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CAS No. : | 90076-65-6 | MDL No. : | MFCD00210017 |
Formula : | C2F6LiNO4S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QSZMZKBZAYQGRS-UHFFFAOYSA-N |
M.W : | 287.09 | Pubchem ID : | 3816071 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 11.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 33.4 |
TPSA : | 85.04 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.11 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.32 |
Log Po/w (WLOGP) : | 5.74 |
Log Po/w (MLOGP) : | 0.07 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 1.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.19 |
Solubility : | 1.86 mg/ml ; 0.00649 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.71 |
Solubility : | 0.564 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.55 |
Solubility : | 8.04 mg/ml ; 0.028 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.81 |
Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P260-P264-P270-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P314-P361+P364-P405-P501 | UN#: | 2923 |
Hazard Statements: | H301+H311-H314-H372-H412 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 70℃; | HTf2N was obtained by sublimation at 70 °C from a solution of LiTf2N in concentrated sulfuric acid under reduced pressure (10−3 mbar). The crude product was resublimed for further purification. Yield: 90percent.1H−NMR D2 O : δppm 4:77s; 1H19 F−NMRD2O : δppm −79:16s; 6F13C 19 Fn o−NMRD2O : δppm 19:27s; 2C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 20℃; for 24 h; | First 0.02 mol imidazolium bromide salt was added to 50 mL of dichloromethane and mixed. Then 0.02 mol bis(trifluoromethanesulfonyl)imide salt of lithium was added to the stirring solution of imidazolium bromide salt. The mixture was left stirring for about 24 h at room temperature. Then the lithium bromide salt was filtered and the concentrated AgNO3 solution was added to the solution. The resulting solution was washed with pure water so that AgBr was allowed to pass into the water phase. Then dichloromethane was evaporated with a rotary evaporator. The yield was calculated as 60percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<Preparation Example 2> Preparation of butyl methylpyrrolidinium <n="10"/>bis(tifluoromethanesulfonate)imide; Methyl pyrrolidine (97%, Aldrich Chemical), iodoethane (99%, AldrichChemical), 1-iodopropane (99%, Aldrich Chemical) and 1-iodobutane (99%, AldrichChemical) were used to provide butylmethylpyrrolidinium cation according to the method of Henderson and Passerni (Handerson and Passerni, Chem. Mater., 2004, 16, 2881-2885).As an anion precursor, lithium bis(trifluoromethanesulfonate)imide (HQ-115 available from 3M Co.) was used.The butylmethylpyrrolidinium cation obtained as described above was mixed with lithium bis(trifluoromethanesulfonate)imide and the mixture was allowed to react to provide butylmethylpyrrolidinium bis(trifluoromethanesulfonate)imide.FIG. 6 shows NMR data for determining the presence of the butylmethylpyrrolidinium bis(trifluoro methanesulfonate)imide. | ||
In water; | Synthesis of N-butyl-N-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide was performed following literature procedure.7 In a dry 500 mL round-bottom flask, stoichiometric amounts of 1-methylpyrrolidine (50 g, 0.59 mol)and 1-iodobutane (108 g, 0.59 mol) in 250 mL of ethylacetate were magnetically stirred at room temperature for 24 h. The product was repeatedly washed with ethylacetate and filtered until pure white salt of BMPI was obtained. BMPI was then dissolved in deionized water and mixed with a stoichiometric amount of LiTFSI dissolvedin deionized water. The organic phase was extracted with methylene chloride and subsequently dried at 100 C for 24 h to remove any residual water. The resulting BMP-TFSI had H2O content of less than 100 ppm as measured with the Karl Fischer method. Ionic liquid solutions of 1 M LiTFSI in N-butyl-N-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide (BMPTFSI) were madeby dissolving LiTFSI at 60 C for 24 hours and drying at 100 C overnight prior to use | |
In water; | Synthesis of N-butyl-N-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide was performed following literatureprocedure.11 12 In a dry 500 mL round-bottom flask,stoichiometric amounts of 1-methylpyrrolidine (50 g,0.59 mol) and 1-iodobutane (108 g, 0.59 mol) in 250 mLof ethyl acetate were magnetically stirred at room temperaturefor 24 h. The product was repeatedly washed withethyl acetate and filtered until pure white salt of BMPI wasobtained. BMPI was then dissolved in deionized water andmixed with a stoichiometric amount of LiTFSI dissolvedin deionized water. The organic phase was extracted withmethylene chloride and subsequently dried at 100 C for24 h to remove any residual water. The resulting BMPTFSIhad H2O content of less than 100 ppm as measuredwith the Karl Fischer method. Ionic liquid solutionsof 1 M LiTFSI in N-butyl-N-methylpyrrolidiniumbis(trifluoromethylsulfonyl)imide (BMPTFSI) were madeby dissolving LiTFSI at 60 C for 24 hours and drying at100 C overnight prior to use. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; at 20℃; for 24h; | General procedure: A dried 250 ml round bottom flask was prepared, and 50 ml of DCM (dichloromethane) was added to 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium chloride (10 g, 0.05 mol) and stirred at room temperature.Lithium bis(fluorosulfonyl)imide (9.2 g, 0.05 mol) and 50 ml of DIW (distilled water) were dissolved in a dropping funnel and added dropwise over 10 minutes.After completion of dropwise addition, the reaction was stirred at room temperature for 24 hours.After completion of the reaction, the organic layer is separated using a separator funnel,The organic layer was washed with 50 ml of DIW. The organic layer was added with MgSO4 and filtered, The solvent was removed by distillation and distillation under vacuum to obtain the desired product, 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium bis(fluorosulfonyl)imide (15g, yield = 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 0.5h;Product distribution / selectivity; | In 4-necked flask of 500ml, 82.1 g (1.000mol) of 1-methylimidazole, 101.8 g (1.100mol) of 1-chlorobutane, and 50.0g of toluene were added and stirred for 15 hours under reflux (approximately 106C). After they were reacted in this way, a reaction solution was cooled (air-cooled) to 70C or below. Then, 100.0g of ultra pure water was added therein, the resultant solution was water-cooled to room temperature. After the cooling, an upper layer (toluene layer) of the solution was separated off from the solution by using a separating funnel. To a lower layer (water layer), 100.0g of toluene was further added. After the resultant solution was stirred for 30 min, an upper layer (toluene layer) was separated off from the solution by using a separating funnel, thereby remaining a water layer in which [BMIm]Cl being a cation portion of an ionic liquid was contained.(Anion-Exchange Reaction) After the separation, 53.8g of the water layer containing [BMIm]Cl (corresponding to 0.200mol of [BMIm]Cl) was transferred to a 300ml conical flask, and mixed with 63.2g (0.220mol) of lithium bis(trifluoromethanesulfonyl)imide and 50.0g of ultra pure water. A resultant mixture was stirred for 30min at room temperature in order to carry out an anion-exchange reaction. After the reaction, an upper layer (water layer) was separated out by using a separating funnel. A lower layer was mixed with 50.0g of ultra pure water and stirred for 30min at room temperature. Then, an upper layer (water layer) was separated out by using a separating funnel. A lower layer containing the cation portion of the ionic liquid was transferred to an egg-plant-shaped flask of 100ml and evaporated under reduced pressure at 60C under 20mmHg for 1 hour, so as to distill off water. In this way, a light yellow solution whose solvent was N-methyl-N'-butyl imidazolium bis(trifluoromethanesulfonyl)imide ([BMIm]NTf2) was obtained.(Salt Removal Step) After 50.0g of acetone was added thereto, the light yellow solution thus obtained was cooled to a temperature in a range of approximately 0 to 5C, and then stirred for 30 min, thereby trying to crystallize out lithium chloride (by-product) and unreacted lithium bis(trifluoromethanesulfonyl)imide. Even though the crystallization yielded no crystals, the resultant solution was filtered with a Buchner funnel having an internal diameter of 55mm, and then washed with 20.0g of acetone. A filtrate obtained from the filtration was then transferred to an egg-plant-shaped flask of 200ml and evaporated under reduced pressure at 60C under 20mmHg for 2 hours, and then further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 1 hour. In this way, 73.8g of a concentrated solution containing the target [BMIm]NTf2 was obtained. The concentrated solution had water content of 0.0111% (111ppm).(Water Removing Step and Purifying Step) Then, 73.8g of the concentrated solution thus obtained was mixed with 0.20g (0.00166mol) of methyl orthoacetate (MOA). A resultant mixture was stirred at 80C for 3 hours so as to react MOA with water not distilled off from an ionic liquid. The reaction caused hydrolysis of MOA with the water thereby giving methanol and methyl acetate. The methanol and methyl acetate thus obtained and unreacted MOA were evaporated off under reduced pressure at 60C under 20mmHg for 1 hour. A concentrated liquid thus obtained was further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 2 hours. In this way, a target material, [BMIm]NTf2 was obtained as a light yellow liquid.(Water Content Analysis of [BMIm]NTf2) Water content of [BMIm]NTf2 was measured by the Karl Fishcer test. Water content after the addition of MOA was 0.0032% (32ppm). Water content after methanol, methyl acetate and the unreacted MOA was evaporated off was 0.0037% (37ppm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With lithium resin; In methanol; for 2h; | 4) Weigh 13.1g bistrifluoromethylsulfamide dissolved in methanol 50mL bistrifluoromethylsulfamide solution,Weigh 20g lithium resin prepared in Example 1 was added to the system, stirred for 2 hours, the rapid direct filtration,The filtrate was washed with 50 mL of methanol three times to recover excess resin lithium, the filtrate was evaporated under reduced pressure to remove methanol,After adding 50 mL of diethyl ether and stirring at room temperature for 1 h, the solid obtained by filtration was washed three times with 50 mL of diethyl ether,Yield 15.87gBenzyl bistrifluoromethylsulfonamide lithium salt,The yield (as bistrifluoromethanesulfonamide) was 79%. |
With lithium hydroxide monohydrate; at 20 - 35℃;Neutral conditions; | Step h: [0370] The reaction medium from the preceding step g) was brought to 20 C. in a jacketed 1 L glass reactor. Lithium hydroxide (33 g), in the form of the solid monohydrate (LiOH, H2O), was added until the solution was neutral. The temperature of the reaction medium was maintained below 35 C. and the pH of the final solution was adjusted to neutrality. Step i: [0371] The aqueous solution from the preceding step h) was concentrated on a rotary evaporator under vacuum and then dried in an oven under vacuum, to give a white powder of LiTFSI (0.225 kg). The analyses of the LiTFSI obtained showed that it contains less than 100 ppm of water, less than 20 ppm of fluorides and sulfates, less than 15 ppm of chlorides, less than 10 ppm of sodium, less than 5 ppm of calcium, potassium and silicon, less than 2 ppm of iron and less than 1 ppm of nickel, boron, aluminum and magnesium | |
0.225 kg | With lithium hydroxide monohydrate; at 20 - 35℃;Large scale; | The reaction medium from the preceding step g), and to 20 in a jacketed 1L glass reactor.Solid monohydrate(LiOH,H2 O) in the form of a lithium hydroxide (33 g), the solution was added until neutrality.The temperature of the reaction medium was maintained at below 35 , the pH of the final solution was adjusted to neutral. An aqueous solution from the preceding step h), and concentrated on a rotary evaporator under vacuum, then dried in an oven under vacuum to give a white powder (0.225kg) of LiTFSI.The resulting analysis of LiTFSI is, it is water of less than 100ppm, fluoride and sulfate of less than 20ppm, chloride of less than 15ppm, sodium of less than 10ppm, calcium of less than 5ppm, potassium and silicon, iron and less than 1ppm of less than 2ppm nickel, showed that it contains boron, aluminum and magnesium. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | In water; | 35 g (0.16 mol) of [C4mim][Br] was diluted with 100 mL of deionized water and 45.7 g (0.16 mol)of Li(Tf2N) was added. After mixing, the reaction mixture was separated into two layers. Thebottom layer was [C4mim] [Tf2N] and the top layer was aqueous LiCl. After decanting the toplayer, 100 mL of fresh deionized water was added and the solution was thoroughly mixed. Thisprocedure was repeated twice. The ionic liquid was dried in vacuo (under 0.1mbar) at 60C for 24hours, producing a colorless liquid (yield: 61.5 g, 87.5%). |
60% | In dichloromethane; at 20℃; for 24h; | First 0.02 mol imidazolium bromide salt was added to 50 mL of dichloromethane and mixed. Then 0.02 mol bis(trifluoromethanesulfonyl)imide salt of lithium was added to the stirring solution of imidazolium bromide salt. The mixture was left stirring for about 24 h at room temperature. Then the lithium bromide salt was filtered and the concentrated AgNO3 solution was added to the solution. The resulting solution was washed with pure water so that AgBr was allowed to pass into the water phase. Then dichloromethane was evaporated with a rotary evaporator. The yield was calculated as 60%. |
In water; at 20℃; for 3h;Electrochemical reaction;Product distribution / selectivity; | An embodiment of a reversible mirror of the invention was fabricated as follows: two electrodes were prepared using 6×8 cm single-side planar ITO coated glass plates having a sheet resistivity of 7 Omega/square. Each plate was provided with a bus bar by attaching a copper electrical contact approximately 1 cm wide along the entire edge of the 6 cm end of each plate. The electrodes were then washed with water, methanol and acetone, and dried in a stream of warm air to remove any dust or grease. An o-ring (2 cm internal diameter (ID) vycor rubber donut-shaped o-ring, 0.3 cm thick) was used as a gasket to seal one electrode to the other. A silver wire (5 cm long, 0.25 mm diameter, 99.9% metal purity) was inserted through the o-ring by first piercing a hollow needle through the o-ring, placing one end of the silver wire through the hollow needle, and then withdrawing the hollow needle from the o-ring. Approximately 0.4 mm of the silver wire protruded through the o-ring. The o-ring was then placed between the two electrodes with the conducting ITO coating in contact with the o-ring (see FIGS. 1 and 2) with the bus bars at opposite ends of the device. Two spring-loaded clips were used to hold the device together and provide a tight seal. A digital ohmmeter was used to ensure that the three electrodes (working, counter and pseudo-reference electrodes) were in electrical isolation of each other. Butylmethylimidazolium bis(trifluoromethylsulfonyl)imide was synthesized as follows: Butylmethylimidazolium bromide (50 g) was dissolved deionized water (100 mL). Decolorizing charcoal or activated carbon (3 g) was added to the solution, which was boiled for 3 minutes and filtered. The filtrate was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (65.5 g) in 100 mL of deionized water. After stirring at room temperature for 3 hrs, two layers formed. The bottom layer containing butylmethylimidazolium bis(trifluoromethylsulfonyl)imide was separated, washed deionized water (3×50 mL), heated at 100 C. under vacuum (0.1 mbar) for 48 hrs, and then filtered through activated alumina to give anhydrous, highly pure, molten butylmethylimidazolium bis(trifluoromethylsulfonyl)imide. The purity of the molten salt was assayed by cyclic voltammetry, absorbance spectroscopy or fluorescence measurements. A solution of 3-butyl-1-methylimadazolium bis(trifluoromethylsulfonyl)imide containing less than 1 ppm water and 0.035 mol/L of bismuth (III) bis(trifluoromethylsulfonyl)imide was prepared in a helium atmosphere drybox. The solution was introduced into the chamber of the device by inserting two hollow needles through the o-ring (one needle for introducing the solution, the other needle for removing displaced gas). Afterward, the needles were removed and the o-ring was checked for leaks. Wire connectors were attached to the bus bars and to a potentiostat that provided the voltage for electrodeposition. A bismuth mirror was deposited at a potential of -0.65 Volts versus the silver reference electrode. The bismuth mirror was deplated at a potential of +0.1 Volts versus the silver reference electrode. Overall, this reversible mirror device exhibited good optical reflectance in the reflective state and good transparency in the non-mirrored state, and was switched repetitively between these two states without degradation of performance. |
In water; at 70℃; for 24h;pH 6.0; | General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C. | |
for 24h;Inert atmosphere; | Ionic liquid [bmim]Br was heated gently at 80C. The lithiumsalt LiTFSI was added to the melt under N2and stirred for 24 h.Adding CH2Cl2, LiBr was precipitated and separated by filtration.The filtrate was evaporated to dryness then the [bmim][TFSI]obtained. | |
In water; at 20℃; for 24h; | Then, the dried precursor BmimBr (0. 05 mmol, 10.5 g) and equimolar LiN (S02) 2 (CF3) 2 (0. 05 mmol, 13.7 g) were each dissolved in 20 mL H20 and mixed at room temperature 24h, After adding 50mL CH2Cl2, the water was removed and the aqueous phase was removed. After 5 times, CH2C12 was removed and dried at 80 C for 12 h to obtain ionic liquid [Bmim] [Tf2N]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 3h;Electrochemical reaction;Product distribution / selectivity; | Butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was synthesized as follows: A solution of butylmethylpyrrolidinium bromide (500 g) in deionized water (1 L) was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (646 g) in 1 L of deionized water. The resulting solution was stirred at room temperature for 3 hrs, after which two layers had formed. The bottom layer containing butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was separated, washed with deionized water (3×500 mL), and then heated at 100 C. under vacuum (0.1 mbar) for 48 hrs. Decolorizing charcoal or activated carbon (30 g) and activated alumina (100 g) were added to the molten salt. After stirring for 1 hr, the solids were removed by filtration. The purity of the molten salt was assayed by cyclic voltammetry, absorbance spectroscopy or fluorescence measurements. The treatment with charcoal or activated carbon and activated alumina may be repeated until the desired purity is obtained. EXAMPLE 6 Butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was prepared as follows: decolorizing charcoal or activated carbon (30 g) was added to a solution of butylmethylpyrrolidinium bromide (500 g) in deionized water (1 L). The resulting mixture was boiled for three minutes, then cooled to room temperature and filtered. The filtrate (a purified solution of butylmethylpyrrolidinium bromide) was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (646 g) in 1 L of deionized water, stirred at room temperature for 3 hrs, after which two layers had formed. The bottom layer containing butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)imide was separated, washed with deionized water (3×500 mL), heated at 100 C. under vacuum (0.1 mbar) for 48 hrs, and then filtered through activated alumina to give the highly pure molten salt. The purity of the molten salt was confirmed by cyclic voltammetry, absorbance spectroscopy, or fluorescence measurements. This preparative method is preferred because it provides highly pure molten salt in high yield. | |
In water; at 20℃; for 5h;Inert atmosphere; | General procedure: A solution of the appropriate amine (275 mmol, 1.2 equiv) in ethyl acetate (120 mL) was degassed for 15 min by argon bubbling. Then, 1-alkylbromide (229 mmol, 1 equiv) was added and the resulting mixture was refluxed for 15 h under argon. Finally, the solvent was evaporated under reduced pressure (rotary evaporator). The residue was washed thoroughly with ethyl acetate (3 x 100 mL) and dried under reduced pressure to afford thefirst-generation ionic liquid as an hygroscopic white solid. The resulting product (210 mmol, 1 equiv) was added to a solution of LiNTf2 (166 mmol, 0.8 equiv) in distilled water (100 mL). The mixture was stirred at room temperature under argon for 5 h and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were then washed with water (2 x 15 mL) and brine (2 x 15 mL), and then dried over MgSO4. After filtration, the resultant mixture was stirred for 2 h with activated charcoal. A filtration on celite to remove charcoal and an evaporation under reduced pressure (rotary evaporator, 2 x 10-3 bar) afforded the colorless desired NTf2--based second-generation ionic liquid (global yield >80%). | |
In water; at 20℃; for 0.0333333 - 0.05h;Sealed tube; Green chemistry; | PYR14TFSI was synthesized from aqueous PYR14Br and LiTFSI by the following reaction. LiTFSI was added, e.g., in slight excess with respect to the stoichiometric amount (Fig. 3), to the aqueous PYR14Br solution obtained from the purification step, resulting in the dissolution of the former immediately followed by its reaction with PYR14Br (through anion exchange which replaces Br- with TFSI-) to form hydrophobic PYR14TFSI and hydrophilic LiBr. The rapid formation of two liquid phases clearly indicated that the anion exchange reaction, driven by the intrinsic hydrophobicity of both the PYR14+ cation and the TFSI- anion, proceeded quickly. For instance, both PYR14+ and TFSI-, in which the charge is well shielded by hydrophobic groups (PYR14+) or extensively delocalized (TFSI-), do not easily form hydrogen bonds with water molecules and tend to separate from the aqueous phase forming a second (denser) liquid phase. Therefore, the disappearance itself of the (ionic liquid) PYR14TFSI product from the aqueous solution drove the exchange reaction to completion. Then, the two liquid phases were vigorously stirred at room temperature to facilitate the anion exchange reaction. After a selected time (Fig. 3) the stirring was interrupted and the phase separation took place in a few minutes. The upper phase (clear and colourless) was mostly composed of water, lithium bromide (LiBr) and LiTFSI excess whereas the lower one (uncoloured and generally slightly cloudy) was mostly constituted of PYR14TFSI ionic liquid with lithium salts (i.e., LiBr and LiTFSI) and traces of water. |
In water-d2; | General procedure: The dialkylpyrrolidinium bromides, BMPBr, HMPBr and DMPBr,were synthesized according to previous literature [26]. Nuclearmagnetic resonance (NMR) spectroscopy confirmed formation ofdialkylpyrrolidinium bromides. Acetone-d6 containing 0.05 vol%tetramethylsilane (TMS, Wako Pure Chemical Industries) was usedas the solvent for the ionic liquids in NMR measurements.BMPTFSA, HMPTFSA and DMPTFSA were prepared by interactingLiTFSA (Solvay) with corresponding dialkylpyrrolidinium bromidesin deionized water. Then the prepared ionic liquids wereextracted with dichloromethane (Junsei Chemical), separated byevaporation andfinally dried at 100 C for 24 hours under vacuumto eliminate residual water and dichloromethane. The watercontent in the prepared ionic liquids was lower than 10 ppm,which was confirmed using Karl Fischer method (Metrohm,831KF). Cyclic voltammetry of a Pt electrode did not show anysignificant cathodic or anodic current assignable to impurities,such as water, bromide, and oxygen in the prepared ionic liquids. Pt(acac)2 purchased from Sigma-Aldrich was used as supplied without further purification. The handling of all the chemicals wascarried out in an argon-filled glove box with a continuous gaspurification apparatus (Miwa MFG, DBO-1K-SH or DBO-1KP-KO1). | |
In water; at 20℃; | In second step, [bmIm][NTf2] or [bmPyrr][NTf2] weresynthesized using metathesis reactions of lithium bis(trifluoromethane)sulfonimide salt(LiNTf2) with [bmIm]Br or [bmPyrr]Br in water at room temperature. Extraction of aproticionic liquids was carried out using the water-dichloromethane solvent system to give pureionic liquids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.1% | In water; at 60℃; for 2h; | 2. Put 200g lithium bistrifluoromethylsulfonimide, 152g 1-ethyl-3-methylimidazole bromide salt and 400g pure water into the reactor,Warm to 60 , react for 2h,After standing for a while, 283 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 3. Wash three times with pure water to obtain 251g of pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water,Finally, it is dried in a vacuum oven at 110 C for 12h.237 g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.23%, and the yield was 87.1%;Ion chromatography detection: halogen ion 450ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |
86% | In water; at 20℃; for 2h;Heating / reflux; | 9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70 C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): delta 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70 C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): delta 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) |
In water; at 70℃; for 24h;pH 6.0; | General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C. |
383.5 g | In water; | Step 1: Take 287.1g of lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) completely dissolved in water to form an aqueous solution with a mass percentage concentration of 50%; Step 2: 191.1 g of 1-ethyl-3-methylimidazolium bromide (EMIBr) was completely dissolved in water to form an aqueous solution having a mass percentage concentration of 50% Step 3: mixing the aqueous solution products obtained in steps 1 and 2 to obtain a crude product; Step 4: The crude product is obtained in step 3, washed with water for 2 times, emulsified by heating and stirring, and heated to 60 DEG C for demulsification, and then high purity product is obtained after liquid separation; Step 5: The high-purity product obtained in Step 4 was vacuum-dried at 100 C for 8 hours to obtain 383.5 g of colorless liquid EMI · TFSI product (melting point: about -15 C), purity: 99.95%, water content: 80 ppm, . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sulfuric acid; at 70℃; | HTf2N was obtained by sublimation at 70 C from a solution of LiTf2N in concentrated sulfuric acid under reduced pressure (10-3 mbar). The crude product was resublimed for further purification. Yield: 90%.1H-NMR D2 O : deltappm 4:77s; 1H19 F-NMRD2O : deltappm -79:16s; 6F13C 19 Fn o-NMRD2O : deltappm 19:27s; 2C |
With cation exchange column; In water; | [00079] 40 g Lithium bis(trifluoromethane sulfonyl)imide (0.14 mol, 99%, 3M) was dissolved in 200 mL distilled water and was passed through a pre-protonated cation exchange column of 4.5 eq. Capacity. The collected acid solution was once again passed through the regenerated cation exchange column to ensure quantitative conversion. The resultant aqueous solution of bis(trifluoromethane sulfonyl)imidic acid was condensed to ca. 2.0 M by evaporating excess water. [00080] The aqueous solution of bis(trifluoromethane sulfonyl)imidic acid was added to solution of EtMeiPr2NMeCO3. After the neutralization the solution was subject to evaporation under reduced pressure to remove water. Resultant solid was repeatedly recrystallized from hot methanol solution, and the final product EtMeiPr2N+Im? is fine needle crystal. |
Yield | Reaction Conditions | Operation in experiment |
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In dichloromethane; water; | General procedure: Tributyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide [P44414][NTf2] (1); 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide [BMMIM][NTf2] (3); 1-butylpyridiniumbis(trifluoromethylsulfonyl)imide [BuPy][NTf2] (2); 1-allylpyridinium bis(trifluoromethylsulfonyl)imide[AllPy][NTf2] (5); 1-allyl-2,3-dimethylimidazoliumbis(trifluoromethylsulfonyl)imide [AlldiMIM][NTf2] (7)and 1,3-diallyl-2-methylimiidazolium bis(trifluoromethylsulfonyl)imide [diAllMIM][NTf2] (6) weresynthesized by metathesis reaction using the general procedure:Pyridinium or imidazolium halide (bromide or chloride) was dissolved in water and it wastransferred to a separator funnel with dichloromethane. Subsequently, 1.1 molar equivalent of LiNTf2(80% solution in water) was added and a separator funnel was shaken vigorously. After phaseseparation, the organic phase was washed twice with water, once with 5% water solution of LiNTf2,and this procedure was repeated until water phase was completely free of halide anion. To confirmabsence of chloride anion, acidic solution of silver nitrate was added to a sample of water phase. Noprecipitate of silver chloride indicated an absence of chloride anion. Subsequently, the organic phasewas separated, evaporated and dried under high vacuum (1 mbar) in 60 C for 24 h. The structure ofobtained salts were confirmed by 1H-NMR analysis. |
Yield | Reaction Conditions | Operation in experiment |
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In water; | EXAMPLE 4; Preparation of 1,1'-dibenzyl-4,4'-dipyridinium bis(bis(trifluoromethylsulfonyl)imide) [28]. A first solution of 1,1'-dibenzyl-4,4'-dipyridinium dichloride (1.795 g) in 10 mL distilled H2O was prepared. A second solution of lithium bis(trifluoromethylsulfonyl)imide (LiNTf2, 1.264 g) in 10 mL distilled H2O was prepared and added slowly by pipette to the first solution with stirring. Salt 28 formed as a white solid. The mixture was filtered, the white solid was collected and dissolved in acetone. The acetone was removed under a vacuum to produce 28 as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In water; at 20℃; for 0.5h; | General procedure: To a solution of the chloride ionic liquid in water lithiumbis(trifluoromethane)sulfonimide (LiN(Tf)2, 1.1 eq.) wasadded. The reaction mixture was vigorously stirred for30 min at room temperature. The formation of a secondphase was observed. The mixture was extracted with DCMand the combined organic layers were subsequently washedwith water until no chloride could be detected in theorganic phase (tested with AgNO3 solution). The organicphase was dried over Na2SO4, filtered and the solvent wasevaporated and the residue was dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.3% | In water; at 20℃; for 3h;Large scale; | Methylacrylcholine chloride (798.2 g, 3.84 mol) was added to the reaction vessel,Lithium bis (trifluoromethanesulfonyl) imide1125. 8 g (3.92 mol),Ion-exchanged water 2141. 4 g,And the mixture was stirred at room temperature for 3 hours.After washing twice with ion-exchanged water, dehydration was carried out,get Methacryloyl choline bistrifluoromethanesulfonimide 1703. 5 g (yield 96.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In acetonitrile; at 20℃; for 48h; | The ionic liquid EMI?TFSI- was synthesized by a one step methathesis: 1-ethyl-3-methylimidazoliumchloride EMI?Cl- (1.465 g, 0.01 mol) and lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) (2.871 g, 0.01 mol) were dissolved in acetonitrile intwo separate vials. An anion-exchange reaction occurred after adding slowly (drop bydrop) LiTFSI solution in a 10 mL round-bottom flask containing the EMI?Cl- solution,whereby the mixture was precipitated. Then, the reaction mixture was stirred at 500 rpm atroom temperature for 48 h. After removal of the solvent, the mixture was washedrepeatedly with water until the Cl- could not be detected by addition of AgNO3 solution.The organic phase was collected in a vial and was passed at least twice through Celitesilica column with ethyl acetate to completely remove Cl-. After removal of the solvent,the final product was dried under vacuum to give a yellowish liquid (2.347 g, 62 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In water; at 20℃; for 5h; | a) Choline bis(trifluoromethanesulfonyl)amide 55.85 g (0.4 mol) of <strong>[67-48-1]choline chloride</strong> (Sigma-Aldrich) were dissolved in 150 ml of MQ water. Under vigorous stirring, the resulting <strong>[67-48-1]choline chloride</strong> solution was mixed with a solution of 120 g (0.41 mol) of lithium bis(trifluoromethanesulfonyl)amide (LiTFSI) in 200 ml of MQ water. Phase separation occurred at once, but the stirring was continued for another 5 hours at room temperature. Then, 100 ml of CH2Cl2 were added and the phases were separated. The water phase was extracted with 50 ml of CH2Cl2 and the combined organic phases were washed 6 times with 50 ml of MQ water. A clear colourless solution was obtained. This was poured into a round bottom flask; the solvent was removed using a rotary evaporator and then under high vacuum at 60 C. In this manner, 127 g (83%) of pure choline bis(trifluoromethanesulfonyl)amide (choline TFSI) were obtained. 1H NMR (300 MHz, DMSO-d6) delta/ppm: 3.11 (s, 9H), 3.31-3.47 (m, 2H), 3.84 (tt, J=5.03, 2.29 Hz, 2H), 5.26 (t, J=4.94 Hz, 1H). 13C NMR (75 MHz, DMSO-d6) delta/ppm: 53.30 (br. t, J=3.50, 3.50 Hz), 55.31 (s), 67.18 (br. t, J=3.20, 3.20 Hz), 119.63 (q, J=321.70 Hz). |
81.4% | In water; at 20℃; for 4h; | Synthesis Example: Synthesis of ionic liquid in the form of [Choline][NTf2] [47] 139.82 g (1.0 mol) of <strong>[67-48-1]choline chloride</strong> (2-hyrdoxyethyltrimethylammoniun chloride or vitamin B4; MW 139.82, mp 302 to 305C) dissolved in 250 ml of distilled water, mixed with 500 ml aqueous solution of 1.0 mol of lithium bis(trifluoromethylsulfonyl)imide ([Li][NTf2], MW 287.08) in a 1 L beaker, stirred at room temperature for 4 hours, and left to stand for phase separation. The upper layer was discarded from the solution, and the remaining ionic liquid was washed with 200 ml of distilled water several times until no chloride ions (Cl-) were detected by silver nitrate test in the washing solution. Upon completion of the purification, the resulting ionic liquid was placed in a rotary evaporator and vacuum-dried at 120C for more than 6 hours, thus removing water. As a result, 312.59 g of ionic liquid (C7H14F6N2O5S2 MW: 384.02) in the form of [Choline][NTf2] was obtained at a yield of 81.4%. The [choline] was the 2-hydroxyethyltrimethylammonium cation, and the [NTf2] was the bis(trifluoromethylsulfonyl)imide anion. [48] The moisture content measured by a Karl Fischer method was 0.493%. NMR results analyzed by 1H-NMR(300 MHz, d6-DMSO) were delta = 3.099(3xCH3), 3.38(O-CH2-), 3.84(N-CH2-), and 5.25(-OH) and the results analyzed by 13C-NMR (d6-DMSO) were delta = 53.51(CH2-O), 55.50(3xCH3), 67.42(N-CH2-), and 120(2xCF3). The results of atomic analysis were C 21.78%, H 3.71%, N 7.83%, and S 17.58%. those were well agreed with the theoretical atomic ratios of [Choline][NTf2] (C7H14N2O5F6S2, MW; 384.02) are C 21.88%, H 3.67%, N 7.29%, and S 16.69%. Freezing point measured by differential scanning calorimetry (DSC) was -16C, melting point was 1.0C, and specific gravity of liquid at 29.3C was 1.520 g·cm-3. |
68.5% | In water; at 20℃; for 2h; | 503.1g (3.60 mol) of <strong>[67-48-1]choline chloride</strong> was added to the reaction vessel,Lithium bis (trifluoromethanesulfonyl) imide 1086. 2 g (3.78 mol),Ion-exchanged water 1838. 9 g, and the mixture was stirred at room temperature for 2 hours.After washing twice with ion-exchanged water, Dehydration 1- (2-hydroxyethyl-N, N, N-trimethylammonium bistrifluoromethanesulfonimide949.2 g (yield 68.5%) |
61% | In water; at 20℃; for 2h; | 76.43 wt% <strong>[67-48-1]choline chloride</strong> solution 53.98g (0.30 mole), 74.90 wt% of lithium bis (trifluoromethanesulfonyl) imide solution 111.00g (0.29 mol) anddeionized water 110. were mixed 01G, the resulting mixture was reacted at room temperature for 2 hours. After completion of the reaction, theorganic layer was separated from the reaction mixture which is an organic layer and an aqueous layer and a binary solution, the resulting organiclayer was washed twice with ion-exchanged water 113 g. The organic layer was washed with water and concentrated to dryness under reducedpressure to give a liquid at 25 C. (2-hydroxyethyl) trimethylammonium bis (trifluoromethanesulfonyl) imide 69.28g (61.00% yield). Hereinafter, the(2-hydroxyethyl) trimethylammonium bis (trifluoromethanesulfonyl) imide shows the 1H-NMR data. |
61% | In water; at 20℃; for 2h; | 53.98 g (0.30 mol) of a 76.43 wt% <strong>[67-48-1]choline chloride</strong> aqueous solution,111.00 g (0.29 mol) of a 74.90 wt% lithium bis (trifluoromethanesulfonyl) imide lithium solution and 110.01 g of ion exchanged water were mixed,The resulting mixture was reacted at room temperature for 2 hours.After completion of the reaction, the organic layer was fractionated from the reaction mixture separated into an organic layer and an aqueous layer,The obtained organic layer was washed twice with 113 g of ion exchanged water.The organic layer after washing with water was concentrated and dried under reduced pressure,(2-hydroxyethyl) trimethylammonium = bis (trifluoromethanesulfonyl) imide69.28 g was obtained (yield 61.00%). |
In water; at 20℃; | Example 3: Synthesis of choline bis(trifluoromethylsulfonyl)imide salt (0039) At room temperature, 0.5 mol of 3 <strong>[67-48-1]choline chloride</strong> and an equi-molar amount of 9 lithium bis(trifluoromethylsulfonyl)imide were dissolved in 10 water for ion exchange, and mechanically stirred for 4 to 6 hours. The resulting reaction product was then extracted with dichloromethane, and then treated to remove the solvent to yield the 13 choline bis(trifluoromethylsulfonyl)imide salt obtained from the anion exchange: 1H NMR (300 MHz, CDCl3): delta 6 3.16 (s, 9H, +N(CH3)3), 3.40 (s, 1H, OH), 3.45 (s, 2H, CH2O), 4.03 (s, 2H, CH2N+); 13C NMR (300 MHz, CDCl3): 54.06, 56.21, 67.66, 119.75 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.3% | In water; at 20℃; for 2h; | General procedure: [C1mim]I (5 g, 22mmol) was dissolved in distilled water (30 mL). The solutionwas added dropwise an aqueous solution (10 mL) of potassiumbis(fluorosulfonyl)amide (Kanto Kagaku) (5 g, 23 mmol). White powder wasprecipitated immediately. The suspension was stirred for two hours at room temperature.After the temperature was up to 353 K, the white powder was melted and dissolved. Theaqueous solution had pale yellow color, then small amount of sodium sulfite was added,the color of the solution was disappeared. After the solution was cooled to roomtemperature, biphasic separation was formed, and then the lower layer was crystallized.The crystals were collected and purified by performing recrystallization from themixture of water and methanol (1 : 1). [C1mim]FSA was obtained as colorless crystals.The final product was dried under vacuum (15 Pa) at 363 K for more than 24 h, and6.04 g of the product was obtained (yield 75%). Elemental analysis calcd. forC5H9N3F2O4S2: C, 21.66; H,3.27; N, 15.15. Found: C, 21.62; H, 3.24; N, 14.85. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; at 20.0℃; for 24.0h; | General procedure: A dried 250 ml round bottom flask was prepared, and 50 ml of DCM (dichloromethane) was added to 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium chloride (10 g, 0.05 mol) and stirred at room temperature.Lithium bis(fluorosulfonyl)imide (9.2 g, 0.05 mol) and 50 ml of DIW (distilled water) were dissolved in a dropping funnel and added dropwise over 10 minutes.After completion of dropwise addition, the reaction was stirred at room temperature for 24 hours.After completion of the reaction, the organic layer is separated using a separator funnel,The organic layer was washed with 50 ml of DIW. The organic layer was added with MgSO4 and filtered, The solvent was removed by distillation and distillation under vacuum to obtain the desired product, 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium bis(fluorosulfonyl)imide (15g, yield = 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 5.0h;Inert atmosphere; | General procedure: A solution of the appropriate amine (275 mmol, 1.2 equiv) in ethyl acetate (120 mL) was degassed for 15 min by argon bubbling. Then, 1-alkylbromide (229 mmol, 1 equiv) was added and the resulting mixture was refluxed for 15 h under argon. Finally, the solvent was evaporated under reduced pressure (rotary evaporator). The residue was washed thoroughly with ethyl acetate (3 x 100 mL) and dried under reduced pressure to afford thefirst-generation ionic liquid as an hygroscopic white solid. The resulting product (210 mmol, 1 equiv) was added to a solution of LiNTf2 (166 mmol, 0.8 equiv) in distilled water (100 mL). The mixture was stirred at room temperature under argon for 5 h and extracted with CH2Cl2 (3 x 50 mL). The combined organic phases were then washed with water (2 x 15 mL) and brine (2 x 15 mL), and then dried over MgSO4. After filtration, the resultant mixture was stirred for 2 h with activated charcoal. A filtration on celite to remove charcoal and an evaporation under reduced pressure (rotary evaporator, 2 x 10-3 bar) afforded the colorless desired NTf2--based second-generation ionic liquid (global yield >80%). | |
In water; at 20℃; for 12.0h; | General procedure: An excess (10 %)of lithium bis(trifluoromethylsulfonyl)imide was reacted with 1-alkylpyridinium halide ([HPYR][Br] or <strong>[2534-66-9][OPYR][Br]</strong>) in water at room temperature for 12 h. Then the product was washed with methylene chloride and water (5:1) until there was no silver bromide found when the product was added in silver nitrate. After filtering and rotary evaporating, the product was set under high vacuum for 24 h 1-alkylpyridinium bis(trifluoromethylsulfonyl)imide ([HPYR][Tf2N] or [OPYR][Tf2N]) was obtained as a light-yellow liquid. | |
In water; | General procedure: 1-Alkylpyridinium bromides ([CnPy]Br), as precursors of the target ILs, were prepared by reacting pyridine with1-bromoalkane under a reflux condition (40 - 60 C) over night. After the [CnPy]Br were purified byrecrystallization from methanol/ethyl acetate or acetonitrile/ethyl acetate solution, the crystalline solids weredissolved in water, and the anion exchange reactions were made by adding 1.2 equivalent amount of Li[NTf2].The resultant ionic liquid layers were repeatedly washed with water. Then, the ionic liquid layers weredissolved in dichloromethane and rigorously stirred with activated carbon until the solutions became colorless.Dichloromethane was then evaporated. The obtained ILs were dried in vacuo at room temperature for morethan 2 days. The yields were approximately 50 %. The analytical data are given in followings. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; formaldehyd; formic acid; magnesium sulfate; triphenylphosphine; In tetrachloromethane; dichloromethane; water, 1,3-dimethyl-1-propylpyrrolidinium bromide; water; | EXAMPLE 1 In this example, a method for producing 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide (abbreviation: 3mP13-TFSA) represented by the structural formula (200) is described. First, <strong>[44565-27-7]4-amino-2-methyl-1-butanol</strong> (24.8 g, 240 mmol) and carbon tetrachloride (111 g, 720 mmol) were mixed under a nitrogen atmosphere at room temperature. Into this mixture, triphenylphosphine (69.2 g, 264 mmol) dissolved in dehydrated dichloromethane (150 ml) was added. Stirring was performed at 40 C. for 1 to 1.5 hours, and then pure water (50 ml) was added to the reacted solution and stirred well. Subsequently, an aqueous phase and a dichloromethane phase were separated. A yellow oily substance was extracted from the dichloromethane phase using pure water (50 ml*2 times). Then, the aqueous phase was washed with toluene (50 ml*3 times), and the solvent was removed by evaporation under reduced pressure to give a yellow oily substance. Sodium hydroxide (19.2 g, 480 mmol) was dissolved in pure water (20 ml), and the sodium hydroxide solution was gradually added to the obtained yellow oily substance, and the mixture was stirred for 12 hours. After that, distillation was performed to give 3-methylpyrrolidine (18.7 g, 219 mmol) which is a colorless transparent liquid. Into formic acid (21.6 g, 470 mmol) being water-cooled, 3-methylpyrrolidine (18.7 g, 219 mmol) was gradually added. Next, a 37% formaldehyde solution (26 ml, 330 mmol) was added to this solution. This solution was heated and refluxed at 100 C., was cooled back to room temperature after a bubble generation, and was stirred for about 30 minutes. Then, the solution was heated and refluxed again for one hour. The formic acid was neutralized with sodium hydroxide, and then the target substance was extracted with diethyl ether and dried using magnesium sulfate, and the solvent was removed by evaporation. Then, distillation was performed, whereby 1,3-dimethylpyrrolidine (13.3 g, 134 mmol) which is a colorless transparent liquid was obtained. Bromopropane (22.3 g, 182 mmol) was added to methylene chloride (10 ml) to which 1,3-dimethylpyrrolidine (12.0 g, 121 mmol) was added, and the mixture was heated and refluxed for 24 hours. The solvent was removed by evaporation, and the obtained white residue was recrystallized in ethanol and ethyl acetate and then dried under reduced pressure at 80 C. for 24 hours, whereby 1,3-dimethyl-1-propylpyrrolidinium bromide (13.9 g, 63.4 mmol) which is a white solid was obtained. In pure water, 1,3-dimethyl-1-propylpyrrolidinium bromide (5.30 g, 23.9 mmol) and lithium bis(trifluoromethanesulfonyl)amide (7.55 g, 26.3 mmol) were mixed and stirred, so that an ionic liquid which is insoluble in water was obtained immediately. After that, the obtained ionic liquid was extracated with methylene chloride and then washed with pure water six times. The solvent was removed by evaporation and dried in vacuum at 100 C., so that 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide (9.37 g, 22.2 mmol) was obtained. The compound obtained through the above steps was identified as 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide which is a target substance by using a nuclear magnetic resonance (NMR) and mass spectrometry. 1H NMR data of the obtained compound is shown below. 1H-NMR (CDCl3, 400 MHz, 298 K): delta=0.97-1.05 (3H), 1.15-1.21 (3H), 1.67-1.99 (3H), 2.28-2.48 (1H), 2.58-2.78 (1H), 2.94-3.08 (1H), 3.06, 3.13 (3H), 3.18-3.34 (2H), 3.47-3.87 (3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | b) Synthesis of Co(L)2(TFSI)2 [0078] To a solution of 250 mg (1.1 mmol) C0CI2.6H2O (Sigma Aldrich) in 20 ml MeOH, 444 mg (2.1 mmol) of ligand L was added. The solution was stirred at room temperature for 1 hour. Excess LiTFSI salt (Sigma Aldrich) was added to the solution and stirred for 30 mins. To this solution, deionized water was added to precipitate the cobalt complex. The compound was collected by filtration and washed thoroughly with deionized water and diethyl ether. The product was dried under vacuum and obtained in 75 % yield (1.09 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.03 g | In water; at 20℃; for 0.5h; | General procedure: The quaternary salt (1.0 equiv.) was dissolved in distilled water to which LiNTf2 (1.1 equiv.) in minimal distilled water was added. The resulting solution was stirred at room temperature for 30 min. CH2Cl2 was added and the separated aqueous layer washed twice more with CH2Cl2. The combined organic layers were washed with cold distilled water until negative to a AgNO3 precipitate test, dried (Na2SO4), filtered, and concentrated under vacuum before drying overnight under high vacuum (0.1 mmHg at 60 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In water; at 20℃; for 1.0h; | [Hbet][Tf2N], (Fig. 1), was synthesised according to themetathesis reaction described by Nockemann and co-workers [6].Lithium bis(trifluoromethylsulfonyl)imide (50.0 g, 0.174 mol) and<strong>[590-46-5]betaine hydrochloride</strong> (26.7 g, 0.174 mol) were dissolved in50 mL of water and stirred for one hour at room temperature.The resulting IL was phase-separated from the aqueous phaseand washed with small amounts of cold distilled water until nochloride impurities could be detected by a silver nitrate test inthe wash effluent. The product was dried in a rotary evaporatorat 150 mbar and 80 C for 6 h to give [Hbet][Tf2N] as a white solidin 78% yield. |
Yield | Reaction Conditions | Operation in experiment |
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39% | Under a nitrogen atmosphere, 3.00 g (0.02 mol) of 4-methyl-5-thiazole ethanol,7.50 g of acetonitrile and 7.43 g (0.03 mol) of <strong>[461-17-6]1,1,1-trifluoro-4-iodobutane</strong> were charged and stirred at 70 C. for 15 hours. The reaction solution was cooled to room temperature and concentrated with a rotary evaporator. The obtained concentrate was washed with 10 g of hexane three times and then charged in a 100 mL glass reactor equipped with a stirring bar and a three-way cock, and 3.02 g of ion exchanged water and 3.0 g of lithium bis (trifluoromethanesulfonyl) imide (73.5% aqueous solution) 9.93 g (0.03 mol), and the mixture was stirred at room temperature for 2 hours. After completion of the stirring, the organic layer was separated from the reaction solution separated into an aqueous layer and an organic layer. This organic layer was washed three times with 10 g of ion exchanged water, then placed in a rotary evaporator, dried under reduced pressure,The liquid 3- (1,1,1-trifluorobutyl)-5-(2-hydroxyethyl) -4-methylthiazolium = bis (trifluoromethanesulfonyl) imide 8.19 g was obtained (yield: 39%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In water; at 20℃; for 24h;Inert atmosphere; | A 2-L four-necked flask equipped with a stirrer and a nitrogen gas inlet tube was charged with 300.9 g of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride (1.12 Mol), ion exchanged water 300.3 g and lithium bistrifluoromethanesulfonylimide 557.4 g (73.5percent aqueous solution) (1.43 mol), and the mixture was stirred at room temperature for 24 hours. After completion of the stirring, the organic layer was separated from the reaction solution separated into an aqueous layer and an organic layer. This organic layer was washed with 300 g of ion exchange water and then charged in a 2 L recovery flask equipped with a stirrer, 307.6 g of acetonitrile and 36.2 g of activated carbon (SW-30) were added and stirred at room temperature for 8 hours. This solution was filtered off, the filtrate was concentrated with a rotary evaporator, and the concentrate was dried under reduced pressure to obtain liquid 3-benzyl-5- (2-hydroxyethyl)-4-methylthiazolium bis(trifluoromethaneSulfonyl)imide553.0 g was obtained (yield: 96percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In water; for 2h; | (0400) 5.5 g of LiNTf2 (19 mmoles) are dissolved in 10 mL of water in a beaker. In the same manner, approximately 17.3 mmoles of corresponding bromide is dissolved in water in another beaker. The two solutions are mixed and left under stirring for two hours. (0401) The contents of the beaker are decanted into a separating funnel. The aqueous phase is extracted with twice 15 mL of methylene chloride. The organic phases are collected and dried over MgSO4. The solvent is then evaporated to dryness and the product is dried under vacuum. (0402) 3c: Colorless viscous oil Yield=84%. (0403) 1H NMR (200 MHz, Acetone D6): 1.40-1.70 (m, 2H); 1.90-2.20 (m, 4H); 3.35 (s, 9H); 3.50-3.70 (m, 4H) (0404) 13C NMR (50 MHz, Acetone D6): 23.13; 25.86; 33.24; 34.58; 54.06 (t, JC-N=4.0 Hz); 67.65; 121.37 (q, JC-F=320.9 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | General procedure: 1-Alkylpyridinium bromides ([CnPy]Br), as precursors of the target ILs, were prepared by reacting pyridine with1-bromoalkane under a reflux condition (40 - 60 C) over night. After the [CnPy]Br were purified byrecrystallization from methanol/ethyl acetate or acetonitrile/ethyl acetate solution, the crystalline solids weredissolved in water, and the anion exchange reactions were made by adding 1.2 equivalent amount of Li[NTf2].The resultant ionic liquid layers were repeatedly washed with water. Then, the ionic liquid layers weredissolved in dichloromethane and rigorously stirred with activated carbon until the solutions became colorless.Dichloromethane was then evaporated. The obtained ILs were dried in vacuo at room temperature for morethan 2 days. The yields were approximately 50 %. The analytical data are given in followings. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Exemplary Compound B-14 was synthesized from the intermediate 3. The intermediate 3 (332 mg, 0,5 mmol), 2-methoxyaniline (370 mg, 3 mmol), and ethanol (10 ml) were charged in a reaction container, and then stirred under heating and refluxing for 8 hours. After the completion of a reaction, the ethanol was vacuum-removed, and then ethyl acetate was added to deposit a precipitate. Filtering was performed, the obtained crystal was dissolved in water, an aqueous solution in which potassium hexafluorophosphate (1 g) was dissolved was added, dropwise, the resultant substance was stirred at room temperature for 3 hours, and then the deposited crystal was filtered. The obtained crystal was recrystallized with isopropyl alcohol to give 270 mg (Yield: 80percent) of Exemplary Compound B-14. The structure of Exemplary Compound B-14 was confirmed by NMR measurement. 1H NMR (CD3CN, 500 MHz) sigma (ppm): 9.02 (d, 2H), 8.91 (s, 1H), 8.86 (d, 1H), 8.28 (d, 2H), 8.13 (d, 1H), 7.75 (m, 2H), 7.62 (m, 2H), 7.40 (m, 2H), 7.30 (m, 2H), 3.93 (s, 3H), 3.92 (s, 3H), 2.54 (s, 3 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 1-Methylimidazole and 12 <strong>[624-75-9]iodoacetonitrile</strong> in 13 ethanol was refluxed and stirred at 50C for 12h, the mole ratio was 1:1. A faint yellow powder forms in the reaction. After evaporation of the solvent, the crude product was washed with ethyl acetate and diethyl ether three times, respectively, and dried under vacuum at 50C for 24h to provide pure [MCNIm][I]. Anion exchange with LiTFSI afforded the liquid-state [MCNIm][TFSI] in high yield over 80%. The chemical structure was further confirmed by 1H NMR (DMSO-d6, 400MHz): 9.26 (s, 1H), 7.90 (t, 1H), 7.81 (t, 1H), 5.60 (s, 2H), 3.89 (s, 3H). Using a similar procedure, [RCNIm][I] and [RCNIm][TFSI] from 14 1-ethylimidazole and 1-buthylimidazole can also be obtained and purified. 1HNMR (DMSO-d6, 400MHz) for [ECNIm][I]: 9.34 (s, 1H), 7.92 (t, 2H), 5.59 (s, 2H), 4.26 (m, 2H), 1.43 (s, 3H). 1HNMR (DMSO-d6, 400MHz) for [BCNIm][I]: 9.34 (s, 1H), 7.93 (t, 1H), 7.91 (t, 1H), 5.59 (s, 2H), 4.23 (m, 2H), 1.78 (m, 2H), 1.26 (m, 2H), 0.91 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In water; at 20℃; for 1h; | Triethylmethylammonium chloride (5.060g, 33 mmol)and lithium bis(trifluoromethanesulfonyl)imide (9.6663 g, 34 mmol)were dissolved separately in 50 ml of water each to get clear solutions.Upon mixing the above solutions, a white precipitate formed instantly,and the solution was left to stir for one hour at room temperature afteraddition of CH2Cl2 (100 ml). The organic layer was washed with water(7 × 50 ml). The organic layer was separated and dried in vacuo for72 h at 50 C to get [N1222][NTf2] (8 g, 61%). This sample wascrystallized from hot water to get colourless single crystals. 1H NMR(400 MHz, ((CD3)2CO): 1.43 (tt, CH3, 9H), 3.16 (s, NCH3, 3H), 3.55(q, NCH2, 6H). 13C NMR (100 MHz, ((CD3)2CO): 7.08 (NCH2CH3),46.31 (NCH3), 55.87 (NCH2), 119.20 (CF3, JCF = 320 Hz). 19F NMR(375 MHz, ((CD3)2CO): -79.9 (CF3) ppm. ES+ m/z 116.2((CH2CH3)3CH3N)+, ES- m/z 279.9 (FSI)-. Anal. Calculated forC9H18N2F6O4S2; C, 27.27; H, 4.57: N, 7.06. Found: C, 27.24; H, 4.6:N, 6.92. Chloride content measured by ISE was 20 ppm. Lithiumcontent measured by ICP-MS was 370 ppm. Visual melting point was 102 C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.5% | In water; at 60 - 80℃; for 2h; | 2. Take 200g lithium bistrifluoromethanesulfonimide,Dissolved in 200g pure water, heated to 60 ,Start dropping 235g of 1-ethyl-3-methylimidazole bicarbonate aqueous solution,At the end of the dropwise addition, the temperature rose to 80 C and the temperature was kept for 2 hours. 3. Lower the reaction solution to room temperature,Filtration to obtain 54g of wet filter residue (lithium carbonate and lithium bicarbonate),The filtrate is allowed to stand for separation,286 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 4. Wash three times with pure water to obtain 243g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Maintain the temperature at 80 , remove most of the water, cool and filter to get 6g of wet filter residue,Finally, it is dried in a vacuum drying oven at 110 for 12 hours, and the moisture content is less than 500ppm.The temperature was lowered and filtered to obtain 203g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt. Liquid chromatography detection product purity was 97.62%, yield was 73.5%;Ion chromatography detection: halogen ion <1ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | In water; at 60℃; for 2h; | 3. Combine 200g of 1-ethyl-3-methylimidazole ethyl sulfate,243g of lithium bistrifluoromethanesulfonimide,500g pure water was put into the reaction kettle,Raise the temperature to 60 , stir the reaction for 2h, let it stand for phase separation,335 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. 4. The crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was washed three times with pure water to obtain 312g of relatively pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide amine,Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water, and finally dry in a vacuum drying cabinet at 110 for 12h.301 g of the target product 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.6%, and the yield reached 90.6%;Ion chromatography detection: halogen ion content <1ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |
Tags: 90076-65-6 synthesis path| 90076-65-6 SDS| 90076-65-6 COA| 90076-65-6 purity| 90076-65-6 application| 90076-65-6 NMR| 90076-65-6 COA| 90076-65-6 structure
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