

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CO₂ capture by 1,2,3-triazole-based deep eutectic solvents: the unexpected role of hydrogen bonds

Effect of Hydrogen Bonds on CO₂ Capture by Functionalized Deep Eutectic Solvents Derived from 4-Fluorophenol

Formation of choline salts and dipolar ions for CO₂ reactive eutectic solvents