| 23.63 g |
at 60℃; for 2h; |
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In toluene cooling; |
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In toluene at 20℃; |
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at 60℃; for 2h; |
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In toluene |
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at 20℃; Inert atmosphere; Cooling with ice; |
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In toluene at 20℃; Cooling with ice; |
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at 40℃; Neat (no solvent); cooling/heating system; |
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In toluene at 40℃; Cooling with ice; Inert atmosphere; |
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Cooling with ice; Heating; |
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In toluene at 20℃; for 4h; Inert atmosphere; Cooling with ice; |
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In neat (no solvent) at 34.84℃; |
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at 60℃; for 24h; |
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In toluene at -15 - 25℃; for 0.00833333h; Inert atmosphere; |
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With ethyl acetate at 0℃; for 24h; |
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In toluene at 39.84℃; for 4h; Cooling with ice; |
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In water at 20℃; for 70h; |
Synthesis of [EMIM][EtSO4]
[EMIM][EtSO4] was prepared by first transferring 10 mmol of 1-methylimidazole (0.82 g) and 20 mL of water to a 100-mL round-bottom flask placed in an ice bath. The resulting mixture was allowed to stir (Scheme 1). Then, 3.6 mmol of diethylsulfate (0.54 g) was added dropwise to control the vigorous nature of the reaction. After 10 h, 3.2 mmol of diethylsulfate (0.5 g) was slowly added under continuous stirring in an ice bath. After 20 h of reaction, 3.2 mmol of diethylsulfate (0.5 g) was added slowly, and the reaction was stirred continuously for 10 h, after which the ice bath was removed and the reaction was stirred further for 30 h at room temperature. After completion of the reaction (monitored via thin layer chromatography (TLC)), water was removed using rotary evaporation, and the ionic liquid obtained was kept in an oven for 1 h at 110 C to remove the residual water. |
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In toluene at 20℃; for 5h; Inert atmosphere; |
Diethylsulfate(0.44 mol, 58 mL) was slowly added drop-wise to anice-cooledmixture of 1-methylimidazole (0.44mol, 35 mL) and toluene(1.88 mol, 200 mL) under an inert atmosphere of argon.When the additionof diethylsulfatewas complete, the reaction mixturewas stirred for5 h at room temperature to allow the reaction to go to completion. Atthe end of this period, the lower layer (ionic liquid phase)was separatedfrom the mixture by using a separating funnel and then washed threetimes with a total volume of 100 mL toluene. The crude product wasdried at 70 °C under reduced pressure for 3 h using a rotary evaporator;to remove organic solvents and water before the characterizationmeasurements. |
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In benzene at 20℃; for 5h; |
Preparation of ILs
[EMIM][EtSO4] was synthesized using a molar ratio of N-methylimidazole (C4H6N2) and diethyl sulfate (C4H10O4S) of 1 : 1. First, the N-methylimidazole was dissolved in benzene through stirring at room temperature. The diethyl sulfate was added drop-wise into the above mixture and allowed toreact for 5 h. The unreacted raw materials were removed by arotary evaporator. [EMIM][EtSO4] was obtained as a viscous liquid. |
| 220 g |
at 50℃; for 24h; |
2.1 Example 2
(1) 82.1 g of N-methylimidazole,169.6 g of diethyl sulfate was added,The reaction was stirred at 50 ° C for 24 hours,Washed with ethyl acetate,80 steaming,Get 220g 1-ethyl-3-methylimidazole sulfuric acidEthyl ester salts,For the light yellow liquid; |
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In water; toluene Inert atmosphere; |
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In toluene Inert atmosphere; |
2.2. Synthesis of the ionic liquid
1-Ethyl-3-methylimidazolium ethyl sulfate was prepared accordingto: 0.42 mol of diethyl sulfate was added dropwise to 0.42 mol of 1-methylimidazole in toluene and cooled in an ice bath under argon at arate tomaintain the reaction temperature below313.15 K due to the reactionbeing highly exothermic. The reaction mixture was stirred atroom temperature for (1 to 4) h depending on the amount of startingmaterials. The upper organic phase of the resulting mixture wasdecanted, and the lower IL phase was washed with ethyl acetate. Afterthe last washing, the remaining ethyl acetate was removed by heatingunder reduced pressure. The IL obtained was dried by heating to(343.15 to 353.15) K and stirring under high vacuum for 48 h. InTable 2, some of the physical properties of synthesized IL are givenand compared with literature. |
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In toluene Cooling with ice; |
Synthesis of the ILs
General procedure: Ionic liquids were synthesized by using the method developed by Holbrey et al. [26].A dialkyl sulfate (0.5 mol) was added drop wise to a solution of 1-methylimidazole(0.5 mol) in toluene (150 mL), while cooled in an ice bath. The reaction mixture yieldedILs immediately with the formation of a biphasic system. After complete addition ofdialkyl sulfate the reaction mixture was stirred overnight. Thereafter, the upper organicphase was decanted and the lower IL phase was washed with toluene (75 mL), thendried with heating at 353 K under reduced pressure to remove residual solvent. |
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In toluene for 4h; Cooling with ice; |
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In toluene at 40℃; for 4h; Inert atmosphere; |
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In toluene at 39.99℃; for 4h; Inert atmosphere; Cooling with ice; |
2.2. Synthesis of EMIES
EMIES was synthesized by reaction of N-methylimidazole anddiethyl sulfate in toluene, the synthetic process of EMIES is shown in Fig. 1 and has been described in the previous papers [19-21]. Diethylsulfate and N-methylimidazole with a molar ratio of 1.2:1 were addedto toluene under protection of nitrogen in an ice-water bath, whichwas kept at 313.15 K for 4 h, the solution was cooled to room temperature,washed three timeswith ethyl acetate, the sampleswere dried in avacuum oven at 70 °C for 72 h. The structures of EMIES were characterizedby 1H NMRwith 13C NMR spectrum (Varian, XL-300) and the solventsof 1H NMR with 13C NMR spectrum of EMIES are CDCl3 andDMSO. The 1H NMR and 13C NMR spectrum were displayed in theFigs. A and B of supporting information. |
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In ethanol; ethyl acetate; acetonitrile at 50 - 120℃; for 0.166667h; Inert atmosphere; |
1-3 Example 1
(1) Add 10mol of N-methylimidazole (colorless and transparent), 10mol of diethyl sulfate and solvent into a closed 10L reactor. The solvent is made by mixing ethyl acetate, ethanol and acetonitrile in a volume ratio of 1:1:1 , The amount of solvent added is 30% of the total mass of N-methylimidazole and diethyl sulfate. After evacuating the reactor to -0.08MPa, it is heated to 50±5 under stirring conditions and the temperature is controlled to react. HP- GC monitors the reaction process;(2) After the reaction is complete, under stirring, the reaction kettle is heated to 120°C and filled with nitrogen. After the pressure in the kettle reaches 0.8MPa, continue to stir for 10 minutes to condense and recover vapors; on the remaining bottom of the kettle Add 10% solvent to the remaining bottom of the kettle. The solvent is made by mixing ethyl acetate, ethanol and acetonitrile in a volume ratio of 1:1:1. Under stirring, the temperature is increased to 120°C and then reacted. Fill the kettle with nitrogen. After the pressure in the kettle reaches 0.8MPa, continue stirring for 10 minutes, then condense and recover the vapors. The final bottom of the kettle is the 1-ethyl-3-methylimidazole ethyl sulfate ionic liquid. |
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