KR20090077976A - 이온성 액체를 이용한 이산화탄소로부터의 테트라플루오로에틸렌의 분리 방법 - Google Patents
이온성 액체를 이용한 이산화탄소로부터의 테트라플루오로에틸렌의 분리 방법 Download PDFInfo
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- KR20090077976A KR20090077976A KR1020097011359A KR20097011359A KR20090077976A KR 20090077976 A KR20090077976 A KR 20090077976A KR 1020097011359 A KR1020097011359 A KR 1020097011359A KR 20097011359 A KR20097011359 A KR 20097011359A KR 20090077976 A KR20090077976 A KR 20090077976A
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- ionic liquid
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 102
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 18
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 18
- 238000000926 separation method Methods 0.000 title abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 159
- 238000000034 method Methods 0.000 claims abstract description 67
- 238000004821 distillation Methods 0.000 claims abstract description 24
- 238000010521 absorption reaction Methods 0.000 claims abstract description 14
- 150000001450 anions Chemical class 0.000 claims description 39
- 150000001768 cations Chemical class 0.000 claims description 31
- -1 Pyridinium pyridazinium Pyrimidinium pyrazinium Imidazolium pyrazolium Chemical compound 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000001924 cycloalkanes Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 7
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- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910016467 AlCl 4 Inorganic materials 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
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- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 5
- 150000001923 cyclic compounds Chemical class 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 5
- 125000001425 triazolyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000009298 Trigla lyra Species 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 235000020030 perry Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- RPGGYYVWJTWVMS-ZPSVQYCPSA-N (8r,9s,10r,13s,14s,17r)-17-ethynyl-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 RPGGYYVWJTWVMS-ZPSVQYCPSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- IMUVIFKTRWHTHW-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,2,2-trifluoroethoxy)ethane trihexyl(tetradecyl)phosphanium Chemical compound FC(C(OC(C(F)(F)F)(F)F)F)F.C(CCCCCCCCCCCCC)[P+](CCCCCC)(CCCCCC)CCCCCC IMUVIFKTRWHTHW-UHFFFAOYSA-N 0.000 description 1
- KZWJWYFPLXRYIL-UHFFFAOYSA-M 1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-M 0.000 description 1
- BGGUZIZLOYTWFU-UHFFFAOYSA-M 1,1,2,3,3,3-hexafluoropropane-1-sulfonate;tributyl(tetradecyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC BGGUZIZLOYTWFU-UHFFFAOYSA-M 0.000 description 1
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 1
- VFKJFIDWVGPBDV-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCC[N+]=1C=CN(C)C=1C VFKJFIDWVGPBDV-UHFFFAOYSA-M 0.000 description 1
- MXDXOYOYMBHGQD-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F MXDXOYOYMBHGQD-UHFFFAOYSA-M 0.000 description 1
- ZIPFNZZMKGEBFU-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F ZIPFNZZMKGEBFU-UHFFFAOYSA-M 0.000 description 1
- MIQNTLMZSDFZQY-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F MIQNTLMZSDFZQY-UHFFFAOYSA-M 0.000 description 1
- BGHQBDVUMIWVAR-UHFFFAOYSA-M 1-dodecyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCCCCCC[N+]=1C=CN(C)C=1 BGHQBDVUMIWVAR-UHFFFAOYSA-M 0.000 description 1
- CTEAXVWYCINNCA-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)F CTEAXVWYCINNCA-UHFFFAOYSA-M 0.000 description 1
- SEGKWNUGNNFXPC-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F SEGKWNUGNNFXPC-UHFFFAOYSA-M 0.000 description 1
- MCZWGKAIQPGCBP-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCC[N+]=1C=CN(C)C=1 MCZWGKAIQPGCBP-UHFFFAOYSA-M 0.000 description 1
- FONRKAHEKCCJDV-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCCCCCCCCCCCC[N+]=1C=CN(C)C=1 FONRKAHEKCCJDV-UHFFFAOYSA-M 0.000 description 1
- LOZOAPSBGHOALW-UHFFFAOYSA-N 1h-imidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [NH2+]1C=CN=C1.[O-]S(=O)(=O)C(F)(F)C(F)F LOZOAPSBGHOALW-UHFFFAOYSA-N 0.000 description 1
- ACVAUFCPHXVLQA-UHFFFAOYSA-N 1h-imidazole;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CNC=N1 ACVAUFCPHXVLQA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- PJTWTUDZGDEPHR-UHFFFAOYSA-N FC(C(F)F)(S(=O)(=O)[O-])F.C(CCC)[N+]1=CNC=C1 Chemical compound FC(C(F)F)(S(=O)(=O)[O-])F.C(CCC)[N+]1=CNC=C1 PJTWTUDZGDEPHR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 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
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- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
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- 239000007791 liquid phase Substances 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
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- 239000011591 potassium Substances 0.000 description 1
- BVZFTIYNEUGOHK-UHFFFAOYSA-M potassium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)F BVZFTIYNEUGOHK-UHFFFAOYSA-M 0.000 description 1
- HOYITZNTNKOLOY-UHFFFAOYSA-M potassium;1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F HOYITZNTNKOLOY-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IWVSKNFJIVKXHH-UHFFFAOYSA-N pyrazine;pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CC=N1 IWVSKNFJIVKXHH-UHFFFAOYSA-N 0.000 description 1
- LDEZROSHPJRREZ-UHFFFAOYSA-N pyridazine;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NN=C1 LDEZROSHPJRREZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- ZPHRQLVXRDQUPM-UHFFFAOYSA-M sodium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F ZPHRQLVXRDQUPM-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/0005—Degasification of liquids with one or more auxiliary substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/40—Extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
- C07C21/185—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine tetrafluorethene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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|---|---|---|---|
| US85756606P | 2006-11-08 | 2006-11-08 | |
| US60/857,566 | 2006-11-08 |
Publications (1)
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|---|---|
| KR20090077976A true KR20090077976A (ko) | 2009-07-16 |
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Family Applications (1)
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| KR1020097011359A Withdrawn KR20090077976A (ko) | 2006-11-08 | 2007-11-08 | 이온성 액체를 이용한 이산화탄소로부터의 테트라플루오로에틸렌의 분리 방법 |
Country Status (6)
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| US (2) | US8313558B2 (enExample) |
| EP (1) | EP2086914A1 (enExample) |
| JP (1) | JP2010509333A (enExample) |
| KR (1) | KR20090077976A (enExample) |
| CN (1) | CN101616882A (enExample) |
| WO (1) | WO2008057574A1 (enExample) |
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| US8715521B2 (en) * | 2005-02-04 | 2014-05-06 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquid as working fluid |
| US8506839B2 (en) | 2005-12-14 | 2013-08-13 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquids and water as working fluids |
| TW200808649A (en) * | 2006-05-31 | 2008-02-16 | Du Pont | Process for purifying perfluorinated products |
| US8075777B2 (en) * | 2007-05-16 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Process for the separation of diastereomers |
| US7964760B2 (en) * | 2007-05-25 | 2011-06-21 | E.I. Du Pont De Nemours And Company | Process for the separation of fluorocarbons using ionic liquids |
| WO2010065873A2 (en) | 2008-12-04 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Carbon dioxide removal and ionic liquid compounds useful therein |
| KR100975897B1 (ko) | 2009-01-05 | 2010-08-13 | 경희대학교 산학협력단 | 트리알콕시히드록시포스포늄 카복실레이트계 이온성 액체를포함하는 이산화탄소 흡수제 |
| US8790445B2 (en) * | 2009-06-02 | 2014-07-29 | Honeywell International Inc. | Approaches for removing CO2, SO2 and other gaseous contaminates from gas emissions |
| US9067953B2 (en) * | 2010-03-12 | 2015-06-30 | E I Du Pont De Nemours And Company | Systems for carbon dioxide and sulfur dioxide removal |
| US9017455B2 (en) | 2010-06-03 | 2015-04-28 | E I Du Pont De Nemours And Company | Sulfur compounds for carbon dioxide and sulfur dioxide removal |
| US20120247327A1 (en) * | 2010-09-27 | 2012-10-04 | Conocophillips Company | Hollow-fiber membrane contactors |
| EP2671860B2 (en) * | 2011-02-04 | 2024-05-29 | AGC Inc. | Method for purifying 2,3,3,3-tetrafluoropropene |
| US8779220B2 (en) | 2011-05-10 | 2014-07-15 | E I Du Pont De Nemours And Company | Capture of fluorinated vinyl monomers using ionic liquids |
| US8906135B1 (en) * | 2011-09-01 | 2014-12-09 | U.S. Department Of Energy | Method of purifying a gas stream using 1,2,3-triazolium ionic liquids |
| US20130267668A1 (en) * | 2012-04-09 | 2013-10-10 | E I Du Pont De Nemours And Company | Polymerization of fluorinated vinyl monomers in a biphasic reaction medium |
| US20140262736A1 (en) * | 2013-03-13 | 2014-09-18 | National Engineering Research Center of Drying Technology and Equipment | Method and device for recycling water vapor evaporated from coal drying with vacuum condensing process |
| US9238193B2 (en) | 2013-07-23 | 2016-01-19 | Chevron Phillips Chemical Company Lp | Separations with ionic liquid solvents |
| CN103752137B (zh) * | 2014-01-20 | 2016-04-27 | 中国科学院过程工程研究所 | 一种含醚基吡啶类离子液体捕集酸性气体的方法 |
| CN105617819A (zh) * | 2016-02-29 | 2016-06-01 | 北京化工大学 | 一种离子液体低温吸收合成气中二氧化碳的方法 |
| CN106316779B (zh) * | 2016-08-18 | 2019-02-05 | 山东东岳高分子材料有限公司 | 一种从四氟乙烯副产物中回收高纯度三氟乙烯的方法 |
| CN108993098B (zh) * | 2018-08-13 | 2021-04-13 | 中国地质大学（北京） | 一种高效捕集co2的低共熔溶剂体系及其制备方法与应用 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN109908707B (zh) * | 2019-04-16 | 2021-03-30 | 中国科学院过程工程研究所 | 一种高效吸收二氧化碳的功能离子型低共熔溶剂 |
| CN115569625B (zh) * | 2022-10-27 | 2023-07-18 | 云南云天化股份有限公司 | 一种烷基磷酸酯低聚物制备装置 |
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| US4388812A (en) | 1979-03-08 | 1983-06-21 | Clark Silas W | Variable valve for refrigeration system |
| US5049241A (en) * | 1990-03-27 | 1991-09-17 | E. I. Du Pont De Nemours And Company | Extractive distillation |
| US5345013A (en) * | 1993-06-10 | 1994-09-06 | E. I. Du Pont De Nemours And Company | Safe handling of tetrafluoroethylene |
| JP2001527553A (ja) * | 1997-05-02 | 2001-12-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 半透膜による不飽和フッ素化化合物からのｃｏ▲下２▼の分離 |
| CN1150144C (zh) | 1997-05-02 | 2004-05-19 | 纳幕尔杜邦公司 | 用半透膜从碳氟化合物中分离出二氧化碳 |
| US6155057A (en) | 1999-03-01 | 2000-12-05 | Arizona Board Of Regents | Refrigerant fluid crystallization control and prevention |
| US6339182B1 (en) | 2000-06-20 | 2002-01-15 | Chevron U.S.A. Inc. | Separation of olefins from paraffins using ionic liquid solutions |
| BR0208176B1 (pt) | 2001-03-20 | 2011-09-20 | processo para separar lìquidos ou gases condensáveis no estado condensado. | |
| US6579343B2 (en) | 2001-03-30 | 2003-06-17 | University Of Notre Dame Du Lac | Purification of gas with liquid ionic compounds |
| WO2003086605A2 (en) | 2002-04-05 | 2003-10-23 | University Of South Alabama | Functionalized ionic liquids, and methods of use thereof |
| DE10313207A1 (de) | 2003-03-25 | 2004-10-07 | Basf Ag | Reinigung oder Aufarbeitung von Ionischen Flüssigkeiten mit adsorptiven Trennverfahren |
| DE10316418A1 (de) | 2003-04-10 | 2004-10-21 | Basf Ag | Verwendung einer ionischen Flüssigkeit |
| DE10336556A1 (de) * | 2003-08-05 | 2005-03-10 | Basf Ag | Destillatives Verfahren zur Trennung von engsiedenden oder azeotropen Gemischen unter Verwendung von ionischen Flüssigkeiten |
| DE102004003958A1 (de) | 2004-01-26 | 2005-08-11 | Basf Ag | Herstellungsmethode für ionische Flüssigkeiten |
| US7955738B2 (en) | 2004-03-05 | 2011-06-07 | Honeywell International, Inc. | Polymer ionic electrolytes |
| JP4964119B2 (ja) | 2004-03-05 | 2012-06-27 | ハネウェル・インターナショナル・インコーポレーテッド | 複素環式アミン類のイオン液体 |
| DE102004024967A1 (de) | 2004-05-21 | 2005-12-08 | Basf Ag | Neue Absorptionsmedien für Absorptionswärmepumpen, Absorptionskältemaschinen und Wärmetransformatoren |
| US7313926B2 (en) | 2005-01-18 | 2008-01-01 | Rexorce Thermionics, Inc. | High efficiency absorption heat pump and methods of use |
| US8715521B2 (en) | 2005-02-04 | 2014-05-06 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquid as working fluid |
| RU2007146973A (ru) | 2005-05-18 | 2009-06-27 | Е.И.Дюпон де Немур энд Компани (US) | Гибридный парокомпрессионно-абсорбционный цикл |
| US7709635B2 (en) | 2005-05-19 | 2010-05-04 | University Of South Alabama | Boronium-ion-based ionic liquids and methods of use thereof |
| DE102005028451B4 (de) | 2005-06-17 | 2017-02-16 | Evonik Degussa Gmbh | Verfahren zum Transport von Wärme |
| AR058054A1 (es) | 2005-09-22 | 2008-01-23 | Du Pont | Utilizacion de liquidos ionicos para la separacion de hidrofluorocarburos |
| US8506839B2 (en) | 2005-12-14 | 2013-08-13 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquids and water as working fluids |
| JP5371747B2 (ja) | 2006-05-31 | 2013-12-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | イオン性液体を圧縮器潤滑剤として用いる蒸気圧縮 |
| US20080153697A1 (en) | 2006-12-22 | 2008-06-26 | E. I. Dupont De Nemours And Company | Mixtures of ammonia and ionic liquids |
| US8075777B2 (en) | 2007-05-16 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Process for the separation of diastereomers |
| US7964760B2 (en) | 2007-05-25 | 2011-06-21 | E.I. Du Pont De Nemours And Company | Process for the separation of fluorocarbons using ionic liquids |
| US8119818B2 (en) | 2008-12-04 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| US8138354B2 (en) | 2008-12-04 | 2012-03-20 | E. I. Du Pont De Nemours And Company | N-substituted pyrrolidonium ionic liquids |
-
2007
- 2007-11-08 US US12/446,769 patent/US8313558B2/en not_active Expired - Fee Related
- 2007-11-08 WO PCT/US2007/023496 patent/WO2008057574A1/en not_active Ceased
- 2007-11-08 EP EP07861811A patent/EP2086914A1/en not_active Withdrawn
- 2007-11-08 JP JP2009536292A patent/JP2010509333A/ja active Pending
- 2007-11-08 KR KR1020097011359A patent/KR20090077976A/ko not_active Withdrawn
- 2007-11-08 CN CN200780041710A patent/CN101616882A/zh active Pending
-
2012
- 2012-11-19 US US13/680,197 patent/US20130231448A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20130231448A1 (en) | 2013-09-05 |
| CN101616882A (zh) | 2009-12-30 |
| US8313558B2 (en) | 2012-11-20 |
| EP2086914A1 (en) | 2009-08-12 |
| WO2008057574A1 (en) | 2008-05-15 |
| US20100144994A1 (en) | 2010-06-10 |
| JP2010509333A (ja) | 2010-03-25 |
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