L-ethyl-3-methylimidazolium chloride

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]. 

Carper, W. R., Pflug, J. L., and Wilkes, J. S., Dual spin probe NMR relaxation studies of ionic structure in l-ethyl-3-methylimidazolium chloride-AlClg molten-salts, Inorg. Chim. Acta, 202,89,1992. 

One type of room-temperature ionic liquid is the mixture of A1C13 and a quaternary ammonium chloride (R+C1 ) like l-ethyl-3-methylimidazolium chloride (EMI+C1 ) and 1-butylpyridinium chloride (BP+Ch) [28]. At 1 1 molar ratio of A1C13 and R+C1 , A1C13 exists as AICI4 but the AICI4 ions slightly dissociate into AI2CI7 and Cl-. 

The reactivity of haloalkanes in alkylation reactions also decreases with increasing chain length. In general, syntheses of salts with short alkyl substituents are more complex due to the low boiling points of the haloalkanes. The most frequently used halide salt in this field, l-ethyl-3-methylimidazolium chloride ([EMIM] Cl), is typically synthesized in an autoclave with the chloroethane cooled to below its boiling point (12 °C) before addition. 

Treatment of a quaternary halide salt Q+X with a Lewis acid MX results in the formation of a salt with the composition Q+MX +i . In general, more than just one anion species is formed, depending on the relative proportions of MX and the halide salt Q X. A representative example is the reaction of l-ethyl-3-methylimidazolium chloride [EMIMJC1 with AICI3 (Scheme 2.3). 

Zinc and its alloys are good materials for corrosion-resistant coatings and they are widely used in the automobile industry. The electrodeposition of zinc or its alloys is normally performed in aqueous electrolyte solutions. However, zinc and its alloys can be obtained in improved quality from ionic liquids. It was shown that Lewis acidic ZnCl2-[EMIM]Cl (l-ethyl-3-methylimidazolium chloride) liquids in which... 

Palladium is employed in a number of industrial applications and fundamental studies because of its high catalytic activity for many chemical reactions, e.g. its ability to absorb hydrogen [41], On the other hand, due to hydrogen absorption, only brittle Pd deposits can be obtained in aqueous solutions. The advantage of performing electrodeposition of Pd in ionic liquids is that hydrogen evolution does not occur. Sun et al. demonstrated that Pd and some of its alloys, namely Pd-Ag [42], Pd-Au [43] and Pd-In [44], can be obtained from the basic l-ethyl-3-methylimidazolium chloride/tetrafluoroborate ionic liquid. Compact alloy deposits were obtained and the Pd content in the deposits increased with the increase in Pd mole fraction in the plating bath. 

Antimony is a brittle silvery-white metal. Although the unalloyed form of antimony is not often used in industry, alloys of antimony have found wide commercial applications. The integration of antimony gives certain desirable properties, such as increased corrosion resistance and hardness. Moreover, antimony is also the component of some semiconductors such as InSb and InAsi %Sb%. Sb electrodeposits with good adherence were obtained in a water-stable l-ethyl-3-methylimidazolium chloride-tetrafluoroborate ([EMIM]C1-BF4) room-temperature ionicliquid [53]. Furthermore, it was stated that a crystalline InSb compound can be obtained through direct electrodeposition in the ionic liquid [EMIM]C1-BF4 containing In(III) and Sb(III) at 120 °C [54]. It is just a question of time until antimony electrodeposition is reported in the third generation of ionic liquids. 

CdTe, a II—VI compound semiconductor with a direct band gap of 1.44 eV at room temperature, is, from its physical properties, a promising photovoltaic material. The electrodeposition of CdTe in ionic liquid was published recently by Sun et al. [38]. They were able to show that the semiconductor can be electrodeposited at elevated temperature (above 120 °C) in the Lewis basic l-ethyl-3-methylimidazolium chloride/tetrafluoroborate ionic liquid containing CdCh and TeCU. CdTe films were obtained by the underpotential deposition (UPD) of Cd on the deposited Te. The deposit composition was independent of the deposition potential within the Cd UPD regime. The crystallinity of the deposits is improved by increasing the deposition temperature, which again demonstrates the high potential of the wide thermal windows of ionic liquids for compound electrodeposition. 

Electrodeposition ofAl from l-Ethyl-3-methylimidazolium chloride/AlCl3... 

In this protocol we describe an electroplating procedure for mild steel with an adhesive aluminum layer in Lewis acidic ionic liquid l-ethyl-3-methylimidazolium chloride [EMIMJC1 containing AICI3. We aim to electroplate mild steel with dense, adherent and uniform aluminum layers in the employed ionic liquids at room temperature. 

Electrodeposition of Alfrom l-EthYl-3-methYlimidazolium chloride/AlCf 355... 

Clusters in which intercluster linkages are minimized can be excised. For example, by mixing l-ethyl-3-methylimidazolium chloride (ImCl) with A1C13 and (Zr6Fe)Br14 in a melt reaction, the compound (Im)4[(Zr6Fe)Clig] can be isolated.50... 

Ll/AICIs-EMIC-LIChSOCI Taphite [12]. EMIC l-ethyl-3-methylimidazolium chloride... 

AlCl3-A-butylpyridinium chloride, AlCl3-l-ethyl-3-methylimidazolium chloride, HCl-l-ethyl-3-methylimidazolium chloride, and AlCl3-LiSCN mixtures have been studied using X-ray and neutron scattering [164-167]. These studies have provided information about the specific interactions between anions and cations within the ILs. Unfortunately, little additional information could be extracted from the data. In particular, no information about the structure of the respective ILs beyond the first coordination sphere could be obtained. Importantly, however, the authors show that in AlCl3-LiSCN, the N and not the S atom of the SCN ion coordinates to the Al ion. This was explained with a hard base/hard acid interaction which can be expected for a Lewis acid compound like A1C13. 

Tsuda T, Hussey CL, Stafford GR (2003) Electrochemistry of titanium and the electrodeposition of Al-Ti alloys in the Lewis acidic aluminum chloride-l-ethyl-3-methylimidazolium chloride melt. J Electrochem Soc 150 C234-C237... 

Yang MH, Yang MC, Sun IW (2003) Electrodeposition of indium antimonide from the water-stable l-ethyl-3-methylimidazolium chloride/tetrafluoroborate ionic liquid. J Electrochem Soc 150 C544-C550... 

Huang JF, Sun IW (2004) Nonanomalous electrodeposition of zinc-iron alloys in an acidic zinc chloride-l-ethyl-3-methylimidazolium chloride ionic liquid. J Electrochem Soc 151 C8-C15... 

Chen PY, Sun IW (2001) Electrodeposition of cobalt and zinc-cobalt alloys from a Lewis acidic zinc chloride-l-ethyl-3-methylimidazolium chloride molten salt. Electrochim Acta 46 1169-1174... 

Hsu HY, Yang CC (2003) Conductivity electrodeposition and magnetic property of cobalt (II) and dysprosium chloride in zinc chloride-l-ethyl-3-methylimidazolium chloride room temperature molten salt. Z Naturforsch 58B 139-145... 

The most common ionic liquids include alkylammonium, alkylphosphonium, A/-alkylpyridinium, and A/A/ -dialkylimidazolium cations. Two general methods for their preparation are acid-base neutralization reactions and metathesis of halide salts with a metal or ammonium salts. Alkylammonium, pyridinium, and imidazo-lium halides can be prepared by the reaction of the appropriate alkyl halide and amine. Preparation of l-ethyl-3-methylimidazolium chloride [emimjCl requires a sealed tube since it has a low boiling point. On the other hand, synthesis of [bmim] Cl can be achieved under conventional reflux conditions [33, 34]. 

The same acidic chloroaluminate ionic liquids have been used as solvent for tungsten aryl oxide complexes for the metathesis of alkenes [24]. Slightly acidic chloroaluminates also dissolve the [Cl2W=NPh(PMe3)3] complex which catalyze ethene oligomerization without the addition of co-catalysts [25]. In a similar way, Ni-catalyzed 1-butene dimerization into linear octenes was carried out in acidic chloroaluminates buffered with small amount of weak bases [26]. Neutral chloroaluminates (l-ethyl-3-methylimidazolium chloride/AlCl3 = 1) were employed to immobilize ruthenium carbene complexes for biphasic ADMET (acyclic diene metathesis) polymerization of an acyclic diene ester [27]. 

The aluminum chloride-promoted Friedel-Crafts acylation can also be successfully performed in ionic media. An easy-to-handle ionic liquid is that prepared from a mixture of one to two equivalents of aluminum chloride and l-ethyl-3-methylimidazolium chloride or iodide (EtMeimCl-AlCl3 and EtMeiml-AlCls, respectively). These solvent-catalysfs can be utilized in the easy and efficient acylation of unprotected indoles with a variety of acyl chlorides to give C-selective acylation at the 3-position in 38%-87% yield. ... 

Diels-Alder reactions." Addition of AICI3 to l-ethyl-3-methylimidazolium chloride forms a chloroaluminate ionic liquid. This substance accelerates and enhances the selectivity of Diels-Alder reactions. 

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