3- methyl-1 - imidazolium chloride

FIG. 11 Titration plot of alkanesulfonates. Sample 60 wt % of Hostapur SAS 60, monosulfonates fraction contents ca. 140 mg/100 ml (10% MeOH) solution to be titrated 10 ml, 5 ml buffer pH 3 (Merck), 5 ml MeOH, diluted to 100 ml with water titrant 0.004 mol/l TEGOtrant A 100 (l,3-didecyl-2-methyl-imidazolium chloride, Metrohm 6.2317.000) titrator Titrino 716 DMS with automatic titrator 727 and propellant stirrer titration mode dynamic end point titration (DET), high-sense electrode Metrohm 6.0504.15Q, reference electrode Ag/AgCl Metrohm 6.0733.100, EP = end point. 

Full dissolution has been reported to proceed in ionic liquids such as butyl- or allyl-methyl-imidazolium chloride under microwave irradiation [59, 60], The Clanton is claimed to be essential to favor the de-agglomerization of the cellulose by breaking its H-bonds that hold it together [61]. The cellulose can subsequently be precipitated from the ionic liquid upon addition of, for example, water, without significant depolymerization. 

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... 

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). 

Recently, the air- and water-stable combinations of l-n-butyl-3-methyl-imidazolium chloride with sodium tetrafluoroborate or sodium hexafluoro-phosphate have been prepared. The rhodium complexes [RhCl(PPh3)3] and [Rh(COD)2](BF4) are completely soluble in these ionic liquids and catalyze the hydrogenation of cyclohexene in a typical two-phase reaction with numbers of turnovers of up to 6000 (131). 

C. Moreau, A. Finiels, and L. Vanoye, Dehydration of fructose and sucrose into 5-hydro-xymethylfurfural in the presence of l-H-3-methyl imidazolium chloride acting both as solvent and catalyst, J. Mol. Catal. A Chem., 253 (2006) 165-169. 

BMIm]BF4 BMImCl [BMIm]PF6 CCS ecu [Choline] [Pro] 1 -butyl-3-methyl-imidazolium tetrafluoroborate 1 -butyl-3-methyl-imidazolium chloride 1 -butyl-3-methyl-imidazolium hexafluorophosphate CO2 capture and storage/sequestration CO2 capture and utilization (2-hydroxyethyl)-trimethyl-ammonium (iS )-2-pyrrolidine-carboxylic acid salt... 

The reaction does not occur obviously in three commonly used ILs l-butyl-3-methyl-imidazolium chloride ([BMIm]Cl), 1-butyl-3-methyl-imidazolium tetra-fluoroborate ([BMIm]BF4), l-butyl-3-methyl-imidazolium hexafluorophosphate ([BMIm]PF6). Only 3 % yield can be obtained in water, indicating PEG is the best solvent for the oxidation of secondary alcohols when using Co(II)/ZnO as catalyst. This is because PEG can form Co(II) complex (Co(II)L), which can activate 02 molecule and thereby promote the oxidation of organic compounds (Scheme 3.3) [26]. 

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

The first electrodeposition of lithium from an ionic liquid was reported in 1985 by Lipsztajn and Osteryoung [2], They were able to deposit lithium from a 1-ethyl-3-methyl-imidazolium chloride/aluminum trichloride ionic liquid. They noticed that a neutral ionic liquid, a neutral basic ionic liquid (neutral + small excess of RC1) and a neutral acidic ionic liquid (neutral + small excess of AICI3) each have unique features. Both the basic and the neutral acidic ionic liquids show an extension of 1.5 V of the electrochemical window, making them interesting for electrochemical applications. 

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. 

Hussey et al. carried out an aluminum bulk deposition on copper foil using a Lewis acidic aluminum chloride 1 -ethyl-3-methyl-imidazolium chloride-based ionic liquid [9]. The thickness of the observed deposits were in the range 24—30 pm. Without additives the deposits were not shiny and only poorly adherent. The addition of benzene enhanced the quality of the deposit. XRD measurements confirmed that the composition of the deposits was 100% aluminum metal. 

Endres et al. were able to deposit nanocrystalline aluminum from an aluminum chloride/1-butyl-3-methyl-imidazolium chloride-based ionic liquid (molar ratio 55/45 mol%) and to characterize it by using XRD and TEM [11], Figure 4.5 shows the corresponding XRD pattern. 

The electrodeposition of gallium is of interest for its extraction and purification and for the production of III-V semiconductors. Sun et al. were the first to report the electrodeposition of gallium from Lewis acidic aluminum chloride-1 -ethyl-3-methyl-imidazolium chloride melts (ratio 60 40 mol%) on tungsten and glassy carbon in 1999 [14] The Ga(I) species was introduced by anodization of the gallium metal. 

Pitner and Hussey studied the electrochemistry of tin in acidic and basic AICI3/I-ethyl-3-methyl-imidazolium chloride-based ionic liquids by using voltammetry and chronoamperometry at 40 °C [15]. They reported that the Sn(II) reduction process is uncomplicated at a platinum substrate, where in the atidic ionic liquid the reduction wave was observed at +0.46 V on the Pt electrode and the oxidation at +0.56 V. When they used a gold electrode instead of platinum, they observed an underpotential deposition of a tin monolayer and an additional underpotential deposition process that was attributed to the formation of tin-gold alloy at the surface. The deposition of tin on glassy carbon was controlled by nudeation. 

Sun et al. used basic melts of Tethyl-3-methyl-imidazolium chloride and aluminum chloride of different molar ratios to dissolve TeCU [18]. At —0.68 V reduction of tellurium was observed, which was clearly controlled by the nudeation/growth rate. The bulk deposition led only to poorly adherent powder which was confirmed to be Te° by XRD. 

Potentiostat, (typically, Echochemie, Autolab PGSTAT), Schlenk tube x 2, aluminum sheet, mild steel rods, P400 sand paper, anhydrous AICI3, l-butyl-3-methyl imidazolium chloride ([BMIM]C1), toluene, acetone, dichloromethane, HC1, HNO3, H3PO4, acetic acid, isopropanol. 

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... 

Liu Z, Chen ZC, Zheng QG (2003) Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in ionic hquid l-buthyl-3-methyl-imidazolium chloride and water. Org Lett 5 3321-3323... 

In another approach, the dehydration has been conducted in ionic liquids (l-alkyl-3-methylimidazolium chloride) under acid or metal chloride catalysis yielding HMF up to more than 80% nearly without any formation of by-products like levulinic acid [32], When using chromium(II) chloride as catalyst even D-glucose could be used as feedstock since this catalyst is effective for the in situ isomerization of o-glucose to o-fructose before dehydration takes place to produce HMF in 70% yield. The catalyst system N-heterocyclic carbene/CrCU in l-butyl-3-methyl imidazolium chloride has been developed for the selective conversion of D-fructose (96% yield) and o-glucose (81% yield) [33]. 

A/-butyl 3-methyl imidazolium chloride 1-A/-allyl 3-methyl imidazolium chloride... 

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... 

Example l-Dodecyl-3-methylimidazolium bromide, l-dodecyl-3-methylimida-zolium hexafluorophosphate, l-hexadecyl-3-methyl-imidazolium chloride. 

Table 5.4-3 Solubilities of i-butene and n-butane in the acidic mixture composed of i-butyl-3-methyl imidazolium chloride aluminum chloride ethylaluminum dichloride (1 1.22 0.06 molar ratio) as a function of temperature and under atmospheric pressure...

During the reaction two clear liquid phases occur (Fig. 9-3) that can easily be separated. The upper phase is the pure product - solvent is no longer needed -the lower phase the pure ionic liquid, l-methyl-imidazolium chloride as an ionic liquid has a great advantage over the classical dialkylated systems it can be switched... 

Figure 1.7 Electrochemical potential windows of Al-butyl-pyridinium chloride (BPC) and 1-ethyl-3-methyl imidazolium chloride (EMIC) in the presence of AlClj and depending on the acidity of the ionic melt, different potential windows exist. (Reproduced with permission from Ref. [25], 2002, Elsevier.)...

Figure 7.21 Side view of an aluminum film on steel deposited from an ionic melt that has been formed of ethyl-methyl-imidazolium-chloride and aluminum-tri-chloride. (Reproduced with permission from Ref. [35], 2006, Elsevier.)...

Figure 4.7 CVs for the oxidation of AA (1.0 mM] at bare [curve a] and l-butyl-3-methyl imidazolium chloride [[BMIM][Cl]]-modified [curve b] GC electrodes in 0.10 M phosphate buffer. Curves a and b represent CVs obtained at the above electrodes in the same solution containing no AA. Scan rate, 100 mV s" Reprinted with permission from Ref. [48]. Copyright 2005 American Chemical Society.

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