Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis

Wilkes, John S.; Levisky, Joseph A.; Wilson, Robert A.; Hussey, Charles L.

doi:10.1021/ic00133a078

Cited by 1,479 publications

(997 citation statements)

References 3 publications

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“…Early studies of this interesting class of aprotic solvents focused on equilibria, how the electrochemistry varied depending on the acid-base character of the melt, the use of electroanalytical approaches to analyze water and oxide impurities, and the use of polypyrrole-and polyvinylferrocene-coated electrodes (57 ). Some studies suggested that ILs might be useful as electrolytes in batteries, photoelectrochemical cells, and electroplating (2,57 ).…”

Section: Electrochemistrymentioning

confidence: 99%

“…Typical ILs have conductivities of >10 -2 S/cm and are often useless as target ions (2,57,58). ILs possessing a zwitterionic structure in which the cation and anion are tethered (and therefore not expected to migrate with the potential gradient) were examined (58 ).…”

Section: Electrochemistrymentioning

confidence: 99%

“…ILs are also interesting because of their other useful and intriguing physicochemical properties. Wilkes et al first reported ambient-temperature ILs based on the 1-alkyl-3-methylimidazolium cation in 1982 (2). Since then, many ILs containing a variety of cations and anions of different sizes have been synthesized to provide specific characteristics.…”

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confidence: 99%

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Ionic Liquids in Analytical Chemistry

Anderson¹,

Armstrong²,

Wei³

2006

Anal. Chem.

491

326

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oom-temperature ionic liquids (RTILs), also known as liquid organic, molten, or fused salts, are a class of nonmolecular ionic solvents with low melting points. The accepted definition of an RTIL is any salt that has a melting point lower than ambient temperature (1). However, "ionic liquid" (IL) is often applied to any compound that has a melting point <100°C. Most common RTILs are composed of unsymmetrically substituted nitrogen-containing cations (e.g., imidazole, pyrrolidine, pyridine) with inorganic anions (e.g., Cl -, PF 6 -, BF 4 -). ILs are also interesting because of their other useful and intriguing physicochemical properties. Wilkes et al. first reported ambient-temperature ILs based on the 1-alkyl-3-methylimidazolium cation in 1982 (2). Since then, many ILs containing a variety of cations and anions of different sizes have been synthesized to provide specific characteristics.Over the past few years, research and applications of ILs have expanded tremendously. The initial impetuses for this expansion were organic synthesis and the growth of green chemistry. In this article, we will give an overview of the structure and properties of ILs and describe their expanding use in various applications in separations and chromatography, MS, spectroscopy, and electrochemistry. Description and propertiesILs have negligible vapor pressures at room temperature, possess a wide range of viscosities, can be custom-synthesized to be miscible or immiscible, often have high stability, and are capable of un-

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Section: Electrochemistrymentioning

confidence: 99%

Section: Electrochemistrymentioning

confidence: 99%

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Ionic Liquids in Analytical Chemistry

Anderson¹,

Armstrong²,

Wei³

2006

Anal. Chem.

491

326

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“…The enhanced thermal stability of imidazolium surfactants as compared with the alkylammonium halides has been reported to be due to the delocalization of the positive charge over the imidazole ring [22] and [23]. Similarly, if the charge delocalization is increased by fusing a benzene ring to imidazole (as in the case of benzimidazole), one might expect further enhanced thermal stability.…”

Section: Morphology Of Polymer-clay Nanocompositesmentioning

confidence: 99%

Benzimidazolium surfactants for modification of clays for use with styrenic polymers

Costache

Heidecker

Manias

et al. 2007

Polymer Degradation and Stability

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Abstract:Nanocomposites of polystyrene (PS), acrylonitrile-butadiene-styrene copolymer (ABS) and high impact polystyrene (HIPS) were prepared with two new homologous benzimidazolium surfactants used as organic modifications for the clays. The morphology of the polymer/clay hybrids was evaluated by powder X-ray diffraction (XRD) and transmission electron microscopy (TEM), showing good overall dispersion of the clay. The thermal stability of the polymer/clay nanocomposites was enhanced, as evaluated by thermogravimetric analysis. From cone calorimetric measurements, the peak heat release rate of the nanocomposites was decreased by about the same amount as seen for other organically-modified, commercially available clays.

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“…[1][2][3] Work has focussed on liquids formed from dialkylimidazolium halides which are readily prepared from 1-methylimidazole and a slight excess of the desired haloalkane. 4 Addition of a suitable molar ratio of aluminium chloride to these salts gives rise to ionic liquids containing complex metal anions which have been used in a number of applications such as electroplating, electrochemical devices and catalysts for organic synthesis. 1,[4][5][6] The main disadvantage of imidazolium-based liquids is their relatively high cost for bulk applications, whilst chloroaluminate ionic liquids have the additional problem of their low tolerance to moisture, necessitating the use of glove box and Schlenk techniques to prepare and investigate their properties.…”

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confidence: 99%

Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains

et al. 2001

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Ionic liquids, or room temperature molten salts, have attracted increasing interest over recent years, particularly in the area of green chemistry, due to their advantageous properties including negligible vapour pressure and wide liquid range. 1-3 Work has focussed on liquids formed from dialkylimidazolium halides which are readily prepared from 1-methylimidazole and a slight excess of the desired haloalkane. 4 Addition of a suitable molar ratio of aluminium chloride to these salts gives rise to ionic liquids containing complex metal anions which have been used in a number of applications such as electroplating, electrochemical devices and catalysts for organic synthesis. 1,[4][5][6] The main disadvantage of imidazolium-based liquids is their relatively high cost for bulk applications, whilst chloroaluminate ionic liquids have the additional problem of their low tolerance to moisture, necessitating the use of glove box and Schlenk techniques to prepare and investigate their properties. The former problem may be overcome by using cheaper ammonium salts whereas the latter may be solved by replacing aluminium with less reactive metals.Recently, Freeman and coworkers have characterised ionic liquids formed from FeCl 2 or FeCl 3 and 1-butyl-3-methylimidazolium chloride. 7 However, other examples of ionic liquids made from metal chlorides other than aluminium are less well characterised and are mainly cited in conference proceedings 8 or in the patent literature. 9,10 Here we report the synthesis and characterisation of new moisture-stable, Lewis-acidic ionic liquids made from metal chlorides and quaternary ammonium salts that are commercially available or simple to synthesise. These offer the potential to tailor the physical properties e.g. melting point, viscosity and conductivity, and to tune the Lewis acidity by choosing a different metal or indeed combinations of metals.To investigate the parameters necessary for a salt to be liquid at or near room temperature we have heated a range of ammonium salts with zinc chloride in a 1+2 molar ratio and the results are shown in Since choline chloride, [Me 3 NC 2 H 4 OH]Cl, gave the lowest freezing point we have characterised this system in more detail. Heating mixtures of choline chloride and zinc chloride in molar ratios between 1+1 and 1+3 gave rise to clear colourless liquids, with the freezing points varying between ca. 65 °C (1+1), 25 °C (1+2) and 45 °C (1+3). Unlike analogous aluminium systems, 4,11,12 ratios with a molar excess of choline chloride, i.e. basic melts, do not form ambient temperature liquids in these systems. This would imply that complex zinc anions, in which the charge can be delocalised, are necessary in the formation of these ionic liquids. Further characterisation of the 1:2 liquid is described below.A 1 H NMR spectrum of the neat ionic liquid was recorded and shows resonances at d 2.97, 3.34 and 3.94 assigned to the methyl groups, N-CH 2 protons, and the CH 2 OH protons, respectively, of the choline cation. All signals were broad and poorly reso...

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Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis

Cited by 1,479 publications

References 3 publications

Ionic Liquids in Analytical Chemistry

Ionic Liquids in Analytical Chemistry

Benzimidazolium surfactants for modification of clays for use with styrenic polymers

Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains

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