Design, Synthesis, and Evaluation of Nonaqueous Silylamines for Efficient CO<sub>2</sub> Capture

Switzer, Jackson R.; Ethier, Amy L.; Hart, Emily C.; Flack, Kyle M.; Rumple, Amber C.; Donaldson, Jordan C.; Bembry, Ashley T.; Scott, Owen M.; Biddinger, Elizabeth J.; Talreja, Manish; Song, Myoung-Geun; Pollet, Paméla; Eckert, Charles A.; Liotta, Charles L.

doi:10.1002/cssc.201300438

Cited by 32 publications

(43 citation statements)

References 19 publications

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“…It is concluded that, in addition to the expected DBU salt of the carbamate (7), an additional species is also present in the reaction mixture. Employing additional NMR experiments, the structure of this species was postulated to be the DBU salt of benzylbicarbamate (8) shown in Figure 8. The experimental details and accompanying interpretation are presented as follows.…”

Section: Reaction Of Benzylamine With 1 Equivalent Of Dbumentioning

confidence: 99%

“…In DMSO or DMF the carbamic acid is the primary product. In a solvent such as acetonitrile and an equivalent amount of strong organic base such as DBU, the amidinium benzylcarbamate (7) is the major product along with the amidinium benzylbicarbamate (8). In contrast, if only 0.5 equivalent of DBU is present the major species appears to be the DBU salt of bis-benzylbicarbamate.…”

Section: In Situ Protection Of Amines With Co2mentioning

confidence: 99%

“…CO2 is known to react with primary and secondary amines to form the corresponding carbamic acid or ammonium carbamate ion pair [1][2][3][4][5][6][7][8][9][10][11]. The CO2-amine reaction can be reversed thermally under relatively mild conditions-a key to developing "in situ, reversible" protection schemes.…”

Section: Introductionmentioning

confidence: 99%

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The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

et al. 2015

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Abstract:The introduction and removal of protecting groups is ubiquitous in multi-step synthetic schemes. From a green chemistry standpoint, however, alternative strategies that employ in situ and reversible protection and deprotection sequences would be attractive. The reversible reactions of CO2 with amines could provide a possible vehicle for realizing this strategy. Herein, we present (1) the products of reaction of benzylamines with CO2 in a variety of solvents with and without the presence of basic additives; (2) 498(4-aminomethyl)phenyl) methanol with isopropenyl acetate in acetonitrile containing DBU in the absence and presence of CO2.

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Section: Reaction Of Benzylamine With 1 Equivalent Of Dbumentioning

confidence: 99%

Section: In Situ Protection Of Amines With Co2mentioning

confidence: 99%

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The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

et al. 2015

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“…28,29 The hypothesis has been that until 60-70% conversion, the ML acts like a solvent to the ionic RevIL species, significantly reducing the ionic and hydrogen bonding between the RevIL. 28,29 The trend with TEtoxySA follows this similar pattern, as shown in Figure 3. However, the conductivity of the system remained relatively constant as a function of conversion, where any change in conductivity is within experimental error.…”

Section: Resultsmentioning

confidence: 99%

“…• C. 28,29,39 The increased CO 2 uptake is due to the formation of carbamic acid. However, literature reports that that the carbamic acid is non-ionic and does not act as a charge carrier.…”

Section: Resultsmentioning

confidence: 99%

Ionicity Analysis of Silylamine-Type Reversible Ionic Liquids as a Model Switchable Electrolyte

Jiménez

Jung

Biddinger

2015

J. Electrochem. Soc.

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Separation of the electrochemical product from an electrolyte can add challenges to the overall process. Use of a switchable electrolyte offers the possibility to reduce or eliminate these separation challenges while maintaining high conductivity. Reversible ionic liquids (RevILs) are a type of switchable solvent that could be used as a switchable electrolyte. Switchable solvents are solvents that can have dramatic step-changes in their properties with the introduction of an external stimulus, in this case CO 2 . In order to determine the feasibility of using TEtoxySA-RevIL, which behaves similarly to protic ionic liquids, as an electrolyte an ionicity analysis utilizing binary mixtures of the RevIL and organic solvents were studied to determine the ionic behavior of the system. Both protic and aprotic solvents with a broad range of dielectric constants were used in order to elucidate the ionicity of the RevIL mixtures. When in the pure RevIL state, the conductivity is prohibitively low due to a heightened viscosity and poor ion mobility due to hydrogen bonding and coulometric attraction. We found that in the presence of protic solvents with high dielectric constants the conductivity of the RevIL increased by up to four orders of magnitude and achieved ideal ionicity.

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Encapsulated Ionic Liquids for CO₂ Capture: Using 1‐Butyl‐methylimidazolium Acetate for Quick and Reversible CO₂ Chemical Absorption.

et al. 2016

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The potential advantages of applying encapsulated ionic liquid (ENIL) to CO capture by chemical absorption with 1-butyl-3-methylimidazolium acetate [bmim][acetate] are evaluated. The [bmim][acetate]-ENIL is a particle material with solid appearance and 70 % w/w in ionic liquid (IL). The performance of this material as CO sorbent was evaluated by gravimetric and fixed-bed sorption experiments at different temperatures and CO partial pressures. ENIL maintains the favourable thermodynamic properties of the neat IL regarding CO absorption. Remarkably, a drastic increase of CO sorption rates was achieved using ENIL, related to much higher contact area after discretization. In addition, experiments demonstrate reversibility of the chemical reaction and the efficient ENIL regeneration, mainly hindered by the unfavourable transport properties. The common drawback of ILs as CO chemical absorbents (low absorption rate and difficulties in solvent regeneration) are overcome by using ENIL systems.

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Design, Synthesis, and Evaluation of Nonaqueous Silylamines for Efficient CO₂ Capture

Cited by 32 publications

References 19 publications

The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

Ionicity Analysis of Silylamine-Type Reversible Ionic Liquids as a Model Switchable Electrolyte

Encapsulated Ionic Liquids for CO₂ Capture: Using 1‐Butyl‐methylimidazolium Acetate for Quick and Reversible CO₂ Chemical Absorption.

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Design, Synthesis, and Evaluation of Nonaqueous Silylamines for Efficient CO2 Capture

Cited by 32 publications

References 19 publications

The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

Ionicity Analysis of Silylamine-Type Reversible Ionic Liquids as a Model Switchable Electrolyte

Encapsulated Ionic Liquids for CO2 Capture: Using 1‐Butyl‐methylimidazolium Acetate for Quick and Reversible CO2 Chemical Absorption.

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Product

Resources

About

Design, Synthesis, and Evaluation of Nonaqueous Silylamines for Efficient CO₂ Capture

Encapsulated Ionic Liquids for CO₂ Capture: Using 1‐Butyl‐methylimidazolium Acetate for Quick and Reversible CO₂ Chemical Absorption.