Decreasing the Viscosity in CO<sub>2</sub> Capture by Amino-Functionalized Ionic Liquids through the Formation of Intramolecular Hydrogen Bond

Luo, Xiao; Fan, Xi; Shi, Gui L.; Li, Hao R.; Wang, Cong M.

doi:10.1021/acs.jpcb.5b10553

Cited by 81 publications

(57 citation statements)

References 67 publications

(98 reference statements)

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“…As was recently pointed out by Wang et al, [50] the formation of an intramolecular hydrogen bond in the carbamic acid prevents the increase of the viscosity of the AAIL. All pre- Table 2.…”

mentioning

confidence: 71%

“…[19-21, 41, 43, 44] The high viscosities of AAILs before CO 2 absorption and their dramatic increase after CO 2 absorption have led to the investigation of methods to reduce the viscosity, prevent its increase, or both. Mixtures of AAILs with water [27,45,46] or low-viscosity ILs, [47,48] the immobilization of AAILs into porous materials, [16,40,42,49] and AAILs with the possibilities to form intramolecular hydrogen bonds [50] have been considered. However, the available theoretical work deals with density functional theory calculations of several aminefunctionalized anions and cations [51,52] to explain the 1:2 or 1:1 absorption capacity owing to the stabilization or destabilization effect of the cation or anion on the carbamic acid.…”

Section: Introductionmentioning

confidence: 99%

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Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Firaha

Kirchner

2016

ChemSusChem

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One of the possible solutions to prevent global climate change is the reduction of CO2 emissions, which is highly desired for the sustainable development of our society. In this work, the chemical absorption of carbon dioxide in amino acid ionic liquids was studied through first-principles methods. The use of readily accessible and biodegradable amino acids as building blocks for ionic liquids makes them highly promising replacements for the widely applied hazardous aqueous solutions of amines. A detailed insight into the reaction mechanism of the CO2 absorption was obtained through state-of-the-art theoretical methods. This allowed us to determine the reason for the specific CO2 capacities found experimentally. Moreover, we have also conducted a theoretical design of ionic liquids to provide valuable insights into the precise tuning of the energetic and kinetic parameters of the CO2 absorption.

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“…As was recently pointed out by Wang et al, [50] the formation of an intramolecular hydrogen bond in the carbamic acid prevents the increase of the viscosity of the AAIL. All pre- Table 2.…”

mentioning

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Firaha

Kirchner

2016

ChemSusChem

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“…Formation of intramolecular excimer by a dipyrenyl probe can be very effective in probing viscosity changes of the medium . For such compounds, observation of red‐shifted, broad emission resulting from an excimer is observed along with the normal structured monomer fluorescence.…”

Section: Resultsmentioning

confidence: 99%

Superbase‐Added Choline Chloride‐Based Deep Eutectic Solvents for CO₂ Capture and Sequestration

Bhawna

Pandey

2017

ChemistrySelect

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Deep eutectic solvents (DESs) have emerged as inexpensive and environmentally‐benign liquid media for potential usage in chemical sciences. CO2 capture and sequestration by various substances is an active area of research in green chemistry. CO2 capture ability of DES‐based systems composed of salt choline chloride mixed with hydrogen bond donors urea (named reline), ethylene glycol (named ethaline), and monoethanolamine (named MEACC), are assessed in the absence and presence of three superbases: 1,5‐diazabicyclo[4.3.0]‐non‐5‐ene (DBN), 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), and 1,5,7‐triazabicyclo[4.4.0]‐dec‐5‐ene (TBD), respectively. Addition of superbase is found to significantly increase the CO2 capture ability of the DESs reline and ethaline; for the DES MEACC, the CO2 capture ability is not changed much as monoethanolamine and MEACC on their own exhibit appreciable CO2 capture efficiency. It is found that the overall efficiency of CO2 capture is the best with superbase DBN as compared to DBU or TBD due to the lower steric hindrance around the imine structure. Presence of glycerol in the superbase‐added DESs results in decrease in CO2 capture ability due to significantly lower solubility of CO2 in glycerol. 13C NMR, FTIR and Raman spectroscopic measurements reveal that major part of the captured CO2 binds covalently to the electron‐rich functionalities present on the components of the DES with superbase assisting this association. The reversibility of the captured CO2 is assessed by introducing N2 gas into the CO2 captured superbase‐added DES system; it is found that only 21–25% CO2 by weight could be removed from the system through five cycles. Heating the CO2 captured superbase‐added DES system to 60 °C and 100 °C results in loss of only 23% and 35% CO2 by weight, respectively. Intramolecular excimer intensity of 1,10‐bis(1‐pyrenyl)decane and steady‐state fluorescence anisotropy of rhodamine 6G fluorescence probes effectively monitor the CO2 capture process as viscosity of the superbase‐added DES increases as more‐and‐more CO2 is captured. Efficiency, effectiveness, and robustness of superbase‐added DES‐based systems towards CO2 capture and sequestration is amply highlighted.

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“…Hydrogen bonding and viscosity correlations in ionic liquids (ILs) have also been discussed at length . TSILs that possess N or O atoms capable of intramolecular hydrogen bonding have significantly lower CO 2 ‐rich viscosity compared to conventional ILs . Upon CO 2 capture, CO 2 BOLs form a zwitterion capable of forming intra‐ or intermolecular hydrogen bonds, as shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

Reinventing Design Principles for Developing Low‐Viscosity Carbon Dioxide‐Binding Organic Liquids for Flue Gas Clean Up

et al. 2017

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Anthropogenic CO emissions from point sources (e.g., coal fired-power plants) account for the majority of the greenhouse gases in the atmosphere. Water-lean solvent systems such as CO -binding organic liquids (CO BOLs) are being developed to reduce the energy requirement for CO capture. Many water-lean solvents such as CO BOLs are currently limited by the high viscosities of concentrated electrolyte solvents, thus many of these solvents have yet to move toward commercialization. Conventional standard trial-and-error approaches for viscosity reduction, while effective, are time consuming and economically expensive. We rethink the metrics and design principles of low-viscosity CO -capture solvents using a combined synthesis and computational modeling approach. We critically study the effects of viscosity reducing factors such as orientation of hydrogen bonding, introduction of higher degrees of freedom, and cation or anion charge solvation, and assess whether or how each factor affects viscosity of CO BOL CO capture solvents. Ultimately, we found that hydrogen bond orientation and strength is the predominant factor influencing the viscosity in CO BOL solvents. With this knowledge, a new CO BOL variant, 1-MEIPADM-2-BOL, was synthesized and tested, resulting in a solvent that is approximately 60 % less viscous at 25 mol % CO loading than our base compound 1-IPADM-2-BOL. The insights gained from the current study redefine the fundamental concepts and understanding of what influences viscosity in concentrated organic CO -capture solvents.

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Decreasing the Viscosity in CO₂ Capture by Amino-Functionalized Ionic Liquids through the Formation of Intramolecular Hydrogen Bond

Cited by 81 publications

References 67 publications

Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Superbase‐Added Choline Chloride‐Based Deep Eutectic Solvents for CO₂ Capture and Sequestration

Reinventing Design Principles for Developing Low‐Viscosity Carbon Dioxide‐Binding Organic Liquids for Flue Gas Clean Up

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Decreasing the Viscosity in CO2 Capture by Amino-Functionalized Ionic Liquids through the Formation of Intramolecular Hydrogen Bond

Cited by 81 publications

References 67 publications

Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Tuning the Carbon Dioxide Absorption in Amino Acid Ionic Liquids

Superbase‐Added Choline Chloride‐Based Deep Eutectic Solvents for CO2 Capture and Sequestration

Reinventing Design Principles for Developing Low‐Viscosity Carbon Dioxide‐Binding Organic Liquids for Flue Gas Clean Up

Contact Info

Product

Resources

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Decreasing the Viscosity in CO₂ Capture by Amino-Functionalized Ionic Liquids through the Formation of Intramolecular Hydrogen Bond

Superbase‐Added Choline Chloride‐Based Deep Eutectic Solvents for CO₂ Capture and Sequestration