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CAS No. : | 65039-09-0 | MDL No. : | MFCD00074843 |
Formula : | C6H11ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BMQZYMYBQZGEEY-UHFFFAOYSA-M |
M.W : | 146.62 | Pubchem ID : | 2734160 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.95 |
TPSA : | 8.81 Ų |
GI absorption : | Low |
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) : | -6.31 cm/s |
Log Po/w (iLOGP) : | -4.0 |
Log Po/w (XLOGP3) : | 1.25 |
Log Po/w (WLOGP) : | -2.66 |
Log Po/w (MLOGP) : | 0.67 |
Log Po/w (SILICOS-IT) : | 0.26 |
Consensus Log Po/w : | -0.9 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.88 |
Solubility : | 1.93 mg/ml ; 0.0131 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.03 |
Solubility : | 13.6 mg/ml ; 0.0926 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.71 |
Solubility : | 28.9 mg/ml ; 0.197 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501 | UN#: | N/A |
Hazard Statements: | H302-H319 | Packing Group: | N/A |
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 |
---|---|---|
100% | In ethanol at 35℃; for 10h; UV-irradiation; | 1.1; 2.1 Example 1 (1) uniformly dispersing 1-methylimidazole and ethyl chloride in a molar ratio of 1:1 in ethanol, After heating to 35 ° C with a circulating heating device, under stirring conditions, Irradiation with ultraviolet light of 600 W/m 2 for 10 h, obtaining a quaternary ammonium salt solution of 1-ethyl-3-methylimidazolium chloride in a yield of 100%; |
79% | ||
71% | In acetonitrile at 70℃; for 168h; |
69.2% | at 76℃; for 72h; | |
for 72h; Heating; | ||
at 174℃; Large scale reaction; | ||
at 90℃; for 96h; Autoclave; | ||
In acetonitrile | ||
Reflux; | ||
Reflux; | 2.1.Materials and physical measurements General procedure: The reagentsandsolventswereuseddirectlyassuppliedcommerciallywithoutfurtherpurification excepttwokindsof1-methyl-3-alkylimidazoliumhalideILssynthesizedfromthere-actions of1-alkylhalidewith1-methylimidazoleaccordingtotheliteratureprocesses. [22] Degassed alkylhalide(alkyl ethylto amyl;XCl, I) wererefluxedwiththedistilled1-methylimi-dazole togivethetwokindsofeightILs.TheILswerewashedwithethylacetate,andthendriedunderavacuumatleastfor10h([EMI]Cl: whitesolid,[PMI]Cl:colorlessoil,[BMI]Cl:whitesolid,[AMI]Cl: colorlessoil,[EMI]I:yellowsolid,[PMI]I:yellowoil,[BMI]I: yellowoil,[PMI]I:yellowoil).ElementalanalysisofC,HandNwascarriedoutonaVarioELIIIelementalanalyzer.FT-IRspectrawerecollectedfromKBrpellets(Aldrich,499%, FT-IRgrade)witha BrukerTensor27FT-IRspectrometerintherangeof4000-400cm-1. TGAwerecarriedoutinN2 atmosphere onaSDTQ600V8.3 Build101instrumentwithaheatingrateof10 °C min1 anda N2 flow rateof20cm3 min1. PXRDdataforthematerialswerecollectedatambienttemperaturewithaRigakuD/Max-3c (Japan)diffractometer(Cu-Kα1,2 X-radiation, λ11.540598Åandλ21.544426Å),equippedwithanX'Celeratordetectorandaflatplate sampleholderinaBragg-Brentano para-focusingopticsconfiguration(40kV,50mA).Intensitydatawerecollectedbythestep countingmethod(stepbeing0.02°) incontinuousmodeinthe rangeof5r2θr60°. FluorescencespectrawereacquiredonaHitachi F-4600 fluorescence spectrophotometerwiththeexcita-tion andemissionslitssettedto5nm. | |
at 70℃; for 24h; | 2.2 Preparation of ILs Bromoethane (0.13 mol, 14 g) was added into 1-methylimidazole(0.1 mol, 8.2 g) in a 100 mL three necked flask. The mixturewas stirred at 70 °C for 24 h. When the reaction was over,the white solid was collected by filtration, washed with ethylacetate (3 × 10 mL) and oven-dried under vacuum at 50 °C for6 h. The precursors EmimCl, 1-butyl-3-methylimidazoliumchloride (BmimCl), 1-hexyl-3-methylimidazolium chloride (HmimCl), 1-ethyl-3-methylimidazolium bromide (EmimBr),1-butyl-3-methylimidazolium bromide (BmimBr), 1-hexyl-3-methylimidazolium bromide (HmimBr) and 1-ethyl-3-methylimidazoliumiodide were synthesized according to the abovemethod. EmimCl-AlCl3, EmimBr-AlCl3, BmimCl-AlCl3,BmimBr-AlCl3, HmimCl-AlCl3, HmimBr-AlCl3, EmimI-AlCl3and EmimCl-FeCl3 ILs were synthesized according to the previousreports [20, 21]. | |
In acetonitrile at 90℃; for 24h; | 3.1.1. Synthesis of the Ionic Liquids Both ionic liquids were synthesized in a one-step reaction. The reaction substrates of the first ionicliquid synthesis were 1-methylimidazole, 1-chloroetane, and acetonitrile at a molar ratio of 1:1:10. The1-methylimidazole, 1-chloropropane, and acetonitrile at a molar ratio of 1:1:10 were used to synthesizethe second ionic liquid. Both mixtures were stirred under a reux condenser at 90 C for 24 h. Theproducts of reactions were washed with heptane at 70 C. Next, the solvent was removed using arotary evaporator (BUCHI Labortechnik AG, Flawil, Switzerland). The final products of synthesisreactions were 1-ethyl-3-methylimidazolium chloride [EMIM][Cl] and 1-propyl-3-methylimidazoliumchloride [PMIM][Cl]. The scheme of the ionic liquids synthesis is shown in Figure 7. | |
In ethyl acetate at 10 - 20℃; Cooling with ice; | 3.1 (1) Take a 1L four-necked flask and place it in an ice bath,To this was added 1-methylimidazole (246.3 g, 3.0 mol),Ethyl acetate (60 mL) was added,Stir for 10min to make it uniform;When the temperature of the system dropped below 10°C, ethyl chloride (214g, 3.3moil) was added dropwise thereto,Control the dropping rate to keep the temperature of the system at 10-20 °C to carry out the reaction,After dripping,Remove the ice bath and continue the reaction at room temperature,A reaction product containing 1-ethyl-3-methylimidazolium chloride is obtained.Post-processing: 1-ethyl-3-methylimidazolium chloride is separated from the reaction product by suction filtration,Rinse twice with a mixture of ethyl acetate and petroleum ether (1:3 by volume),Dry in vacuo for 1 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In water-d2 at 100℃; for 15h; | ||
With water-d2 at 100℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium fluorosulfonate In diethyl ether; acetonitrile for 1h; | |
57% | With fluorosulphonic acid at 0 - 60℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water at 20℃; | |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrafluoroborate; at 79.84℃; for 10h;Glovebox; Inert atmosphere; | EMIC was prepared and purified according to a procedure in theliterature [39]. EMI-BF4was prepared by modifying the literaturemethod [40] without using acetone as the solvent. Briefly, EMICand sodium tetrafluoroborate (NaBF4, 98%, ACROS) were mixedand stirred in a 1:1.1 molar ratio at 353 K for 10 h inside a glovebox (Vacuum Atmosphere Co. (VAC), HE-493-SB) filled with highlypure nitrogen and equipped with a regeneration system (VAC, Dri-Train HE-493). Afterwards, the mixture was moved out of the glovebox and an appropriate amount of dichloromethane (CH2Cl2) wasadded to it and stirred for 30 min to reduce the viscosity of themixture and the solubility of NaCl in EMI-BF4. EMI-BF4is solublein CH2Cl2but NaCl is not. After the NaCl had been removed viavacuum filtration through a fine frit, the CH2Cl2was removed witha rotary evaporator. The EMI-BF4RTIL was then completely driedunder vacuum at 383 K for at least 10 h. The dried EMI-BF4wasstored in the glove box for subsequent experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: trimethylsilyl trifluoroacetate; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride for 3h; Heating / reflux; Stage #2: With chloro-trimethyl-silane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; [(2)H6]acetone | 2.2 1-Ethyl-3-methylimidazolium methoxide: 2.2 1-Ethyl-3-methylimidazolium methoxide: A mixture of 1-ethyl-3-methyl imidazolium chloride (3.66 g, 25 mmol) and potassium t-butoxide (3.96 g, 35 mmol) was placed in a 50 cm3 round bottomed flask in a glove box. The flask was transferred to a Kugelrohr apparatus and the mixture was heated at 140° C., at about 130 Pa (1 mm Hg) pressure A colourless oil (1-ethyl-3-methylimidazol-2-ylidine) was collected The reaction was adjudged to be complete after 30 minutes and the apparatus was repressurised with dry nitrogen. Anhydrous methanol (1.0 cm3, 27 mmol) was added to the carbene by syringe. Excess methanol was removed by reconnecting to the vacuum line (1 mm Hg) and rotating the reaction vessel for 1 hour. The NMR spectra were recorded neat, using an acetone-d6 external lock. Yield estimated at 85-90% (based on NMR) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In acetone at 26℃; for 12h; | 4 Example 4 Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,3,3,3-hexafluoropropanesulfonate (Emim-HFPS) (Cation, imidazolium; Anion, Formula 1) To a 1l round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml). The mixture was gently warmed (50° C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,3,3,3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml). This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved. These solutions were combined and stirred under positive N2 pressure at 26° C. for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 2 hr. The product was a viscous light yellow oil (103.8 g, 89% yield). 19F NMR (DMSO-d6) δ -73.8 (s, 3F); -114.5, -121.0 (ABq, J=258 Hz, 2F); -210.6 (m, 1F, JHF=41.5 Hz). 1H NMR (DMSO-d6) δ 1.4 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H,); 5.8 (m, JHF=41.5 Hz, 1H,); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.12%. Analytical calculation for C9H12N2O3F6S: C, 31.5: H, 3.5: N, 8.2. Experimental Results: C, 30.9: H, 3.3: N, 7.8. TGA (air): 10% wt. loss (at) 342° C., 50% wt. loss (at) 373° C. TGA (N2): 10% wt. loss (at) 341° C., 50% wt. loss (at) 374° C. The reaction scheme is shown below |
89% | In acetone at 26℃; for 12h; | H To a 11 round bottom flask was added l-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml). The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,3,3,3- hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml). This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved. These solutions were combined and stirred under positive N2 pressure at 26 degrees C for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it.The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr. The product was a viscious light yellow oil (103.8 g, 89% yield).The reaction scheme is shown below:+ KC119F NMR (DMSOd6) ? -73.8 (s, 3F); -114.5, -121.0 (ABq, J = 258 Hz, 2F); -210.6 (m, IF, JHF = 41.5 Hz).1R NMR (DMSOd6) ? 1.4 (t, J = 7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J = 7.3 Hz, 2H5);5.8 (m, JHF= 41.5 Hz, IH5); 7.7 (s, IH); 7.8 (s, IH); 9.1 (s, IH).% Water by Karl-Fisher titration: 0.12 %.Analytical calculation for C9H12N2O3F6S: C, 31.5: H, 3.5: N, 8.2. ExperimentalResults: C, 30.9: H, 3.3: N5 7.8. TGA (air): 10% wt. loss @ 342 degrees C, 50% wt. loss @ 373 degrees C.TGA (N2): 10% wt. loss @ 341 degrees C, 50% wt. loss @ 374 degrees C. |
89% | In acetone at 20 - 26℃; for 12h; | J (J) Synthesis of 1-ethyl-3-methylimidazolium1,1,2,3,3,3-hexafluoropropanesulfonate (Emim-HFPS) To a 1 liter round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 mL). The mixture was gently warmed (50° C.) until almost all of the Emim-Cl dissolved. To a separate 500 mL flask was added potassium 1,1,2,3,3,3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 mL). This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved. These solutions were combined and stirred under positive N2 pressure at 26° C. for 12 hr producing a milky white suspension. The KCI precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 2 hr. The product was a viscous light yellow oil (103.8 g, 89% yield). 19F NMR (DMSO-d6) δ -73.8 (s, 3F); -114.5, -121.0 (ABq, J=258 Hz, 2F); -210.6 (m, 1F, JHF=41.5 Hz). 1H NMR (DMSO-d6) δ 1.4 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H,); 5.8 (m, JHF=41.5 Hz, 1H,); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.12%. Analytical calculation for C9H12N2O3F6S: C, 31.5: H, 3.5: N, 8.2. Experimental Results: C, 30.9: H, 3.3: N, 7.8. TGA (air): 10% wt. loss ã 342° C., 50% wt. loss ã 373° C. TGA (N2): 10% wt. loss ã 341° C., 50% wt. loss ã 374° C. The reaction scheme is shown below: |
89% | In acetone at 26℃; for 12h; | H To a 11 round bottom flask was added l-ethyl-3- methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1, 1,2, 3, 3, 3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml) . This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved.These solutions were combined and stirred under positive N2 pressure at 26 degrees C for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr . The product was a viscious light yellow oil (103.8 g, 89% yield) . 19F NMR (DMSO-de) δ -73.8 (s, 3F) ; -114.5, -121.0 (ABq, J = 258 Hz, 2F) ; -210.6 (m, IF, JHF = 41.5 Hz) .1H NMR (DMSO-de) δ 1.4 (t, J = 7.3 Hz, 3H) ; 3.9 (s, 3H) ; 4.2 (q, J = 7.3 Hz, 2H, ) ;5.8 (m, JHF = 41.5 Hz, IH, ) ; 7.7 (s, IH) ; 7.8 (s, IH) ; 9.1 (s, IH) .% Water by Karl-Fisher titration: 0.12 %. Analytical calculation for C9H12N2O3F6S: C, 31.5: H, 3.5:N, 8.2. Experimental Results: C, 30.9: H, 3.3: N, 7.8.TGA (air) : 10% wt . loss (at) 342 degrees C, 50% wt . loss (at) 373 degrees C.TGA (N2) : 10% wt . loss (at) 341 degrees C, 50% wt . loss (at) 374 degrees C. |
89% | In acetone at 26℃; for 12h; | H To a 11 round bottom flask was added l-ethyl-3- methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1, 1,2, 3, 3, 3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml) . This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved.These solutions were combined and stirred under positive N2 pressure at 26 degrees C for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it.The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr . The product was a viscious light yellow oil (103.8 g, 89% yield) .19F NMR (DMSO-de) δ -73.8 (s, 3F); -114.5, -121.0 (ABq, J = 258 Hz, 2F); -210.6 (m, IF, JHF = 41.5 Hz) . 1H NMR (DMSO-de) δ 1.4 (t, J = 7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J = 7.3 Hz, 2H, ) ; 5.8 (m, JHF = 41.5 Hz, IH, ) ; 7.7 (s, IH) ; 7.8 (s, IH) ; 9.1 (s, IH) .% Water by Karl-Fisher titration: 0.12 %. Analytical calculation for C9H12N2O3F6S: C, 31.5: H, 3.5: N, 8.2. Experimental Results: C, 30.9: H, 3.3: N, 7.8. TGA (air) : 10% wt . loss (at) 342 degrees C, 50% wt . loss (at) 373 degrees C.TGA (N2) : 10% wt . loss (at) 341 degrees C, 50% wt . loss (at) 374 degrees C. |
89% | In acetone at 26℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In acetone at 24℃; for 24h; | G (G) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethanesulfonate (Emim-TFES); To a 500 ml round bottom flask was added 1-ethyl-3methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml). The mixture was gently warmed (50 degrees C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml). This second mixture was stirred magnetically at 24 degrees C. until all of the TFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24 degrees C. for 24 hrs. The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 2 hr. The product was a viscous light yellow oil (76.0 g, 64% yield). 19F NMR (DMSO-d6) δ -124.7. (dt, JFH=6 Hz, JFF=6 Hz, 2F); -138.4 (dt, JFH=53 Hz, 2F). 1H NMR (DMSO-d6) δ 1.3 (t, J=7.3 Hz, 3H); 3.7 (s, 3H); 4.0 (q, J=7.3 Hz, 2H); 6.1 (tt, JFH=53 Hz, JFH=6 Hz, 1H); 7.2 (s, 1H); 7.3 (s, 1H); 8.5 (s, 1H). % Water by Karl-Fisher titration: 0.18%. Analytical calculation for C8H12N2O3F4S: C, 32.9; H, 4.1; N, 9.6. Found: C, 33.3; H, 3.7; N, 9.6. Mp 45-46 degrees C. TGA (air): 10% wt. loss (at) 379 degrees C., 50% wt. loss (at) 420 degrees C. TGA (N2): 10% wt. loss (at) 378 degrees C., 50% wt. loss (at) 418 degrees C. |
64% | In acetone at 24℃; for 24h; | 3 Example 3 Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethanesulfonate (Emim-TFES) (Cation, imidazolium; Anion, Formula 1) To a 500 ml round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml). The mixture was gently warmed (50° C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml). This second mixture was stirred magnetically at 24° C. until all of the TFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24° C. for 24 hrs. The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 2 hr. The product was a viscous light yellow oil (76.0 g, 64% yield). 19F NMR (DMSO-d6) δ -124.7 (dt, JFH=6 Hz, JFF=6 Hz, 2F); -138.4 (dt, JFH=53 Hz, 2F). 1H NMR (DMSO-d6) δ 1.3 (t, J=7.3 Hz, 3H); 3.7 (s, 3H); 4.0 (q, J=7.3 Hz, 2H); 6.1 (tt, JFH=53 Hz, JFH=6 Hz, 1H); 7.2 (s, 1H); 7.3 (s, 1H); 8.5 (s, 1H). % Water by Karl-Fisher titration: 0.18%. Analytical calculation for C8H12N2O3F4S: C, 32.9: H, 4.1: N, 9.6 Found: C, 33.3: H, 3.7: N, 9.6. Mp 45-46° C. TGA (air): 10% wt. loss (at) 379° C., 50% wt. loss (at) 420° C. TGA (N2): 10% wt. loss (at) 378° C., 50% wt. loss (at) 418° C. The reaction scheme is shown below: |
64% | In acetone at 24℃; for 24h; | G To a 500 ml round bottom flask was added l-ethyl-3methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml). The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,2- tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml). This second mixture was stirred magnetically at 24 degrees C until all of the TFES-K dissolved.These solutions were combined in a 11 flask producing a milky white suspension. The mixture was stirred at 24 degrees C for 24 hrs. The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr. The product was a viscous light yellow oil (76.0 g, 64% yield).The reaction scheme is shown below:19F NMR (DMSOd6) ? -124.7. (dt, JFH = 6 Hz, JFF = 6 Hz, 2F); -138.4 (dt, JFH =53 Hz, 2F).1R NMR (DMSOd6) ?. 1.3 (t, J = 7.3 Hz, 3H); 3.7 (s, 3H); 4.0 (q, J = 7.3 Hz,2H); 6.1 (tt, JPH = 53 Hz, JFH = 6 Hz, IH); 7.2 (s, IH); 7.3 (s, IH); 8.5 (s, IH).% Water by Karl-Fisher titration: 0.18 %.Analytical calculation for C8H12N2O3F4S: C, 32.9: H, 4.1: N, 9.6 Found: C,33.3: H, 3.7: N, 9.6.Mp 45-46 degrees C. TGA (air): 10% wt. loss @ 379 degrees C, 50% wt. loss @ 420 degrees C.TGA (N2): 10% wt. loss @ 378 degrees C, 50% wt. loss @ 418 degrees C. |
64% | In acetone at 24℃; for 24h; | I (I) Synthesis of 1-ethyl-3-methylimidazolium1,1,2,2-tetrafluoroethanesulfonate (Emim-TFES) To a 500 mL round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 mL). The mixture was gently warmed (50° C.) until almost all of the Emim-Cl dissolved. To a separate 500 mL flask was added potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 mL). This second mixture was stirred magnetically at 24° C. until all of the TFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24° C. for 24 hrs. The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 2 hr. The product was a viscous light yellow oil (76.0 g, 64% yield). 19F NMR (DMSO-d6) δ -124.7. (dt, JFH=6 Hz, JFF=6 Hz, 2F); -138.4 (dt, JFH=53 Hz, 2F). 1H NMR (DMSO-d6) δ 1.3 (t, J=7.3 Hz, 3H); 3.7 (s, 3H); 4.0 (q, J=7.3 Hz, 2H); 6.1 (tt, JFH=53 Hz, JFH=6 Hz, 1H); 7.2 (s, 1H); 7.3 (s, 1H); 8.5 (s, 1H). % Water by Karl-Fisher titration: 0.18%. Analytical calculation for C8H12N2O3F4S: C, 32.9: H, 4.1: N, 9.6 Found: C, 33.3: H, 3.7: N, 9.6. Mp 45-46° C. TGA (air): 10% wt. loss ã 379° C., 50% wt. loss ã 420° C. TGA (N2): 10% wt. loss ã 378° C., 50% wt. loss ã 418° C. The reaction scheme is shown below: |
64% | In acetone at 24℃; for 24h; | G To a 500 ml round bottom flask was added 1 -ethyl- 3-methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1, 1, 2, 2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml) . This second mixture was stirred magnetically at 24 degrees C until all of the TFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24 degrees C for 24 hrs . The KCl precipitate was then allowed to settle leaving a clear green solution above it.The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line(4 Pa, 25 degrees C) for 2 hr . The product was a viscous light yellow oil (76.0 g, 64% yield) .19F NMR (DMSO-d6) δ -124.7 (dt, JFH = 6 Hz, JFF = 6 Hz, 2F) ; -138.4 (dt, JFH = 53 Hz, 2F) .1H NMR (DMSO-d6) δ 1.3 (t, J = 7.3 Hz, 3H) ; 3.7 (s,3H) ; 4.0 (q, J = 7.3 Hz, 2H) ;6.1 (tt, JFH = 53 Hz, JFH = 6 Hz, IH) ; 7.2 (s, IH) ;7.3 (s, IH) ; 8.5 (s, IH) . % Water by Karl-Fisher titration: 0.18 %.Analytical calculation for C8H12N2O3F4S: C, 32.9: H,4.1: N, 9.6 Found: C, 33.3: H, 3.7: N, 9.6.Mp 45-46 degrees C.TGA (air) : 10% wt . loss (at) 379 degrees C, 50% wt . loss (at) 420 degrees C. |
64% | In acetone at 24℃; for 24h; | G To a 500 ml round bottom flask was added 1 -ethyl-3methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium1, 1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml) . This second mixture was stirred magnetically at 24 degrees C until all of theTFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24 degrees C for 24 hrs . The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr . The product was a viscous light yellow oil (76.0 g, 64% yield) .19F NMR (DMSO-de) δ . . -124.7 . (dt, JFH = 6 Hz, JFF = 6 Hz, 2F) ; -138.4 (dt, JFH = 53 Hz, 2F) .1H NMR (DMSO-d6) δ 1.3 (t, J = 7.3 Hz, 3H) ; 3.7 (s, 3H) ;4.0 (q, J = 7.3 Hz, 2H) ;6.1 (tt, JFH = 53 Hz, JFH = 6 Hz, IH) ; 7.2 (s, IH) ; 7.3 (s, IH) ; 8.5 (s, IH) .% Water by Karl-Fisher titration: 0.18 %.Analytical calculation for C8H12N2O3F4S: C, 32.9: H, 4.1:N, 9.6 Found: C, 33.3: H, 3.7: N, 9.6.Mp 45-46 degrees C.TGA (air) : 10% wt . loss (at) 379 degrees C, 50% wt . loss (at) 420 degrees C.TGA (N2) : 10% wt . loss (at) 378 degrees C, 50% wt . loss (at) 418 degrees C. |
64% | In acetone at 24℃; for 24h; | G To a 500 ml round bottom flask was added 1 -ethyl- 3methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1, 1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml) . This second mixture was stirred magnetically at 24 degrees C until all of the TFES-K dissolved.These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24 degrees C for 24 hrs . The KCl precipitate was then allowed to settle leaving a clear green solution above it.The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr . The product was a viscous light yellow oil (76.0 g, 64% yield) .19F NMR (DMSO-d6) δ -124.7 (dt, JFH = 6 Hz, JFF = 6 Hz, 2F) ; -138.4 (dt, JFH = 53 Hz, 2F) .1H NMR (DMSO-de) δ 1.3 (t, J = 7.3 Hz, 3H) ; 3.7 (s, 3H) ; 4.0 (q, J = 7.3 Hz, 2H) ;6.1 (tt, JFH = 53 Hz, JFH = 6 Hz, IH) ; 7.2 (s, IH) ; 7.3 (s, IH) ; 8.5 (s, IH) .% Water by Karl-Fisher titration: 0.18 %. Analytical calculation for C8H12N2O3F4S: C, 32.9: H, 4.1 :N, 9.6 Found: C, 33.3: H, 3.7 : N, 9.6.Mp 45-46 degrees C.TGA (air) : 10% wt . loss (at) 379 degrees C, 50% wt . loss (at)420 degrees C. TGA (N2) : 10% wt . loss (at) 378 degrees C, 50% wt . loss (at) 418 degrees C. |
64% | In acetone at 24℃; for 24h; | |
64% | In acetone at 24℃; for 24h; | G (G) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethanesulfonate (Emim-TFES); To a 500 ml round bottom flask was added 1-ethyl-3methylimidazolium chloride (Emim-Cl, 98%, 61.0 g) and reagent grade acetone (500 ml). The mixture was gently warmed (50 degrees C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 90.2 g) along with reagent grade acetone (350 ml). This second mixture was stirred magnetically at 24 degrees C. until all of the TFES-K dissolved. These solutions were combined in a 1 liter flask producing a milky white suspension. The mixture was stirred at 24 degrees C. for 24 hrs. The KCl precipitate was then allowed to settle leaving a clear green solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 2 hr. The product was a viscous light yellow oil (76.0 g, 64% yield). 19F NMR (DMSO-d6) δ -124.7. (dt, JFH=6 Hz, JFF=6 Hz, 2F); -138.4 (dt, JFH=53 Hz, 2F). 1H NMR (DMSO-d6) δ 1.3 (t, J=7.3 Hz, 3H); 3.7 (s, 3H); 4.0 (q, J=7.3 Hz, 2H); 6.1 (tt, JFH=53 Hz, JFH=6 Hz, 1H); 7.2 (s, 1H); 7.3 (s, 1H); 8.5 (s, 1H). % Water by Karl-Fisher titration: 0.18%. Analytical calculation for C8H12N2O3F4S: C, 32.9; H, 4.1; N, 9.6. Found: C, 33.3; H, 3.7; N, 9.6. Mp 45-46 degrees C. TGA (air): 10% wt. loss (at) 379 degrees C., 50% wt. loss (at) 420 degrees C. TGA (N2): 10% wt. loss (at) 378 degrees C., 50% wt. loss (at) 418 degrees C. |
Yield | Reaction Conditions | Operation in experiment |
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89% | In acetone at 26℃; for 12h; | H (H) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,3,3,3-hexafluoropropanesulfonate (Emim-HFPS); To a 11 round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml). The mixture was gently warmed (50 degrees C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,3,3,3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml). This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved. These solutions were combined and stirred under positive N2 pressure at 26 degrees C. for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 2 hr. The product was a viscous light yellow oil (103.8 g, 89% yield). 19F NMR (DMSO-d6)δ -73.8 (s, 3F); -114.5, -121.0 (ABq, J=258 Hz, 2F); -210.6 (m, 1F, JHF=41.5 Hz). 1H NMR (DMSO-d6) δ 1.4 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H,); 5.8 (m, JHF=41.5 Hz, 1H,); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.12%. Analytical calculation for C9H12N2O3F6S: C, 31.5; H, 3.5; N, 8.2. Experimental Results: C, 30.9; H, 3.3; N, 7.8. TGA (air): 10% wt. loss (at) 342 degrees C., 50% wt. loss (at) 373 degrees C. TGA (N2): 10% wt. loss (at) 341 degrees C., 50% wt. loss (at) 374 degrees C. |
89% | In acetone at 26℃; for 12h; | H To a 11 round bottom flask was added l-ethyl-3- methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml) . The mixture was gently warmed (50 degrees C) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1, 1, 2, 3, 3, 3-hexafluoropropanesulfonate (HFPS- K, 92.2 g) along with reagent grade acetone (300 ml) . This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved.These solutions were combined and stirred under positive N2 pressure at 26 degrees C for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 2 hr . The product was a viscious light yellow oil (103.8 g, 89% yield) .19F NMR (DMSO-de) δ -73.8 (s, 3F); -114.5, -121.0 (ABq,J = 258 Hz, 2F); -210.6 (m, IF, JHF = 41.5 Hz) . 1H NMR (DMSO-de) δ 1.4 (t, J = 7.3 Hz, 3H); 3.9 (s,3H); 4.2 (q, J = 7.3 Hz, 2H, ) ;5.8 (m, JHF = 41.5 Hz, IH,); 7.7 (s, IH); 7.8 (s, IH);9.1 (s, IH) .% Water by Karl-Fisher titration: 0.12 %. Analytical calculation for C9H12N2O3F6S: C, 31.5: H,3.5: N, 8.2. Experimental Results: C, 30.9: H, 3.3:N, 7.8.TGA (air) : 10% wt . loss (at) 342 degrees C, 50% wt . loss (at)373 degrees C. TGA (N2) : 10% wt . loss (at) 341 degrees C, 50% wt . loss (at)374 degrees C. |
89% | In acetone at 26℃; for 12h; | H (H) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,3,3,3-hexafluoropropanesulfonate (Emim-HFPS); To a 11 round bottom flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 50.5 g) and reagent grade acetone (400 ml). The mixture was gently warmed (50 degrees C.) until almost all of the Emim-Cl dissolved. To a separate 500 ml flask was added potassium 1,1,2,3,3,3-hexafluoropropanesulfonate (HFPS-K, 92.2 g) along with reagent grade acetone (300 ml). This second mixture was stirred magnetically at room temperature until all of the HFPS-K dissolved. These solutions were combined and stirred under positive N2 pressure at 26 degrees C. for 12 hr producing a milky white suspension. The KCl precipitate was allowed to settle overnight leaving a clear yellow solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 2 hr. The product was a viscous light yellow oil (103.8 g, 89% yield). 19F NMR (DMSO-d6)δ -73.8 (s, 3F); -114.5, -121.0 (ABq, J=258 Hz, 2F); -210.6 (m, 1F, JHF=41.5 Hz). 1H NMR (DMSO-d6) δ 1.4 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H,); 5.8 (m, JHF=41.5 Hz, 1H,); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.12%. Analytical calculation for C9H12N2O3F6S: C, 31.5; H, 3.5; N, 8.2. Experimental Results: C, 30.9; H, 3.3; N, 7.8. TGA (air): 10% wt. loss (at) 342 degrees C., 50% wt. loss (at) 373 degrees C. TGA (N2): 10% wt. loss (at) 341 degrees C., 50% wt. loss (at) 374 degrees C. |
Yield | Reaction Conditions | Operation in experiment |
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In acetone at 24℃; for 8h; | T (T) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (Emim-TPENTAS); To a 500 ml round bottomed flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 ml). The mixture was gently warmed (50 degrees C.) until all of the Emim-Cl dissolved. In a separate 500 ml flask, potassium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 ml). These solutions were combined in a 1 liter flask producing a white precipitate (KCl). The mixture was stirred at 24 degrees C. for 8 hr. The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil which was then diluted with chloroform (100 ml). The chloroform was washed three times with deionized water (50 ml), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 8 hr. The product was a light yellow oil (22.5 g). 19F NMR (DMSO-d6) δ -82.9.(m, 2F); -87.3 (s, 3F); -89.0 (m, 2F); -118.9 (s, 2F). 1H NMR (DMSO-d6) δ 1.5 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.17%. Analytical calculation for C10H11N2O4F9S: C, 28.2; H, 2.6; N, 6.6 Experimental results: C, 28.1; H, 2.9; N, 6.6. TGA (air): 10% wt. loss (at) 351 degrees C., 50% wt. loss (at) 401 degrees C. TGA (N2): 10% wt. loss (at) 349 degrees C., 50% wt. loss (at) 406 degrees C. | |
In acetone at 24℃; for 8h; | 16 Example 16 Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (Emim-TPENTAS) (Cation, imidazolium; Anion, Formula II) To a 500 ml round bottomed flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 ml). The mixture was gently warmed (50° C.) until all of the Emim-Cl dissolved. In a separate 500 ml flask, potassium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 ml). These solutions were combined in a 1 liter flask producing a white precipitate (KCl). The mixture was stirred at 24° C. for 8 hr. The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil which was then diluted with chloroform (100 ml). The chloroform was washed three times with deionized water (50 ml), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 8 hr. The product was a light yellow oil (22.5 g). 19F NMR (DMSO-d6) δ -82.9 (m, 2F); -87.3 (s, 3F); -89.0 (m, 2F); -118.9 (s, 2F). 1H NMR (DMSO-d6) δ 1.5 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.17%. Analytical calculation for C10H11N2O4F9S: C, 28.2: H, 2.6: N, 6.6 Experimental results: C, 28.1: H, 2.9: N, 6.6. TGA (air): 10% wt. loss (at) 351° C., 50% wt. loss (at) 401° C. TGA (N2): 10% wt. loss (at) 349° C., 50% wt. loss (at) 406° C. | |
In acetone at 24℃; for 8h; | T To a 500 ml round bottomed flask was added l-ethyl-3- methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 ml). The mixture was gently warmed (50 degrees C) until all of the Emim- Cl dissolved. In a separate 500 ml flask, potassium l,l,2,2-tetrafluoro-2- (pentafluoroethoxy)sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 ml).These solutions were combined in a 11 flask producing a white precipitate(KCl). The mixture was stirred at 24 degrees C for 8 hr. The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil, which was then diluted with chloroform (100 ml). The chloroform was washed three times with deionized water (50 ml), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 8 hr. The product was a light yellow oil (22.5 g).19F NMR (DMSO-d6) ? -82.9.(m, 2F); -87.3 (s, 3F); -89.0 (m, 2F); -118.9 (s, 2F).1H NMR (DMSO-d6) ? . 1.5 (t, J = 7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J = 7.3 Hz,2H);7.7 (s, IH); 7.8 (s, IH); 9.1 (s, IH). % Water by Karl-Fisher titration: 0.17 %.Analytical calculation for ClOHl 1N2O4F9S: C, 28.2: H, 2.6: N, 6.6Experimental results: C, 28.1: H, 2.9: N, 6.6.TGA (air): 10% wt. loss @ 351 degrees C, 50% wt. loss @ 401 degrees C.TGA (N2): 10% wt. loss @ 349 degrees C, 50% wt. loss @ 406 degrees C. |
In acetone at 24℃; for 8h; | V (V) Synthesis of 1-ethyl-3-methylimidazolium1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (Emim-TPENTAS) To a 500 mL round bottomed flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 mL). The mixture was gently warmed (50° C.) until all of the Emim-Cl dissolved. In a separate 500 mL flask, potassium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 mL). These solutions were combined in a 1 liter flask producing a white precipitate (KCl). The mixture was stirred at 24° C. for 8 hr. The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil which was then diluted with chloroform (100 mL). The chloroform was washed three times with deionized water (50 mL), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25° C.) for 8 hr. The product was a light yellow oil (22.5 g). 19F NMR (DMSO-d6) δ -82.9.(m, 2F); -87.3 (s, 3F); -89.0 (m, 2F); -118.9 (s, 2F). 1H NMR (DMSO-d6) δ 1.5 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.17%. Analytical calculation for C10H11N2O4F9S: C, 28.2: H, 2.6: N, 6.6 Experimental results: C, 28.1: H, 2.9: N, 6.6. TGA (air): 10% wt. loss ã 351° C., 50% wt. loss ã 401° C. TGA (N2): 10% wt. loss ã 349° C., 50% wt. loss ã 406° C. | |
In acetone at 24℃; for 8h; | T (T) Synthesis of l-ethyl-3-methylimidazolium 1,1,2,2- tetrafluoro-2- (pentafluoroethoxy) sulfonate (Emim-TPENTAS)To a 500 ml round bottomed flask was added l-ethyl-3- methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 ml) . The mixture was gently warmed (50 degrees C) until all of the Emim-Cl dissolved. In a separate 500 ml flask, potassium 1, 1, 2, 2-tetrafluoro- 2- (pentafluoroethoxy) sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 ml) .These solutions were combined in a 1 liter flask producing a white precipitate (KCl) . The mixture was stirred at 24 degrees C for 8 hr . The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil which was then diluted with chloroform (100 ml) . The chloroform was washed three times with deionized water (50 ml), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C) for 8 hr . The product was a light yellow oil (22.5 g) .19F NMR (DMSO-de) δ -82.9 (m, 2F); -87.3 (s, 3F); -89.0 (m, 2F) ; -118.9 (s, 2F) .1H NMR (DMSO-de) δ 1.5 (t, J = 7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J = 7.3 Hz, 2H); 7.7 (s, IH); 7.8 (s, IH); 9.1 (s, IH) .% Water by Karl-Fisher titration: 0.17 %. Analytical calculation for C10H11N2O4F9S : C, 28.2: H, 2.6: N, 6.6 Experimental results: C, 28.1: H, 2.9: N, 6.6.TGA (air) : 10% wt . loss @ 351 degrees C, 50% wt . loss @ 5 401 degrees C.TGA (N2) : 10% wt . loss @ 349 degrees C, 50% wt . loss @ 406 degrees C. | |
In acetone at 24℃; for 8h; | T (T) Synthesis of 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (Emim-TPENTAS); To a 500 ml round bottomed flask was added 1-ethyl-3-methylimidazolium chloride (Emim-Cl, 98%, 18.0 g) and reagent grade acetone (150 ml). The mixture was gently warmed (50 degrees C.) until all of the Emim-Cl dissolved. In a separate 500 ml flask, potassium 1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)sulfonate (TPENTAS-K, 43.7 g) was dissolved in reagent grade acetone (450 ml). These solutions were combined in a 1 liter flask producing a white precipitate (KCl). The mixture was stirred at 24 degrees C. for 8 hr. The KCl precipitate was then allowed to settle leaving a clear yellow solution above it. The KCl was removed by filtration through a celite/acetone pad. The acetone was removed in vacuo to give a yellow oil which was then diluted with chloroform (100 ml). The chloroform was washed three times with deionized water (50 ml), dried over magnesium sulfate, filtered, and reduced in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 8 hr. The product was a light yellow oil (22.5 g). 19F NMR (DMSO-d6) δ -82.9.(m, 2F); -87.3 (s, 3F); -89.0 (m, 2F); -118.9 (s, 2F). 1H NMR (DMSO-d6) δ 1.5 (t, J=7.3 Hz, 3H); 3.9 (s, 3H); 4.2 (q, J=7.3 Hz, 2H); 7.7 (s, 1H); 7.8 (s, 1H); 9.1 (s, 1H). % Water by Karl-Fisher titration: 0.17%. Analytical calculation for C10H11N2O4F9S: C, 28.2; H, 2.6; N, 6.6 Experimental results: C, 28.1; H, 2.9; N, 6.6. TGA (air): 10% wt. loss (at) 351 degrees C., 50% wt. loss (at) 401 degrees C. TGA (N2): 10% wt. loss (at) 349 degrees C., 50% wt. loss (at) 406 degrees C. |
Yield | Reaction Conditions | Operation in experiment |
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88% | In dichloromethane at 20℃; for 0.5h; | 14; S11 1-ethyl-3-methylimidazolium chloride (EMI+Cl-) (0.73 g, 5 mmol) and methylene chloride (10 mL) were weighed out into a 25 mL flask. CF3SO2N(CN)(Si(CH3)3) (1.29 g, 5.25 mmol) was added, and the mixture was stirred for 30 minutes at room temperature. As the CF3SO2N(CN)(Si(CH3)3), that obtained through Synthesis Example 9 was used. After the reaction was completed, post-treatment was carried out as in Synthesis Example 13, thus obtaining an ionic liquid (B1). The yield was 1.48 g (88%). The ionic liquid (B1) obtained through the present synthesis example exhibited substantially the same spectral data as the ionic liquid (B 1) synthesized in Synthesis Example 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In water equimolar organic ligand and K-compound dissolved in water; stirred at room temp. for 2 h; extracted 6 times with small portions of CH2Cl2; dried over Na2SO4; solvent removed; dried in vacuum; | |
In acetonitrile at 20℃; for 1h; | General procedure: Seven kinds of onium salts, 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl) (Tokyo Chemical Industry Co., Ltd.), 1-butyl-3-methylimidazolium chloride ([C4mim]Cl) (Kanto Chemical Co., Inc.), 1-butylpyridinium chloride ([C4py]Cl) (Tokyo Chemical Industry Co., Ltd.), 1-butyl-1-methylpyrrolidinium chloride ([C4mpyr]Cl) (Sigma-Aldrich, Inc.), 1-butyl-1-methylpiperidinium chloride ([C4mpip]Cl) (Tokyo Chemical Industry Co., Ltd.), trimethylpropylammonium bromide ([N1,1,1,3]Br) (Tokyo Chemical Industry Co., Ltd.), and tributylmethylammonium chloride ([N4,4,4,1]Cl) (Sigma-Aldrich, Inc.) were used as the cationic species for the preparation of the [PhBF3]--based organic salts. K[PhBF3] was prepared via the previously mentioned protocol and was used as the anion source. The synthesis of the [PhBF3]--based organic salts was performed using the metathesis protocol explained below. K[PhBF3] (40mmol) was added to a solution of an onium halide (40mmol) in acetonitrile (60mL), and the mixture was stirred for 1h at ambient temperature. After the reaction, the mixture was filtered to remove the precipitated by-product, KCl or KBr, and the filtrate was condensed under vacuum. The crude product was extracted by CH2Cl2 and rinsed with ultrapure water several times to remove the unreacted halides and by-product. The organic layer was concentrated in vacuo. The resultant onium phenyltrifluoroborate was dried at 373K under vacuum for 12h. The final product was confirmed by NMR spectroscopy, mass spectrometry, and elemental analysis. 1-Butyl-3-methylimidazolium tetrafluoroborate ([C4mim][BF4]) was purchased from Kanto Chemical Co. and used for comparison. It was thoroughly vacuum dried for 24h before use to remove any residual water. |
Yield | Reaction Conditions | Operation in experiment |
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100% | at 60℃; for 60h; | 4 Example 4 1-Ethyl-3-methylimidazolium methylsulfite A mixture of 4.90 g (33.4 mmol) of 1-ethyl-3-methylimidazolium chloride and 5.67 g (41.0 mmol) of diethyl sulfite is stirred at 60° C. (temperature of the oil bath) for 60 hours under an inert-gas atmosphere (nitrogen) in a sealed reaction vessel with pressure valves for 1-1.5 bar above atmospheric pressure. The end of the reaction is determined by NMR measurement. The product is pumped off over the course of 2 hours in vacuo at 13.3 Pa and 60° C. (temperature of the oil bath), giving 7.23 g of liquid 1-ethyl-3-methylimidazolium ethylsulfite. The yield is virtually quantitative. The product is investigated by means of NMR spectroscopy. 1H NMR (reference: TMS; solvent: CD3CN), ppm: 1.06 t (CH3); 1.43 t (CH3); 3.56 q (CH2O); 3.87 s (CH3); 4.22 q (CH2); 7.47 m (CH); 7.53 m (CH); 9.49 br. s. (CH); 3JH,H=7.3 Hz. |
Yield | Reaction Conditions | Operation in experiment |
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100% | at 110 - 115℃; under 750.075 - 1125.11 Torr; for 72.0h; | Example 4 1-Ethyl-3-methylimidazolium methanesulfonate A mixture of 10.64 g (72.6 mmol) of 1-ethyl-3-methylimidazolium chloride and 14.39 g (130.7 mmol) of dimethyl sulfite is stirred at 110-115 C. (temperature of the oil bath) for 72 hours under an inert-gas atmosphere (nitrogen) in a sealed reaction vessel with pressure valve for 1-1.5 bar above atmospheric pressure. The end of the reaction is determined by NMR measurement. The product is pumped off over the course of 5 hours in vacuo at 13.3 Pa and 115 C. (temperature of the oil bath), giving 14.78 g of liquid 1-ethyl-3-methylimidazolium methanesulfonate. The yield is virtually quantitative. The residual chloride content is less than 5 ppm. The product is investigated by means of NMR spectroscopy. 1H NMR (reference: TMS; solvent: CD3CN), ppm: 1.41 t (CH3); 2.44 s (CH3); 3.85 s (CH3); 4.19 q (CH2); 7.51 d,d (CH); 7.57 d,d (CH); 9.26 br. s. (CH); 3JH,H=7.4 Hz; JH,H=1.5 Hz. |
Yield | Reaction Conditions | Operation in experiment |
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75% | Stage #1: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With potassium hydroxide In ethanol for 2h; Stage #2: With ammonium fluoride In ethanol at 50℃; for 12h; | 2 Example 2: Synthesis of 1-ethyl 3-methylimidazolium fluoride ionic liquid: First, weigh 0.02 mol of 1-ethyl 3-methylimidazole chloride salt and dissolve in 50 ml of ethanol, then weigh 0.02 mol of potassium hydroxide and dissolve in 50 ml of ethanol, mix the two solutions and stir for 2 hours, then filter and separate after standing. Obtain the supernatant, add 0.02 mol of ammonium fluoride to the supernatant, react for 12 hours at 50°C in a ventilated window, and separate after standing overnight. The obtained supernatant is evaporated under reduced pressure at 50°C to remove the organic solvent, and vacuum Drying in a drying oven at 50° C. for 24 hours to obtain 1-ethyl 3-methylimidazolium fluoride ionic liquid, whose structure is characterized by nuclear magnetism, and the yield is >75% by weighing the mass. |
8.8 g | With hydrogen fluoride In water at 50 - 100℃; for 3h; Sealed tube; | 1 Example 1: Synthesis of ethyl-3-methylimidazolium fluoride, the steps are: (1) Take 10g of 99% purity by mass of 1-ethyl-3-methylimidazolium chloride was dissolved in 25mL of distilled water was added50mL mass concentration of 40% hydrofluoric acid, sealed stirred and heated to 50oC;(2) the raw material at least sufficient reaction 3h, then heated to 100oC, evaporating the excess hydrogen fluoride gas and chlorine productGaseous hydrogen, and gases through the absorption of calcium oxide, not dehydrated to give 1-ethyl-3-methyl-imidazol-fluorinated liquid;(3) not dehydrated to 1-ethyl-3-methylimidazolium fluoride ionic liquid was diluted with distilled water, dehydrated notThe volume of ethyl-3-methyl-fluorinated ionic liquid with distilled water, is less than 1:50, the diluted solution was added AgNO3 solution, if precipitation production, continue to add 20mL hydrofluoric acid, repeating (a) and (2) step until no precipitate was produced, purifiedNon-dehydrated 1-ethyl-3-methylimidazolium fluoride ionic liquids;(4) non-purified dehydrated ethyl-3-methyl-fluorinated ionic liquid was dried under high vacuum at 80oCAt least 48h, in addition to the depth of the water, in addition to hydrogen fluoride to give a viscous liquid, viscous liquid to be detected, in addition to the viscous liquidThe volume of distilled water, viscous liquid with distilled water is less than 1:50, sealed and heated to 80oC, with a dilute HF detectorRelease liquid residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue to 80oC dried under high vacuum in addition to hydrogen fluoride untilInspection hydrogen fluoride concentration <0.1ppm; if detected hydrogen fluoride concentration <0.1ppm, the resulting liquid is 1-ethyl-3-methyl imidazole fluorideOxazole ionic liquids, weighing 8.80g. |
19.76 g | With ammonium fluoride at 50℃; for 8h; | 1.1; 1.2; 1.3; 1.4 1) Take 29.32 g of 1-ethyl-3-methylimidazolium chloride (purity 99%) and 7.6 g of NH4F (purity 98%), respectively, and place the two solids directly in an Erlenmeyer flask and take a water bath at 50 °C. After 8 hours of ultrasonic vibration, the solid will undergo a metathesis reaction to produce a white precipitate, which is allowed to stand, precipitated and settled, and the upper layer is a liquid phase with suspended particles to obtain a layered mixture after standing;2) pumping the layered phase at a low pressure three times to obtain a filtrate and a filter residue;3) The liquid phase obtained by filtration is vacuum-screwed at 60 ° C to obtain a pale yellow clear liquid;4) Dry the light yellow clear solution at 70 ° C for 24 h to obtain a pale yellow viscous liquid, which is 1-ethyl-3-methylfluorinated imidazole product, number L1, using a small glass bottle and taking two drops of product Perform Raman spectroscopy test to check whether the product contains NH4+, compare the spectral results of the sample with the standard Raman spectrum of NH4+. If the Raman vibration band of NH4+ is found in comparison, continue to dry at 100 °C under high vacuum until no The Raman vibration band of NH4+ appeared. If a Raman vibration band without NH4+ was detected, the obtained 1-ethyl-3-methylfluorinated imidazolium ionic liquid was weighed 19.76 g. |
With silver fluoride In ethanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
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97.9% | at 80℃; for 3h; | A mixture of 1.32 g (9.0 mmol) of 1-ethyl-3-methylimidazolium chloride and 3.45 g (9.0 mmol) of triethyloxonium bis(trifluoromethylsulfonyl)imide from Example 3 is heated to 70-80 C. (temperature of the oil bath) and stirred for four hours under a nitrogen atmosphere. Volatile constituents are pumped off over the course of one hour under reduced pressure (7 Pa) at 70 C. (temperature of the oil bath), giving 3.45 g of a liquid. The yield of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide is 97.9%, based on the 1-ethyl-3-methylimidazolium chloride employed. The product is investigated by NMR spectroscopy.1H NMR spectrum, ppm: 1.45 t (CH3); 3.83 s (CH3); 4.17 q (CH2); 7.37 m (CH); 7.43 m (CH); 8.57 br. s. (CH); 3JH,H=7.3 Hz.19F NMR spectrum, ppm: -78.91 s (CF3). |
Yield | Reaction Conditions | Operation in experiment |
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99.2% | In acetonitrile at 20℃; for 3h; | 3 Example 3; 1-Ethyl-3-methylimidazolium tris(pentafluoroethyl)difluorochlorophosphate; A mixture of 4.1 g (28.0 mmol) of 1-ethyl-3-methylimidazolium chloride and 13.1 g (30.8 mmol) of tris(pentafluoroethyl)difluorophosphorane is stirred at room temperature for three hours. Volatile constituents (excesses of tris(pentafluoroethyl)difluorophosphorane) are removed in vacuo, and the residue is dried in vacuo for two hours at 7 Pa and at 40-50° C. (temperature of the oil bath). 15.9 g of a viscous, oily material are obtained. The yield of 1-ethyl-3-methylimidazolium tris(pentafluoroethyl)difluorochlorophosphate is 99.2%, based on the 1-ethyl-3-methylimidazolium chloride employed. The compound is analysed by NMR spectroscopy.NMR data:1H NMR spectrum, ppm: 1.45 t (CH3); 3.83 s (CH3); 4.17 q (CH2); 7.37 m (CH); 7.43 m (CH); 8.57 br. s. (CH); 3JH,H=7.3 Hz.19F NMR spectrum, ppm: -25.52 d,m (PF), -69.83 d,m (PF), -77.48 t (CF3), -80.04 m (2CF3), -105.12 d,d (CF2, FA), -105.87 d,d (CF2, FB), -108.87 d,m (CF2), -114.72 d,m (CF2, FA), -115.47 d,m (CF2, FB), J1P,F=933 Hz, J1P,F=863 Hz, J2P,F=98 Hz, J2P,F=84 Hz, J2P,F=119 Hz, J2A,B=281 Hz, J4F,F=21 Hz.31P NMR spectrum, ppm: -147.4 d,d,m. |
Yield | Reaction Conditions | Operation in experiment |
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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 |
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90% | In water | |
69% | In water | 2 Example 2: 1-Ethyl-3-methylimidazoliumcyanodifluorotrifluoro- methylborate - [Οβ H 11 NJ [C F3B F2(C )]; K[CF3BF2(CN)] (5.9 g, 32.5 mmol), prepared as described in Example 1 , is dissolved in deionized water (20ml_) and 1-ethyl-3- methylimidazoliumchloride, [emim]CI (5.0 g, 34.1 mmol) dissolved in deionized water (20 mL) is added by the mixing of the reaction mixture with the magnetic stirring bar. The ionic liquid is separated, washed with deionized water and dried in vacuo at 50 °C. The yield of liquid 1-ethyl-3- methylimidazoliumcyanodifluorotrifluoromethylborate is 5.7g (22.4 mmol), 69% based on the potassium cyanodifluorotrifluoromethylborate employed. Melting point: 13°C.Water content (Karl-Fischer Titration) is 40 ppm.Dynamic viscosity (20°C): 16.5 mPa s. H-NMR: δ, ppm = 1.5 1 (CH3, 3H), 3JH,H = 7 Hz; 4.0 s (CH3> 3H); 4.3 q (CH2, 2H), 3JH,H = 7 Hz; 7.6 m (CH, 1 H); 7.7 m (CH, 1 H); 8.9 br.s (CH, 1 H).JC{'H}-NMR (cation): δ, ppm = 136.8 s (1 C), 124.6 s (1 C), 122.9 s (1 C), 45.6 s (1 C), 36.5 s (1 C), 15.4 s (1 C). |
69% | In water for 0.166667h; | 11 Example 11 1-Ethyl-3-methylimidazolium cyanodifluorotrifluoromethylborate-[C6H11N2][CF3BF2(CN)] K[CF3BF2(CN)] (5.9 g, 32.5 mmol), prepared as described in Example 2, is added with vigorous stirring to a solution of 1-ethyl-3-methylimidazolium chloride, [EMIM]Cl (5.0 g, 34.1 mmol), in deionised water (20 ml), and the mixture is stirred for 10 min. The aqueous phase is subsequently separated off from the ionic liquid using a pipette, washed with bidistilled water (4*5 ml) and dried at 50° C. in a high vacuum. Yield of liquid 1-ethyl-3-methylimidazolium cyanodifluorotrifluoromethylborate is 5.7 g (22.4 mmol), 69%, based on the potassium cyanodifluorotrifluoromethylborate employed. Melting point: 13° C. Water content (Karl Fischer titration): 40 ppm. Dynamic viscosity (20° C.): 16.5 mPa·s, (40° C.): 10.3 mPa·s, (60° C.) 6.9 mPa·s, (80° C.) 5.0 mPa·s. 1H-NMR: δ, ppm=1.5 t (CH3, 3H), 3JH,H=7 Hz; 4.0 s (CH3, 3H); 4.3 q (CH2, 2H), 3JH,H=7 Hz; 7.6 m (CH, 1H); 7.7 m (CH, 1H); 8.9 br.s (CH, 1H). 13C{1H}-NMR (cation): δ, ppm=136.8 s (1C), 124.6 s (1C), 122.9 s (1C), 45.6 s (1C), 36.5 s (1C), 15.4 s (1C). 11B-NMR: δ, ppm=-3.8 tq (1B), 1JF,B=49.0 Hz, 2JF,B=34.5 Hz. 19F-NMR: δ, ppm=-77.4 q (CF3, 3F), 2JF,B=34.5 Hz; -169.1 q (BF2, 2F), 1JF,B=49.3 Hz |
Yield | Reaction Conditions | Operation in experiment |
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59% | In water | 11 Example 11. 1-Ethyl-3-methylimidazolium dicyanomethoxypenta- fluoroethylborate; K[C2F5B(OCH3)(CN)2] (5.2 g, 20.6 mmol), prepared as described in Example 4, is dissolved in deionized water (10 ml), and 1-ethyl-3- methylimidazolium chloride [EMIM]CI (3.5 g, 23.9 mmol), dissolved in deionized water (10 ml), is added by the mixing of the reaction mixture with the magnetic stirring bar. The ionic liquid is separated, washed with deionized water (4 x 2 ml) and dried in vacuo at 60° C. The yield of liquid 1-Ethyl-3-methylimidazolium dicyanomethoxypentafluoroethylborate is 4.0 g (12.3 mmol), 59 % based on the potassium dicyanomethoxypentafluoro- ethylborate, K[C2F5B(OCH3)(CN)2], employed. The product is analyzed by ion chromatography and showed the low content of impurities on halides; chloride: 20 ppm, fluoride: 5 ppm. Water content (Karl-Fischer Titration) is 27 ppm.Raman: v (CN) = 22041H{11B}-NMR: 6", ppm = 8.90 d,d (CH, 1 H), 4JH,H = 1.8 Hz; 7.70 d,d (CH, 1H), 3JH,H = 4JH,H = 1 -7 Hz; 7.63 d,d (CH, 1 H) 3JH,H * 4JH,H = .7 Hz; 4.39 t (CH2, 2H), JH,H = 7.36 Hz; 4.06 s (CH3, 3H); 3.25 s (OCH3, 3H); 1.50 t (CH3, 3H), JH,H = 7.41 Hz. 3C{ H}-NMR: δ, ppm = 136.78 s (CH, 1C); 125.07 s (CH, 1C); 122.38 s (CH, 1C); 53.15 s (OCH3, 1C); 45.61 s (CH2, 1C); 36.46 s (CH3, 1C); 15.34 s (CH3, 1C). 11B{1H}-NMR: δ, ppm = -12.7 t (1B), 2JF, B = 23.1 Hz.19F{ H}-NMR: δ, ppm = -82.0 s (CF3, 3F); -128.9 q (CF2, 2F), 2JF, B = 23.3 Hz.Elemental analysis: found, %: C 40.83, H 4.52, N 17.54; calculated for C11H14BF5N4O: C 40.77, H 4.35, N 17.29. |
59% | In water | 11 EXAMPLE 11 1-Ethyl-3-methylimidazolium dicyanomethoxypentafluoroethylborate-[C6H11N2][C2F5B(OCH3)(CN)2] K[C2F5B(OCH3)(CN)2] (5.2 g, 20.6 mmol), prepared as described in Example 4, is dissolved in deionized water (10 ml), and 1-ethyl-3-methylimidazolium chloride [EMIM]Cl (3.5 g, 23.9 mmol), dissolved in deionized water (10 ml), is added by the mixing of the reaction mixture with the magnetic stirring bar. The ionic liquid is separated, washed with deionized water (4*2 ml) and dried in vacuo at 60° C. The yield of liquid 1-Ethyl-3-methylimidazolium dicyanomethoxypentafluoroethylborate is 4.0 g (12.3 mmol), 59% based on the potassium dicyanomethoxypentafluoroethylborate, K[C2F5B(OCH3)(CN)2], employed. The product is analyzed by ion chromatography and showed the low content of impurities on halides; chloride: 20 ppm, fluoride: 5 ppm. Water content (Karl-Fischer Titration) is 27 ppm. Raman: v (CN)=2204 cm-1. 1H{11B}-NMR: δ, ppm=8.90 d, d (CH, 1H), 4JH,H≈1.8 Hz; 7.70 d, d (CH, 1H), 3JH,H≈4JH,H≈1.7 Hz; 7.63 d, d (CH, 1H) 3JH,H≈4JH,H≈1.7 Hz; 4.39 t (CH2, 2H), JH,H=7.36 Hz; 4.06 s (CH3, 3H); 3.25 s (OCH3, 3H); 1.50 t (CH3, 3H), JH,H=7.41 Hz. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In water | 7 Example 7. 1-Ethyl-3-methylimidazolium dicyanomethoxytrifluoro- methylborate; K[CF3B(OCH3)(CN)2] (5.5 g, 27.2 mmol), prepared as described in Example 2, is dissolved in deionized water (10 ml), and 1-ethyl-3-methylimidazolium chloride [EMIM]CI (4.1 g, 27.9 mmol), dissolved in deionized water (10 ml), is added by the mixing of the reaction mixture with the magnetic stirring bar. The ionic liquid is separated, washed with deionized water (4 x 2 ml) and dried in vacuo at 60° C. The yield of liquid 1-Ethyl-3-methylimidazolium dicyanomethoxytrifluoromethylborate is 3.7 g (13.5 mmol), 49 % based on the potassium dicyanomethoxytrifluoromethyl-borate, K[CF3B(OCH3)(CN)2], employed. The product is analyzed by ion chromatography and showed the low content of impurities on halides; chloride: 104 ppm, fluoride: 41 ppm. Water content (Karl-Fischer Titration) is 58 ppm.Raman specroscopy: v (CN) = 2205 cm-1 0H{11B}-NMR: δ, ppm = 8.95 d,d (CH, 1 H), 4JH,H = 1.7 Hz; 7.71 d,d (CH, 1 H), 3JH,H = 4JH,H == 1 - Hz; 7.61 d,d (CH, 1 H) 3JH,H = 4JH,H = 1.6 Hz; 4.39 t (CH2, 2H), JH,H = 7.36 Hz; 4.07 s (CH3, 3H); 3.20 s (OCH3, 3H); 1.50 1 (CH3, 3H), JH,H = 7.40 Hz153C{1H}-NMR: δ, ppm = 136.28 s (CH, 1C); 125.01 s (CH, 1C); 122.28 s (CH, 1 C); 53.15 s (OCH3, 1C); 45.52 s (CH2, 1C); 36.40 s (CH3, 1C); 15.28 s (CH3, 1C)20 11B{1H}-NMR: δ, ppm = -13.5 q (1 B), 2JF, B = 33.3 Hz.19F{1H}-NMR: δ, ppm = -71.2 q (CF3, 3F), 2JF, B = 33.4 Hz.Elemental analysis: found, %: C 43.77, H 5.28, N 20.59; calculated for ol- CioH14BF3N40: C 43.83, H 5.15, N 20.44. |
49% | In water at 60℃; | 7 K[CF3B(OCH3)(CN)2] (5.5 g, 27.2 mmol), prepared as described in Example 2, is dissolved in deionized water (10 ml), and 1-ethyl-3-methylimidazolium chloride [EMIM]Cl (4.1 g, 27.9 mmol), dissolved in deionized water (10 ml), is added by the mixing of the reaction mixture with the magnetic stirring bar. The ionic liquid is separated, washed with deionized water (4×2 ml) and dried in vacuo at 60° C. The yield of liquid 1-Ethyl-3-methylimidazolium dicyanomethoxytrifluoromethylborate is 3.7 g (13.5 mmol), 49% based on the potassium dicyanomethoxytrifluoromethyl-borate, K[CF3B(OCH3)(CN)2], employed. The product is analyzed by ion chromatography and showed the low content of impurities on halides; chloride: 104 ppm, fluoride: 41 ppm.Water content (Karl-Fischer Titration) is 58 ppm.Raman spectroscopy: v (CN)=2205 cm-1 1H{11B}-NMR: δ, ppm=8.95 d, d (CH, 1H), 4JH,H=1.7 Hz; 7.71 d, d (CH, 1H), 3JH,H=4JH,H=1.7 Hz; 7.61 d, d (CH, 1H) 3JH,H=4JH,H=1.6 Hz; 4.39 t (CH2, 2H), JH,H=7.36 Hz; 4.07 s (CH3, 3H); 3.20 s (OCH3, 3H); 1.50 t (CH3, 3H), JH,H=7.40 Hz13C{1H}-NMR: δ, ppm=136.28 s (CH, 1C); 125.01 s (CH, 1C); 122.28 s (CH, 1C); 53.15 s (OCH3, 1C); 45.52 s (CH2, 1C); 36.40 s (CH3, 1C); 15.28 (CH3, 1C)11B{1H}-NMR: δ, ppm=-13.5 q (1B), 2JF,B=33.3 Hz.19F{1H}-NMR: δ, ppm=-71.2 q (CF3, 3F), 2JF,B=33.4 Hz.Elemental analysis: found, %: C, 43.77; H, 5.28; N, 20.59; calculated for C10H14BF3N4O: C, 43.83; H, 5.15; N, 20.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene at 25 - 50℃; for 2.75h; | 3 EXAMPLE 31807 g of toluene were initially introduced in a 7 l jacketed reactor and heated to 50° C. and 147 g (1 mol) of ethylmethylimidazolium chloride were added. 264 g (1.98 mol) of aluminum chloride were added in portions over the course of 15 min. The mixture was then stirred for 1 h at 50° C. and for a further 1.5 h at 25° C. After phase separation, 864 g of a black-green catalyst phase consisting of EMIM [Al2Cl7] as 47.6% strength solution in toluene and 1333 g of a greenish toluene phase were obtained. | |
In neat (no solvent) at 60℃; Glovebox; | ||
at 20℃; |
at -20℃; for 4h; Sealed tube; | ||
at 70℃; for 3h; Inert atmosphere; | Synthesis of ionic liquids General procedure: Ionic liquids were synthesized bythe direct reaction of metal halides with Et3N•HCl, EMIMCl,and BMIMCl. A 50-mL glass fl ask was charged with Et3N•HCl,EMIMCl or BMIMCl (10 mmol) and AlCl3, FeCl3, ZnCl2, SnCl2or CuCl2 (10-20 mmol) under argon. The mixture was stirredat 70 C for 3 h. If additive of copper(II) sulfate was required, the obtained ionic liquid was treated with CuSO4 (0.05 mmol) andthe mixture was stirred for 1 h at room temperature | |
at 70℃; for 3h; Inert atmosphere; | Synthesis of ionic liquids General procedure: Ionic liquids were synthesized bythe direct reaction of metal halides with Et3N•HCl, EMIMCl,and BMIMCl. A 50-mL glass fl ask was charged with Et3N•HCl,EMIMCl or BMIMCl (10 mmol) and AlCl3, FeCl3, ZnCl2, SnCl2or CuCl2 (10-20 mmol) under argon. The mixture was stirredat 70 C for 3 h. If additive of copper(II) sulfate was required, the obtained ionic liquid was treated with CuSO4 (0.05 mmol) andthe mixture was stirred for 1 h at room temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In diethyl ether; water at 30℃; for 24h; | 1 Example 1: Synthesis of di(l-ethyl-3-methylimidazolium) ethylenbis-(dithiocarbamate),[ C2mim]2ebdtc; A 250 mL round bottom flask was charged with 50 mL of diethylether and 5 g (83 mmol) of freshly distilled ethylenediamine. To the mixture was then added l-ethyl-3- methylimidazolium chloride (24.34 g, 166 mmol) to form a suspension. The suspension was stirred at room temperature and water (50 mL) was then added to completely dissolve the 1 - ethyl-3-methylimidazolium chloride. Upon addition of the water, a biphasic system formed with a yellow lower phase. Sodium hydroxide (6.64 g, 166 mmol) in 10 mL water was added, followed by the dropwise addition of carbondisulfide (12.63 g, 166 mmol). The reaction temperature was maintained below 30°C. After 24 hours of stirring, the suspension turned red. The volatiles were removed by evaporation and the water traces were removed by freeze drying. The residue was dissolved in ethanol, yielding a ruby solution with a colorless crystalline precipitate. The solid was filtered and the volatile material was removed under reduced pressure to yield the product as a red sticky solid. XH-NMR (300 MHz, d6-DMSO) δ (ppm) = 9.6 (s, 2H), 8.4 (s, 2H1H), 7.8 (s, 2H), 7.7 (s, 2H), 4.2 (q, 4H), 3.9 (s, 6H), 3.4 (s, 4H), 1.4 (t, 6H). 13C-NMR (75 MHz, d6-DMSO) δ (ppm) = 167.9, 161.8, 134.5, 118.9, 71.9, 70.4, 67.7, 60.3, 55.6, 53.5. FT-IR: 3074.57, 1567.88, 1467.07, 1380.84, 1316.88, 1264.86, 1164.97, 998.15, 952.04, 864.30, 726.35, 671.73, 646.07, 616.07, 547.23, 530.15, 475.06. MS: 1 11 (Emim+), 321 (ebdtc2 ). Tg - 37.5, T 147.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 4-methoxy-phenol In acetonitrile at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane; water at 20℃; for 0.25h; | |
71% | In water | 11 Na[B(CN)3OC2H5] (7.0 g, 44.6 mmol) is dissolved in distilled water (10 ml), 1-ethyl-3-methylimidazolium chloride, [EMIM]CI (6.5 g, 44.3 mmol), in distilled water (10 ml) is added, and the mixture is stirred vigorously. CH2CI2 (50 ml) is then added, and the emulsion is stirred for 15 minutes. The CH2CI2 phase is separated off, washed with distilled water (3 * 2-3 ml), subsequently dried using MgS04 and filtered. The solution is evaporated in vacuo, and the ionic liquid is dried in vacuo. Yield of 1-ethyl-3- methylimidazolium [B(CN)3OC2H5], which is liquid at room temperature: 7.8 g (31.8 mmol, 71 %). Viscosity (20°C): 27 mPa-s. The product is characterized by means of NMR and Raman spectroscopy:1 B{1H} NMR (solvent: acetone-D6), δ, ppm: -19.03 s.1H{1 B} NMR (solvent: acetone-D6), <5, ppm: 8.97 s (1 H, CH); 7.73 d,d (1 H, CH), 3JH-H = 1.8 Hz; 7.66 d,d (1 H, CH), 3JH-H = 1.7 Hz; 4.38 q (2H, CH2), 3JH- H = 7.3 Hz; 4.05 s (3H, CH3); 3.43 q (2H, OCH2), 3JH-H = 7.0 Hz; 1.57 t (3H, CH3), 3JH-H = 7.3 Hz; 1.10 t (3H, CH3), 3JH-H = 7.0 Hz.13C{1H} NMR (solvent: acetone-D6), δ, ppm: 137.00 s (CH), 129.01 q(3CN), 1 JC-B = 69.8 Hz; 124.76 s (CH); 123.09 s (CH); 61.17 s (OCH2), 45.75 s (CH2); 36.66 s (CH3); 17.73 q (CH3), 3JC-B = 3.2 Hz; 15.42 s (CH3). Raman spectroscopy: v (CN) = 2204, 2216 cm-1.Elemental analysis, found, %: C 53.45, H 6.87, N 27.81 ; calculated for CnH^BNsO, %: C 53.91 , H 6.58, N 28.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In water | 7 Na[B(CN)3OCH3] (8.0 g, 55.9 mmol) is taken up in distilled water (10 ml) with 1-ethyl-3-methylimidazolium chloride, [EMIM]CI (8.2 g, 55.9 mmol), and the mixture is stirred vigorously. An emulsion of 1-ethyl-3-methyl- imidazolium [BOMe(CN)3] in water forms. CH2CI2 (50 ml) is then added to the reaction mixture, and the emulsion is stirred for 15 minutes. The CH2CI2 phase is separated off, washed with distilled water (3 * 2-3 ml), subsequently dried using MgS04 and filtered. The solution is evaporated in vacuo, and the ionic liquid obtained is dried in vacuo. Yield of 1-ethyl-3- methylimidazolium [BOMe(CN)3], which is liquid at room temperature: 9.1 g (39.4 mmol, 70%). Viscosity (20°C): 20 mPa s. The product is characterized by means of NMR and Raman spectroscopy:1B{1H} NMR (solvent: acetone-D6), δ, ppm: -18.48 s.1H{11B} NMR (solvent: acetone-D6), δ, ppm: 8.95 br.s (1 H, CH); 7.72 d,d (1 H, CH), 3JH-H = 1 -8 Hz; 7.65 d,d (1 H, CH), 3JH-H = 1.7 Hz; 4.38 q (2H, CH2), 3JH-H = 7.3 Hz; 4.04 s (3H, CH3); 3.19 s (3H, OCH3), 1.57 t (3H, CH3), 3JH-H = 7.3 Hz. 13C{1H} NMR (solvent: acetone-D6), <5, ppm: 136.91 s (CH), 128.60 q (3 CN), 1JC-B = 70.0 Hz; 124.69 s (CH); 123.02 s (CH); 52.98 q (OCH3), 2JC-B < 1 Hz; 45.70 s (CH2); 36.61 s (CH3), 15.49 s (CH3).Raman spectroscopy: v (CN) = 2205, 2214 cm-1.Elemental analysis, found, %: C 51.35, H 6.35, N 30.76; calculated for C10H14BN5O, %: C 51.98, H 6.11 , N 30.31 |
70% | In dichloromethane; water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: tris(pentafluoroethyl)difluorophosphorane With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With water In tetrahydrofuran at 0℃; for 0.5h; | 2 8.1 g (19 mmol) of (C2F5)3PF2 are slowly added at 0° C. to 20 ml of a one molar LiAlH4/THF solution (20 mmol), and the mixture is stirred for 30 minutes. The solution is hydrolysed using water at 0° C., giving a colourless precipitate (aluminium hydroxide), and 2.8 g (19 mmol) of 1-ethyl-3-methylimidazolium chloride, dissolved in 2 ml of water, are added. After stirring for 30 minutes, the precipitate is filtered off. A second phase deposits, which is separated off and extracted twice with water. It is subsequently dried in vacuo, leaving a colourless liquid. Yield (based on 1-ethyl-3-methylimidazolium chloride): 3.4 g (33%) Analytical data of [EMIM][P(C2F5)3F2H]: |
33% | Stage #1: tris(pentafluoroethyl)difluorophosphorane With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In tetrahydrofuran; water for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; potassium trifluoro(1,1,2,2,2-pentafluoroethyl)borate In water for 0.25h; Stage #2: sodium cyanide With chloro-trimethyl-silane In water at 60℃; for 10h; | 17.B B. Potassium trifluoropentafluoroethylborate, K[C2F5BF3] (1.0 g, 4.42 mmol) and 1-ethyl-3-methylimidazolium chloride, [EMIM]Cl (650 mg, 4.43 mmol), are weighed out into a 10 ml reaction vessel with a glass valve and a PTFE spindle (Young, London) and a magnetic stirrer. Deionised water (1 ml) is added, and the reaction mixture is stirred for 15 minutes. The aqueous phase is separated off, and ionic liquid remaining is washed with deionised water (1 ml) and dried at 50° C. in vacuo for 4 hours. NaCN (660 mg, 13.46 mmol) and trimethylsilyl chloride, (CH3)3SiCl (1.7 ml, 13.45 mmol), are then added, and the reaction mixture is stirred at 60° C. (oil-bath temperature) for 10 hours. The volatile constituents are removed in vacuo, the suspension obtained is washed with deionised water (3*2 ml), and the clear ionic liquid is dried at 50° C. in vacuo. The yield of liquid 1-ethyl-3-methylimidazolium cyanodifluoropentafluoroethylborate at room temperature is 1.2 g (3.93 mmol), 89%, based on the potassium trifluoropentafluoroethylborate, K[C2F5BF3], employed. The purity of the product is 98% according to the 11B- and 19F-NMR spectroscopic investigations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In water | 29 Example 29 1-Ethyl-3-methylimidazolium dicyanofluoropentafluoroethylborate-[C6H11N2[C2F5BF(CN)2] Potassium dicyanofluoropentafluoroethylborate, K[C2F5BF(CN)2] (7.0 g, 29.2 mmol), prepared as described in Example 6, and 1-ethyl-3-methylimidazolium chloride, [EMIM]CI (5.0 g, 34.1 mmol), are taken up in bidistilled water (15 ml) and stirred. The aqueous phase is subsequently separated off, the ionic liquid is washed with bidistilled water (4*5 ml), separated off and subsequently dried at 50° C. in a high vacuum. Yield virtually colourless liquid 1-ethyl-3-methylimidazolium dicyanofluoropentafluoroethylborate is 6.4 g (20.5 mmol), 70%, based on the potassium dicyanofluoropentafluoroethylborate, K[C2F5BF(CN)2], employed. Melting point: -48° C. Water content (Karl Fischer titration): 6 ppm. Dynamic viscosity (20° C.): 16.4 mPa·s, (40° C.): 9.8 mPa·s, (60° C.) 6.5 mPa·s, (80° C.) 4.6 mPa·s. 1H-NMR: δ, ppm=1.5 t (CH3,3H), 3,4JH,H=7 Hz; 4.0 s (CH3, 3H); 4.3 q (CH2, 2H), 3,4JH,H=7 Hz; 7.63 s (CH, 1H); 7.70 s (CH, 1H); 8.9 s (CH, 1H). 13C{1H}-NMR (cation): δ, ppm=136.8 s (1C), 124.6 s (1C), 122.9 s (1C), 45.6 s (1C), 36.5 s (1C), 15.4 s (1C). 11B-NMR: δ, ppm=-12.0 d,t (1B), 1JF,B=51.6 Hz, 2JF,B=25.2 Hz. 19F-NMR: δ, ppm=-82.6 d,t (CF3, 3F), 3JF,F=1.0 Hz, 4JF,F=6.3 Hz; -132.0 q,d (CF2, 2F), 3JF,F=5.0 Hz, 2JF,B=25.3 Hz; -219.1 q,q,t (BF, 1F), 1JF,B=52 Hz, 3JF,F=5-6 Hz, 4JF,F=5-6 Hz. |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In dichloromethane; water for 1h; | 17.A A. Potassium cyanodifluoropentafluoroethylborate, K[C2F5BF2(CN)] (6.9 g, 29.6 mmol), prepared as described in Example 5, and 1-ethyl-3-methylimidazolium chloride, [EMIM]CI (4.5 g, 30.7 mmol), are taken up in a mixture of CH2Cl2 (100 ml) and deionised water (20 ml) and stirred for 1 hour. The aqueous phase is subsequently separated off, and the organic phase is washed with deionised water (5*50 ml) until the test for chloride ions using AgNO3 is negative. The dichloromethane phase is dried using MgSO4, filtered and evaporated at 60° C. using a rotary evaporator. The virtually colourless liquid obtained is dried at 50° C. in vacuo. The yield of liquid 1-ethyl-3-methylimidazolium cyanodifluoropentafluoroethylborate is 6.5 g (21.3 mmol), 72%, based on the potassium cyanodifluoropentafluoroethylborate, K[C2F5BF2(CN)], employed. Melting point: -1 1H-NMR: δ, ppm=1.5 t (CH3, 3H), 3JH,H=7 Hz; 4.0 s (CH3, 3H); 4.3 q (CH2, 2H), 3JH,H=7 Hz; 7.6 m (CH, 1H); 7.7 m (CH, 1H); 8.9 br.s (CH, 1H). 13C{1H}-NMR (cation): δ, ppm=136.8 s (1C), 124.6 s (1C), 122.9 s (1C), 45.6 s (1C), 36.5 s (1C), 15.4 s (1C). 11B-NMR: δ, ppm=-2.7 tt (1B), 1JF,B=51.0 Hz, 2JF,B=25.3 Hz 19F-NMR: δ, ppm=-83.3 t (CF3, 3F), 4JF,F=5.2 Hz; -136.3 q (CF2, 2F), 2JF,B=23.3 Hz; -167.2 qq (BF2, 2F), 1JF,B=51.1 Hz, 4JF,F=5.1 Hz Elemental analysis: found, %, C, 35.44; H, 3.50; N, 13.81; calculated for C3H11BF7N3, %, C, 35.44; H, 3.64; N, 13.78. |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In water for 0.166667h; | 16 Example 16 1-Ethyl-3-methylimidazolium dicyanofluorotrifluoromethylborate-[C6H11N2][CF3BF(CN)2] Potassium dicyanofluorotrifluoromethylborate, K[CF3BF(CN)2] (5.0 g, 26.3 mmol), prepared as described in Example 3, is dissolved in deionised water (15 ml), and a solution of 1-ethyl-3-methylimidazolium chloride, [EMIM]Cl (3.8 g; 26.3 mmol), in deionised water (15 ml) is added with vigorous stirring. The mixture is stirred for 10 min. The aqueous phase is subsequently removed using a pipette, and the colourless ionic liquid obtained is washed with bidistilled water (4*5 ml) and subsequently dried at 50° C. in vacuo. Yield of liquid 1-ethyl-3-methylimidazolium dicyanofluorotrifluoromethylborate is 5.5 g (21.1 mmol, 80%). Melting point: -29° C. Water content (Karl Fischer titration): 20 ppm. Dynamic viscosity (20° C.): 14.0 mPa·s, (40° C.): 8.6 mPa·s, (60° C.) 5.8 mPa·s, (80° C.) 4.2 mPa·s. 1H-NMR: δ, ppm=1.5 t (CH3,3H), 3JH,H=7 Hz; 4.0 s (CH3, 3H); 4.3 q (CH2, 2H), 3JH,H=7 Hz; 7.6 m (CH, 1H); 7.7 m (CH, 1H); 8.9 br.s (CH, 1H). 13C{1H}-NMR (cation): δ, ppm=136.8 s (1C), 124.6 s (1C), 122.9 s (1C), 45.6 s (1C), 36.5 s (1C), 15.4s (1C). 11B-NMR: δ, ppm=-12.8 dq (1B), 1JF,B=49.3 Hz, 2JF,B=35.7 Hz. 19F-NMR: δ, ppm=-74.0 qd (CF3, 3F), 2JF,B=35.7 Hz, 3JF,F=8.3 Hz; -219.7 qq (BF, 1F), 1JF,B=49.2 Hz, 3JF,F=8.0 Hz |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In water | 35 Example 351-Ethyl-3-methylimidazolium tricyanotrifluoromethylborate-[C6H11N2][CF3B(CN)3] Potassium tricyanotrifluoromethylborate K[CF3B(CN)3] (96 mg, 0.48 mmol) is dissolved in deionised water (1 ml), and a solution of 1-ethyl-3-methylimidazolium chloride [EMIM]CI (100 mg, 0.68 mmol) in 1 ml of deionised water is added. The aqueous phase is separated off, and ionic liquid obtained is washed with deionised water (2×2 ml), separated off and dried at 50° C. in vacuo. The yield of 1-ethyl-3-methylimidazolium tricyanotrifluoromethylborate is 98 mg (0.39 mmol). This corresponds the yield 75%, based on the potassium tricyanotrifluoromethylborate K[CF3B(CN)3] employed. The product is characterised by means of NMR spectroscopy.1H-NMR: δ, ppm=8.85 d,d (CH, 1H), 4JH,H≈1.7 Hz; 7.79 d,d (CH, 1H), 3JH,H≈4JH,H≈1.8 Hz; 7.66 d,d (CH, 1H) 3JH,H≈4JH,H≈1.7 Hz; 4.42 t (CH2, 2H), JH,H=7.36 Hz; 4.07 s (CH3, 3H); 1.57 t (CH3, 3H), JH,H=7.40 Hz.13C{1H}-NMR (cation): δ, ppm=136.98 s (CH, 1C); 125.21 s (CH, 1C); 122.54 s (CH, 1C); 45.69 s (CH2, 1C); 36.57 s (CH3, 1C); 15.42 s (CH3, 10).11B-NMR: δ, ppm=-32.0 q (1B), 2JF,B=36.3 Hz.19F-NMR: δ, ppm=-66.4 q (CF3, 3F), 2JF,B=36.3 Hz. |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In water | 36 Example 361-Ethyl-3-methylimidazolium tricyanopentafluoroethylborate-[C6H11N2][C2F5B(CN)3] Potassium tricyanopentafluoroethylborate K[C2F5B(CN)3] (160 mg, 0.64 mmol) is dissolved in deionised water (1 ml), and a solution of 1-ethyl-3-methylimidazolium chloride [EMIM]CI (120 mg, 0.81 mmol) in 1 ml of deionised water is added. The aqueous phase is separated off, and ionic liquid obtained is washed with deionised water (2×2 ml), separated off and dried at 50° C. in vacuo. The yield of 1-ethyl-3-methylimidazolium tricyanopentafluoroethylborate is 180 mg (0.56 mmol). This corresponds the yield 87%, based on the potassium tricyanopentafluoroethylborate K[C2F5B(CN)3] employed. The product is characterised by means of NMR spectroscopy.1H-NMR: δ, ppm=8.77 d,d (CH, 1H), 4JH,H≈1.7 Hz; 7.71 d,d (CH, 1H), 3JH,H≈4JH,H≈1.8 Hz; 7.62 d,d (CH, 1H) 3JH,H≈4JH,H≈1.7 Hz; 4.37 t (CH2, 2H), JH,H=7.31 Hz; 4.02 s (CH3, 3H); 1.50 t (CH3, 3H), JH,H=7.40 Hz.13C{1H}-NMR (cation): δ, ppm=136.48 s (CH, 1C); 125.02 s (CH, 1C);122.34 s (CH, 1C); 45.51 s (CH2, 1C); 36.51 s (CH3, 1C); 15.38 s (CH3, 1C).11B-NMR: δ, ppm=-31.9 t (1B), 2JF,B=25.2 Hz.19F-NMR: δ, ppm=-82.3 s (CF3, 3F); -124.2 q (CF2, 2F), 2JF,B=25.2 Hz. |
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With water | 5 10.0 g (79 mmol) K[BH(CN)3] dissolved in 50 cm3 water and 11.6 g (79 mmol) 1-ethyl-3-methylimidazolium chloride, [EMIMjCI in 50 cm3 water are mixed together at room temperature. The product, 1-ethyl-3- methylimidazolium tricyanohydridoborate is extracted with dichloromethane (100 + 50 + 50 cm3 of CH2CI2). The organic phase is washed two times with water (50 + 50 cm3) and dried with Na2S04. The solvent is distilled off and the residue is dried in vacuum at ca. 40 °C for 15 hours. The yield of liquid at room temperature 1-ethyl-3-methylimidazolium tricyanohydridoborate, [EMIM] [BH(CN)3], is 12.2 g (77%).Residual water: 15 ppm.Chloride impurities: 9 ppm (ion-chromatography)Viscosity: 12.2 mPa s (20 °C).Decomposition temperature: above 277 °C (DSC/TGA; onset). H{11B}-NMR (Solvent: Acetonitrile-D3): δ, ppm = 1.49 1 (CH3> 3H), 3JH,H = 7.3 Hz; 1.77 s (BH, 1 H); 3.86 s (CH3, 3H); 4.20 q (CH2) 2H), 3JH,H = 7.3 Hz; 7.36 d.d (CH, H); 7.42 d,d (CH, H), 3JH,H = 1 7 Hz; 8.46 br.s (CH, 1 H).11B-NMR (Solvent: Acetonitrile-D3): δ, ppm = -40.2 s, 1JB,H = 97 Hz. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | at 50℃; for 16h;Inert atmosphere; | Examples 3 and 4: methylene diacetate A 50 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (20.0 g, 117.0 mmol), and 0.5 equivalents of dichloromethane (5.0 g, 58.7 mmol) were added at room temperature and the reaction was stirred at 50C for 16h. After reaction the pure Product was distilled from the reaction mixture at 80C under reduced pressure (85.0-%). When dibromomethane was used as substrate the reaction was fast even at room temperature and highly exothermic. The reaction proceeds via homogeneous path way and the pure product distilled from the reaction mixture at 80C under reduced pressure (86.0% yield). Methylene diacetate: 1H NMR (CD3CN, 400.13 MHz): delta = 2.04 (s, 6H, CH3), 5.64 (s, 2H, CH2); 13C NMR: delta = 20.9 (CH3), 79.7 (CH2), 170.8 (CO); FTIR (ATR mode): v = 2996 (br), 1758 (s), 1190 (s), 1009 (s), 978 (s) |
Yield | Reaction Conditions | Operation in experiment |
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95% | at 20℃; for 2h;Inert atmosphere; | Example 5 benzyl acetate A 100 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (40.0 g, 0.235 mol), and benzyl chloride (28.0 g, 0.221 mol) were added at room temperature and reaction mixture was stirred for 2h at room temperature (rt), the reaction was fast and exothermic. After reaction two phases were obtained, the desired product formed the upper layer and was decanted (95.0% yield). 1H NMR (CDCl3, 400.13 MHz): delta = 2.09 (s, 3H, CH3), 5.1 (s, 2H, CH2), 7.35 (m, 5H, Ph); 13C NMR: delta = 21.2 (CH3), 66.5 (CH2), 122.4, 128.7, 136.1(Ph), 171.0 (CO); FTIR (ATR mode): v = 3034 (br), 1736 (s), 1222 (s), 1025 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 70℃; for 3h;Inert atmosphere; | Example 1 and 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 70C 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 (90.0% 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 100C under reduced pressure (90.0% yield). Ethylene glycol diacetate: 1H NMR (CDCl3, 400.13 MHz): delta = 2.02 (s, 6 H, CH3), 4.2 (s, 4H, CH2); 13C NMR: delta = 20.9 (CH3), 62.3 (CH2), 170.9 (CO); FTIR (ATR mode): v = 2961 (br), 1735 (s), 1371 (m), 1213 (s), 1048 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | at 80℃; for 16h;Inert atmosphere; | Examples 6 and 7: sec-butyl acetate A 50 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (20.0 g, 0.117 mol), and 1.0 equivalents of 2-bromobutane (15.9 g, 0.116 mmol) were added at room temperature and the reaction was stirred at room temperature for 16h. After reaction two phases were obtained and the upper layer (product) was decanted (83.0% yield). When 2-chlorobutane was used as substrate the reaction was stirred at 80C for 16h. After reaction two phases were obtained. To get the pure product upper layer was decanted (82.0% yield). 1H NMR (CD3CN, 400.13 MHz): delta = 0.87 (t, 3H, CH3), 1.15 (d, 3H, CH3), 1.53 (m, 2H, CH2), 4.75 (m, 1H, CH) 13C NMR: delta = 10.0 (CH3), 19.8 (CH3), 21.5 (CH3), 29.6 (CH2), 72.8 (CH), 171.3 (CO); FTIR (ATR mode): v = 2974 (br), 1733 (s), 1371 (m), 1238 (s), 1030 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 20℃; for 2h;Inert atmosphere; | Example 9 Methyl (R)- (+)-2-acetoxy propionate An optically pure halide compound which is methyl-(R)-(+)-2- chloro propionate and EMIM-acetate were used as starting compounds (Scheme 3). A 25 mL Schlenk flask was equipped with a magnetic stirring bar, EMIM-acetate (1.0 g, 5.875 mmol), and 1.0 equivalents of methyl (R)- (+)-2-chloro propionate (0.72 g, 5.875mmol) were added at room temperature and reaction was stirred at room temperature for 2h. After the reaction, two phases were obtained upper layer was decanted which was contained pure compound (90.0% yield). 1H NMR (CDCl3, 400.13 MHz): delta = 1.46 (d, 3H, CH3), 1.12 (s, 3H, CH3), 3.74 (s, 3H, CH3), 5.06 (q, 1H, CH); FTIR (ATR mode): v = 1738 (s), 1372 (m), 1207 (m), 1097 (m). Optical activity: Optical activity of the starting material as well as product was measured with polarimeter. Sample was prepared in 20 mL heptane by dissolving 0.7g of methyl (R)- (+)-2-chloro propanate. The solution of 0.7 g of methyl (R)- (+)-2-acetoxy propionate was prepared in the same solvent. The specific rotation was found to be (alpha) = -3.20 at room temperature, whereas that of the starting material was 2.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54 mg | In water | 8 Example 8: 1-Ethyl-3-methylimidazolium methyldicyanofluoroborate Example 8: 1-Ethyl-3-methylimidazolium methyldicyanofluoroborate -Potassium methyldicyanofluoroborate (50 mg, 0.367 mmol) and 1-ethyl-3- methylimidazolium chloride, EMIM CI (100 mg, 0.684 mmol), are combined in deionized water (1 ml) and mixed. The reaction solution is extracted with CH2CI2 (2 * 1 ml), and the CH2CI2 is subsequently removed in vacuo. The liquid remaining is dried in vacuo for 12 hours.The yield of EMIM [CH3BF(CN)2] is 54 mg (0.259 mmol). The NMR spectra of EMIM [CH3BF(CN)2]:1 B{ H}-NMR: <5, ppm = -8.9 d (1JF,B = 56.5 Hz).11B-NMR: <5, ppm = -8.9 d.q (1 JF,B = 56.5 Hz, 2JB,H = 4.3 Hz).19F-NMR: δ, ppm = -202.8 q.q (1JF,B = 56.2 Hz, 3JF>H = 14.2 Hz, BF).1H{1 B}-NMR: <5, ppm = 9.03 br. s (CH, 1 H), 7.75 t (3 H.H = H = 1.8 Hz, CH, 1 H), 7.68 t (3JH,H = 4JH.H ¾ 1 -7 Hz, CH, 1 H), 4.40 q (3JH,H = 7.3 Hz, CH2, 2H), 4.05 s (CH3, 3H), 1.57 t (3JH.H = 7.3 Hz, CH3, 3H), -0.12 d (3JF,H = 14.4 Hz, BCH3, 3H).1H-NMR: δ, ppm = 9.03 br. s (CH, 1 H), 7.75 t (3JH,H == H ¾ 1-8 Hz, CH, 1 H), 7.68 t (3JH,H = H = 1 -7 Hz, CH, 1 H), 4.40 q (3JH,H = 7.3 Hz, CH2, 2H), 4.05 s (CH3, 3H), 1.57 t (3JH.H = 7.3 Hz, CH3, 3H), -0.12 d,q (3JF,H = 14.4 Hz, 2JB,H ¾ 4.3 Hz, BCH3, 3H).13C{ H}-NMR: δ, ppm = 136.4 s (EMIM, 1C), 134.0 q,q (1JC,B = 62 Hz, 2JF,C = 39 Hz, 2CN, 2C), 124.0 s (EMIM, 1C), 122.3 s (EMIM, 1C), 45.0 s (EMIM, 1C), 35.9 s (EMIM, 1C), 14.8 s (EMIM, 1C), 8.1 m (BCH3, 1C). |
8.8 g | In dichloromethane at 20℃; for 5h; | 24 Example 24. 1-Ethyl-3-methylimidazolium methyldicyanofluoroborate Example 24. 1-Ethyl-3-methylimidazolium methyldicyanofluoroborate -K[CH3BF(CN)2] (6.0 g, 44.1 mmol) and 1-ethyl-3-methylimidazolium chloride, [EMIM]CI, (6.45 g, 44.0 mmol) are suspended in CH2CI2 (50 ml_) and stirred for 5 hours at room temperature. Magnesium sulfate is added (1g) and the reaction mixture is stirred for 30 min and filtered. The precipitate is washed with 15 ml of CH2CI2 and the organic phases are combined. All volatile compounds are removed in vacuo and the resulted ionic liquid is dried in vacuo for 2 days. 8.8 g (42.31 mmol) of EMIM [CH3BF(CN)2]The spectroscopic data correspond to Example 8.Dynamic viscosity:°c mPa s20 16.240 9.360 6.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol; water for 5h; Reflux; | Synthesis of the ionic liquid (EMIm-Pic) 1-Ethyl-3-methylimidazolium chloride (1.47 g, 10.00 mmol)and potassium picrate (2.67 g, 10.00 mmol) were added to a solutionof deionized water:methanol (2:1, 60 mL). The reaction mixturewas stirred for 5 h under reflux. After which time it wasallowed to cool down to room temperature (ca. 30 °C) and the compound1-ethyl-3-methylimidazolium picrate (EMIm-Pic) was extractedfrom the reaction medium with dichloromethane (ca.60 mL). This solution was them washed three times with deionizedwater (ca. 100 mL in each time). The solvent was evaporated underreduced pressure and the yellow compound was dried over CaCl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane; water at 20℃; for 3h; | 5 Example 5: Synthesis of compound of formula (3) Example 5: Synthesis of compound of formula (3) A solution of 1-Ethyl-3-methyl-1H-imidazolium chloride (2.89 g, 19.7 mmol), compound of formula (1) (4.0 g, 19.7 mmol, prepared according to example 2) in water (14.5 ml) was mixed with DCM (29 ml) and stirred at room temperature for 3 hours. After separation of the aqueous from the organic phase, the organic phase was washed with water (5.8 ml), driedover K2C03 and evaporated on a rotary evaporator yielding 4.33 g (80%) of compound of formula (3) as a slightly yellow solid with a melting point (DSC) of ca. 62°C1H-NMR (400 MHz, CD3CN, TMS): delta [ppm] = 1.46 (t, J = 8Hz, 3H); 3.29 (s, 3H); 3.43 to 3.48 (m, 4H); 3.82 (s, 3H); 4.11 (q, J = 8Hz, 3H); 7.33 (s, 1H); 7.38 (s, 1H); 8.42 (s,1H)13C-NMR (100.6 MHz, CD3CN, TMS): delta [ppm] = 15.5 (s); 36.8 (s); 45.8 (s); 58.8 (s);65.5 (s); 74.0 (q: J = 4 Hz); 123.0 (s); 124.7 (s); 128.8 (q: J = 70 Hz)11B-NMR (160.5 MHz, CD3CN, TMS): delta [ppm] = -19.07 (t, 1.6 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In dichloromethane at 20℃; for 26h; | 9 Example 9: Synthesis of compound of formula (7) Example 9: Synthesis of compound of formula (7) Example 9: Synthesis of compound of formula (7)To compound of formula (2) (5.17 g, 19.8 mmol), prepared according to example 4, were added dichloromethane (40 ml) and 1 -ethyl-3-methylimidazolium chloride (2.95 g, 20.1 mmol). The mixture was stirred at room temperature for 26 h. The mixture was then filteredand concentrated under reduced pressure, to yield 6.49 g (98%) of compound of formula (7) as a colorless oil.1H NMR (400 MHz, CDC13) delta [ppm] = 1.05 (t, J = 7 Hz, 3H), 1.60 (t, J = 7 Hz, 3H), 3.44 (quart, J = 7 Hz, 2H), 3.57 (m, 2H), 3.66 (m, 6H), 3.98 (s, 3H), 4.28 (quart, J = 7 Hz, 2H),7.32 (s, 2H), 9.01 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In hexane at 0 - 20℃; for 26h; | 11 Example 11Preparation of 1 -ethyl-3-methylimidazolium bis(pentafluoroethyl)-phosphinate, [EMIM] [(C2F5)2P(0)0] 10128] Purified 1 -ethyl-3-methylimidazolium chloride, [EMIM]Cl, (0.304 g; 2.1 mmol) is suspended in n-hexane (about 4 ml) in a 10 ml glass flask, cooled (0° C.), and methyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(0)OCH3, (0.676 g; 2.1 mmol) is added. The reaction mixture is warmed (room temperature) and stirred for 26 h. The readily volatile constituents are removed in vacuo (10-s mbar) at room temperature. 1 -Ethyl-3-methylimidazolium bis(pentafluoroethyl)phosphinate, [EMIM][(C2F5)2P(0)0], (0.86 g; 2.1 mmol) is isolated as pale-yellow, highly viscous liquid in quantitative yield with a purity of 99%.10129] The isolated product is characterised by means of ‘H, ‘9F and 3’P NMR spectra in CD3CN.j0130] ‘H NMR: ö in ppm: 8.77 bts (1H), 7.47 d,d (1H), 3JH,H=1.8 Hz; 7.41 d,d (1H), 3JH,H=1.8 Hz; 4.20 q (2H), HJI73 Hz; 3.85 s (3H); 1.47 t (3H), Hz.j0131] ‘9F NMR: ö in ppm: -81.5 m (6F), -126.2 d (4F), 2JF?=66.8 Hz.10132] 3’P NMR: ö in ppm: -1.4 quin,m, 2JF,,=66.9 Hz. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Iron(III) nitrate nonahydrate; dihydrogen peroxide; nitric acid at 70℃; for 4h; | Fenton experiments General procedure: The oxidation runs were carried out at atmospheric pressure in a 500 mL glass batch reactor equipped with a magnetic stirrer (700 rpm) and temperature control. The initial pH value was adjusted to 3 with nitric acid. The starting concentration of IL was always 1 g L-1 and the theoretical stoichiometric amount of H2O2 for complete mineralization was used in all the experiments experiments(3.9, 5.0, 5.5 and 6.0 g L-1for [emim][Cl], [bmpyr][Cl], [tbN][Cl] and[tbP][Cl], respectively). The Fe3+ dose was varied within the range of 10 to 125 mg L-1 and temperatures between 50 and 90 °C were tested. Temperature above the ambient is used in order to increase the efficiency of hydrogen peroxide consumption and reduce the reaction time [20]. As recently demonstrated, increasing the temperature does not imply an extra cost since heat can be recovered from the exit stream and it has also to be considered the exothermic character of the oxidation process [24]. Blank experiments in the absence of catalyst were carried outat all the temperatures tested and negligible conversions of all ILs(<5%) were always observed. All the experiments were performed by duplicate being the standard deviation lower than 5% in all cases. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In dichloromethane; water | |
74% | In water at 20℃; for 2h; | |
69% | In water | 3 Example 3 1-Ethyl-3-methylimidazolium dicyanodihydridoborate-EMIM [BH2(CN)2] Example 31-Ethyl-3-methylimidazolium dicyanodihydridoborate-EMIM [BH2(CN)2]14.04 g (135 mmol) of potassium dicyanodihydridoborate, K[BH2(CN)2], and 19.8 g (135 mmol) of 1-ethyl-3-methylimidazolium chloride, [EMIM]Cl, are each dissolved in 20 ml of water and mixed. 1-Ethyl-3-methylimidazolium dicyanodihydridoborate, [EMIM][BH2(CN)2], is extracted with 130+50+50 ml of CH2Cl2. The combined organic phases are washed with 80 ml of water, dried using Na2SO4, and the solvent is distilled off. [EMIM][BH2(CN)2] is dried at about 50° C. in vacuo for two days with stirring. The yield is 16.3 g (93 mmol, 69%). Water content: 44 ppm; chloride content: 18 ppm; viscosity: 10.2 mPa·s (20° C.). Decomposition temperature (onset): about 290° C. (DSC/TGA) 11B NMR (solvent: CD3CN; reference: Et2O.BF3), δ, ppm: -42.0 t, 1JH,B=95 Hz. 1H{11B} NMR (solvent: CD3CN; reference: TMS), δ, ppm: 8.56 br.s (1H, CH); 7.45 d, d (1H, CH), 3JH,H=1.8 Hz; 7.39 d, d (1H, CH), 3JH,H=1.7 Hz; 4.20 q (2H, CH2), 3JH,H=7.3 Hz; 3.86 s (3H, CH3); 1.48 t (3H, CH3), 3JH,H=7.3; 0.93 br. s (2H, BH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With ion exchange resin (DOWEX); ion excahnge water Stage #2: 3-(2-ethoxyethoxy)propanoic acid In water at 20℃; for 24h; | 1-8 EXAMPLE 1-8 EXAMPLE 1-8 170 mL (102 mmol) of ion exchange resin (DOWEX (registered trademark), manufactured by The Dow Chemical Company) was admixed with ion exchanged water and filled in a column. Then, a solution in which 5.01 g (34.17 mmol) of 1-ethyl-3-methylimidazolium chloride is dissolved in 30.48 g of ion exchanged water was allowed to flow through it two times. Further, 19.99 g of ion exchanged water was divided to two portions and allowed to flow through the ion exchange resin to give 79.64 g of a reaction solution. From the resulting reaction solution, 50.04 g was drawn and added with 4.43 g (23.62 mmol) of 3-(2-ethoxyethoxy)propanoic acid, which has been obtained in Preparation Example 2, followed by stirring for 24 hours at room temperature. The resulting reaction solution was concentrated and dried to obtain 6.20 g of 1-ethyl-3-methylimidazolium 3-(2-ethoxyethoxy)propanoate (hereinbelow, abbreviated as [C2mim] [EEEPA]) (yield: 100%). (0159) 1H-NMR analysis data of the obtained [C2mim] [EEEPA] is given below. (0160) 1H-NMR(CDCl3) δ(ppm)=10.45(s,1H), 10.09(br,2H), 4.32(q,2H), 4.01(s,3H), 3.60(t,2H), 3.55-3.51(m,4H), 3.49(q,3H), 2.52(q,2H), 1.56-1.51(m,2H), 1.15(t,3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | EXAMPLE 1-4 170 mL (102 mmol) of ion exchange resin (DOWEX (registered trademark), manufactured by The Dow Chemical Company) was admixed with ion exchanged water and filled in a column. Then, a solution in which 5.01 g (34.17 mmol) of 1-ethyl-3-methylimidazolium chloride was dissolved in 30.48 g of ion exchanged water was allowed to flow through it two times. Further, 19.99 g of ion exchanged water was divided to two portions and allowed to flow through the ion exchange resin to obtain 79.64 g of a reaction solution. From the obtained reaction solution, 13.66 g (5.85 mmol) was drawn and then added with 0.86 g (5.84 mmol) of <strong>[149577-05-9]3-(2-methoxyethoxy)propanoic acid</strong>, which has been obtained in Preparation Example 1, followed by stirring for 24 hours at room temperature. The resulting reaction solution was concentrated and dried to obtain 1.38 g of 1-ethyl-3-methylimidazolium 3-(2-methoxyethoxy)propanoate (hereinbelow, abbreviated as [C2mim] [MEEPA]) (yield: 91%). 1H-NMR analysis data of the obtained [C2mim] [MEEPA] is given below. 1H-NMR(CDCl3) delta(ppm)=10.79(s,1H), 7.49(s,1H), 7.48(s,1H), 4.33(q,2H), 4.03(s,3H), 3.79(t,2H), 3.60(t,2H), 3.52(t,2H), 3.33(s,3H), 2.52(t,2H), 1.55(t,3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In propan-2-one at 57℃; | 3.2 (2) in step (1), when raw material 1-methylimidazole detected content<0.1wt%, dissolving sodium dicyanamide in acetone, stirring evenly, adding it to the reaction system at room temperature, in reflux state (57 °C) reflux reaction overnight.The feeding amount in step (2) is respectively: sodium dicyanamide: 80.2g (0.9mol),1-Ethyl-3-methylimidazolium chloride (ie, 1-ethyl-3-methylimidazolium chloride): 132.0 g (0.9 mol)Post-treatment: firstly carry out suction filtration treatment, the product filtered out is rotary evaporated to remove the solvent,Add dichloromethane to it, there is precipitation, add it for several times until no precipitation is precipitated, filter to remove the solid, rotary evaporate to remove the dichloromethane,1-ethyl-3-methylimidazolium dicyanamide salt ionic liquid was obtained.After the reaction is detected by GC, it is concentrated in vacuo.The target product was obtained with a yield of 89% and a purity of ≥99%. |
at 49.84 - 89.84℃; for 17h; Darkness; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.9% | With selenium; hydrazine hydrate; sodium stannate trihydrate at 160℃; for 144h; Autoclave; | For the synthesis of 1: A mixture of Na2SnO3·3H2O (0.267g, 1mmol), Se powder (0.198g, 2.5mmol) and 0.50mL hydrazine hydrate (85%) in 1.0g [Emim]Cl was sealed in a 20mL Teflon-lined stainless-steel autoclave at 160°C for 6days, followed by slowly cooling to room temperature under a cooling rate of ~5.4Kh-1. The product was washed with N,N-dimethylformamide and ethanol for several times. Red block-like crystals of 1 were obtained by manually selection (Yield: 0.121g, 29.9% based on Sn). Elemental analysis: calcd. (%) for C30H55N10ClSe14Sn6: C 14.96, H 2.30, N5.81; found: C 14.92, H 2.27, N 5.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-Mercaptobenzothiazole With potassium hydroxide In methanol at 30℃; for 0.833333h; Stage #2: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In methanol for 16h; | 4 Example 4 33.45 g of mercaptobenzothiazole and 11.22 g of potassium hydroxide were respectively dissolved in 40 mL of methanol,The two were then mixed in a 500 mL three-necked round bottom flask equipped with a condenser and a thermometer,30 conditions,Stirring for 50min,The solution is always clear and transparent.After cooling the solution to room temperature,43.94 g of 1-methyl-3-ethylimidazolium chloride was added,Stirring reaction for 16h,The process of gradual precipitation generation.The product was filtered through a slow filter paper,Washed three times with 150 mL of methanol,The filtrate was distilled off to remove the solvent,And then vacuum drying at 80 for 24 h to get mercaptobenzothiazole anti-corrosive ionic liquid,Remember [EMIM] [MBT].3 g of mercaptobenzothiazole-based corrosion resistant ionic liquid [EMIM] [MBT] was dissolved in 97 g of base oil PEG200,By ultrasonic dispersion 3min,It is possible to obtain 100 g of a lubricant composition containing a mercaptobenzothiazole-based corrosion-resistant ionic liquid,Recorded as PEG200 + 3% [EMIM] [MBT]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In methanol; acetonitrile at 20℃; for 3h; | 1.5 Preparation of ionic liquid (A-1) (1-ethyl-3-methylimidazolium-1-cyano-1,1-difluoromethanesulfonate) 7.66 g of sodium 1-cyano-1,1-difluoromethanesulfonate obtained in (4) was placed in a 100 ml Erlenmeyer flask, 60 ml of dehydrated acetonitrile was added to dissolve it, and 5 ml of dehydrated methanol was added, 6.31 g of 1-ethyl-3 methylimidazolium chloride dissolved in 15 ml of dehydrated acetonitrile, stirred at room temperature for 3 hours, filtered, concentrated, and vacuum-dried at 50 °C for 3 hours, and 11.2 g (yield 98%) of ionic liquid (A-1) (1-ethyl-3-methylimidazolium-1-cyano-1,1-difluoromethanesulfonate) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In acetonitrile at 20℃; for 168h; | |
81% | In acetonitrile at 25℃; for 168h; | 2.2 (2) 20 mmol1-Ethyl-3-methyl-1H-imidazolium chloride and 24 mmolAfter adding the sodium tetrazolium borate salt to 30 mL of acetonitrile,Stir the reaction at 25°C for 7 days,Filter and collect the filtrate;After rotovaping to remove the acetonitrile solvent from the filtrate,Dissolve with 50 mL of dichloromethane firstThen wash three times with water,Then dry with anhydrous sodium sulfate.Then vacuum distillation,Finally vacuum drying,3.549 g of 1-ethyl-3-methyl-1H-imidazole tetrazolium cyanoborate are obtained,Yield 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: trifluoroacetic acid; potassium (pentafluoroethyl)trimethoxyborate With potassium hydrogenfluoride at 20℃; for 2h; Stage #2: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In water | 3.2.2. Preparation of potassium pentafluoroethyltrifluoroborate K[C2F5BF3] 3.2.2.3. Method 3. K[C 2 F 5 B(OCH 3 ) 3 ] (8.80 g, 33.6 mmol) and KHF 2(11.5 g, 147 mmol) were placed into a glass ask and dissolved intriuoroacetic acid (65 mL). The reaction mixture was stirred at roomtemperature for 2 h. All volatiles were removed in vacuum, the residualsolid was extracted with acetonitrile (20 mL), and the suspension wasltered. All volatiles were evaporated in vacuum and the residue wassuspended in chloroform (60 mL). The precipitate that consists of amixture of K[C 2 F 5 BF 3 ] and CF 3 C(O)OK was ltered o. Yield: 23.5 g; K[C 2 F 5 BF 3 ]:CF 3 C(O)OK = ca. 1:6. This mixture can be separated bytreatment with EMIM Cl in water (see part 3.2.5, Method 2). |
Yield | Reaction Conditions | Operation in experiment |
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In acetone at 20℃; for 48h; Inert atmosphere; | ||
In acetone at 20℃; for 96h; Inert atmosphere; | 2.2. Synthetic protocol for ILs ILswere synthesized by procedure described earlier [28]. 0.5 molof chloride-based reactant IL (1-ethyl-3-methylimidazolium, Nbutylpyridinium,1-benzyl-3-methylimidazolium, 1-butyl-3-methylimidazolium, 1-butyl-1methylpyrrolidinium, morpholiniumand (vinylbenzyl)trimethylammonium) was taken in round bottomflask and 25 mL of acetone was further poured inside. Then 0.5 molof Na-salt of 2-acrylamido-2-methyl-1-propanesulfonic acid wastransferred to reaction mixture. The resultant mixture wasmagnetically stirred at ambient temperature under inert atmospherefor 4 days. The vacuum filtration of the mixture was doneand solvent in the filtrate was evaporated. The respective ILs obtainedafter evaporation of solvent were dissolved in DCM andextracted thrice with 10mL of cold water to get rid of traces of NaClissued from metathesis reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetonitrile at 25℃; for 168h; | 2.2 Example 2 Synthesis of 1-ethyl-3-methyl-1H-imidazole bis (tetrazolium) borate (2) 40 mmol of 3-ethyl-1-methyl-1H-imidazol-3-ium chloride and 44 mmol of sodium bis(1H-1,2,3,4-tetrazol-1-yl)boranuide were added to 100 mL of acetonitrile,The reaction solution II was stirred at 25 ° C. for 7 days, filtered and the filtrate was collected. The acetonitrile solvent was removed by rotary evaporation from the filtrate and then dissolved in 50 mL of methylene chloride and then washed three times with water,Then dried over anhydrous sodium sulfate, then vacuum distillation,Finally, it was dried in vacuo to give 8.387 g of 1-ethyl-3-methyl-1H-imidazole bis (tetrazole) borate in 80% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: didodecyl phosphate; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With sodium hydroxide In ethanol at 20℃; Stage #2: In dichloromethane; water for 1.5h; | 3 Synthesis of solid organic salt 17 parts by mass of phosphoryl chloride,Using 42 parts by mass of 1-dodecanol as a raw material, Alan Aitken, Chris J. Collett, Shaun T. E. 34 parts by mass of didodecyl phosphate are obtained by the method described in Mesher, SYNTHESIS 2012, 44, 25152518. 10 parts by mass of commercially available ethylmethylimidazolium chloride,26 parts by mass of didodecyl phosphate synthesized as described above are dispersed in 20 parts by mass of ethanol, 3.6 parts by mass of sodium hydroxide is added, and the mixture is stirred at room temperature overnight. Thereafter, 30 parts by mass of water and 30 parts by mass of dichloromethane were added to the reaction solution, and the mixture was stirred for 1 hour and then left to stand for 30 minutes. The organic phase is taken out, dichloromethane is distilled off and dried under reduced pressure to obtain 27 parts by mass of a solid organic salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 40℃; for 18h;UV-irradiation; | (2) mixing the quaternary ammonium salt solution obtained in the step (1) with sodium tetrafluoroborate (the molar ratio of 1-methylimidazole to sodium tetrafluoroborate is 1:1), After heating to 40 C, Under agitation, Irradiation with ultraviolet light of 600 W/m2, The exposure time is 18h, a mixed solution containing a tetrafluoroborate ionic liquid; (3) filtering the mixture obtained in the step (2) twice, Get the filtrate, The filtrate was concentrated at 60 C. Remove ethanol, Obtaining 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid, The yield was 94%. See Table 1 for the properties of the resulting ionic liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.9% | With lithium perchlorate In dichloromethane; water for 12h; | 1; 4; 2-3 Example 1 Preparation of 1-ethyl-3-methylimidazolium acetate ionic liquid: 1.0 mol of 1-ethyl-3-methylimidazolium chloride was dissolved in 48 g of water.Solution A was obtained, and 1.2 mol of lithium perchlorate was dissolved in 254 g of water.Solution B was obtained; solution A was mixed with solution B, 575 g of dichloromethane was added, and the reaction was mechanically stirred for 12 hours;The aqueous phase is separated into waste liquid, recovered, and the organic phase is washed with 260 g of pure water each time.After washing 5 times, no precipitation was detected using AgNO3 solution; the organic phase was vacuum-screwed at 80 ° C.193 g of 1-ethyl-3-methylimidazolium perchlorate ionic liquid intermediate were obtained in a yield of 91.9%;Add 579g of ethanol and slowly add a total of 90.1g of potassium acetate in 4 batches with vigorous stirring.During the addition process, solids are dissolved and precipitated continuously, and the reaction is continuously stirred for 24 hours;Stirring was stopped, frozen to -15 ° C for 24 hours, filtered, and the filter cake was recovered. The filtrate was steamed at 80 ° C; cooled to room temperature.Add 4 volumes of a mixed solution of dichloromethane and 18-crown-6 (crown ether is mixed with dichloromethane in advance,1% of the mass of methylene chloride, frozen to -15 ° C for 24 hours, filtered, the filtrate was steamed at 60 ° C; 18-crown-6 liquid separation,A total of 154.0 g of 1-ethyl-3-methylimidazolium acetate ionic liquid was obtained, and the yield was 90.5%.The purity was 99.3% by high performance liquid chromatography, ≤120ppm of K ion residue, and ≤5ppm of Cl ion residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.0% | In ethanol; for 24h; | 1.0 mol of 1-ethyl-3-methylimidazolium chloride was added to 880 g of ethanol with vigorous stirring.Slowly add a total of 90.1 g of potassium acetate in 4 batches, during the addition process,The solids were dissolved and precipitated continuously, and the reaction was stirred for 24 hours; the stirring was stopped, and the mixture was frozen to -15 C for 24 hours.Filtration, recovery of the cake, and evaporation of the filtrate at 80 degrees to obtain a total of 153.0 g of 1-ethyl-3-methylimidazolium acetate ionic liquid, the yield was 90.0%.The purity was determined by high performance liquid chromatography to be 97.0%, the K ion residue was about 8200 ppm, and the Cl ion residue was about 6400 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 0.166667h; Darkness; | Synthesis of imidazolium-based ionic liquids A solution of silver benzoate (20.46 mmol) in methanol (10 mL) was added to a solution of1-ethyl-3-methylimidazolium chloride (20.46 mmol) in methanol (10 mL) and stirred underexclusion of light at room temperature for 10 min. The reaction mixture was filtrated anddried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 20℃; for 0.166667h; Darkness; | To a solution of 1-ethyl-3-methylimidazolium chloride (20.46 mmol) in acetone (10 mL), asolution of silver salicylate (20.46 mmol) in acetone (10 mL) was added. The reaction wasstirred for 10 min under exclusion of light at room temperature. After the reaction, the mixturewas filtrated and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With titanium tetrachloride In acetonitrile at 0℃; for 1h; Inert atmosphere; | 1 [Production of 1-Ethyl-3-methylimidazolium cyanosulfonyl (trifluoromethylsulfonylamide)] Lithium chlorosulfonyl (trifluoromethylsulfonylamide) under an argon atmosphere1.67 g was dissolved in 17 mL of acetonitrile and 1.06 g of 1-ethyl-3-methylimidazolium chloride was added.Then, 2.8 g of trimethylsilyl cyanide was added.After cooling to 0 ° C. in an ice bath, 3.4 g of titanium tetrachloride was added dropwise.After the dropwise addition, the solvent of the reaction solution aged for 1 hour was distilled off, water (100 ml) was added, and the mixture was stirred at room temperature for 40 minutes.Then, it was extracted with ethyl acetate (50 mL × 3) and washed with saturated brine.After adding sodium sulfate to the organic layer, filtering, and distilling off the solvent,Add methylene chloride (20 mL)Wash with 20 mL of water and methylene chloride (20 ml x 2) in the aqueous layer.The organic layer was washed with water (20 ml × 2).The organic layer was distilled off and vacuum dried to give 185 mg.1-Ethyl-3-methylimidazolium cyanosulfonyl(Trifluoromethylsulfonylamide)(Yield 7%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | Stage #1: sodium 2-amino-1,1-difluoro-2-oxoethanesulfonyl(trifluoromethylsulfonylamide) With phosphorus pentoxide at 200℃; for 3h; Inert atmosphere; Stage #2: acetonitrile Stage #3: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In water at 20℃; for 0.5h; | 2 [Production of 1-Ethyl-3-methylimidazolium cyanodifluoromethylsulfonyl (trifluoromethylsulfonylamide)] In an argon atmosphere, 36.8 g of diphosphorus pentoxide in a 300 mL three-necked round bottom flask,28.2 g of the sodium (2-amino-1,1-difluoro-2-oxoethanesulfonyl) (trifluoromethylsulfonylamide) obtained above was added, and the mixture was vigorously stirred at 200 ° C. for 3 hours.Then let it cool300 ml of dehydrated acetonitrile was added, and vacuum filtration was performed with a membrane filter (manufactured by Nippon Millipol) having a pore size of 0.45 μm.Concentrate the filtrate120 mL each of ultrapure water and ethyl acetate were added to the obtained sample.The ethyl acetate layer was extracted and concentrated.Place the resulting sample in a 100 mL Ellenmeier flask and placeAfter adding 20 mL of ultrapure water and dissolving it,12.6 g of 1-ethyl-3-methylimidazolium chloride was dissolved in 20 mL of ultrapure water.added.After stirring at room temperature for 30 minutes, 20 mL of dichloromethane was added.The mixture was stirred for 2 hours.After stirring, the dichloromethane layer is separated, concentrated, andBy performing vacuum drying at 60 ° C for 3 hours,7.2 g (yield 21%) of 1-ethyl-3-methylimidazolium cyanodifluoromethylsulfonyl (trifluoromethylsulfonylamide) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In water at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Amberlite IRA-400 cinnamate exchange resin In methanol | 2.7.16 [C2mim][Cin], [C4mim][Cin], [C2py][Cin], [C4py][Cin], [Ch][Cin], [C2OHmim][Cin], [C2OHpy][Cin], [C4py-Cin][Cin], [C4mim-Cin][Cin] General procedure: A methanol solution (50mM, 10mL) of the appropriate IL was slowly passed through a “crude” column with the Amberlite IRA-400 anion exchange resin (cinnamate form) five times; 80-99% substitution of the anion was achieved in this way. After that, the crude product solution was slowly passed through a “fresh” column. The solvent was evaporated under reduced pressure at room temperature; traces of the solvent were removed by drying over P2O5 under vacuum. |
Tags: 65039-09-0 synthesis path| 65039-09-0 SDS| 65039-09-0 COA| 65039-09-0 purity| 65039-09-0 application| 65039-09-0 NMR| 65039-09-0 COA| 65039-09-0 structure
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