DE2239817A1 - Bis-perfluoroalkane sulphonic acid imides - useful as catalysts and tensi-des, prepd eg from N-trimethyl-silyl-perfluoroalkane sulphonamide - Google Patents
Bis-perfluoroalkane sulphonic acid imides - useful as catalysts and tensi-des, prepd eg from N-trimethyl-silyl-perfluoroalkane sulphonamideInfo
- Publication number
- DE2239817A1 DE2239817A1 DE19722239817 DE2239817A DE2239817A1 DE 2239817 A1 DE2239817 A1 DE 2239817A1 DE 19722239817 DE19722239817 DE 19722239817 DE 2239817 A DE2239817 A DE 2239817A DE 2239817 A1 DE2239817 A1 DE 2239817A1
- Authority
- DE
- Germany
- Prior art keywords
- perfluoroalkane
- bis
- sulphonamide
- prepd
- silyl
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Abstract
Description
Bis-perfluoralkansulfonsäureimide sowie Verfahren zu ihrer Herstellung Die vorliegende Erfindung betrifft neue Bis-perfluoralkansulfonsäureimide bzw. deren Derivate sowie ein Verfahren zu ihrer Herstellung.Bis-perfluoroalkanesulfonic acid imides and processes for their preparation The present invention relates to new bis-perfluoroalkanesulfonic acid imides or their Derivatives and a process for their preparation.
Die erfindungsgemäße Substanzklasse besitzt die allgemeine Formel worin Rf und Rf gleiche oder verschiedenartige, géradket tige oder verzweigte Perfluoralkanreste mit 1 bis 12 Kohlenstoffatomen sind und X entweder Wasserstoff, Metall oder Ammonium bedeus ten kann.The substance class according to the invention has the general formula where Rf and Rf are identical or different, straight-chain or branched perfluoroalkane radicals with 1 to 12 carbon atoms and X can denote either hydrogen, metal or ammonium.
Die Bis-perfluoralkansulfonimide sind nach den üblichen Methoden der organischen Chemie aus den technisch durch elektrochemische Fluorierung relativ leicht herstellbaren Perfluoralkansulfonylfluoriden nicht zugangli chD Aliphatische Disulfonimide azeton entstehen beispielsweise bereits bei der Umsetzung von Alkansulfc'nsäurechloriden mit Ammoniak unter geeigneten Bedingungen, während man aromatische Disulfonimide aus dem Natriumsalz der Sulfonamide mit Sulfonylchlorid herstellt, (vgl. Houben Weyl, Methoden der organischen Chemie 2, S. 398, 400 und 636).The bis-perfluoroalkanesulfonimides are according to the usual methods of organic chemistry from the technical through electrochemical fluorination relative easily prepared perfluoroalkanesulfonyl fluorides not accessible to chD Aliphatic Acetone disulfonimides are formed, for example, during the reaction of alkanesulfonic acid chlorides with ammonia under suitable conditions while using aromatic disulfonimides from the sodium salt of the sulfonamides with sulfonyl chloride, (cf. Houben Weyl, Methods of Organic Chemistry 2, pp. 398, 400 and 636).
Setzt man jedoch ein Perfluoralkansulfonylfluorid mit Ammoniak um, so kann man lediglich die entsprechenden Perfluoralkansulfonamide R RrS02NH2 isolieren. Auch die Natriumsalze der Perfluoralkansulfonamide reagieren mit weiterem Perfluoralkansulfonyl-florid nicht analog den aromatischen Sulfonamiden unter Bildung der freien Imide neben Alkalifluorid.However, if a perfluoroalkanesulfonyl fluoride is reacted with ammonia, so one can only isolate the corresponding perfluoroalkanesulfonamides R RrS02NH2. The sodium salts of the perfluoroalkanesulfonamides also react with additional perfluoroalkanesulfonyl-fluoride not analogous to the aromatic sulfonamides with the formation of the free imides alongside Alkali fluoride.
Eine weitere, im Anschluß an Arbeiten zur Umsetzung von Perfluoralkansulfonylfluoriden mit funktionellen Siliciumverbindungen bearbeitete Herstellungsreaktion (vgl. Annalen der Chemie i, 58 (1970)> die untersucht wurde, führte ebenfalls nicht zum Ziel: N-Trimethylsilyl-perfluorbutansulfonamid reagiert selbst bei 200°C im Autoklav, auch unter Zusatz basischer Katalysatoren (z.B. Fluorid-Ionen), nicht mit Perfluorbutansulfonylfluorid unter Abspaltung von Trimethylfluorsilan.Another, following work on the implementation of perfluoroalkanesulfonyl fluorides Production reaction processed with functional silicon compounds (cf. Annalen der Chemie i, 58 (1970)> which was investigated also did not achieve the goal: N-trimethylsilyl-perfluorobutanesulfonamide reacts even at 200 ° C in the autoclave, also with the addition of basic catalysts (e.g. fluoride ions), not with perfluorobutanesulfonyl fluoride with elimination of trimethylfluorosilane.
Uberraschenderweise konnte nun ein einfaches Verfahren zur Herstellung von Bis-perfluoralkansulfonimiden durch Reaktion von Alkalisalzen von N-trimethylsilyl-substituierten Perfluoralkansuifonamiden mit PerRluoralkansulSonylfluoriden nach (Me = Metall, wie z.B. Na, X, Cs, Li) gefunden werden.Surprisingly, a simple process for the preparation of bis-perfluoroalkanesulfonimides by reacting alkali salts of N-trimethylsilyl-substituted perfluoroalkanesulfonamides with perfluoroalkanesulfonyl fluorides has now been found (Me = metal, such as Na, X, Cs, Li) can be found.
Die erfindungsgemäße Umsetzung ird zweckmäßigerweise in einem polaren Lösungsmittel wie zoBo Tetrahydrofuran, Dioxan, Diglyme, Dimethylformamid oder Tetramethylensulfon bei erhöhten Temperaturen, vorzugsweise zwischen 50 und 150 0C, durchgeführt. Das gebildete Trimethylfluorsilan (Kp N 16°C) entweicht aus dem Reaktionsgefäß und kann durch Kondensation gewonnen werden Die Ausgangsprodukte für die Herstellung der erfindungsgemäßen Produkte sind nach folgender, bislang nicht beschriebener Methode zugänglich: 1) Umsetzung eines Alkali-bis-trimethylsilylamides, hergestellt aus- Hexamethyldisilazan und Alkaliamiden bzw.The reaction according to the invention is expediently carried out in a polar one Solvents such as tetrahydrofuran, dioxane, diglyme, dimethylformamide or tetramethylene sulfone at elevated temperatures, preferably between 50 and 150 ° C., carried out. That Trimethylfluorosilane formed (bp N 16 ° C) escapes from the reaction vessel and can can be obtained by condensation The starting products for the production of Products according to the invention are made by the following method, which has not yet been described accessible: 1) Implementation of an alkali-bis-trimethylsilylamide, prepared from- Hexamethyldisilazane and alkali amides or
-hydriden oder -alkylen (vgl. Inorg. Syntheses, Vol. hydrides or alkylene (cf. Inorg.Syntheses, Vol.
VIII, S. 15 (1966)) mit Perfluoralkansulfonylfluoriden bei 0 bis 50°C, z.B. nach 2) Reaktion von Hexamethyldisilazan mit Alkalisalzen von Perfluoralkansulfonamiden, z,B. nach Eine weitere Möglichkeit zur Darstellung der Bis-perfluoralkansulfonimide ergibt sich aus der Umsetzung der Alkalisalze der Perfluoralkans.ulfonamlde mit Perfluoralkansuifonylfluorid, wobei nicht das freie Imid entsteht, sondern gemäß folgender Gleichung Perfluoralkansulfonamid, Alkalifluorid und das Alkali-bis-perfluoralkansulfonimid entstehen: Die Reaktion wird zweckmäßigerweise in polaren Lösungsmitteln, wie Dioxan, Diglyme u.a., unter Druck in Autoklaven bei Temperaturen von 50 bis 150°C ausgeführt. Eine Abtrennung der Perfluoralkansulfonamide ist durch einfache Trennoperationen wie z.B. Destillation oder Sublimation im Hochvakuum möglich.VIII, p. 15 (1966)) with perfluoroalkanesulfonyl fluorides at 0 to 50 ° C, for example after 2) Reaction of hexamethyldisilazane with alkali salts of perfluoroalkanesulfonamides, e.g. after Another possibility for the preparation of the bis-perfluoroalkanesulfonimides results from the reaction of the alkali salts of the perfluoroalkanesulfonamlde with perfluoroalkanesulfonyl fluoride, whereby the free imide is not formed, but according to the following equation, perfluoroalkanesulfonamide, alkali fluoride and the alkali-bis-perfluoroalkanesulfonimide are formed: The reaction is expediently carried out in polar solvents, such as dioxane, diglyme, etc., under pressure in an autoclave at temperatures from 50 to 150.degree. The perfluoroalkanesulfonamides can be separated off by simple separation operations such as distillation or sublimation in a high vacuum.
Die freien Imide sind aus den Alkalisalzen durch Umsetzung mit starken Säuren, wie Schwefelsäure oder Phosphorsäure, oder sauren Ionenaustauschern nun leicht zugänglich.The free imides are obtained from the alkali salts by reacting with strong ones Acids, such as sulfuric acid or phosphoric acid, or acidic ion exchangers now easily accessible.
Die Identifizierung der neuen Bis-perfluoralkansulfonimide erfolgte durch 1H- und 19F- El, IR- und Massenspektroskopie, Acidimetrie -und quantitative Analyse.The new bis-perfluoroalkanesulfonimides were identified by 1H and 19F El, IR and mass spectroscopy, acidimetry and quantitative Analysis.
Die freien Bis-perfluoralkansulfonimide sind extrem starke Säuren - vergleichbar mit den Perfluoralkansulfonsäuren -und können deshalb als Katalysatoren Verwendung finden, z.B. als Veresterungskatalysator. Weiterhin sind diese Verbindungen aufgrund der Perfluoralkanreste als Tenside einsetzba-r.The free bis-perfluoroalkanesulfonimides are extremely strong acids - comparable to perfluoroalkanesulfonic acids - and can therefore be used as catalysts Find use, e.g. as an esterification catalyst. Furthermore, these connections are Can be used as surfactants due to the perfluoroalkane residues.
Nach diesen aufgeführten Verfahren konnten z.B. folgende Bis-perfluoralkansulfonylimide hergestellt werden: Sdp.3,4 850C Smp. 560C Sdp.0,2 800C Smp. 90°C Sdp. 0,2 10400 Smp. 1020C unter Smp. 1060C Smp. 112°C Anhand der folgenden Beispiele soll das erfindungsgemäße Verfahren näher erläutert werden: Beispiel 1: N-Trimethylsilyl -perfluorbutansulfonamid-Natrium, C4F9SO2N(Na)Si ( Cm3)3 1 Mol (299 g) C4F9'SO2NH2 in 100 ml CH30 wird mit 1 Mol frisch zubereitetem CHDONa in 50 ml CH3OH versetzt. Am Rotationsverdampfer wird anschließend das gesamte Methanol im Vakkum abdestilliert und der verbleibende Rückstand mit 300 ml Hexamethyldisilazan am Rückfluß gekocht. Sobald die NH3-Entwicklung beendet ist, wird das überschüssige Hexamethyldisilazan abdestilliert. Der verbleibende weiße, feuchtigkeitsempfindliche Rückstand stellt die gesuchte Verbindung dar.The following bis-perfluoroalkanesulfonylimides, for example, could be produced using these processes: Bp 3.4 850C mp 560C bp 0.2 800C mp 90 ° C bp 0.2 10400 mp 1020C below mp 1060C mp 112 ° C The following examples are intended to explain the process according to the invention in more detail: Example 1: N-trimethylsilyl-perfluorobutanesulfonamide-sodium, C4F9SO2N (Na) Si (Cm3) 3 1 mol (299 g) C4F9'SO2NH2 in 100 ml CH30 is mixed with 1 mol freshly prepared CHDONa in 50 ml CH3OH. All of the methanol is then distilled off in vacuo on a rotary evaporator and the residue that remains is refluxed with 300 ml of hexamethyldisilazane. As soon as the evolution of NH3 has ended, the excess hexamethyldisilazane is distilled off. The remaining white, moisture-sensitive residue is the compound we are looking for.
Bis-perfluorbutansulfonylimid, tC4F9S02)2NH 0,5 Mol C4F9SO2N(Na)Si(CH3)3 werden in 300 ml Dioxan gelöst und mit 0,52 Mol C4FgS02F versetzt. Da zuweilen diese Reaktion selbst bei ca. 700C (Ruckflußtemperatur) noch gehemmt ist, wird die Umsetzung bevorzugt in Autoklaven ausgeführt. Die Reaktionstemperatur liegt hier bei ca.Bis-perfluorobutanesulfonylimide, tC4F9S02) 2NH 0.5 mol C4F9SO2N (Na) Si (CH3) 3 are dissolved in 300 ml of dioxane and treated with 0.52 mol of C4FgS02F. Sometimes this The reaction is still inhibited even at about 700C (reflux temperature) preferably carried out in an autoclave. The reaction temperature here is approx.
100°C. Die Umsetzung ist beendet, sobald bei konstanter Temperatur kein weiterer Druckanstieg mehr erfolgt (ca.100 ° C. The reaction is complete as soon as the temperature is constant no further pressure increase occurs (approx.
1/2 Stunde). Nach Abkühlung wird der Autoklav entspannt.1/2 hour). After cooling, the pressure in the autoclave is released.
Es entweicht hierbei das Trimethylfluorsilan. Daraufhin wird das Lösungsmittel abgezogen, der Rückstand mit 150 ml conz. Schwefelsäure versetzt. Unter Vakuum kann daraus das freie (C4FgS02)2NH herausdestilliert werden. Die Ausbeute beträgt ca. 85 %. Die acidimetrische Analyse ergab einen Verbrauch an 17,14 ml 0,1 n NaOH rUr 1 g (C4FgS02)2NH Das (c4F9s02)2NH bildet relativ schwerlösliche Kaliumsalze, so daß hierdurch eine weitere Reinigungsmöglichkeit besteht.The trimethylfluorosilane escapes. Thereupon the solvent withdrawn, the residue with 150 ml of conc. Sulfuric acid added. Under vacuum can from this the free (C4FgS02) 2NH are distilled out. The yield is approx. 85%. The acidimetric analysis showed consumption of 17.14 ml of 0.1 N NaOH rUr 1 g (C4FgS02) 2NH The (c4F9s02) 2NH forms relatively poorly soluble potassium salts, see above that this provides a further cleaning option.
Beispiel 2: Bis-perfluorbutansulfonylimid, (C4F9SO2) 2NH 0,2 Mol (64,2 g) Natriumfluorbutansulfonamid werden mit 0>1 Mol (30,2 g) Perfluorbutansulfonylfluorid in 100 ml Dioxan im Autoklav 2 Stunden auf 1500C erhitzt. Das Lösungsmittel und das Perfluorbutansulfonamid werden vom Reaktionsgemisch unter Vakuum abdestilliert und der verbleibende Rückstand mit 150 ml Wasser versetzt, wobei das Natrium-bis-perfluorbutansulfonimid in Lösung geht. Durch Zusatz von KCl-Lösung fällt sofort das entsprechende, schwerlösliche Kaliumbis-perfluorbutansulfonimid in reiner Form aus, woraus sich mit conz. Schwefelsäure wieder das Bis-perfluorbutansulfonimid gewinnen läßt.Example 2: bis-perfluorobutanesulfonylimide, (C4F9SO2) 2NH 0.2 mol (64.2 g) Sodium fluorobutanesulfonamide with 0> 1 mol (30.2 g) of perfluorobutanesulfonyl fluoride heated in 100 ml of dioxane in an autoclave to 1500C for 2 hours. The solvent and the perfluorobutanesulfonamide are distilled off from the reaction mixture under vacuum and the remaining residue is mixed with 150 ml of water, the sodium bis-perfluorobutanesulfonimide goes into solution. By adding KCl solution, the corresponding, poorly soluble one falls immediately Potassium bis-perfluorobutanesulfonimide in pure form, from which with conc. sulfuric acid can again win the bis-perfluorobutanesulfonimide.
Sdp.0,2 1040C Smp. l020C unter Eigendruck.Bp 0.2 1040C mp 1020C under autogenous pressure.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722239817 DE2239817A1 (en) | 1972-08-12 | 1972-08-12 | Bis-perfluoroalkane sulphonic acid imides - useful as catalysts and tensi-des, prepd eg from N-trimethyl-silyl-perfluoroalkane sulphonamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722239817 DE2239817A1 (en) | 1972-08-12 | 1972-08-12 | Bis-perfluoroalkane sulphonic acid imides - useful as catalysts and tensi-des, prepd eg from N-trimethyl-silyl-perfluoroalkane sulphonamide |
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| Publication Number | Publication Date |
|---|---|
| DE2239817A1 true DE2239817A1 (en) | 1974-02-21 |
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| DE19722239817 Pending DE2239817A1 (en) | 1972-08-12 | 1972-08-12 | Bis-perfluoroalkane sulphonic acid imides - useful as catalysts and tensi-des, prepd eg from N-trimethyl-silyl-perfluoroalkane sulphonamide |
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Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057327A1 (en) * | 1981-01-30 | 1982-08-11 | Minnesota Mining And Manufacturing Company | Cyclic perfluoroaliphatic disulfonimides |
| FR2637284A1 (en) * | 1988-10-05 | 1990-04-06 | Elf Aquitaine | SYNTHESIS OF SULFONYLIMIDURES |
| FR2645533A1 (en) * | 1989-04-06 | 1990-10-12 | Centre Nat Rech Scient | PROCESS FOR SYNTHESIZING SULFONYLIMIDURES |
| US5021308A (en) * | 1986-10-30 | 1991-06-04 | Hydro-Quebec | New ion conductive material composed of a salt in solution in a liquid electrolyte |
| US5256821A (en) * | 1988-10-05 | 1993-10-26 | Societe Nationale Elf Aquitaine | Method of synthesis of sulphonylimides |
| US5260145A (en) * | 1986-10-30 | 1993-11-09 | Hydro-Quebec | Production of organic cation radicals in an electrochemical cell |
| EP0571832A2 (en) * | 1992-05-26 | 1993-12-01 | Bayer Ag | Imides and their salts and their use as surface active agents |
| US5514493A (en) * | 1995-03-06 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them |
| US5652072A (en) * | 1995-09-21 | 1997-07-29 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
| US5691081A (en) * | 1995-09-21 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
| WO1998045039A1 (en) * | 1997-04-04 | 1998-10-15 | The Regents Of The University Of California | Polymerization catalysts containing electron-withdrawing amide ligands |
| WO1998050349A1 (en) * | 1997-05-01 | 1998-11-12 | Minnesota Mining And Manufacturing Company | Fluorinated sulphonamide and sulphone derivatives |
| US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
| WO1999030381A1 (en) * | 1997-12-10 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Bis(perfluoroalkylsulfonyl)imide surfactant salts in electrochemical systems |
| US6235921B1 (en) * | 1995-02-13 | 2001-05-22 | Central Glass Company, Limited | Amines or salts thereof and methods of preparing same |
| WO2002092211A2 (en) * | 2001-05-10 | 2002-11-21 | 3M Innovative Properties Company | Bis (perfluoroalkanesulfonyl) imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| JP2006505654A (en) * | 2002-11-04 | 2006-02-16 | ソリユテイア・インコーポレイテツド | Functional fluid composition containing an erosion inhibitor |
| FR2993556A1 (en) * | 2012-07-23 | 2014-01-24 | Rhodia Operations | PROCESS FOR PREPARING A SULFONIMIDE COMPOUND AND ITS SALTS |
| EP3705470A1 (en) | 2019-03-08 | 2020-09-09 | Shanghai Rolechem Co., Ltd. | New process for bistrifluoromethanesulfonylimide salt |
-
1972
- 1972-08-12 DE DE19722239817 patent/DE2239817A1/en active Pending
Cited By (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057327A1 (en) * | 1981-01-30 | 1982-08-11 | Minnesota Mining And Manufacturing Company | Cyclic perfluoroaliphatic disulfonimides |
| US5021308A (en) * | 1986-10-30 | 1991-06-04 | Hydro-Quebec | New ion conductive material composed of a salt in solution in a liquid electrolyte |
| US5260145A (en) * | 1986-10-30 | 1993-11-09 | Hydro-Quebec | Production of organic cation radicals in an electrochemical cell |
| FR2637284A1 (en) * | 1988-10-05 | 1990-04-06 | Elf Aquitaine | SYNTHESIS OF SULFONYLIMIDURES |
| EP0364340A1 (en) * | 1988-10-05 | 1990-04-18 | Societe Nationale Elf Aquitaine | Method for the synthesis of sulfonyl imides |
| WO1990003968A1 (en) * | 1988-10-05 | 1990-04-19 | Societe Nationale Elf Aquitaine | Method for the synthesis of sulfonylimidides |
| US5256821A (en) * | 1988-10-05 | 1993-10-26 | Societe Nationale Elf Aquitaine | Method of synthesis of sulphonylimides |
| FR2645533A1 (en) * | 1989-04-06 | 1990-10-12 | Centre Nat Rech Scient | PROCESS FOR SYNTHESIZING SULFONYLIMIDURES |
| WO1990011999A1 (en) * | 1989-04-06 | 1990-10-18 | Centre National De La Recherche Scientifique (Cnrs) | Process for synthesis of sulfonylimidides |
| EP0571832A3 (en) * | 1992-05-26 | 1994-01-05 | Bayer Ag | |
| US5502251A (en) * | 1992-05-26 | 1996-03-26 | Bayer Ag | Imides and their salts, as well as their use |
| EP0571832A2 (en) * | 1992-05-26 | 1993-12-01 | Bayer Ag | Imides and their salts and their use as surface active agents |
| US6642404B2 (en) * | 1995-02-13 | 2003-11-04 | Central Glass Company, Limited | Amines or salts thereof and methods of preparing same |
| US6235921B1 (en) * | 1995-02-13 | 2001-05-22 | Central Glass Company, Limited | Amines or salts thereof and methods of preparing same |
| US5514493A (en) * | 1995-03-06 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them |
| US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
| US5652072A (en) * | 1995-09-21 | 1997-07-29 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
| US5691081A (en) * | 1995-09-21 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
| US5962546A (en) * | 1996-03-26 | 1999-10-05 | 3M Innovative Properties Company | Cationically polymerizable compositions capable of being coated by electrostatic assistance |
| US6335303B1 (en) * | 1997-04-04 | 2002-01-01 | The Regents Of The University Of California | Polymerization catalysts containing electron-withdrawing amide ligands |
| WO1998045039A1 (en) * | 1997-04-04 | 1998-10-15 | The Regents Of The University Of California | Polymerization catalysts containing electron-withdrawing amide ligands |
| WO1998050349A1 (en) * | 1997-05-01 | 1998-11-12 | Minnesota Mining And Manufacturing Company | Fluorinated sulphonamide and sulphone derivatives |
| US6420607B1 (en) | 1997-05-01 | 2002-07-16 | 3M Innovative Properties Company | Cationically polymerizable compositions capable of being coated by electrostatic assistance |
| US6280883B1 (en) | 1997-12-10 | 2001-08-28 | 3M Innovative Properties Company | Bis (perfluoralkanesulfonyl)imide surfactant salts in electrochemical systems |
| WO1999030381A1 (en) * | 1997-12-10 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Bis(perfluoroalkylsulfonyl)imide surfactant salts in electrochemical systems |
| WO2002092211A2 (en) * | 2001-05-10 | 2002-11-21 | 3M Innovative Properties Company | Bis (perfluoroalkanesulfonyl) imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| 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 |
| WO2002092211A3 (en) * | 2001-05-10 | 2003-05-30 | 3M Innovative Properties Co | Bis (perfluoroalkanesulfonyl) imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| US7030067B2 (en) | 2001-05-10 | 2006-04-18 | 3M Innovative Properties Company | Bis(perfluoroalkanesulfonyl)imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| JP2006505654A (en) * | 2002-11-04 | 2006-02-16 | ソリユテイア・インコーポレイテツド | Functional fluid composition containing an erosion inhibitor |
| FR2993556A1 (en) * | 2012-07-23 | 2014-01-24 | Rhodia Operations | PROCESS FOR PREPARING A SULFONIMIDE COMPOUND AND ITS SALTS |
| WO2014016130A1 (en) * | 2012-07-23 | 2014-01-30 | Rhodia Operations | Method for preparing a sulfonimide compound and salts thereof |
| US9394247B2 (en) | 2012-07-23 | 2016-07-19 | Rhodia Operations | Method for preparing a sulfonimide compound and salts thereof |
| EP3705470A1 (en) | 2019-03-08 | 2020-09-09 | Shanghai Rolechem Co., Ltd. | New process for bistrifluoromethanesulfonylimide salt |
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