1-methylimidazolium chloride

Finally, several imidazolium-based polymers have been synthesized, including poly[3-(4-vinylbenzyl)-1 -methylimidazolium chloride and bis(tri-fiuoromethylsulfonyl)imide], and recent studies have evidenced their ability to stabilize metal nanoparticles (Figure 4.13). ... 

As they are rather polar materials they often do not mix with solvents or nonpolar product molecules. Using the BASF product 1-methylimidazole as an acid scavenger, an ionic liquid is formed 1-methylimidazolium chloride (HMIMCl), which has a... 

Protic ionic liquids are technically attractive because they represent a range of materials that may be readily prepared simply by mixing a suitable proton acceptor and a Bronsted acid. Because of the reversibility of protonation, the conponent acid and base may, in principle, be separated, purified and the salt subsequently reformed, a route to recovery and recycle not generally available for fully allq lated ionic liquids. Indeed, the ionic liquid, 1-methylimidazolium chloride, a vital conponent of the BASIL process, is attractive for this very reason. 

The first industrial process to involve ionic liquids was introduced by BASF in 2002. Called BASIL", this technology addresses the problem of HCl formed as a byproduct in the synthesis of alkoxyphenylphosphanes (eq. 9.86). Before the advent of ionic liquids, HCl was scavenged by a tertiary amine, forming a solid [RsNHJCl salt which was separated by filtration. On a commercial scale, this operation is expensive. BASF now uses 1-methylimidazole to scavenge HCl (eq. 9.87). 1-Methylimidazolium chloride is an ionic liquid (mp 348 K) which is immiscible with the reaction solvent. Separation of the two liquid phases is achieved at a lower cost than the filtration previously needed. Deprotonation of the 1-methylimidazolium cation regenerates imidazole which is recycled. 

Anionic surfactants like alkanesulfonates can also be determined by poten-tiometric titration with ion-selective electrodes. Recently, a special PVC electrode was offered as a high-sense surfactant electrode in combination with the new titrant l,3-didecyl-2-methylimidazolium chloride [20]. This one-phase... 

The dehydration of fructose 40 or glucose into 5-hydroxymethylfurfural 41 is a process which has been exploited to convert biomass into higher value products. The reaction has been achieved using a chromium NHC complex, formed in situ from CrCl and the NHC 42 (Scheme 11.10) [16], The reaction is performed in the ionic liquid BMIM+Cl (l-butyl-3-methylimidazolium chloride). 

When the same [NiI (NHC)2] complexes are employed as alkene dimerisation catalysts in ionic liquid (IL) solvent [l-butyl-3-methylimidazolium chloride, AICI3, A-methylpyrrole (0.45 0.55 0.1)] rather than toluene, the catalysts were found to be highly active, with no evidence of decomposition. Furthermore, product distributions for each of the catalyst systems studied was surprisingly similar, indicating a common active species may have been formed in each case. It was proposed that reductive elimination of the NHC-Ni did indeed occur, as outlined in Scheme 13.8, however, the IL solvent oxidatively adds to the Ni(0) thus formed to yield a new Ni-NHC complex, 15, stabilised by the IL solvent, and able to effectively catalyse the dimerisation process (Scheme 13.9) [25-27],... 

Recently several pubhcations have examined replacing aqueous solvents with ionic liquids. Since simple and complex sugars are soluble in many imidazolium hahdes, water is not required as a co-solvent and degradation of HMF is minimal. Lansalot-Matras et al. reported on the dehydration of fmctose in imidazolium ionic liquids using acid catalyst (6). Moreau et al. reported that l-H-3-methylimidazolium chloride has sufficient acidity to operate without added acid (7). And we reported that a 0.5 wt% loading (6 mole% compared to substrate) of many metal halides in 1-ethyl-3-methylimidazohum chloride ([EMIM]C1) result in catalytically active materials particularly useful for dehydration reactions (8). 

For the sulfonation step, amino acids were added as their sodium salts. The reactions were carried out in cold aqueous solution, in which the sulfonamides were immediately precipitated. By the same method dansylations of amino acids could be accomplished with N-( 1 -dimethylaminonaphthalene-5-sulfonyl)-Af -methylimidazolium chloride ... 

Khadilkar and Rebeiro have investigated a new method [107] that overcomes all these problems and is far safer. The authors used closed pressure reactor [108], with no apparent loss of yield. The microwave reactor used for these reactions has a possibility for recording temperature and pressure during irradiation. For example, 1-bu-tyl-3-methylimidazolium chloride was isolated in 91% yield in 24 min [109] at 150 °C and 57 psig was the maximum pressure reached. 

In the BASF BASIL process that utilizes A-methylimidazole to scavenge HCl byproduct, the acidic ionic liquid A-methylimidazolium chloride [HMIMJCl was formed, with a melting point of 75°C (13,102). Recently, the group of Bronsted acidic ionic liquids with the same cation was extended to include other anions, such as BFF, TfO , and TsO . The melting point of the salt is between 30 and 109°C. Strong hydrogen bonding in the tosylate salt was characterized by IR spectroscopy. 

C. 1- Butyl-3-methylimidazolium hexafluorophosphate. A 1-L, one-necked, round-bottomed flask (Note 13) is charged with 65.6 g (0.37 mol, 1 equiv) of 1- butyl-3-methylimidazolium chloride, and 69.3 g (0.37 mol, 1 equiv) of potassium hexafluorophosphate (Note 19) in 70 ml of distilled water. The reaction mixture is stirred at room temperature for 2 hr affording a two-phase system. The organic phase is washed with 3 X 50 mL of water and dried under reduced pressure (0.1 mbar, 0.001 mm). Then 100 ml of dichloromethane and 35 g of anhydrous magnesium sulfate are added. After 1 hr, the suspension is filtered and the volatile material is removed under reduced pressure (0.1 bar, 0. 1 mm) at 30°C for 2 hr to afford 86.4 g (0.29 mol, 81%) of 1- butyl-3-methylimidazolium hexafluorophosphate as alight yellow viscous liquid, mp 10°C (Notes 20 and 21). 

Butyl-3-methylimidazolium chloride IH-lmidazolium, 1-butyl-3-methyl-, chloride (10) (79917-90-1)... 

Chloroaluminate ILs derived from l-butyl-3-methylimidazolium chloride having two equivalents of aluminum chloride were effective catalysts for the Pechmann condensation of phenol with ethylacetoacetonate, Scheme 26. ... 

The electrochemical reduction of TiCU and ZrCl4, in chloroaluminate melts and other molten salt systems, to lower valent halides has been fairly widely studied [4-7]. This has also been extended to studies of centered hexanuclear Zr halide clusters. Thus, ambient temperature AICI3 -1 -ethyl-3-methylimidazolium chloride (ImCl) molten salts, both basic (40/60 mol% AlCls/ImCl) and acidic (60/40 mol% AICI3 /ImCl), were used in an electrochemical investigation of clusters... 

The combination of quaternary ammonium chloride salt, such as l-ethyl-3-methylimidazolium chloride (EMIC), with... 

Voltammetry at a glassy carbon (GC) electrode was used to study of the electrochemical deposition of CdTe from the Lewis basic l-ethyl-3-methylimidazolium chloride/tetrafluoroborate room temperature ionic liquid [208]. 

The electrochemistry of Cd(II) was investigated at different electrodes (GC, polycrystalline tungsten, Pt, Ni) in a basic l-ethyl-3-methylimidazolium chloride/tet-rafluoroborate, at room temperature molten salt [312], and in acidic zinc chloride-l-ethyl-3-methylimidazolium [284]. 

Three ionic liquids were purchased from Aldrich l-butyl-3-methylimidazolium chloride, l-butyl-3-methylimidazolium hexafluorophosphate and l-butyl-3-methylimidazolium tetrafluoroborate. Homogeneous Co (II) catalyst precursors used in our experiments include Co(BF4)2, Co(OAc)2, and Co(C104)2 each of which have high solubilities in above ionic liquids. High surface area catalyst supports Si02 and AI2O3 were obtained from Davison and Engelhard, respectively. 

Domarfeka, U., Bogel-Lukasik, E., and Bogel-Lukasik, R., 1-Octanol/water partition coefficients of l-alkyl-3-methylimidazolium chloride, Chem. Eur. J., 9,3033,2003. 

Domariska, U. and Bogel-Lukasik, E., Measurements and correlation of the (solid + liquid) equilibria of [l-decyl-3-methylimidazolium chloride + alcohols (C2-CJ2)], Ind. Eng. Chem. Res., 42,6986, 2003. 

Arce, A., Rodriguez, O., and Soto A., Experimental determination of liquid-liquid equilibrium using ionic liquids tert-amyl ethyl ether + ethanol + l-octyl-3-methylimidazolium chloride system at 298.15 K, f. Chem. Eng. Data, 49, 514, 2004. 

Zhang, H., Wu, ]., Zhang, J., and He, J., l-Allyl-3-methylimidazolium chloride room temperature ionic liquid A new and powerful nonderivatizing solvent for cellulose. Macromolecules, 38,8272-827/ 2005. 

Schlufter, K., Schmauder, H.P., Dorn, S., and Heinze, T., Bacterial cellulose in the ionic liquid l-n-butyl-3-methylimidazolium chloride, Macromol. Rapid Commun., 27, 1670-1676,2006. 

Remsing, R.C., Swatloski, R.P., Rogers, R.D., and Moyna, G., Mechanism of cellulose dissolution in the ionic liquid l-n-butyl-3-methylimidazolium chloride a and 35/37(21 NMR relaxation study on model systems, Chem. Commun., 1271-1273, 2006. 

Wasserscheid and coworkers were the first to attempt to use ILs for the desulfurization of model solutions (dibenzothiophene [DBT], in n-dodecane) and real diesel fuels [41]. For extraction, the authors used ILs with l-alkyl-3-methylimidazolium cations ([C CiIm], n = 2, 4, 6) and various anions. Also, binary mixtures of l-alkyl-3-methylimidazolium chloride with AICI3 (Lewis-acidic ILs), the equimolar mixture of cyclohexyldiethylammonium and tri-butylammonium mefhanesulfonates (Brnnsted-acidic IL) and the equimolar mixture of cyclohexyldiefhylmethylammonium and tributylmefhylammo-nium methanesulfonafes were tested. 

Saha, S., Hayashi, S., Kobayashi, A., and Hamaguchi, H., Crystal structure of l-butyl-3-methylimidazolium chloride. A clue to the elucidation of the ionic liquid structure, Chem. Let., (Japan), 32, 740-741, 2003. 

Downard, A., Earle, M. J., Hardacre, C., McMath, S. E. J., Nieuwenhuyzen, M., and Teat, S. J., Structural studies of crystalline l-alkyl-3-methylimidazolium chloride salts, Chem. Mater., 16, 43-48, 2004. 

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