JP2017510528A - フッ素含有および硫黄含有化合物ならびにその塩を水性媒体中で製造する方法 - Google Patents
フッ素含有および硫黄含有化合物ならびにその塩を水性媒体中で製造する方法 Download PDFInfo
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- JP2017510528A JP2017510528A JP2016536651A JP2016536651A JP2017510528A JP 2017510528 A JP2017510528 A JP 2017510528A JP 2016536651 A JP2016536651 A JP 2016536651A JP 2016536651 A JP2016536651 A JP 2016536651A JP 2017510528 A JP2017510528 A JP 2017510528A
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- sulfur
- fluorine
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- salt
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 150000003839 salts Chemical class 0.000 title claims abstract description 69
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 53
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 51
- 239000011737 fluorine Substances 0.000 title claims abstract description 51
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 45
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 239000011593 sulfur Substances 0.000 title claims abstract description 43
- 239000012736 aqueous medium Substances 0.000 title description 4
- -1 halogeno sulfoxide compound Chemical class 0.000 claims abstract description 46
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 239000002216 antistatic agent Substances 0.000 claims abstract description 5
- 239000003792 electrolyte Substances 0.000 claims abstract description 4
- 239000004094 surface-active agent Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 18
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 235000003270 potassium fluoride Nutrition 0.000 claims description 8
- 239000011698 potassium fluoride Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 238000005341 cation exchange Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 4
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 150000004010 onium ions Chemical class 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 7
- 238000003682 fluorination reaction Methods 0.000 description 19
- 150000001768 cations Chemical group 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- 239000002609 medium Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- PVMUVDSEICYOMA-UHFFFAOYSA-N n-chlorosulfonylsulfamoyl chloride Chemical compound ClS(=O)(=O)NS(Cl)(=O)=O PVMUVDSEICYOMA-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- MHEBVKPOSBNNAC-UHFFFAOYSA-N potassium;bis(fluorosulfonyl)azanide Chemical compound [K+].FS(=O)(=O)[N-]S(F)(=O)=O MHEBVKPOSBNNAC-UHFFFAOYSA-N 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LTPGVRJWDQWUGN-UHFFFAOYSA-N 1h-imidazol-1-ium;fluoride Chemical compound F.C1=CNC=N1 LTPGVRJWDQWUGN-UHFFFAOYSA-N 0.000 description 4
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- DVERFJXHCKPMNM-UHFFFAOYSA-N fluorophosphane Chemical compound PF DVERFJXHCKPMNM-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004693 imidazolium salts Chemical class 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- HJBZFPLBRXFZNE-UHFFFAOYSA-M tetrabutylphosphanium fluoride hydrofluoride Chemical compound F.[F-].CCCC[P+](CCCC)(CCCC)CCCC HJBZFPLBRXFZNE-UHFFFAOYSA-M 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- MKWANFMVPUWHFR-UHFFFAOYSA-M 1-butylpyridin-1-ium;fluoride Chemical compound [F-].CCCC[N+]1=CC=CC=C1 MKWANFMVPUWHFR-UHFFFAOYSA-M 0.000 description 1
- SHCXVPFGWISLBK-UHFFFAOYSA-M 1-decyl-3-methylimidazol-3-ium;fluoride Chemical compound [F-].CCCCCCCCCCN1C=C[N+](C)=C1 SHCXVPFGWISLBK-UHFFFAOYSA-M 0.000 description 1
- OPVBQRUBBJUSSN-UHFFFAOYSA-M 1-ethyl-2,3-dimethylimidazol-3-ium;fluoride Chemical compound [F-].CCN1C=C[N+](C)=C1C OPVBQRUBBJUSSN-UHFFFAOYSA-M 0.000 description 1
- XQTFNBQBERLQQH-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;fluoride Chemical compound [F-].CC[N+]=1C=CN(C)C=1 XQTFNBQBERLQQH-UHFFFAOYSA-M 0.000 description 1
- UGDYSZBHTRVGOR-UHFFFAOYSA-M 1-ethylpyridin-1-ium;fluoride Chemical compound [F-].CC[N+]1=CC=CC=C1 UGDYSZBHTRVGOR-UHFFFAOYSA-M 0.000 description 1
- GFLLWAWCKDGPRN-UHFFFAOYSA-M 1-hexadecyl-3-methylimidazol-3-ium;fluoride Chemical compound [F-].CCCCCCCCCCCCCCCC[N+]=1C=CN(C)C=1 GFLLWAWCKDGPRN-UHFFFAOYSA-M 0.000 description 1
- RDEQYSBMTXQVRX-UHFFFAOYSA-M 1-hexyl-2,3-dimethylimidazol-3-ium;fluoride Chemical compound [F-].CCCCCC[N+]=1C=CN(C)C=1C RDEQYSBMTXQVRX-UHFFFAOYSA-M 0.000 description 1
- JJZVFQPXLKWBAO-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;fluoride Chemical compound [F-].CCCCCCN1C=C[N+](C)=C1 JJZVFQPXLKWBAO-UHFFFAOYSA-M 0.000 description 1
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 1
- DASYRTXUTZVMTO-UHFFFAOYSA-M 1-hexylpyridin-1-ium;fluoride Chemical compound [F-].CCCCCC[N+]1=CC=CC=C1 DASYRTXUTZVMTO-UHFFFAOYSA-M 0.000 description 1
- KAHZLELVNYWKRI-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;fluoride Chemical compound [F-].CCCCCCCCCCCCCCCCCC[N+]=1C=CN(C)C=1 KAHZLELVNYWKRI-UHFFFAOYSA-M 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910000599 Cr alloy Inorganic materials 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910000914 Mn alloy Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 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
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WSLQHGMJTGELSF-UHFFFAOYSA-L dipotassium;difluoride Chemical compound [F-].[F-].[K+].[K+] WSLQHGMJTGELSF-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZPQINZAVTLGLIW-UHFFFAOYSA-N guanidine;hydrofluoride Chemical compound F.NC(N)=N ZPQINZAVTLGLIW-UHFFFAOYSA-N 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 229910001119 inconels 625 Inorganic materials 0.000 description 1
- 229910000816 inconels 718 Inorganic materials 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 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
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- GVXHSMAJJFVLGD-UHFFFAOYSA-N methyl 5-chloro-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C1=C(Cl)N=C2C(C(=O)OC)=CSC2=C1C(F)(F)F GVXHSMAJJFVLGD-UHFFFAOYSA-N 0.000 description 1
- NVVLMKLCGJCBMM-UHFFFAOYSA-M methyl(trioctyl)azanium;fluoride Chemical compound [F-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC NVVLMKLCGJCBMM-UHFFFAOYSA-M 0.000 description 1
- DNNRJKWCZPNAMV-UHFFFAOYSA-M methyl-bis(2-methylpropyl)-octylphosphanium;fluoride Chemical compound [F-].CCCCCCCC[P+](C)(CC(C)C)CC(C)C DNNRJKWCZPNAMV-UHFFFAOYSA-M 0.000 description 1
- JBPOCXRUEVZQNL-UHFFFAOYSA-M methyl-tris(2-methylpropyl)phosphanium;fluoride Chemical compound [F-].CC(C)C[P+](C)(CC(C)C)CC(C)C JBPOCXRUEVZQNL-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XJMFORMFPOEHCH-UHFFFAOYSA-M tributyl(methyl)azanium;fluoride Chemical compound [F-].CCCC[N+](C)(CCCC)CCCC XJMFORMFPOEHCH-UHFFFAOYSA-M 0.000 description 1
- IYRRNWPLLPEWEF-UHFFFAOYSA-M tributyl(methyl)phosphanium;fluoride Chemical compound [F-].CCCC[P+](C)(CCCC)CCCC IYRRNWPLLPEWEF-UHFFFAOYSA-M 0.000 description 1
- ZTMFERDEXVFCET-UHFFFAOYSA-M trimethyl(phenyl)phosphanium;fluoride Chemical compound [F-].C[P+](C)(C)C1=CC=CC=C1 ZTMFERDEXVFCET-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
- C01B21/0935—Imidodisulfonic acid; Nitrilotrisulfonic acid; Salts thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
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- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract
Description
X−SO−R’+MF→F−SO−R+MXまたはX−SO2−R’+MF→F−SO2−R+MX
− −NHSO2F基、
− −NHSOF基、
− −NM’SO2F基、
− −NM’SOF基、
− −NR1R10基、
− −NHSO2R1基、
− −NHSOR1基、および
− −NHCOR1基
からなる群から選択されてもよく、
ここで、M’は、アルカリもしくはアルカリ土類金属またはオニウムイオンであり、R1およびR10は、同一であっても異なってもよく、水素原子、1〜15個の炭素原子を有する飽和または不飽和の直鎖、分岐または環状炭化水素系鎖、1〜15個の炭素原子を有するフルオロアルキル、パーフルオロアルキルまたはフルオロアルケニル鎖、および芳香族基からなる群から選択される。
[式中、
−Wは、NまたはPを表し、
−R2、R3、R4およびR5は、同一であっても異なってもよく、
. 1〜16個の炭素原子を有し、1個以上のヘテロ原子またはフェニル、ヒドロキシル、ハロゲン、ニトロ、アルコキシもしくはアルコキシカルボニル基(アルコキシ基は、1〜4個の炭素原子を有する)で任意選択で置換された、直鎖または分岐アルキル基;
. 2〜12個の炭素原子を有する、直鎖または分岐アルケニル基;
. 1個以上のヘテロ原子、または1〜4個の炭素原子を有するアルキル基、アルコキシ基、アルコキシカルボニル基(アルコキシ基は、1〜4個の炭素原子を有する)、もしくはハロゲン基で任意選択で置換された、6〜10個の炭素原子を有するアリール基
を表す]
に対応する塩である。
(式中、
R6基は、1〜20個の炭素原子を有するアルキル基を表わし、
R7基は、水素原子、または1〜4個の炭素原子を有するアルキル基を表わし、
R8基は、1〜4個の炭素原子を有するアルキル基を表わし、
R9基は、1〜6個の炭素原子を有するアルキル基を表わす)
に対応する。
フッ化カリウムの水性溶液を、ガラス製反応器中で反応温度にする。HCSIと表示される、ビス(クロロスルホニル)イミド(10グラム、47ミリモル)を、30秒の経過をかけて添加し、攪拌を反応温度で2時間維持する。カリウムビス(フルオロスルホニル)イミド(KFSI)の収率を計算するために、19FNMRにより実施される分析用に反応媒体を水に希釈する。
フッ化亜鉛(5.1g;49ミリモル)を、90グラムのバレロニトリルに溶解させる。次いで、ビス(クロロスルホニル)イミドを添加し、攪拌を周囲温度で24時間維持する。
フッ化カリウム(27g、0.46モル)の水性溶液(23gの水)を、ガラス製反応器中で100℃の温度にする。KCSIと表示される、カリウムビス(クロロスルホニル)イミド(11.8グラム、46ミリモル)を30秒の経過をかけて添加し、攪拌をこの反応温度で2時間維持する。反応媒体を水に希釈し、周囲温度に戻す。19FNMR分析は、得られたカリウムビス(フルオロスルホニル)イミド(KFSI)の収率が69%であることを示す。
N,N,N−トリ−n−オクチル−N−メチルアンモニウムビス(クロロスルホニル)イミド(27g;46ミリモル)を、120℃の温度にした、フッ化カリウム(27g、0.46モル)の水(23g)溶液に添加する。この媒体を2時間撹拌したままにする。周囲温度に戻した後、19F NMR分析は、N,N,N−トリ−n−オクチル−N−メチルアンモニウムビス(フルオロスルホニル)イミドの収率が49%であることを示す。
カリウムビス(クロロスルホニル)イミド(10g;46ミリモル)を、120℃の温度にした、フッ化カリウム(27g、0.46モル)の水(23g)溶液に添加する。この媒体を30分間攪拌したままにする。周囲温度に戻した後、19FNMR分析は、カリウムビス(フルオロスルホニル)イミドの収率が76%であることを示す。
Claims (14)
- 式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法であって、フッ化物アニオンを与える少なくとも1種の塩の、少なくとも1種の、式X−SO−R’(I0)のハロスルホキシド化合物、それぞれ式X−SO2−R’(II0)のハロスルホニル化合物の、水の存在下での反応を含み、Xは、フッ素以外のハロゲン原子であり、RおよびR’は、それぞれ、硫黄原子に共有結合を介して結合した基であり、前記結合は前記硫黄原子を窒素原子に結合する、方法。
- 前記R基が、
− −NHSO2F基、
− −NHSOF基、
− −NM’SO2F基、
− −NM’SOF基、
− −NR1R10基、
− −NHSO2R1基、
− −NHSOR1基、
− −NHCOR1基;
(ここで、M’は、アルカリもしくはアルカリ土類金属またはオニウムイオンであり、R1およびR10は、同一であっても異なってもよく、水素原子、1〜15個の炭素原子を有する飽和もしくは不飽和の直鎖、分岐もしくは環状炭化水素系鎖、1〜15個の炭素原子を有するフルオロアルキル、パーフルオロアルキルもしくはフルオロアルケニル鎖、および芳香族基からなる群から選択される)
からなる群から選択される、請求項1に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。 - 式(II0)X−SO2−NH−SO2−Xのハロスルホニル化合物が、化合物F−SO2−NH−SO2−F(II)を調製するために使用される、請求項1または2に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 式(II0)X−SO2−NH−SO2−CF3のハロスルホニル化合物が、化合物F−SO2−NH−SO2−CF3(II)を調製するために使用される、請求項1または2に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記フッ化物アニオンを与える塩が、金属フッ化物、フッ化オニウムおよびそれらの混合物から選択される、請求項1〜4のいずれか一項に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記フッ化物アニオンを与える塩が、フッ化カリウムである、請求項4に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記式(I0)のハロスルホキシド化合物または前記式(II0)のハロスルホニル化合物が、酸形態である、請求項1〜6のいずれか一項に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記式(I0)のハロスルホキシド化合物または前記式(II0)のハロスルホニル化合物が、塩化形態、好ましくはアルカリ金属塩、アルカリ土類金属塩またはオニウム塩の形態である、請求項1〜6のいずれか一項に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物が、塩化形態、好ましくはカリウム塩の形態で得られる、請求項1〜8のいずれか一項に記載の、式F−SO−R(I)または式F−SO2−R(II)のフッ素含有および硫黄含有化合物を調製する方法。
- 前記式(I)または式(II)のフッ素含有および硫黄含有化合物の少なくとも1種の塩を調製する方法であって、請求項1〜9に定義されたとおりの方法による塩化形態の前記式(I)または式(II)の化合物の調製と、続いて、液/液抽出の工程と、次いで、酸性化、得られた酸を回収、および中和の工程を含む連続の実施とを含む方法。
- 前記式(I)または式(II)のフッ素含有および硫黄含有化合物の少なくとも1種の塩を調製する方法であって、請求項1〜9に定義されたとおりの方法による塩化形態の前記式(I)または式(II)の化合物の調製と、続いて、液/液抽出の工程と、次いで、カチオン交換反応の実施とを含む方法。
- 前記式(I)または式(II)のフッ素含有および硫黄含有化合物の前記塩が、アルカリ金属の塩、アルカリ土類金属の塩、遷移金属の塩、またはランタニドから選択される塩である、請求項10または11に記載の、前記式(I)または式(II)のフッ素含有および硫黄含有化合物の少なくとも1種の塩を調製する方法。
- リチウムビス(フルオロスルホニル)イミドが調製される、請求項10〜12のいずれか一項に記載の、前記式(I)または式(II)のフッ素含有および硫黄含有化合物の少なくとも1種の塩を調製する方法。
- 電解質塩、帯電防止剤前駆体、または界面活性剤前駆体としての、請求項1〜9のいずれか一項に定義されたとおりの方法によって調製された前記式F−SO−R(I)もしくは式F−SO2−R(II)のフッ素含有および硫黄含有化合物、または請求項10〜13のいずれか一項に記載されたとおりに調製された前記式F−SO−R(I)もしくは式F−SO2−R(II)のフッ素含有および硫黄含有化合物の塩の使用。
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EP3077333A1 (fr) | 2016-10-12 |
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TWI654135B (zh) | 2019-03-21 |
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US20160304347A1 (en) | 2016-10-20 |
US11613465B2 (en) | 2023-03-28 |
KR102351641B1 (ko) | 2022-01-17 |
FR3014438B1 (fr) | 2017-10-06 |
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CA2931997C (fr) | 2022-03-01 |
CA2931997A1 (fr) | 2015-06-11 |
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