DE60311795T2 - Katalytisches verfahren zur herstellung von perfluorethansulfonylfluorid und/oder perfluordiethylsulfon - Google Patents
Katalytisches verfahren zur herstellung von perfluorethansulfonylfluorid und/oder perfluordiethylsulfon Download PDFInfo
- Publication number
- DE60311795T2 DE60311795T2 DE60311795T DE60311795T DE60311795T2 DE 60311795 T2 DE60311795 T2 DE 60311795T2 DE 60311795 T DE60311795 T DE 60311795T DE 60311795 T DE60311795 T DE 60311795T DE 60311795 T2 DE60311795 T2 DE 60311795T2
- Authority
- DE
- Germany
- Prior art keywords
- catalytic process
- fluoride
- solvent
- reactor
- process according
- 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 - Fee Related
Links
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 44
- 230000008569 process Effects 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title claims description 6
- JUZCVRZJGRPWJZ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)S(F)(=O)=O JUZCVRZJGRPWJZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- UIUJTRZXBNWJDL-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,1,2,2,2-pentafluoroethylsulfonyl)ethane Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)C(F)(F)C(F)(F)F UIUJTRZXBNWJDL-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910001512 metal fluoride Inorganic materials 0.000 claims abstract description 28
- 150000003983 crown ethers Chemical class 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims description 65
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 63
- 239000002904 solvent Substances 0.000 claims description 27
- 239000006184 cosolvent Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 8
- 239000005935 Sulfuryl fluoride Substances 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 2
- UNTITLLXXOKDTB-UHFFFAOYSA-N dibenzo-24-crown-8 Chemical compound O1CCOCCOCCOC2=CC=CC=C2OCCOCCOCCOC2=CC=CC=C21 UNTITLLXXOKDTB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 239000010702 perfluoropolyether Substances 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 75
- 239000000047 product Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000003426 co-catalyst Substances 0.000 description 10
- 239000011698 potassium fluoride Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006555 catalytic reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- -1 methide anions Chemical class 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- YYBMGVRXEFBHTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonyl fluoride Chemical compound FC(F)(F)C(F)(C(F)(F)F)S(F)(=O)=O YYBMGVRXEFBHTL-UHFFFAOYSA-N 0.000 description 2
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 2
- 244000089742 Citrus aurantifolia Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940087305 limonene Drugs 0.000 description 2
- 235000001510 limonene Nutrition 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- PQMAKJUXOOVROI-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(trifluoromethyl)morpholine Chemical compound FC(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F PQMAKJUXOOVROI-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- IWNGKGJOOLMUMM-UHFFFAOYSA-N N,1,1,2,2,2-hexafluoroethanesulfonamide Chemical compound FNS(=O)(=O)C(F)(F)C(F)(F)F IWNGKGJOOLMUMM-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 206010043458 Thirst Diseases 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007960 acetonitrile Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- KBDSLGBFQAGHBE-MSGMIQHVSA-N limonin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@@H]2[C@]34COC(=O)C[C@@H]3OC2(C)C)C=COC=1 KBDSLGBFQAGHBE-MSGMIQHVSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/137,165 US6580006B1 (en) | 2002-05-02 | 2002-05-02 | Catalytic process for preparing perfluoroethanesulfonyl fluoride and/or perfluorodiethylsulfone |
| US137165 | 2002-05-02 | ||
| PCT/US2003/007886 WO2003095422A2 (en) | 2002-05-02 | 2003-03-13 | Catalytic process for preparing perfluoroethanesulfonyl fluoride and/or perfluorodiethylsulfone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60311795D1 DE60311795D1 (de) | 2007-03-29 |
| DE60311795T2 true DE60311795T2 (de) | 2007-12-06 |
Family
ID=22476089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60311795T Expired - Fee Related DE60311795T2 (de) | 2002-05-02 | 2003-03-13 | Katalytisches verfahren zur herstellung von perfluorethansulfonylfluorid und/oder perfluordiethylsulfon |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6580006B1 (enExample) |
| EP (1) | EP1501792B1 (enExample) |
| JP (1) | JP4417833B2 (enExample) |
| CN (1) | CN1290827C (enExample) |
| AT (1) | ATE353872T1 (enExample) |
| AU (1) | AU2003220279A1 (enExample) |
| DE (1) | DE60311795T2 (enExample) |
| DK (1) | DK1501792T3 (enExample) |
| WO (1) | WO2003095422A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004316117A1 (en) * | 2003-08-11 | 2005-09-01 | E.I. Dupont De Nemours And Company | Methods using fluorosulfones for extinguishing and preventing fire, |
| CA2660449A1 (en) * | 2006-08-11 | 2008-09-04 | California Institute Of Technology | Dissociating agents, formulations and methods providing enhanced solubility of fluorides |
| US8658309B2 (en) * | 2006-08-11 | 2014-02-25 | California Institute Of Technology | Dissociating agents, formulations and methods providing enhanced solubility of fluorides |
| WO2009000748A1 (en) * | 2007-06-27 | 2008-12-31 | Solvay Fluor Gmbh | Preparation of compounds with a perfluoroalkylsulfonyl group |
| WO2010053962A1 (en) * | 2008-11-04 | 2010-05-14 | California Institute Of Technology | Hybrid electrochemical generator with a soluble anode |
| CN112004651A (zh) | 2018-04-26 | 2020-11-27 | 3M创新有限公司 | 氟砜 |
| CN112041114B (zh) | 2018-05-01 | 2022-12-06 | 3M创新有限公司 | 可适形的磨料制品 |
| CN116472635A (zh) | 2020-11-03 | 2023-07-21 | 3M创新有限公司 | 电子部件浸渍冷却用流体 |
| CN114917855B (zh) * | 2022-05-25 | 2024-03-12 | 金华永和氟化工有限公司 | 一种连续制备全氟烷基乙烯基醚的反应系统及方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519983A (en) | 1948-11-29 | 1950-08-22 | Minnesota Mining & Mfg | Electrochemical process of making fluorine-containing carbon compounds |
| US3542864A (en) | 1966-07-13 | 1970-11-24 | Minnesota Mining & Mfg | Process for the production of perfluoroalkanesulfonyl fluorides |
| GB1189561A (en) | 1967-02-21 | 1970-04-29 | E I Du Pont De Neomours And Co | Process for Preparing Fluorinated Organic Sulfonyl Derivatives and Sulfones |
| US3920738A (en) * | 1974-03-20 | 1975-11-18 | Pennwalt Corp | Preparation of methane sulfonyl fluoride |
| US4269790A (en) * | 1978-03-23 | 1981-05-26 | Chevron Research Company | Hydrocarbylethyl sulfonyl fluoride |
| US5206440A (en) * | 1992-01-21 | 1993-04-27 | E. I. Du Pont De Nemours And Company | Oxidation of fluorine containing sulfides to sulfones |
| US5318674A (en) * | 1993-06-30 | 1994-06-07 | Minnesota Mining And Manufacturing Company | Process for preparing perfluoroalkanesulfonyl fluorides |
| DE69625336T2 (de) | 1995-02-06 | 2003-09-11 | E.I. Du Pont De Nemours And Co., Wilmington | Amorphe tetrafluoroethylen-hexafluoropropylencopolymere |
| US5780682A (en) | 1995-04-04 | 1998-07-14 | Haldor Topsoe A/S | Process for the synthesis of fluorinated alkyl sulphonyl halides |
| US6372829B1 (en) | 1999-10-06 | 2002-04-16 | 3M Innovative Properties Company | Antistatic composition |
-
2002
- 2002-05-02 US US10/137,165 patent/US6580006B1/en not_active Expired - Lifetime
-
2003
- 2003-03-13 DE DE60311795T patent/DE60311795T2/de not_active Expired - Fee Related
- 2003-03-13 AT AT03716577T patent/ATE353872T1/de not_active IP Right Cessation
- 2003-03-13 JP JP2004503443A patent/JP4417833B2/ja not_active Expired - Fee Related
- 2003-03-13 WO PCT/US2003/007886 patent/WO2003095422A2/en not_active Ceased
- 2003-03-13 EP EP03716577A patent/EP1501792B1/en not_active Expired - Lifetime
- 2003-03-13 AU AU2003220279A patent/AU2003220279A1/en not_active Abandoned
- 2003-03-13 DK DK03716577T patent/DK1501792T3/da active
- 2003-03-13 CN CNB03809990XA patent/CN1290827C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005524718A (ja) | 2005-08-18 |
| EP1501792B1 (en) | 2007-02-14 |
| WO2003095422A3 (en) | 2004-04-08 |
| CN1290827C (zh) | 2006-12-20 |
| ATE353872T1 (de) | 2007-03-15 |
| CN1649835A (zh) | 2005-08-03 |
| DE60311795D1 (de) | 2007-03-29 |
| DK1501792T3 (da) | 2007-06-04 |
| JP4417833B2 (ja) | 2010-02-17 |
| AU2003220279A1 (en) | 2003-11-11 |
| EP1501792A2 (en) | 2005-02-02 |
| WO2003095422A2 (en) | 2003-11-20 |
| US6580006B1 (en) | 2003-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5969192A (en) | Process for preparing hydrogen-terminated polyoxyperfluoroalkanes | |
| EP1135356B1 (de) | Verfahren zur herstellung von säurefluoriden aus säurechloriden | |
| DE60311795T2 (de) | Katalytisches verfahren zur herstellung von perfluorethansulfonylfluorid und/oder perfluordiethylsulfon | |
| EP0634383B1 (de) | Verfahren zur Addition von HF an halogenierte Alkene | |
| WO2011036281A1 (en) | Continuous preparation of carbonates | |
| EP0980345B1 (fr) | Procede de preparation de 1,1,1,3,3-pentachlorobutane | |
| DE3032471C2 (enExample) | ||
| DE60014673T2 (de) | Verfahren zum herstellen eines vic-dichlorsäurefluorids | |
| DE69207818T2 (de) | Verfahren zur Herstellung von einer Fluorverbindung | |
| DE60315761T2 (de) | Verfahren zur Herstellung von Acylfluoriden | |
| Sheppard | N-Fluoroalkylamines. I. Difluoroazomethines | |
| EP0164954B1 (en) | Process for the preparation of 1-chloro-1,2,2,2-tetrafluorethane | |
| CA1145360A (en) | Preparation of cyanoacetamide and 2,2 -dibromo-3-nitrilopropionamide compositions | |
| DE69501716T2 (de) | Verfahren zur Herstellung von Halogendifluoressigsäurealkylester | |
| DE69828777T2 (de) | Verfahren zur herstellung von buttersäureester-derivaten | |
| DE69702961T2 (de) | Herstellung von 1,1-difluorethan | |
| CA1041542A (en) | Process for the production of n, n-diallyldichloroacetamide | |
| JP6463364B2 (ja) | スルフィン化によるオキシスルフィドおよびフッ素化誘導体の製造方法 | |
| EP0070485B1 (de) | Verfahren zur Herstellung von omega-Fluorsulfato-perfluoralkansäurederivaten | |
| JP2972163B2 (ja) | アルキルハロジフルオロアセテートの製造方法 | |
| DE3880490T2 (de) | Perfluoramino-oxaziridine und Verfahren zu ihrer Herstellung. | |
| DE69635059T2 (de) | Herstellung fluorinierter verbindungen | |
| DE602004012906T2 (de) | Verfahren zur Herstellung von perfluorierten monofunktionellen Carbonylverbindungen | |
| DE68906214T2 (de) | Fluorinierte alkoximine, deren n-chlor-und n-brom derivate sowie verfahren zur herstellung davon. | |
| JP2523936B2 (ja) | ジカルボニルフロライドの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |