Oligoether Carboxylates: Task-Specific Room-Temperature Ionic Liquids

Klein, Regina; Zech, Oliver; Maurer, Eva; Kellermeier, Matthias; Kunz, Werner

doi:10.1021/jp200624g

Cited by 42 publications

(41 citation statements)

References 72 publications

(243 reference statements)

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“…244 1-Ethyl-3-methylimidazolium 2-(2-methoxyethoxy) ethylsulfate was used as a solvent for the extraction of linalool from citrus essential oil. 318 Klein et al 319 prepared quaternary ammonium salts (including choline salts) of an oligoether carboxylate (2,5,8,11-tetraoxatridecan-13-oate) (Scheme 44) with a T g of −60 °C and viscosities in the range of 260–840 mPa s at 25 °C; these organic liquids exhibit significantly lower viscosities, higher conductivities, and higher polarities than alkali oligoether carboxylates.…”

Section: Anion-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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Section: Anion-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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“…Indeed, a competition occurs for hydrogen bonding between the anions and cations, which can influence the proton transfer equilibrium position. The carboxylate anion is a better hydrogen‐bond acceptor than the Tf 2 N anion, and gives rise to stronger interactions with the proton of the IL cation (Figure ), causing the equilibrium position to move forwards as much as the hydrogen‐bond donating ability of the cation increases.…”

Section: Resultsmentioning

confidence: 99%

“…[34] Notably,f or all the investigated pyridines, the calculated K eq IL increaseo ni ncreasing the hydrogen-bond donating ability of the IL cation, quantitatively expressed by the solvent parameter a,f ollowst he order Indeed,acompetition occurs for hydrogen bondingb etween the anions and cations, which can influence the proton transfer equilibrium position. The carboxylate anion is ab etter hydrogen-bond acceptort han the Tf 2 Na nion, [35] and gives rise to stronger interactions with the proton of the IL cation (Figure 3), causingt he equilibrium positiont o move forwards as much as the hydrogen-bond donating ability of the cation increases.…”

Section: Effect Of the Il Cationmentioning

confidence: 99%

Ionic Liquids as “Masking” Solvents of the Relative Strength of Bases in Proton Transfer Reactions

et al. 2018

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Equilibrium constants for the proton transfer reaction between pyridines and trifluoroacetic acid were measured in room‐temperature ionic liquids (ILs) of different cation–anion compositions. The experimental equilibrium constants for ion‐pair formation were corrected according to the Fuoss equation. The calculated equilibrium constants for the formation of free ions were taken as a quantitative measure of the base strength in IL solutions and compared with the relative constants in water. The effect of IL composition is discussed for a series of fixed IL anions and fixed IL cations. Finally, the sensitivity of the proton transfer reaction to the electronic effects of the substituent groups on the pyridine ring was quantified by applying the Hammett equation. A more marked levelling effect on the base strength was observed in ILs than in water. The Hammett reaction constants ρ were then correlated with solvent parameters according to a multi‐parametric analysis, which showed that both specific hydrogen‐bond donor/acceptor and non‐specific interactions play an important role, with α and permittivity being the main parameters affecting the ability of the IL to differentiate the strength of the base.

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“…1-Ethyl-3-methylimidazolium 2-(2-methoxyethoxy) ethylsulfate was used as a solvent for the extraction of linalool from citrus essential oil [ 141 ]. Klein et al [ 142 ] …”

Section: Anion-functionalized Ilsmentioning

confidence: 99%

Task-Specific Ionic Liquids for Electrochemical Applications

Zhao

2015

Electrochemistry in Ionic Liquids

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Ionic liquids (ILs) have been widely examined as solvents, additives, or catalysts in a variety of applications including organic catalysis [ 1 -5 ], inorganic and materials synthesis [ 6 ], biocatalysis [ 7 -12 ], electrochemistry [ 13 ], pharmaceutical chemistry [ 14 ], polymerization [ 15 , 16 ], and engineering fl uids [ 17 -19 ]. The physicochemical properties of ILs are tunable through a careful selection of a variety of different cations and anions and a rational combination of ion pairs. More interestingly, cations and/or anions can be further functionalized to form so-called task-specifi c ionic liquids (TSILs). The notion of TSILs carrying specifi c functionality tailored for particular applications has proven visionary, and a variety of different functional groups have been grafted onto ILs [ 20 -22 ]. In particular, there is an exponential growth in constructing new TSILs as electrolytes for electrochemical applications. This chapter focuses on a critical discussion of some major types of TSILs and their electrochemical properties and applications. Ether/Thioether-and Hydroxyl/Thiol-Functionalized ILs General Physical PropertiesOur recent review has captured some key physical properties of ether-and alcoholfunctionalized ILs [ 22 ]. The inclusion of alkyloxy or alkyloxyalkyl groups in ILs often lowers the melting points ( T m ) [ 23 -26 ]. Additionally, the lowering of the

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Oligoether Carboxylates: Task-Specific Room-Temperature Ionic Liquids

Cited by 42 publications

References 72 publications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ionic Liquids as “Masking” Solvents of the Relative Strength of Bases in Proton Transfer Reactions

Task-Specific Ionic Liquids for Electrochemical Applications

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