DE69835427T2 - Verfahren zur herstellung von perfluorsulfonamiden, perfluorsulfonamiden und ihren salzen sowie sulfonierungsreagens - Google Patents
Verfahren zur herstellung von perfluorsulfonamiden, perfluorsulfonamiden und ihren salzen sowie sulfonierungsreagens Download PDFInfo
- Publication number
- DE69835427T2 DE69835427T2 DE69835427T DE69835427T DE69835427T2 DE 69835427 T2 DE69835427 T2 DE 69835427T2 DE 69835427 T DE69835427 T DE 69835427T DE 69835427 T DE69835427 T DE 69835427T DE 69835427 T2 DE69835427 T2 DE 69835427T2
- Authority
- DE
- Germany
- Prior art keywords
- alkylatable
- process according
- organic
- fat
- organic base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 229940124530 sulfonamide Drugs 0.000 title claims description 18
- 150000003456 sulfonamides Chemical class 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title description 6
- 238000006277 sulfonation reaction Methods 0.000 title description 4
- 150000007530 organic bases Chemical class 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012038 nucleophile Substances 0.000 claims abstract description 17
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 17
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 125000005270 trialkylamine group Chemical group 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 8
- 125000005265 dialkylamine group Chemical group 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical class O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 238000005694 sulfonylation reaction Methods 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 230000006103 sulfonylation Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- -1 sulphonyl halide Chemical class 0.000 abstract description 9
- 125000004429 atom Chemical group 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000002585 base Substances 0.000 description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- 150000003949 imides Chemical class 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 150000003461 sulfonyl halides Chemical class 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
- 239000000243 solution Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 5
- 150000003254 radicals Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002641 lithium Chemical class 0.000 description 2
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- USPTVMVRNZEXCP-UHFFFAOYSA-N sulfamoyl fluoride Chemical class NS(F)(=O)=O USPTVMVRNZEXCP-UHFFFAOYSA-N 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical group [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001344 alkene derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SRGBVXWKCOEGJK-UHFFFAOYSA-N octane-1,2,7,8-tetramine Chemical compound NCC(N)CCCCC(N)CN SRGBVXWKCOEGJK-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940066765 systemic antihistamines substituted ethylene diamines Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 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
- C07C303/36—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
- C07C303/38—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 reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9706064A FR2763331B1 (fr) | 1997-05-16 | 1997-05-16 | Procede de synthese de sulfonimides et de leurs sels |
| FR9706064 | 1997-05-16 | ||
| PCT/FR1998/000973 WO1998052886A1 (fr) | 1997-05-16 | 1998-05-15 | Procede de synthese de perfluorosulfonamides, de perfluorosulfonimides et de leurs sels, ainsi qu'un reactif de sulfonylaton |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69835427D1 DE69835427D1 (de) | 2006-09-14 |
| DE69835427T2 true DE69835427T2 (de) | 2007-02-01 |
Family
ID=9506986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69835427T Expired - Lifetime DE69835427T2 (de) | 1997-05-16 | 1998-05-15 | Verfahren zur herstellung von perfluorsulfonamiden, perfluorsulfonamiden und ihren salzen sowie sulfonierungsreagens |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6297398B1 (enExample) |
| EP (1) | EP0983216B1 (enExample) |
| JP (1) | JP4865115B2 (enExample) |
| CN (1) | CN1264785C (enExample) |
| AT (1) | ATE334955T1 (enExample) |
| AU (1) | AU7773398A (enExample) |
| BR (1) | BR9809837B1 (enExample) |
| CA (1) | CA2289005C (enExample) |
| DE (1) | DE69835427T2 (enExample) |
| EA (1) | EA004498B1 (enExample) |
| ES (1) | ES2270519T3 (enExample) |
| FR (1) | FR2763331B1 (enExample) |
| HU (1) | HUP0002297A3 (enExample) |
| NO (1) | NO322194B1 (enExample) |
| WO (1) | WO1998052886A1 (enExample) |
| ZA (1) | ZA984155B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6252111B1 (en) * | 1999-02-16 | 2001-06-26 | Central Glass Company, Limited | Method for producing sulfonimide or its salt |
| EP1122240A3 (en) * | 2000-01-31 | 2003-11-26 | Morita Chemical Industries Co., Ltd. | Process for producing sulfonylimide compound |
| FR2818994B1 (fr) * | 2000-12-29 | 2004-01-09 | Rhodia Chimie Sa | Procede de preparation par voie electrochimique de sels metalliques |
| US20030054172A1 (en) | 2001-05-10 | 2003-03-20 | 3M Innovative Properties Company | Polyoxyalkylene ammonium salts and their use as antistatic agents |
| US6555510B2 (en) * | 2001-05-10 | 2003-04-29 | 3M Innovative Properties Company | Bis(perfluoroalkanesulfonyl)imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| US6885025B2 (en) * | 2003-07-10 | 2005-04-26 | Universal Display Corporation | Organic light emitting device structures for obtaining chromaticity stability |
| JP2008222659A (ja) * | 2007-03-14 | 2008-09-25 | Asahi Kasei Corp | スルホンアミド化合物の製造方法 |
| US20090043021A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043017A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043016A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| JP5191267B2 (ja) * | 2008-04-23 | 2013-05-08 | 旭化成株式会社 | スルホンイミド塩の精製方法 |
| JP2010083764A (ja) * | 2008-09-29 | 2010-04-15 | Asahi Kasei Corp | 新規スルホンイミド塩の精製方法 |
| US8258341B2 (en) * | 2009-07-10 | 2012-09-04 | E.I. Du Pont De Nemours And Company | Polyfluorosulfonamido amine and intermediate |
| JP5730513B2 (ja) * | 2009-08-13 | 2015-06-10 | 三菱マテリアル株式会社 | 含フッ素スルホニルイミド化合物の製造方法 |
| JP2011037784A (ja) * | 2009-08-13 | 2011-02-24 | Mitsubishi Materials Corp | ペルフルオロアルキルスルホンアミドの製造方法 |
| CN102405189B (zh) | 2009-11-27 | 2014-07-09 | 株式会社日本触媒 | 氟磺酰亚胺盐以及氟磺酰亚胺盐的制备方法 |
| PL2578533T3 (pl) * | 2010-05-28 | 2019-07-31 | Nippon Shokubai Co., Ltd. | Sól metalu alkalicznego fluorosulfonyloimidu i sposób jej wytwarzania |
| CN102180816B (zh) * | 2011-03-15 | 2013-06-12 | 浙江大学 | 非对称型双氟代磺酰亚胺钾的制备方法 |
| CN102617414B (zh) * | 2012-03-02 | 2014-12-17 | 苏州氟特电池材料有限公司 | 含氯磺酰/磷酰亚胺碱金属盐和含氟磺酰/磷酰亚胺碱金属盐的制备方法 |
| FR2993556B1 (fr) | 2012-07-23 | 2014-08-15 | Rhodia Operations | Procede de preparation d'un compose sulfonimide et de ses sels |
| CN104710639B (zh) * | 2015-03-03 | 2017-12-01 | 上海交通大学 | 一种基于全氟磺酰胺阴离子交换膜的制备方法 |
| JP2018039760A (ja) * | 2016-09-08 | 2018-03-15 | 三菱マテリアル電子化成株式会社 | ペルフルオロアルカンスルホンアミドアンモニウムの製造方法 |
| CN114470826B (zh) * | 2022-02-17 | 2023-03-14 | 中船(邯郸)派瑞特种气体股份有限公司 | 一种双(三氟甲磺酰)亚胺的纯化装置和方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3466979D1 (en) * | 1983-12-16 | 1987-12-03 | Ciba Geigy Ag | Process for the protection of keratinic material against the attack of keratin eating insects and phenoxytrifluoromethane sulfonanilides |
| FR2637284B1 (fr) * | 1988-10-05 | 1991-07-05 | Elf Aquitaine | Methode de synthese de sulfonylimidures |
| FR2645533B1 (fr) * | 1989-04-06 | 1991-07-12 | Centre Nat Rech Scient | Procede de synthese de sulfonylimidures |
| DE4217366A1 (de) * | 1992-05-26 | 1993-12-02 | Bayer Ag | Imide und deren Salze sowie deren Verwendung |
| JP3117369B2 (ja) * | 1994-09-12 | 2000-12-11 | セントラル硝子株式会社 | スルホンイミドの製造方法 |
| US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
| GB9702194D0 (en) * | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
-
1997
- 1997-05-16 FR FR9706064A patent/FR2763331B1/fr not_active Expired - Lifetime
-
1998
- 1998-05-15 CN CNB988051737A patent/CN1264785C/zh not_active Expired - Lifetime
- 1998-05-15 JP JP55003598A patent/JP4865115B2/ja not_active Expired - Lifetime
- 1998-05-15 AU AU77733/98A patent/AU7773398A/en not_active Abandoned
- 1998-05-15 CA CA002289005A patent/CA2289005C/fr not_active Expired - Lifetime
- 1998-05-15 EP EP98925721A patent/EP0983216B1/fr not_active Expired - Lifetime
- 1998-05-15 EA EA199901039A patent/EA004498B1/ru not_active IP Right Cessation
- 1998-05-15 HU HU0002297A patent/HUP0002297A3/hu unknown
- 1998-05-15 BR BRPI9809837-3A patent/BR9809837B1/pt not_active IP Right Cessation
- 1998-05-15 US US09/423,486 patent/US6297398B1/en not_active Expired - Lifetime
- 1998-05-15 WO PCT/FR1998/000973 patent/WO1998052886A1/fr not_active Ceased
- 1998-05-15 DE DE69835427T patent/DE69835427T2/de not_active Expired - Lifetime
- 1998-05-15 ES ES98925721T patent/ES2270519T3/es not_active Expired - Lifetime
- 1998-05-15 AT AT98925721T patent/ATE334955T1/de not_active IP Right Cessation
- 1998-05-18 ZA ZA984155A patent/ZA984155B/xx unknown
-
1999
- 1999-11-15 NO NO19995595A patent/NO322194B1/no not_active IP Right Cessation
-
2001
- 2001-08-07 US US09/923,493 patent/US6399821B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0002297A3 (en) | 2002-09-30 |
| CN1273573A (zh) | 2000-11-15 |
| CN1264785C (zh) | 2006-07-19 |
| US6297398B1 (en) | 2001-10-02 |
| HUP0002297A2 (hu) | 2000-11-28 |
| EP0983216A1 (fr) | 2000-03-08 |
| EP0983216B1 (fr) | 2006-08-02 |
| AU7773398A (en) | 1998-12-11 |
| US20020004613A1 (en) | 2002-01-10 |
| NO322194B1 (no) | 2006-08-28 |
| WO1998052886A1 (fr) | 1998-11-26 |
| JP2001525844A (ja) | 2001-12-11 |
| CA2289005A1 (fr) | 1998-11-26 |
| BR9809837A (pt) | 2000-06-20 |
| FR2763331B1 (fr) | 1999-06-25 |
| EA004498B1 (ru) | 2004-04-29 |
| JP4865115B2 (ja) | 2012-02-01 |
| ES2270519T3 (es) | 2007-04-01 |
| ATE334955T1 (de) | 2006-08-15 |
| BR9809837B1 (pt) | 2010-02-09 |
| ZA984155B (en) | 1998-12-28 |
| DE69835427D1 (de) | 2006-09-14 |
| FR2763331A1 (fr) | 1998-11-20 |
| NO995595L (no) | 2000-01-14 |
| CA2289005C (fr) | 2007-04-17 |
| EA199901039A1 (ru) | 2000-04-24 |
| NO995595D0 (no) | 1999-11-15 |
| US6399821B2 (en) | 2002-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69835427T2 (de) | Verfahren zur herstellung von perfluorsulfonamiden, perfluorsulfonamiden und ihren salzen sowie sulfonierungsreagens | |
| DE19533711B4 (de) | Verfahren zur Herstellung von einem Sulfonimid oder seinem Salz | |
| EP1658262A2 (de) | Verfahren zur herstellung ionischer flüssigkeiten, ionischer feststoffe oder gemische derselben | |
| DE1966931A1 (de) | Perfluoralkylsubstituierte, quartaere ammoniumsalze | |
| DE69107220T2 (de) | Verfahren zur herstellung von fluoroaliphatischen aminocarboxyltensiden. | |
| DE60107706T2 (de) | Aromatische sulfonierung-reaktionen | |
| DE1942264B2 (de) | Polyfluorsulfonsäuren und deren Sulfonate, Verfahren zur Herstellung der Polyfluorsulfonate, sowie Verwendung der genannten Verbindungen als oberflächenaktive Mittel | |
| DE1620236A1 (de) | Verfahren zur Herstellung neuer N,N'-Disulfide | |
| EP1569921A1 (de) | IONISCHE FL SSIGKEITEN MIT N(CF sb 3 /sb ) sb 2 /sb &r sqb; sp - /sp -ANIONEN | |
| EP0190992A2 (de) | Perfluoralkylalkylthio-,-sulfinyl- oder -sulfonylalkyl-glycidylether, Verfahren zu deren Herstellung und deren Verwendung | |
| DE889898C (de) | Verfahren zur Herstellung von Phosphorverbindungen | |
| DE60314094T2 (de) | Verfahren zur behandlung einer organischen lösung eines sulfonylgruppe tragenden imids | |
| DE69604513T2 (de) | Verfahren zur Herstellung substituierter Carbodiimide | |
| DE60013644T2 (de) | Verfahren zur Reinigung von Phosphinoxiden | |
| EP0560178A2 (de) | Verfahren zur Herstellung von Sulfonylharnstoffen | |
| DE1929295A1 (de) | Verfahren zur Herstellung von Methansulfonamiden | |
| DE69929453T2 (de) | Zur sulfonierung von perhalogenierten sulfanilid verwendbare verfahren und reagenz zur sulfonierung | |
| DE2558508C3 (de) | Verfahren zur Racematspaltung von DL-Pantolacton | |
| DE2512498C2 (de) | Verfahren zur herstellung von sulfonsaeurefluoriden | |
| DE69811358T2 (de) | Verfahren zur herstellung von 1-chlorocarbonyl-4-piperidinopiperidin oder dem hydrochlorid davon | |
| DE2305517C3 (de) | 2-Imino-13-dithiacyclobutane, Verfahren zu ihrer Herstellung und sie enthaltende Warmblüterschutzmittel gegen Schildzecken | |
| EP0011794B1 (de) | Verfahren zur Herstellung von Sulfamidsäurehalogeniden | |
| DE3729416A1 (de) | Verfahren zur sulfonierung und/oder sulfatierung organischer komponenten mit so(pfeil abwaerts)3(pfeil abwaerts) in einem organischen reaktionsmedium | |
| DD139716A5 (de) | Verfahren zur herstellung von dialkyl-phosphorchloridothionaten | |
| DE10321112A1 (de) | Verfahren zur Fluorierung organischer Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |