DE60209814T2 - Verfahren zur herstellung von ionischen flüssigkeiten - Google Patents
Verfahren zur herstellung von ionischen flüssigkeiten Download PDFInfo
- Publication number
- DE60209814T2 DE60209814T2 DE60209814T DE60209814T DE60209814T2 DE 60209814 T2 DE60209814 T2 DE 60209814T2 DE 60209814 T DE60209814 T DE 60209814T DE 60209814 T DE60209814 T DE 60209814T DE 60209814 T2 DE60209814 T2 DE 60209814T2
- Authority
- DE
- Germany
- Prior art keywords
- halide
- imidazolium
- reaction
- solvent
- khz
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 pyridinium halide Chemical class 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 150000001450 anions Chemical class 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000001768 cations Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims abstract description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims abstract description 7
- 238000005349 anion exchange Methods 0.000 claims abstract description 5
- 239000000376 reactant Substances 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000009210 therapy by ultrasound Methods 0.000 claims description 5
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 4
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 238000000527 sonication Methods 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000002525 ultrasonication Methods 0.000 abstract description 2
- 230000002110 toxicologic effect Effects 0.000 abstract 1
- 231100000027 toxicology Toxicity 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WVDDUSFOSWWJJH-UHFFFAOYSA-N 1-methyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1 WVDDUSFOSWWJJH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- BMWDUGHMODRTLU-UHFFFAOYSA-N azanium;trifluoromethanesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C(F)(F)F BMWDUGHMODRTLU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- FRZPYEHDSAQGAS-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+]=1C=CN(C)C=1 FRZPYEHDSAQGAS-UHFFFAOYSA-M 0.000 description 1
- NNLHWTTWXYBJBQ-UHFFFAOYSA-N 1-butyl-4-methylpyridin-1-ium Chemical compound CCCC[N+]1=CC=C(C)C=C1 NNLHWTTWXYBJBQ-UHFFFAOYSA-N 0.000 description 1
- LESUBZNRBDUXOH-UHFFFAOYSA-N 1-butylpyridin-1-ium;nitrate Chemical compound [O-][N+]([O-])=O.CCCC[N+]1=CC=CC=C1 LESUBZNRBDUXOH-UHFFFAOYSA-N 0.000 description 1
- UYYXEZMYUOVMPT-UHFFFAOYSA-J 1-ethyl-3-methylimidazol-3-ium;tetrachloroalumanuide Chemical compound [Cl-].Cl[Al](Cl)Cl.CCN1C=C[N+](C)=C1 UYYXEZMYUOVMPT-UHFFFAOYSA-J 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UCCKRVYTJPMHRO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCC[N+]=1C=CN(C)C=1C.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F UCCKRVYTJPMHRO-UHFFFAOYSA-N 0.000 description 1
- UQWLFOMXECTXNQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F UQWLFOMXECTXNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- IODDQGMEFSNLGV-UHFFFAOYSA-N butane;hydrochloride Chemical compound Cl.CCCC IODDQGMEFSNLGV-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- GBJFFNJJPBMORJ-UHFFFAOYSA-N octyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCC)C1=CC=CC=C1 GBJFFNJJPBMORJ-UHFFFAOYSA-N 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01128403 | 2001-12-04 | ||
| EP01128403 | 2001-12-04 | ||
| PCT/EP2002/013499 WO2003048078A2 (en) | 2001-12-04 | 2002-11-29 | Production of ionic liquids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60209814D1 DE60209814D1 (de) | 2006-05-04 |
| DE60209814T2 true DE60209814T2 (de) | 2006-08-31 |
Family
ID=8179398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60209814T Expired - Lifetime DE60209814T2 (de) | 2001-12-04 | 2002-11-29 | Verfahren zur herstellung von ionischen flüssigkeiten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20050005840A1 (https=) |
| EP (1) | EP1453838B1 (https=) |
| JP (1) | JP2005511666A (https=) |
| CN (1) | CN1269824C (https=) |
| AT (1) | ATE319720T1 (https=) |
| AU (1) | AU2002356761A1 (https=) |
| DE (1) | DE60209814T2 (https=) |
| ES (1) | ES2258670T3 (https=) |
| WO (1) | WO2003048078A2 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763186B2 (en) * | 2002-06-21 | 2010-07-27 | Los Alamos National Security, Llc | Preparation and purification of ionic liquids and precursors |
| DE10313207A1 (de) | 2003-03-25 | 2004-10-07 | Basf Ag | Reinigung oder Aufarbeitung von Ionischen Flüssigkeiten mit adsorptiven Trennverfahren |
| US7402711B2 (en) | 2005-09-22 | 2008-07-22 | E.I. Du Pont De Nemours And Company | Preparation of poly(tetramethylene) glycol |
| US7625941B2 (en) | 2005-09-22 | 2009-12-01 | E.I. Du Pont De Nemours And Company | Ionic liquids |
| WO2007038362A1 (en) | 2005-09-22 | 2007-04-05 | E. I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol and copolymers thereof |
| US7464580B2 (en) * | 2005-09-26 | 2008-12-16 | Oakland University | Ionic liquid high temperature gas sensors |
| GB2431517B (en) * | 2005-10-19 | 2008-08-27 | Kidde Ip Holdings Ltd | Temperature switch |
| US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
| US7886577B2 (en) | 2006-03-30 | 2011-02-15 | Oakland University | Devices with surface bound ionic liquids and method of use thereof |
| US8375768B2 (en) * | 2006-03-30 | 2013-02-19 | Oakland University | Ionic liquid thin layer sensor for electrochemical and/or piezoelectric measurements |
| US8721770B2 (en) | 2008-12-04 | 2014-05-13 | E I Du Pont De Nemours And Company | Carbon dioxide removal and ionic liquid compounds useful therein |
| US8138354B2 (en) | 2008-12-04 | 2012-03-20 | E. I. Du Pont De Nemours And Company | N-substituted pyrrolidonium ionic liquids |
| EP2358672B1 (en) | 2008-12-04 | 2013-04-17 | E. I. du Pont de Nemours and Company | N-substituted pyrrolidonium ionic liquids with expanded linker |
| US8350056B2 (en) | 2008-12-04 | 2013-01-08 | E I Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| US8119818B2 (en) | 2008-12-04 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| CN104211620B (zh) | 2009-08-07 | 2016-05-25 | 和光纯药工业株式会社 | 双季铵盐的制造法和其中间体 |
| CN102372676A (zh) * | 2010-08-05 | 2012-03-14 | 昆山科技大学 | 利用超音波促进合成反应快速制造离子液体的方法及设备 |
| JP5579677B2 (ja) * | 2010-08-30 | 2014-08-27 | 日本乳化剤株式会社 | イオン液体の製造方法 |
| KR20130073822A (ko) * | 2011-12-23 | 2013-07-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 이온 액체, 비수 전해질 및 축전 장치 |
| CN102863387B (zh) * | 2012-09-29 | 2015-07-08 | 四川大学 | 一种咪唑类鎓盐的合成方法 |
| CN103755638B (zh) * | 2014-01-21 | 2017-01-18 | 四川大学 | 由硼酸制备咪唑类鎓盐的方法 |
| JP2018090527A (ja) * | 2016-12-02 | 2018-06-14 | 大阪瓦斯株式会社 | イオン液体製造方法 |
| US11567031B2 (en) * | 2017-09-08 | 2023-01-31 | Oakland University | Selective real-time gas sensing |
| WO2019113513A1 (en) | 2017-12-08 | 2019-06-13 | Baker Hughes, A Ge Company, Llc | Ionic liquid based well asphaltene inhibitors and methods of using the same |
| EA202091413A1 (ru) | 2018-07-11 | 2020-09-24 | Бейкер Хьюз Холдингз Ллк | Скважинные ингибиторы асфальтенов на основе ионной жидкости и способы их применения |
| CN109731612B (zh) * | 2018-12-20 | 2022-01-07 | 万华化学集团股份有限公司 | 一种功能化离子液体及制备全反式维生素a醋酸酯的方法 |
| CN109824596B (zh) * | 2019-03-08 | 2020-12-11 | 杭州华樾新材料有限公司 | 离子液体的制备方法 |
| CN115850182A (zh) * | 2022-12-27 | 2023-03-28 | 合肥学院 | 一种用于碳酸二甲酯-甲醇分离的离子液体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3520724A (en) * | 1967-06-23 | 1970-07-14 | Dynamics Corp America | Dual tank sonic processing system and method |
| EP0467742A1 (fr) * | 1990-07-16 | 1992-01-22 | Rhone-Poulenc Chimie | Procédé de synthèse de dérivés fluorés |
| DE19919494A1 (de) * | 1999-04-29 | 2000-11-02 | Celanese Chem Europe Gmbh | Ionische Flüssigkeiten, ihre Herstellung und ihre Verwendung |
-
2002
- 2002-11-29 US US10/497,806 patent/US20050005840A1/en not_active Abandoned
- 2002-11-29 ES ES02804206T patent/ES2258670T3/es not_active Expired - Lifetime
- 2002-11-29 AU AU2002356761A patent/AU2002356761A1/en not_active Abandoned
- 2002-11-29 EP EP02804206A patent/EP1453838B1/en not_active Expired - Lifetime
- 2002-11-29 WO PCT/EP2002/013499 patent/WO2003048078A2/en not_active Ceased
- 2002-11-29 JP JP2003549273A patent/JP2005511666A/ja active Pending
- 2002-11-29 DE DE60209814T patent/DE60209814T2/de not_active Expired - Lifetime
- 2002-11-29 AT AT02804206T patent/ATE319720T1/de not_active IP Right Cessation
- 2002-11-29 CN CNB02824172XA patent/CN1269824C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1453838B1 (en) | 2006-03-08 |
| EP1453838A2 (en) | 2004-09-08 |
| DE60209814D1 (de) | 2006-05-04 |
| ATE319720T1 (de) | 2006-03-15 |
| AU2002356761A1 (en) | 2003-06-17 |
| WO2003048078A3 (en) | 2003-11-27 |
| US20050005840A1 (en) | 2005-01-13 |
| ES2258670T3 (es) | 2006-09-01 |
| CN1269824C (zh) | 2006-08-16 |
| WO2003048078A2 (en) | 2003-06-12 |
| JP2005511666A (ja) | 2005-04-28 |
| CN1606561A (zh) | 2005-04-13 |
| AU2002356761A8 (en) | 2003-06-17 |
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