L-ethyl-3-methyl imidazolium

The imidazolium compounds l-ethyl-3-methyl-imidazolium-chloride (EMIM-Cl), l-butyl-3-methyl-imidazolium-chloride (n-BuMIM-Cl), and l-hexyl-3-methyl-imidazolium-chloride (n-HeMIM-Cl), toluene (anhydrous, 99.99%), and HCl were obtained from Sigma Aldrich whereas, l-octyl-3-methyl-imidazolium-chloride (n-OcMIM-Cl), l-Dodecyl-3-methyl-imidazolium-chloride (n-DoMIM-Cl) were... 

Rhinebarger et al. [35] and Eyring et al. [36,37] have used lithium-7 nuclear magnetic resonance (NMR) chemical shift data to determine the stability constants for crown-ether complexes of Li+ in two IL systems consisting of 55/45 mole% N-butylpyridinium chloride-aluminum chloride and l-ethyl-3-methyl-imidazolium chloride-aluminum chloride. The stability constants for... 

Takahashi, S., Curtiss, L. A., Gosztola, D., Koura, N., and Saboungi, M.-L., Molecular orbital calculations and raman measurements for l-ethyl-3-methyl-imidazolium chloroaluminates, Inorg. Chem., 34, 2990-2993, 1995. 

Wilkes, J.S. and Zaworodtko, M.J., Air and water stable l-ethyl-3-methyl-imidazolium based ionic liquids. /. Chem. Soc. Chem. Comm., 13, 965-967, 1992. 

Ionic liquids are a class of solvents and they are the subject of keen research interest in chemistry (Freemantle, 1998). Hydrophobic ionic liquids with low melting points (from -30°C to ambient temperature) have been synthesized and investigated, based on 1,3-dialkyl imidazolium cations and hydrophobic anions. Other imidazolium molten salts with hydrophilic anions and thus water-soluble are also of interest. NMR and elemental analysis have characterized the molten salts. Their density, melting point, viscosity, conductivity, refractive index, electrochemical window, thermal stability, and miscibility with water and organic solvents were determined. The influence of the alkyl substituents in 1,2, 3, and 4(5)-positions on the imidazolium cation on these properties has been scrutinized. Viscosities as low as 35 cP (for l-ethyl-3-methylimi-dazolium bis((trifluoromethyl)sulfonyl)amide (bis(triflyl)amide) and trifluoroacetate) and conductivities as high as 9.6 mS/cm were obtained. Photophysical probe studies were carried out to establish more precisely the solvent properties of l-ethyl-3-methyl-imidazolium bis((trifluoromethyl)sulfonyl)amide. The hydrophobic molten salts are promising solvents for electrochemical, photovoltaic, and synthetic applications (Bon-hote et al., 1996). 

Seddon showed that l-ethyl-3-methyl imidazolium chloride-aluminum(lll) chlorides are ionic liquids at temperatures as low as -90°C (Seddon, 1996 Earle and Seddon, 2000). These nonvolatile ionic liquids can solvate a wide range of organic reactions including oligomerisations, polymerizations (Lynn et al., 2000), alkylations (Ross et al., 2001), and acylations (Seddon, 1997 Welton, 1999). 

Fig. 4.1 Simplified electrochemical windows of 1-butyl-pyridinium chloride and l-ethyl-3-methyl-imidazolium chloride.

The first work in this field was reported by Winnick et al. in 1995 [4], In order to design a sodium/iron(II) chloride battery, they examined a l-ethyl-3-methyl-imidazolium chloride/aluminum chloride-based system. As described by Lipsztajn and Osteryoung for lithium it was first necessary to synthesize the acidic ionic liquid by adding an excess of AICI3 and then adding an equivalent amount of sodium chloride as a buffer to obtain again the neutral species. 

The structure of a vanadyl tetrachloride salt has been characterized with the l-ethyl-3-methyl-imidazolium cation (152).698 The coordination chemistry of V02+ with F was investigated in ionic melts.699 X(o) calculations were carried out to characterize the electronic structures and d-d... 

Yeh FH, Tai CC, Huang JF et al (2006) Formation of porous silver by electrochemical alloying/ dealloying in a water-insensitive zinc chloride-l-ethyl-3-methyl imidazolium chloride ionic liquid. J Phys Chem B 110 5215-5220... 

The photoisomerization of cis-and trans-stilbenes has been studied in ionic liquids and evidence is presented that the mechanism depends on the particular ionic liquid used. In basic N-butylpyridinium chloride/AlCb the photoequilibration involves stilbene radical cations, whereas in basic l-ethyl-3-methyl-imidazolium chloride/AlCb the process occurs via the standard singlet state photoisomerization mechanism. It has been found that the tetra-O-acetylribo-flavin (126) sensitized dehydrogenation of substituted benzyl alcohols, giving the... 

N, N, N, N -trimethylbutylammonium l-ethyl-3-methyl-imidazolium l-n-hexyl-3-methyl-imidazolium l-n-butyl-3-methyl-imidazolium l-ethyl-3-methyl-imidazolium l-n-butyl-3-methyl-imidazolium l-n-hexyl-3-methyl-imidazolium trihexyl (tetradecyl) -phosphonium trihexyl (tetradecyl) -phosphonium... 

Blends were prepared with cellulose or silk as soon as a common solvent was available [63, 69-71]. Recently, ionic liquids were used. The solvent l-ethyl-3-methyl-imidazolium acetate completely dissolves raw crustacean shells allowing to recover high purity chitin powder or films and fibres by direct spinning [72]. Films of poly(e-caprolactone) (PCL) blends with a-chitin and chitosan were produced. They are completely biodegradable and the crystallinity of PCL is suppressed in the blends due to hydrogen bond interaction between PCL and polysaccharides [73]. Blends were also realized with poly (3-hydroxybutyric acid) (PHB) and chitin or chitosan. They show faster biodegradation than the pure-state component polymers [74,75]. 

Hantel, M. M., A. Platek, T. Kaspar, R. Nesper, A. Wokaun, and R. Kotz. 2013. Investigation of diluted ionic liquid l-ethyl-3-methyl-imidazolium tetrafluoroborate electrolytes for intercalation-like electrodes used in supercapacitors. Electrochimica Acta 110 234-239. 

The ionic liquid, l-ethyle-3-methyle imidazolium ethyl sulfate, is synthesized by alkylation of methyllimidazole as follows [29]... 

Pig. 8.13 Differential capacitance of l-ethyl-3-methyl imidazolium (emim) and bisfluorosnlfonyl imide (FSI) with alow concentration of LjFSI [123], Reprinted with permission from [123] Copyright 2011 American Chemical Society... 

Geometrical trans to cis isomerization of 3,3 -, 4,4 -, and 5,5 -disubstituted 2,2 -diphenoquinones has been studied by computational methods.The double bond isomerization of butene-catalysed l-ethyl-3-methyl-imidazolium chloride ionic liquid has been similarly examined and stepwise isomerization is suggested.The reaction of l,2-di(l-adamantyl)-2-thioxoethanone with diazomethane and 2-diazopropane gave 2-acylthiiranes via 2 - - 3-cycloaddition, elimination of nitrogen, and 1,3-dipolar electrocyclization of the intermediate acyl-substituted thiocarbonyl ylides. Rearrangement of pyrimidine-5-carboxylic acids esters to 5-acylpyrimidones does not occur in the examples studied and a [l,4]-phospho-Fries rearrangement has been reported. ... 

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