DE10126929A1 - Production of compounds with perfluoroalkanesulfonic acid residues, used e.g. in electrolytes and batteries, involves reacting perfluoroalkanesulfonic anhydride with dialkyl carbonate in presence of perfluoroalkanesulfonic acid - Google Patents

Production of compounds with perfluoroalkanesulfonic acid residues, used e.g. in electrolytes and batteries, involves reacting perfluoroalkanesulfonic anhydride with dialkyl carbonate in presence of perfluoroalkanesulfonic acid

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Publication number
DE10126929A1
DE10126929A1 DE10126929A DE10126929A DE10126929A1 DE 10126929 A1 DE10126929 A1 DE 10126929A1 DE 10126929 A DE10126929 A DE 10126929A DE 10126929 A DE10126929 A DE 10126929A DE 10126929 A1 DE10126929 A1 DE 10126929A1
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Prior art keywords
compounds
perfluoroalkanesulfonic
perfluoroalkanesulfonic acid
alkyl
salts
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DE10126929A
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German (de)
Inventor
Nicolai Ignatyev
Michael Schmidt
Udo Heider
Peter Sartori
Andrei Kucheryna
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Merck Patent GmbH
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Merck Patent GmbH
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Priority to DE10126929A priority Critical patent/DE10126929A1/en
Priority to EP09006446A priority patent/EP2085378A1/en
Priority to AU2002344346A priority patent/AU2002344346A1/en
Priority to EP02776502A priority patent/EP1399417B1/en
Priority to PCT/EP2002/004917 priority patent/WO2002098844A1/en
Priority to US10/478,969 priority patent/US7084290B2/en
Priority to DE50213765T priority patent/DE50213765D1/en
Priority to JP2003501834A priority patent/JP4317918B2/en
Priority to CA002449060A priority patent/CA2449060A1/en
Priority to AT02776502T priority patent/ATE439340T1/en
Publication of DE10126929A1 publication Critical patent/DE10126929A1/en
Priority to IN1656KO2003 priority patent/IN2003KO01656A/en
Priority to US11/443,278 priority patent/US7585994B2/en
Priority to JP2009030513A priority patent/JP4564092B2/en
Priority to US12/499,446 priority patent/US20130316248A9/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65688—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphonium compound
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/02—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof using combined reduction-oxidation reactions, e.g. redox arrangement or solion
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
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    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/13—Energy storage using capacitors

Abstract

A method for the production of compounds with perfluoroalkanesulfonic acid residues (II) involves reacting perfluoroalkanesulfonic acid anhydride with dialkyl carbonate in presence of perfluoroalkanesulfonic acid. Independent claims are also included for: (a) a method for the production of perfluoroalkanesulfonate salts (II) by reacting esters (I) with compounds of formula XR<1>R<2>R<3> (III); (b) a method for the production of (II) by reacting (I) with compounds of formulae (III)-(X); (c) compounds of formula Mn+(OSO2CF3)n-; (d) liquid, gel-like or solid electrolytes containing compounds as described in (c), optionally mixed with other salts; and (e) primary and secondary batteries, condensers, super-condensers and/or galvanic cells containing compounds as in (c) or electrolytes as in (d) or compounds (I) obtained by this method. X = P or N; R<1>-R<3> = H, 1-16C alkyl (optionally partly substituted with other groups, preferably F, Cl, N(1-6C fluoroalkyl with up to 13 F atoms)2, O-fluoroalkyl (as above), SO2-(fluoroalkyl) or fluoroalkyl, optionally substituted aryl or optionally substituted heterocyclic groups), or (1-16C alkyl)-aryl, aryl or heteroaryl (all optionally partly substituted, preferably with F, Cl, Br, NO2, CN, alkyl, aryl or heterocyclic groups), in which 1, 2 or 3 CH2 groups in alkyl or alkylene residues may be replaced by hetero-atoms, preferably O, NH or N(1-6C alkyl), and not all of the groups R<1>-R<3> may be perfluorinated or perchlorinated at once; R<1>-R<5> = H, halogen (preferably fluorine, but with no N-halogen bonds), 1-8C alkyl (optionally partly substituted as above), aryl, alkylaryl or (alkyl)-heterocyclic groups; Mn+ = formulae (XI)-(XIX); X, Y = P or N.

Description

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Verbindungen mit Perfluoralkansulfonsäureresten sowie die Verwendung von Leitsalzen in Batterien, Kondensatoren, Superkondensatoren und galvanischen Zellen.The present invention relates to a method for producing Compounds with perfluoroalkanesulfonic acid residues and the Use of conductive salts in batteries, capacitors, Supercapacitors and galvanic cells.

Die Verbreitung von tragbaren elektronischen Geräten, wie z. B. Laptop- und Palmtop-Computern, Mobiltelefonen, oder Videokameras und damit auch der Bedarf nach leichten und leistungsfähigen Batterien hat in den letzten Jahren weltweit dramatisch zugenommen.The proliferation of portable electronic devices, such as. B. laptop and palmtop computers, cell phones, or video cameras and thus also the need for light and powerful batteries has increased dramatically worldwide in recent years.

Angesichts dieses sprunghaft gestiegenen Bedarfs nach Batterien und den damit verbundenen ökologischen Problemen kommt der Entwicklung von wiederaufladbaren Batterien mit einer langen Lebensdauer eine stetig wachsende Bedeutung zu.Given this surge in demand for batteries and the associated ecological problems Development of rechargeable batteries with a long Lifetime a growing importance.

Lithium-Ionen-Batterien und Doppelschichtkondensatoren mit sehr hohen Kapazitäten (sogenannte Super- oder Ultracapacitors) stellen den derzeitigen Stand der Technik dar. In beiden Systemen werden mit LiPF6 bzw. N(C2H5)4BF4 derzeit hydrolyseempfindliche und thermisch instabile Substanzen als Leitsalz verwendet. Im Kontakt mit feuchter Luft bzw. mit Restwasser aus den Lösungsmitteln kann schnell HF entstehen. Neben den toxischen Eigenschaften wirkt HF sehr negativ auf das Zyklenverhalten und somit auf die Performance der elektrochemischen Zellen.Lithium-ion batteries and double-layer capacitors with very high capacities (so-called super or ultra capacitors) represent the current state of the art. In both systems, LiPF 6 and N (C 2 H 5 ) 4 BF 4 are currently hydrolysis-sensitive and thermally unstable Substances used as conductive salt. HF can quickly develop in contact with moist air or with residual water from the solvents. In addition to the toxic properties, HF has a very negative effect on the cycle behavior and thus on the performance of the electrochemical cells.

Als Alternative wurden Imide, wie das Bis(trifluormethylsulfonyl)imid oder das Bis(pentafluorethylsulfonyl)imid oder Methanide, wie das Tris(trifluormethylsulfonyl)methanid und deren Derivate vorgestellt.As an alternative, imides such as the bis (trifluoromethylsulfonyl) imide or the bis (pentafluoroethylsulfonyl) imide or methanides such as that Tris (trifluoromethylsulfonyl) methanide and its derivatives presented.

Aber auch quaternäre Ammonium- und Phosphoniumsalze mit Perfluoralkansulfonat-Anionen wurden als Leitsalze für galvanische Zellen entwickelt. Die Synthese dieser Salze ist jedoch relativ aufwendig, da ein Zwischenprodukt, der Trifluormethansulfonsäuremethylester (Methyltriflat), schwer darzustellen ist.But also quaternary ammonium and phosphonium salts Perfluoroalkanesulfonate anions have been used as conductive salts for galvanic Cells developed. However, the synthesis of these salts is relative complex, because an intermediate product, the Trifluoromethanesulfonic acid methyl ester (methyl triflate), heavy is to be presented.

Das Methyltriflat ist ein starkes Methylierungsreagenz. Es wird in der präparativen Chemie zur Einführung von Methylgruppen genutzt, z. B. bei der Methylierung von heterocyclischen Verbindungen (Yu, Teylor, Tetrahedron Letter, 1999 (36), 6661-6664) oder der Methylierung von Schwefel-organischen Verbindungen (Tsuge, Hatta, Chem. Letter, 1997 (9), 945-946). Methyltriflat ist wesentlich reaktiver als Methyliodid, Dimethylsulfat und Methyltoluensulfonat, die üblicherweise verwendeten Methylierungsreagenzien bei der Synthese von quaternären Ammonium- und Phosphoniumsalzen.The methyl triflate is a strong methylation reagent. It will be in the preparative chemistry used to introduce methyl groups, e.g. B.  in the methylation of heterocyclic compounds (Yu, Teylor, Tetrahedron Letter, 1999 (36), 6661-6664) or the methylation of Organic sulfur compounds (Tsuge, Hatta, Chem. Letter, 1997 (9), 945-946). Methyl triflate is much more reactive than methyl iodide, Dimethyl sulfate and methyl toluenesulfonate, which are common used methylation reagents in the synthesis of quaternary ammonium and phosphonium salts.

Es gibt verschiedene Synthesewege für das Methyltriflat (Gramstad, J. Chem. Soc., 1956, 173-180 oder Beard, J. Org. Chem., 1973 (21), 3673-3677). Alle beschriebenen Synthesewege eignen sich nicht für eine Übertragung in einen großen Maßstab, da sie entweder sehr toxische Ausgangsmaterialien, wie z. B. Dimethylsulfat, verwenden, die Ausbeuten sehr niedrig sind, das Reaktionsprodukt aufgereinigt werden muß, oder gefährliche Neben- bzw. Abfallprodukte anfallen, wie z. B. Schwefelsäure die mit Dimethylsulfat verunreinigt ist.There are various synthetic routes for methyl triflate (Gramstad, J. Chem. Soc., 1956, 173-180 or Beard, J. Org. Chem., 1973 (21), 3673 to 3677). All of the synthetic routes described are not suitable for a transfer on a large scale since it is either very toxic starting materials such as B. dimethyl sulfate, use the Yields are very low, the reaction product can be purified must, or dangerous by-products or waste products arise, such. B. Sulfuric acid contaminated with dimethyl sulfate.

Aufgabe der Erfindung war es daher, ein einfaches Verfahren für die Synthese von Perfluoralkansulfonsäurealkylestern und daraus herstellbare Leitsalze zur Verfügung zu stellen.The object of the invention was therefore to provide a simple method for Synthesis of perfluoroalkanesulfonic acid alkyl esters and therefrom to provide conductive salts that can be produced.

Die Aufgabe wird gelöst durch ein Verfahren zur Herstellung von Verbindungen mit Perfluoralkansulfonsäureresten, unter der Verwendung eines Verfahrensschrittes bei dem Perfluoralkansulfonsäureanhydrid in Gegenwart von Perfluoralkansulfonsäure mit Dialkylcarbonat zu Perfluoralkansulfonsäurealkylester umgesetzt wird.
The object is achieved by a process for the preparation of compounds having perfluoroalkanesulfonic acid residues, using a process step in which perfluoroalkanesulfonic anhydride is reacted with dialkyl carbonate to give perfluoroalkanesulfonic acid alkyl ester in the presence of perfluoroalkanesulfonic acid.

Überraschend wurde gefunden, daß die Umsetzung von Perfluoralkansulfonsäureanhydrid nahezu quantitativ zum Perfluoralkansulfonsäurealkylester erfolgt. Es sind nur katalytische Mengen an Perfluoralkansulfonsäure erforderlich. Es werden nur 0,01-0,1 mol Perfluoralkansulfonsäure pro 1 mol Perfluoralkansulfonsäureanhydrid benötigt.It was surprisingly found that the implementation of Perfluoroalkanesulfonic anhydride almost quantitative for Perfluoroalkanesulfonsäurealkylester takes place. They are only catalytic Amounts of perfluoroalkanesulfonic acid required. Only 0.01-0.1 mol Perfluoroalkanesulfonic acid per 1 mol Perfluoroalkanesulfonic anhydride is required.

Über das erfindungsgemäße Verfahren erhält man Perfluoralkansulfonsäurealkylester, die als Methylierungsreagenzien verwendet werden können. Sie können zur Methylierung von heterocyclischen Verbindungen oder Phosphor- und Schwefel- organische Verbindungen verwendet werden, oder zur Darstellung von N-Methylaminosäure mit geringer Racematbildung.One obtains via the method according to the invention Perfluoroalkanesulfonic acid alkyl esters used as methylation reagents can be used. You can use it to methylate heterocyclic compounds or phosphorus and sulfur  organic compounds are used, or for the representation of N-methyl amino acid with low racemate formation.

Das Reaktionsprodukt muß nicht isoliert werden, da nicht umgesetzte Dialkylcarbonate bei einer Umsetzung mit
The reaction product does not have to be isolated, since unreacted dialkyl carbonates react with

XR1R2R3,
XR 1 R 2 R 3 ,

wobei
X P oder N und
R1, R2, R3
unabhängig voneinander H, Alkyl, Alkylaryl oder Aryl bedeuten, und mindestens ein R + H ist, zu den entsprechenden Salzen für die Verwendung in Elektrolyten für galvanische Zellen als Lösungsmittel enthalten sein kann.in which
XP or N and
R 1 , R 2 , R 3
independently of one another denote H, alkyl, alkylaryl or aryl, and at least one R + H is, to the corresponding salts for use in electrolytes for galvanic cells can be contained as a solvent.

Beispielsweise können folgende Umsetzungen erfolgen:
For example, the following implementations can take place:

CF3SO2OCH3 + (C2H5)3N → ((C2H5)3NCH3]+ CF3SO2O-
CF 3 SO 2 OCH 3 + (C 2 H 5 ) 3 N → ((C 2 H 5 ) 3 NCH 3 ] + CF 3 SO 2 O -

oder
or

CF3SO2OCH3 + (C2H5)3P → [(C2H5)3PCH3]+ CF3SO2O-.CF 3 SO 2 OCH 3 + (C 2 H 5 ) 3 P → [(C 2 H 5 ) 3 PCH 3 ] + CF 3 SO 2 O - .

Nach der Umsetzung muß lediglich der nicht umgesetzte Perfluoralkansulfonsäurealkylester abdestilliert werden, die restliche Perfluoralkansulfonsäure kann für weitere Umsetzungen genutzt werden.After the implementation, only the unconverted must Perfluoroalkanesulfonsäurealkylester be distilled off, the rest Perfluoroalkanesulfonic acid can be used for further reactions become.

Diese Salze können sowohl in reiner Form als auch in Form ihrer Mischungen als Leitsalze in primären und sekundären Batterien, Kondensatoren, Superkondensatoren und galvanischen Zellen eingesetzt werden. Es ist auch möglich, die Salze gemeinsam mit weiteren, dem Fachmann bekannten Salzen als Leitsalz zu verwenden.These salts can be in both pure form and in the form of their Mixtures as conductive salts in primary and secondary batteries, Capacitors, supercapacitors and galvanic cells be used. It is also possible to use the salts together to use further salts known to the person skilled in the art as the conductive salt.

Die Leitsalze werden im Elektrolyten mit geeigneten Lösungsmitteln eingesetzt. Besonders bevorzugt werden als Lösungsmittel solche Lösungsmittel oder deren Gemische eingesetzt, die zur Anwendung in einer primären oder sekundären Batterie, einem Kondensator, einem Superkondensator oder einer galvanischen Zelle geeignet sind, wie beispielsweise Dimethylcarbonat, Diethylcarbonat, Propylencarbonat, Ethylencarbonat, Ethylmethylcarbonat, Methylpropylcarbonat, 1,2- Dimethoxyethan, 1,2-Diethoxyethan, Methylacetat, γ-Butyrolacton, Ethylacetat, Methylpropionat, Ethylpropionat, Methylbutyrat, Ethylbutyrat, Dimethylsulfoxid, Dioxolan, Sulfolan, Acetonitril, Acrylnitril, Tetrahydrofuran, 2-Methyl-Tetrahydrofuran oder deren Gemische, hergestellt.The conductive salts are in the electrolyte with suitable solvents used. Such solvents are particularly preferred Solvents or mixtures thereof are used in a primary or secondary battery, a capacitor, a Supercapacitor or a galvanic cell are suitable, such as for example dimethyl carbonate, diethyl carbonate, propylene carbonate, Ethylene carbonate, ethyl methyl carbonate, methyl propyl carbonate, 1,2- Dimethoxyethane, 1,2-diethoxyethane, methyl acetate, γ-butyrolactone, Ethyl acetate, methyl propionate, ethyl propionate, methyl butyrate,  Ethyl butyrate, dimethyl sulfoxide, dioxolane, sulfolane, acetonitrile, acrylonitrile, Tetrahydrofuran, 2-methyl-tetrahydrofuran or mixtures thereof, manufactured.

Die so erhaltenen Elektrolyte eignen sich zum Einsatz in primären Batterien, sekundären Batterien, Kondensatoren, Superkondensatoren und galvanischen Zellen und stellen ebenfalls einen Gegenstand der vorliegenden Erfindung dar.The electrolytes thus obtained are suitable for use in primary ones Batteries, secondary batteries, capacitors, supercapacitors and galvanic cells and also represent an object of present invention.

Gegenstand der Erfindung sind auch primäre Batterien, sekundäre Batterien, Kondensatoren, Superkondensatoren und galvanische Zellen, die wenigstens ein Salz, erhalten durch die Umsetzung von Perfluoralkansulfonsäurealkylester mit einer Verbindung gemäß der Formel XR1R2R3, und ggf. weitere Salze und/oder Zusatzstoffe enthalten. Diese weiteren Salze und Zusatzstoffe sind dem Fachmann z. B. aus Doron Aurbach, Nonaqueous Electrochemistry, Marc Dekker Inc., New York 1999; D. Linden, Handbook of Batteries, Second Edition, McGraw-Hill Inc., New York 1995 und G. Mamantov und A. I. Popov, Chemistry of Nonaqueous Solutions, Current Progress, VCH Verlagsgemeinschaft, Weinheim 1994 bekannt. Sie werden hiermit als Referenz eingeführt und gelten somit als Teil der Offenbarung. The invention also relates to primary batteries, secondary batteries, capacitors, supercapacitors and galvanic cells which contain at least one salt obtained by reacting alkyl perfluoroalkanesulfonic acid ester with a compound of the formula XR 1 R 2 R 3 , and optionally further salts and / or Contain additives. These other salts and additives are known to the expert z. B. from Doron Aurbach, Nonaqueous Electrochemistry, Marc Dekker Inc., New York 1999; D. Linden, Handbook of Batteries, Second Edition, McGraw-Hill Inc., New York 1995 and G. Mamantov and AI Popov, Chemistry of Nonaqueous Solutions, Current Progress, VCH Verlagsgemeinschaft, Weinheim 1994. They are hereby introduced as a reference and are therefore considered part of the disclosure.

BeispieleExamples

Im folgenden wird die Erfindung anhand von Beispielen erläutert. Diese Beispiele dienen lediglich der Erläuterung der Erfindung und schränken den allgemeinen Erfindungsgedanken nicht ein.In the following the invention will be explained with the aid of examples. This Examples serve only to illustrate the invention and limit it the general idea of the invention.

Beispiel 1example 1 Darstellung von Methyltrifluormethansulfonat (Methyltriflat)Preparation of methyl trifluoromethanesulfonate (methyl triflate)

In einem 1-l-Rundhalskolben werden 646 g (2,29 mol) Trifluoressigsäureanhydrid und 36 g (0,24 mol) Trifluoressigsäure vorgelegt. Unter ständigem Rühren und Rückflußkühlung werden 206 g (2,29 mol) Dimethylcarbonat bei Raumtemperatur zugegeben. Innerhalb von 10 min erwärmt sich die Lösung auf 50-60°C und wird anschließend noch eine Stunde bei dieser Temperatur weiter gerührt. Anschließend wird die Lösung mit einem Ölbad auf 100-110°C erwärmt und weitere 2 Stunden gerührt. Es werden nach einer Destillation 733 g Methyltrifluormethansulfonat mit einer Reinheit über 99% isoliert.
Siedebereich: 98-99°C, Ausbeute: 97,7%
19F und 1H-NMR sind identisch mit den Literaturdaten (Paquette, Encyclopedia of Reagents for Organic Synthesis, 1995, 3617-3622).646 g (2.29 mol) of trifluoroacetic anhydride and 36 g (0.24 mol) of trifluoroacetic acid are placed in a 1 liter round-necked flask. 206 g (2.29 mol) of dimethyl carbonate are added at room temperature with constant stirring and reflux cooling. The solution heats up to 50-60 ° C. within 10 minutes and is then stirred at this temperature for a further hour. The solution is then heated to 100-110 ° C. with an oil bath and stirred for a further 2 hours. After distillation, 733 g of methyl trifluoromethanesulfonate with a purity of over 99% are isolated.
Boiling range: 98-99 ° C, yield: 97.7%
19 F and 1 H NMR are identical to the literature data (Paquette, Encyclopedia of Reagents for Organic Synthesis, 1995, 3617-3622).

Zu dem Rückstand werden 731 g (2,59 mol) Trifluoressigsäureanhydrid und 232 g (2,58 mol) Dimethylcarbonat gegeben und der oben beschriebene Prozeß wiederholt. Es werden 837 g Methyltrifluormethansulfonat mit einer Reinheit über 99% isoliert.
Ausbeute: 99,1%.731 g (2.59 mol) of trifluoroacetic anhydride and 232 g (2.58 mol) of dimethyl carbonate are added to the residue and the process described above is repeated. 837 g of methyl trifluoromethanesulfonate with a purity of over 99% are isolated.
Yield: 99.1%.

Der Prozeß kann mehrmals wiederholt werden. The process can be repeated several times.  

Beispiel 2Example 2 Darstellung von MethylpentafluorethansulfonatPreparation of methyl pentafluoroethanesulfonate

In einem 10-ml-Rundhalskolben werden 5,74 g (15,0 mmol) Pentafluorethansulfonsäureanhydrid und 0,31 g (1,55 mmol) Pentafluorethansulfonsäure vorgelegt. Unter ständigem Rühren und Rückflußkühlung werden 1,35 g (15,0 mmol) Dimethylcarbonat bei Raumtemperatur zugegeben. Die Lösung wird eine Stunde bei einer Temperatur von 60°C und anschließend bei 110°C 3 Stunden weiter gerührt. Es werden nach einer Destillation 5,41 g Methylpentafluorethansulfonat isoliert.
Siedebereich: 114-115°C, Ausbeute: 84,1%
NMR 19F, ppm: (Lösungsmittel: CDCl3; Standard: CCl3F)
-80,44 s (CF3);
-115,34 s (CF2)
NMR 1H, ppm: (Lösungsmittel: CDCl3; Standard: TMS)
4,23 s (CH3).5.74 g (15.0 mmol) of pentafluoroethanesulfonic anhydride and 0.31 g (1.55 mmol) of pentafluoroethanesulfonic acid are placed in a 10 ml round-necked flask. With constant stirring and reflux cooling, 1.35 g (15.0 mmol) of dimethyl carbonate are added at room temperature. The solution is stirred for one hour at a temperature of 60 ° C and then at 110 ° C for 3 hours. After distillation, 5.41 g of methyl pentafluoroethanesulfonate are isolated.
Boiling range: 114-115 ° C, yield: 84.1%
NMR 19 F, ppm: (solvent: CDCl 3 ; standard: CCl 3 F)
-80.44 s (CF 3 );
-115.34 s (CF 2 )
NMR 1 H, ppm: (solvent: CDCl 3 ; standard: TMS)
4.23 s (CH 3 ).

Das Spektrum wurde auf einem Bruker Spektrometer WP 80 SY erstellt.The spectrum was recorded on a Bruker WP 80 SY spectrometer created.

Beispiel 3Example 3 Darstellung von N-methyl-N-triethylammoniumtrifluormethansulfonatPreparation of N-methyl-N-triethylammonium trifluoromethanesulfonate

Bei Raumtemperatur wird eine Lösung aus 8,35 g (82,7 mmol) Triethylamin in 150 cm3 Hexan vorgelegt. Unter ständigem Rühren werden innerhalb von 10 min 13,56 g (82,7 mmol) Methyltriflat, hergestellt wie in Beispiel 1, bei Raumtemperatur zugegeben. Die Lösung erwärmt sich und wird eine halbe Stunde weiter gerührt. Dabei wird die Lösung wieder auf Raumtemperatur gebracht. Ein weißer Niederschlag wird abfiltriert und mit Hexan gewaschen. Das Hexan- Filtrat kann für eine weitere Umsetzung genutzt werden. Nach der Trocknung im Vakuum bei 60°C werden 21,81 g eines weißen feinkristallinen Materials werden isoliert.
Ausbeute: 99,5%
NMR 19F, ppm: (Lösungsmittel: Acetonitril D3; Standard: CCl3F)
-78,04 s (CF3SO3 -)
NMR 1H, ppm: (Lösungsmittel: Acetonitril D3; Standard: TMS)
1,25 tm (3CH3);
2,86 s (CH3);
3,26 q (3CH2);
J3 H,H = 7,3 HzA solution of 8.35 g (82.7 mmol) of triethylamine in 150 cm 3 of hexane is initially introduced at room temperature. With constant stirring, 13.56 g (82.7 mmol) of methyl triflate, prepared as in Example 1, are added at room temperature within 10 min. The solution warms up and is further stirred for half an hour. The solution is brought back to room temperature. A white precipitate is filtered off and washed with hexane. The hexane filtrate can be used for a further reaction. After drying in vacuo at 60 ° C., 21.81 g of a white, finely crystalline material are isolated.
Yield: 99.5%
NMR 19 F, ppm: (solvent: acetonitrile D 3 ; standard: CCl 3 F)
-78.04 s (CF 3 SO 3 - )
NMR 1 H, ppm: (solvent: acetonitrile D 3 ; standard: TMS)
1.25 tm (3CH 3 );
2.86 s (CH 3 );
3.26 q (3CH 2 );
J 3 H, H = 7.3 Hz

Beispiel 4Example 4 Darstellung von Methyl(triethyl)phosphoniumtrifluormethansulfonatPreparation of methyl (triethyl) phosphonium trifluoromethanesulfonate

Bei Raumtemperatur wird eine Lösung aus 8,05 g (68,2 mmol) Triethylphosphin in 150 cm3 Hexan vorgelegt. Unter ständigem Rühren werden innerhalb von 10 min 11,19 g (68,2 mmol) Methyltriflat, hergestellt wie in Beispiel 1, bei Raumtemperatur zugegeben. Die Lösung erwärmt sich und wird eine halbe Stunde weiter gerührt. Dabei wird die Lösung wieder auf Raumtemperatur gebracht. Ein weißer Niederschlag wird abfiltriert und mit Hexan gewaschen. Das Hexan- Filtrat kann für eine weitere Umsetzung genutzt werden. Nach der Trocknung im Vakuum bei 60°C werden 19,02 g eines weißen feinkristallinen Materials isoliert.
Ausbeute: 98,9%
NMR 19F, ppm: (Lösungsmittel: Aceton D6; Standard: CCl3F)
-77,82 s (CF3SO3 -)
NMR 1H, ppm: (Lösungsmittel: Aceton D6; Standard: TMS)
1,30 dt (3CH3);
1,95d (CH3);
2,40 dq (3CH2);
J3 H,H = 7,7 Hz
J2 P,H = 13,7 Hz
J2 P,H = 13,8 Hz
J3 P,H = 18,8 Hz A solution of 8.05 g (68.2 mmol) of triethylphosphine in 150 cm 3 of hexane is initially introduced at room temperature. With constant stirring, 11.19 g (68.2 mmol) of methyl triflate, prepared as in Example 1, are added at room temperature within 10 min. The solution warms up and is further stirred for half an hour. The solution is brought back to room temperature. A white precipitate is filtered off and washed with hexane. The hexane filtrate can be used for a further reaction. After drying in vacuo at 60 ° C., 19.02 g of a white, finely crystalline material are isolated.
Yield: 98.9%
NMR 19 F, ppm: (solvent: acetone D 6 ; standard: CCl 3 F)
-77.82 s (CF 3 SO 3 - )
NMR 1 H, ppm: (solvent: acetone D 6 ; standard: TMS)
1.30 dt (3CH 3 );
1.95d (CH 3 );
2.40 dq (3CH 2 );
J 3 H, H = 7.7 Hz
J 2 P, H = 13.7 Hz
J 2 P, H = 13.8 Hz
J 3 P, H = 18.8 Hz

Beispiel 5Example 5 Darstellung von 1,3-DimethylimidazoliumtrifluormethansulfonatPreparation of 1,3-dimethylimidazolium trifluoromethanesulfonate

Zu 6,67 g (81,2 mmol) 1-Methylimidazol werden in einem Rundkolben unter Rühren und Eisbad-Kühlung 13,70 g (83,5 mmol) Methyltriflat innerhalb von 10 Minuten zugetropft. Das Reaktionsgemisch erwärmt sich und wird unter Rückflußkühlung 1 Stunde bei 70-75°C gerührt. Der Überschuß an Methyltriflat wird im Vakuum bei 60°C entfernt. 20,00 g eines weißen Pulvers werden isoliert.
NMR 19F, ppm: (Lösungsmittel: Acetonitril D3; Standard: CCl3F)
-78,14 s (CF3SO3 -)
NMR 1H, ppm: (Lösungsmittel: Acetonitril D3; Standard: TMS)
3,82 s (2CH3);
7,35d (2H);
8,53 t (1H);
J4 H;H = 1,6 Hz13.70 g (83.5 mmol) of methyl triflate are added dropwise to 6.67 g (81.2 mmol) of 1-methylimidazole in a round bottom flask with stirring and cooling in an ice bath over the course of 10 minutes. The reaction mixture heats up and is stirred under reflux for 1 hour at 70-75 ° C. The excess methyl triflate is removed in vacuo at 60 ° C. 20.00 g of a white powder are isolated.
NMR 19 F, ppm: (solvent: acetonitrile D 3 ; standard: CCl 3 F)
-78.14 s (CF 3 SO 3 - )
NMR 1 H, ppm: (solvent: acetonitrile D 3 ; standard: TMS)
3.82 s (2CH 3 );
7.35d (2H);
8.53 t (1H);
J 4 H; H = 1.6 Hz

Claims (9)

1. Verfahren zur Herstellung von Verbindungen mit Perfluoralkansulfonsäureresten, unter der Verwendung eines Verfahrensschrittes bei dem Perfluoralkansulfonsäureanhydrid in Gegenwart von Perfluoralkansulfonsäure mit Dialkylcarbonat zu Perfluoralkansulfonsäurealkylester umgesetzt wird.1. Method of making connections with Perfluoroalkanesulfonic acid residues, using a Process step in the perfluoroalkanesulfonic anhydride in Presence of perfluoroalkanesulfonic acid with dialkyl carbonate Perfluoroalkanesulfonsäurealkylester is implemented. 2. Verfahren zur Herstellung von Verbindungen mit Perfluoralkansulfonsäureresten nach Anspruch 1, dadurch gekennzeichnet, daß das Dialkylcarbonat ausgewählt ist aus der Gruppe: Dimethylcarbonat, Diethylcarbonat, Dipropylcarbonat, Dibutylcarbonat oder deren Mischungen.2. Method of making connections with Perfluoroalkanesulfonic acid residues according to claim 1, characterized characterized in that the dialkyl carbonate is selected from the Group: dimethyl carbonate, diethyl carbonate, dipropyl carbonate, Dibutyl carbonate or mixtures thereof. 3. Verfahren zur Herstellung von Perfluoralkansulfonsäureresten nach Anspruch 1 dadurch gekennzeichnet, daß der Perfluoralkansulfonsäurealkylester mit einer Verbindung gemäß der Formel
XR1R2R3,
wobei
X P oder N und
R1, R2, R3
unabhängig voneinander H, Alkyl, Alkylaryl oder Aryl bedeuten, und mindestens ein R ≠ H ist, umgesetzt wird.3. A process for the preparation of perfluoroalkanesulfonic acid residues according to claim 1, characterized in that the perfluoroalkanesulfonic acid alkyl ester with a compound according to the formula
XR 1 R 2 R 3 ,
in which
XP or N and
R 1 , R 2 , R 3
independently of one another denote H, alkyl, alkylaryl or aryl, and at least one R ≠ H is reacted. 4. Verbindung [P(C2H5)3CH][SO3CF3].4. Compound [P (C 2 H 5 ) 3 CH] [SO 3 CF 3 ]. 5. Verwendung der Verbindungen [P(C2H5)3CH3][SO3CF3] und/oder [N(C2H5)3CH3][SO3CF3] in Elektrolyten allein oder in Mischungen mit anderen Salzen und Lösungsmitteln.5. Use of the compounds [P (C 2 H 5 ) 3 CH 3 ] [SO 3 CF 3 ] and / or [N (C 2 H 5 ) 3 CH 3 ] [SO 3 CF 3 ] in electrolytes alone or in mixtures with other salts and solvents. 6. Verwendung der Verbindungen [P(C2H5)3CH3][SO3CF3] und/oder (N(C2H5)3CH3][SO3CF3] gemäß Anspruch 5 als Leitsalz in primären Batterien, sekundären Batterien, Kondensatoren, Superkondensatoren und/oder galvanischen Zellen, ggf. auch in Kombination mit weiteren Salzen.6. Use of the compounds [P (C 2 H 5 ) 3 CH 3 ] [SO 3 CF 3 ] and / or (N (C 2 H 5 ) 3 CH 3 ] [SO 3 CF 3 ] according to claim 5 as the conductive salt in primary batteries, secondary batteries, capacitors, supercapacitors and / or galvanic cells, possibly also in combination with other salts. 7. Elektrolyt, enthaltend die Verbindungen [P(C2H5)3CHj[SO3CF3] und/oder [N(C2H5)3CH3[SO3CF3] allein oder in Mischungen mit anderen Salzen und Lösungsmitteln.7. Electrolyte containing the compounds [P (C 2 H 5 ) 3 CHj [SO 3 CF 3 ] and / or [N (C 2 H 5 ) 3 CH 3 [SO 3 CF 3 ] alone or in mixtures with other salts and solvents. 8. Primäre Batterien, sekundären Batterien, Kondensatoren, Superkondensatoren und/oder galvanischen Zellen enthaltend Elektrolyte nach Anspruch 7.8. Primary batteries, secondary batteries, capacitors, Containing supercapacitors and / or galvanic cells Electrolytes according to claim 7. 9. Verwendung von Perfluoralkansulfonsäurealkylester hergestellt nach einem Verfahren gemäß Anspruch 1 als Methylierungsreagenz.9. Use of perfluoroalkanesulfonic acid alkyl ester prepared by a method according to claim 1 as a methylation reagent.
DE10126929A 2001-06-01 2001-06-01 Production of compounds with perfluoroalkanesulfonic acid residues, used e.g. in electrolytes and batteries, involves reacting perfluoroalkanesulfonic anhydride with dialkyl carbonate in presence of perfluoroalkanesulfonic acid Withdrawn DE10126929A1 (en)

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DE10126929A DE10126929A1 (en) 2001-06-01 2001-06-01 Production of compounds with perfluoroalkanesulfonic acid residues, used e.g. in electrolytes and batteries, involves reacting perfluoroalkanesulfonic anhydride with dialkyl carbonate in presence of perfluoroalkanesulfonic acid
JP2003501834A JP4317918B2 (en) 2001-06-01 2002-05-04 Method for producing perfluoroalkanesulfonic acid ester
CA002449060A CA2449060A1 (en) 2001-06-01 2002-05-04 Process for the preparation of compounds containing perfluoroalkanesulfonic acid groups
EP02776502A EP1399417B1 (en) 2001-06-01 2002-05-04 Method for producing perfluoroalkanesulfonic acid esters
PCT/EP2002/004917 WO2002098844A1 (en) 2001-06-01 2002-05-04 Method for producing perfluoroalkanesulfonic acid esters
US10/478,969 US7084290B2 (en) 2001-06-01 2002-05-04 Method for producing perfluoroalkanesulfonic acid esters
DE50213765T DE50213765D1 (en) 2001-06-01 2002-05-04 PROCESS FOR PREPARING PERFLUOROAL KANSULFONIC ACID ESTERS
EP09006446A EP2085378A1 (en) 2001-06-01 2002-05-04 Perfluor alkane sulphonic acid salts
AU2002344346A AU2002344346A1 (en) 2001-06-01 2002-05-04 Method for producing perfluoroalkanesulfonic acid esters
AT02776502T ATE439340T1 (en) 2001-06-01 2002-05-04 METHOD FOR PRODUCING PERFLUORALKANSULPHONIC ACID ESTERS
IN1656KO2003 IN2003KO01656A (en) 2001-06-01 2003-12-22
US11/443,278 US7585994B2 (en) 2001-06-01 2006-05-31 Process for the preparation of compounds containing perfluoroalkanesulfonic acid groups
JP2009030513A JP4564092B2 (en) 2001-06-01 2009-02-12 Method for producing perfluoroalkanesulfonic acid ester
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2085378A1 (en) 2001-06-01 2009-08-05 Merck Patent GmbH Perfluor alkane sulphonic acid salts
CN114156535A (en) * 2020-09-07 2022-03-08 比亚迪股份有限公司 Electrolyte, lithium ion battery and power vehicle

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2085378A1 (en) 2001-06-01 2009-08-05 Merck Patent GmbH Perfluor alkane sulphonic acid salts
CN114156535A (en) * 2020-09-07 2022-03-08 比亚迪股份有限公司 Electrolyte, lithium ion battery and power vehicle
CN114156535B (en) * 2020-09-07 2023-09-05 比亚迪股份有限公司 Electrolyte, lithium ion battery and power vehicle

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