Ether-Functionalized Imidazolium Hexafluorophosphate Ionic Liquids for Improved Water Miscibilities

Schrekker, Henri Stephan; Stracke, Marcelo Paulo; Schrekker, Clarissa M. L.; Dupont, Jaı̈rton

doi:10.1021/ie0709685

Cited by 51 publications

(39 citation statements)

References 45 publications

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“…For example, 1-(2-hydroxypropyl)-3-methylimidazolium based ILs (paired with various anions such as Cl − , NO 3 − , PF 6 − and Tf 2 N − ) are more hygroscopic and more miscible with water than the alkyl-substituted analogues. 75 Schrekker et al 139 observed that the incorporation of an ether chain into the imidazolium cation greatly improves hydrophilicity and water miscibility of PF 6 − based ILs; the hydrophilicity increases in the order of [BMIM][PF 6 ] < [MeO(CH 2 ) 2 -MIM][PF 6 ] < [Me(OCH 2 CH 2 ) 3 -MIM][PF 6 ], and at 50 °C the latter is completely miscible with water. A dimethylammonium-based IL containing two PEG-350 methyl ether chains is completely miscible with water due to the hydrophilic nature of the two long alkoxy chains 59 while 1-(2-hydroxyethyl)-3-methylimidazolium hexafluorophosphate ([(HOCH 2 CH 2 )-MIM][PF 6 ]), is soluble in water at >50 kg m –3 at 25 °C.…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

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: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 99%

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

2012

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“…[21][22][23] These functionalized ILs increased water solubility compared to their alkyl-derivatized counterparts. 24 The potential of such ILs in gas separations has been recently reported with polymer gas separation membranes based on polymerizable etherderivatized ILs. 25 No thermodynamic property of cyanoalkyl-substituted ILs was found in the literature.…”

Section: Introductionmentioning

confidence: 99%

Study of Ether-, Alcohol-, or Cyano-Functionalized Ionic Liquids Using Inverse Gas Chromatography

et al. 2010

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Activity coefficients of 52 organic compounds in four ionic liquids (ILs), 1,3-dimethoxyimidazolium bis((trifluoromethyl)sulfonyl)imide, 1-(methylethylether)-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide, 1-ethanol-3-methylimidazolium bis((trifluoromethyl)-sulfonyl)imide, and 1-(3-cyanopropyl)-3-methylimidazolium dicyanamide, were measured using inverse gas chromatography from (312 to 353) K. The retention data were also converted in gas-to-IL partition coefficients and water-to-IL partition coefficients using the corresponding gas-to-water partition coefficients. Both sets of partition coefficients were analyzed using the modified Abraham solvation parameter model. The derived equations correlated the experimental gas-to-IL and water-to-IL partition coefficient data to within (0.09 and 0.14) log units, respectively.

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“…Contrary to conventional volatile organic compounds (VOCs), most ILs are generally regarded as "green" solvents due to their immensely low vapor pressure [4]. The class of imidazolium cation-based RTILs has been demonstrated to be highly attractive in extraction and separation processes because their structural modifications in both the cation (especially the 1 and 3 positions of the imidazolium ring) and anion permit the tuning of properties such as miscibility with water and organic solvents, the melting point and viscosity [2]. Effort has been made with imidazolium ionic liquids as extraction solvents in liquid phase microextraction (LPME).…”

Section: Introductionmentioning

confidence: 99%

“…Room-temperature ionic liquids (RTILs) are a special class of ionic liquids (ILs) with the melting point at or below 25 °C [1][2][3]. Contrary to conventional volatile organic compounds (VOCs), most ILs are generally regarded as "green" solvents due to their immensely low vapor pressure [4].…”

Section: Introductionmentioning

confidence: 99%

Temperature-controlled ionic liquid dispersive liquid phase microextraction combined with ultra-high-pressure liquid chromatography for the rapid determination of triclosan, triclocarban and methyl-triclosan in aqueous samples

Guo

Cao

et al. 2010

Sci. China Chem.

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As extraction solvents, ionic liquids have green characteristics. In this study, an environmentally benign analytical method termed temperature-controlled ionic liquid dispersive liquid phase microextraction (TIL-DLME) combined with ultra-highpressure liquid chromatography (UHPLC)-tunable ultraviolet detection (TUV) was developed for the pre-concentration and determination of triclosan (TCS), triclocarban (TCC) and methyl-triclosan (M-TCS) in water samples. Significant parameters that may affect extraction efficiencies were examined and optimized, including the types and amount of ionic liquids, volume of the diluent, heating temperature, cooling time, salt effect and pH value. Under the optimum conditions, linearity of the method was observed in the ranges of 0.0100-100 g L 1 for TCS and M-TCS, and 0.00500-50.0 g L 1 for TCC with correlation coefficients (r 2 ) > 0.9903. The limits of detection (LODs) ranged from 1.15 to 5.33 ng L 1. TCS in domestic water and TCC in reclaimed water were detected at the concentrations of 1.01 and 0.126 g L 1 , respectively. The spiked recoveries of the three target compounds in reclaimed water, irrigating water, waste water and domestic water samples were obtained in the ranges of 68.4%-71.9%, 61.6%-87.8%, 58.9%-74.9% and 64.9%-92.4%, respectively. Compared with the previous dispersive liquid-liquid microextraction method (DLLME) about the determination of TCS, TCC and M-TCS, this method is not only more environmentally friendly but also more sensitive.ionic liquid, temperature-controlled ionic liquid dispersive liquid phase microextraction, UHPLC, aqueous samples

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Ether-Functionalized Imidazolium Hexafluorophosphate Ionic Liquids for Improved Water Miscibilities

Cited by 51 publications

References 45 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

Study of Ether-, Alcohol-, or Cyano-Functionalized Ionic Liquids Using Inverse Gas Chromatography

Temperature-controlled ionic liquid dispersive liquid phase microextraction combined with ultra-high-pressure liquid chromatography for the rapid determination of triclosan, triclocarban and methyl-triclosan in aqueous samples

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