1-Ethyl-3-methylimidazolium bromide

pale yellow to yellow crystals, crystalline powder

General procedure: The ligands (except 3) were all synthesized by adaptation of the methods of Starikova et al. [20]. A typical and generic procedure is described. Spectroscopic and analyses data are presented. N-monosubstituted azole (0.1mmol) and dry toluene were placed in a two-neck flask and stirred until a homogeneous solution was formed; then alkyl halide (0.3mmol) was added drop wise with continuous stirring. After addition of the alkyl halide, the mixture was stirred while heating at 40°C for 24h. The solvent was removed and the ligand was dried under vacuum. 2.2.2 The intermediate 1-ethyl-3-methylimidazolium bromide[EMIM]Br was prepared with equimolar bromoethane(>99percent) and 1-methylimidazolium (>99percent) in a closed glass reactor and the reaction was enhanced by microwave(Milestone microwave lab station, Italy). Firstly, the reactor was heated to 80°C (80 w) during a period of 30 seconds and the temperature was kept for another 90 seconds(100 w) to complete this reaction. The forming of AlClStep 1; Synthesis of l-ethyl-3-methylimidazolium bromide; Into a flask equipped with a thermometer, a nitrogen gas inlet tube, a reflux condenser tube, a stirrer, and a dropping funnel, methylimidazole 82 g (1.0 mol) and 2-butanone(hereinafter, described as MEK) 400 g were charged. While the mixture was maintained at 50°C under nitrogen flow, ethyl bromide163.5 g (1.5 mol) was added dropwise into the mixture over 2 hours. Then, the mixture was maintained at 80°C for 2 hours and then the reaction was completed. Then, the reaction liquid was filtered to obtain l-ethyl-3-methylimidazolium bromide (hereinafter, described as EMImBr) whichwas a slight brown-white crystal. Then, this crystal was washed with MEK two times in a glove box, the inside of which was substituted with nitrogen, to obtain white EMImBr 172g (yield of 90percent) .General procedure: The salts 15a-15e were prepared by the reported procedures. The reactions of neat alkyl halides with 1-methyl imidazole were carried out under nitrogen atmosphere. The white solid compounds were formed in the reaction mixture. These reaction mixtures were evaporated to dryness in vacuum to give white solid salts in good yield. The solid salts were highly hygroscopic in nature. All salts 15a-15e were characterized by common spectroscopic techniques.Ionic liquid 1-ethyl-3-methylimidazolium bromidePreparation of the compound:In a 100 ml three-necked flask with a condensing reflux unit, Add 1-methylimidazole (8.2 g, 0.1 mol), Ethyl bromide (11.99 g, 0.11 mol) was stirred at 35 ° C for 5 hours.A white crystalline powder was obtained which was washed with ethyl acetate to remove ethyl bromide.Dry at 80 ° C for 3 h under vacuum. The yield was 85percent.0.82g (10 mmol) 1-methylimidazole and 1.09 g (10 mmol) bromoethane were slowly added to 50 mL acetonitrile under stirring with continuous heating at 70–80C and refluxing for 10 h. It was then filtered off and recrystallized with methanol and ether, and dried under vacuum. The yield of MLDE ¢Brreached about 49.7percent. The synthesis method can be showedas the followed Scheme 2.Examples 3 and 4: methylene diacetateand 2: ethylene glycol diacetate; A 100 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (50.0 g, 0.293 mol), and 0.5 equivalents of 1, 2-dichloroethane (14.5 g, 0.146 mol) were added at room temperature and reaction was stirred at 70°C for 3h. After reaction two phases were obtained upper layer was decanted and the reaction mixture was extracted 3 times with diethyl ether, all fractions were combined and diethyl ether was removed under vacuum. The final pure product was obtained as color less liquid (90.0percent yield) When 1, 2-dibromoethane was used as substrate the reaction was very fast even at room temperature and was highly exothermic. The reaction proceeds via homogeneous pathway; the pure product was distilled from the reaction mixture at 100°C under reduced pressure (90.0percent yield). Ethylene glycol diacetate: Examples 6 and 7: sec-butyl acetate

Ionic liquid

Molecular Weight:191.07
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:190.01056
Monoisotopic Mass:190.01056
Topological Polar Surface Area:8.8
Heavy Atom Count:9
Complexity:72.9
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes