DE3034538A1 - -fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellung - Google Patents
-fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellungInfo
- Publication number
- DE3034538A1 DE3034538A1 DE19803034538 DE3034538A DE3034538A1 DE 3034538 A1 DE3034538 A1 DE 3034538A1 DE 19803034538 DE19803034538 DE 19803034538 DE 3034538 A DE3034538 A DE 3034538A DE 3034538 A1 DE3034538 A1 DE 3034538A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acid
- fluorosulfato
- electrolysis
- compounds
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000002253 acid Substances 0.000 title description 22
- 238000004519 manufacturing process Methods 0.000 title description 7
- 238000005868 electrolysis reaction Methods 0.000 claims description 33
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 23
- 239000003792 electrolyte Substances 0.000 claims description 16
- -1 platinum group metals Chemical class 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- 229910021397 glassy carbon Inorganic materials 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000010405 anode material Substances 0.000 claims description 3
- 239000010406 cathode material Substances 0.000 claims description 3
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 14
- 239000002585 base Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000001103 potassium chloride Substances 0.000 description 7
- 235000011164 potassium chloride Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000197 pyrolysis Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004812 organic fluorine compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 2
- CRLSHTZUJTXOEL-UHFFFAOYSA-N 2,2-difluoroacetyl fluoride Chemical compound FC(F)C(F)=O CRLSHTZUJTXOEL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- VGFKXVSMDOKOJZ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)F VGFKXVSMDOKOJZ-UHFFFAOYSA-N 0.000 description 1
- LOUICXNAWQPGSU-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxirane Chemical class FC1(F)OC1(F)F LOUICXNAWQPGSU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZKKNDJYEQNIUQM-UHFFFAOYSA-N 2-fluorosulfonylacetic acid Chemical class OC(=O)CS(F)(=O)=O ZKKNDJYEQNIUQM-UHFFFAOYSA-N 0.000 description 1
- CKEXGJMBTYXHMT-UHFFFAOYSA-N 2-propoxypropanoic acid hydrofluoride Chemical compound F.CCCOC(C)C(O)=O CKEXGJMBTYXHMT-UHFFFAOYSA-N 0.000 description 1
- PYIMQPQWCZJYNU-UHFFFAOYSA-N 2-propoxypropanoyl fluoride Chemical compound CCCOC(C)C(F)=O PYIMQPQWCZJYNU-UHFFFAOYSA-N 0.000 description 1
- NYECZJPHHACZAQ-UHFFFAOYSA-N C(CCC)C(=O)F.[F] Chemical compound C(CCC)C(=O)F.[F] NYECZJPHHACZAQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-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
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001260 Pt alloy Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DCWRLHBFXAWEKA-UHFFFAOYSA-N [F].OS(O)(=O)=O Chemical compound [F].OS(O)(=O)=O DCWRLHBFXAWEKA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- CTHHBLWYPDKYFP-UHFFFAOYSA-N ctk3i9005 Chemical compound FS(=O)(=O)OOS(F)(=O)=O CTHHBLWYPDKYFP-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- HKMFZXSQIPJRHN-UHFFFAOYSA-N fluorosulfonylformyl fluoride Chemical class FC(=O)S(F)(=O)=O HKMFZXSQIPJRHN-UHFFFAOYSA-N 0.000 description 1
- KRRYGFCJUCTWMH-UHFFFAOYSA-N fluorosulfonyloxyethane Chemical compound CCOS(F)(=O)=O KRRYGFCJUCTWMH-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- KSGGIONYAUAWPY-UHFFFAOYSA-N pentanoyl fluoride Chemical compound CCCCC(F)=O KSGGIONYAUAWPY-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- VXJAYNWISQFORV-UHFFFAOYSA-M potassium fluorosulfate Chemical compound [K+].[O-]S(F)(=O)=O VXJAYNWISQFORV-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- XCXLEIPEAAEYTF-UHFFFAOYSA-M sodium fluorosulfate Chemical compound [Na+].[O-]S(F)(=O)=O XCXLEIPEAAEYTF-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803034538 DE3034538A1 (de) | 1980-09-12 | 1980-09-12 | -fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellung |
| DE8181107002T DE3161036D1 (en) | 1980-09-12 | 1981-09-07 | Omega-fluorosulphato-perfluorocarboxylic-acid derivatives and process for their production |
| EP81107002A EP0047950B1 (de) | 1980-09-12 | 1981-09-07 | Omega-Fluorsulfato-perfluorcarbonsäurederivate und Verfahren zu deren Herstellung |
| CA000385689A CA1163646A (en) | 1980-09-12 | 1981-09-11 | .omega.-FLUOROSULFATO-PERFLUOROCARBOXYLIC ACID DERIVATIVES AND PROCESSES FOR THEIR PREPARATION |
| JP56142550A JPS5785367A (en) | 1980-09-12 | 1981-09-11 | Omega-fluorosulfate-perfluorocarboxylic acid derivative and manufacture |
| US06/482,570 US4460512A (en) | 1980-09-12 | 1983-04-06 | ω-Fluorosulfato-perfluorocarboxylic acid derivatives and processes for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803034538 DE3034538A1 (de) | 1980-09-12 | 1980-09-12 | -fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3034538A1 true DE3034538A1 (de) | 1982-05-06 |
Family
ID=6111836
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803034538 Withdrawn DE3034538A1 (de) | 1980-09-12 | 1980-09-12 | -fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellung |
| DE8181107002T Expired DE3161036D1 (en) | 1980-09-12 | 1981-09-07 | Omega-fluorosulphato-perfluorocarboxylic-acid derivatives and process for their production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181107002T Expired DE3161036D1 (en) | 1980-09-12 | 1981-09-07 | Omega-fluorosulphato-perfluorocarboxylic-acid derivatives and process for their production |
Country Status (5)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4647350A (en) * | 1985-10-15 | 1987-03-03 | Monsanto Company | Electrolytic preparation of perfluoroalkanoic acids, perfluoroalkanols and perfluoroalkyl esters |
| FR2661620B1 (fr) * | 1990-05-03 | 1992-07-17 | Norsolor Sa | Procede de refroidissement associe a un procede utilisant de l'acide fluorhydrique anhydre. |
| WO1998043952A1 (fr) * | 1997-03-31 | 1998-10-08 | Daikin Industries, Ltd. | Procede de production de derives d'acide ethersulfonique de perfluorovinyle et copolymere correspondant |
| WO2008150487A2 (en) * | 2007-05-31 | 2008-12-11 | Texas Tech University | Synthesis of half esters |
| RU2484081C2 (ru) * | 2011-06-16 | 2013-06-10 | Федеральное государственное унитарное предприятие "Ордена Ленина и ордена Трудового Красного Знамени научно-исследовательский институт синтетического каучука имени академика С.В. Лебедева" | Способ получения фторангидрида дифтор(фторсульфат)уксусной кислоты |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5259111A (en) * | 1975-11-11 | 1977-05-16 | Asahi Glass Co Ltd | Process for preparation of acid-fluoride-containing fluoride having an ester group |
-
1980
- 1980-09-12 DE DE19803034538 patent/DE3034538A1/de not_active Withdrawn
-
1981
- 1981-09-07 EP EP81107002A patent/EP0047950B1/de not_active Expired
- 1981-09-07 DE DE8181107002T patent/DE3161036D1/de not_active Expired
- 1981-09-11 JP JP56142550A patent/JPS5785367A/ja active Granted
- 1981-09-11 CA CA000385689A patent/CA1163646A/en not_active Expired
-
1983
- 1983-04-06 US US06/482,570 patent/US4460512A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4460512A (en) | 1984-07-17 |
| JPS5785367A (en) | 1982-05-28 |
| EP0047950B1 (de) | 1983-09-28 |
| EP0047950A1 (de) | 1982-03-24 |
| JPH0363545B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-01 |
| DE3161036D1 (en) | 1983-11-03 |
| CA1163646A (en) | 1984-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69105275T2 (de) | Verfahren zur herstellung von tertiären perfluoraminen. | |
| DE69404312T2 (de) | Verfahren zur herstellung von perfluoralkylsulfonylfluoriden | |
| DE2849065A1 (de) | Verwendung von quartaeren ammoniumsalzen als leitsalze | |
| DE60014673T2 (de) | Verfahren zum herstellen eines vic-dichlorsäurefluorids | |
| DE3034538A1 (de) | -fluorsulfato-perfluorcarbonsaeurederivate und verfahren zu deren herstellung | |
| DE69501716T2 (de) | Verfahren zur Herstellung von Halogendifluoressigsäurealkylester | |
| US4603017A (en) | Fluorosulfonate containing polyfluorocarbonyl compounds | |
| EP0166293A2 (de) | Verfahren zur Herstellung halogenierter aliphatischer Carbonsäurefluoride | |
| EP0029995B1 (de) | Verfahren zur Herstellung von 4-tert. Butylbenzaldehyd | |
| EP0047945B1 (de) | Verfahren zur Herstellung von Perfluorcarbonylsulfonsäurefluoriden sowie die dabei als Zwischenprodukte auftretenden Fluorsulfatoperfluoralkansulfonsäurehalogenide | |
| EP0070485B1 (de) | Verfahren zur Herstellung von omega-Fluorsulfato-perfluoralkansäurederivaten | |
| DE2708677C3 (de) | Verfahren zur Herstellung von Alkoxycarbonylperfluoralkylperfluorvinyläthern | |
| EP0207445B1 (de) | Verfahren zur Herstellung von Acyloxybenolsulfonsäuren und deren Salzen | |
| EP0243607B1 (de) | Verfahren zur Herstellung von Biscarbamaten | |
| DE69512042T2 (de) | Verfahren zur herstellung verzweigter perfluoroverbindungen | |
| DE3034499A1 (de) | (omega)-fluorsulfato-perfluor-(2-methylalkan-3-one) sowie verfahren zur herstellung von perfluorisopropylketocarbonsaeurefluoriden ueber die erstgenannten verbindungen | |
| EP0071064B1 (de) | Verfahren zur Herstellung von alpha, omega-Bis-fluorsulfato-perfluoralkanen | |
| EP0047946B1 (de) | Verfahren zur Herstellung von Monohydroperfluoralkansulfonsäurehalogeniden sowie einige spezielle Vertreter dieser Verbindungsklasse | |
| EP0071808B1 (de) | Verfahren zur Herstellung von alpha-ständig sulfonierten, alpha, beta-ungesättigten Carbonsäurealkylestern sowie danach erhältliche Verbindungen | |
| EP0023293A1 (de) | Verfahren zur Herstellung von 2.3-Perfluor-bzw.trifluormethyl-1,4-dioxanen | |
| EP0164705A2 (de) | Verfahren zur Herstellung von Phthalaldehydacetalen | |
| EP0179377B1 (de) | Verfahren zur Herstellung von 1-Alkoxyisochromanen und neue 1-Alkoxy-alkylisochromane | |
| DE2048772A1 (de) | Cyclische Perfluorolefme und Ver fahren zu ihrer Herstellung | |
| EP0047949B1 (de) | Verfahren zur Herstellung perfluorierter Carbonsäurefluoride | |
| EP0261501A2 (de) | Halogenhaltige Ether |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |