WO2009132740A2 - Reaktive ionische flüssigkeiten - Google Patents

Reaktive ionische flüssigkeiten Download PDF

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Publication number
WO2009132740A2
WO2009132740A2 PCT/EP2009/002329 EP2009002329W WO2009132740A2 WO 2009132740 A2 WO2009132740 A2 WO 2009132740A2 EP 2009002329 W EP2009002329 W EP 2009002329W WO 2009132740 A2 WO2009132740 A2 WO 2009132740A2
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WIPO (PCT)
Prior art keywords
lithium
ionic liquids
alkyl
fluoroalkyl
potassium
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.)
Ceased
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PCT/EP2009/002329
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German (de)
English (en)
French (fr)
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WO2009132740A3 (de
Inventor
Michael Schmidt
Nikolai Ignatyev (Mykola)
William-Robert Pitner
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Merck Patent GmbH
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Merck Patent GmbH
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to JP2011506585A priority Critical patent/JP5778575B2/ja
Priority to US12/990,029 priority patent/US9006457B2/en
Priority to EP09737784.0A priority patent/EP2274291B1/de
Priority to CN200980115361.8A priority patent/CN102015666B/zh
Publication of WO2009132740A2 publication Critical patent/WO2009132740A2/de
Publication of WO2009132740A3 publication Critical patent/WO2009132740A3/de
Anticipated expiration legal-status Critical
Priority to US14/620,861 priority patent/US9624160B2/en
Ceased legal-status Critical Current

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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
    • H01M10/056—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
    • H01M10/0569—Liquid materials characterised by the solvents
    • 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
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion 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
    • Y02E60/10—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

Definitions

  • the invention relates to reactive ionic liquids containing organic cations with electrochemically reduction-susceptible groups or substituents and anions of fluoroalkyl phosphates,
  • Fluoroalkyl phosphinates, fluoroalkyl phosphonates, acetates, triflates, methides, borates, phosphates and aluminates for use in electrochemical cells such as lithium ion batteries and double layer capacitors.
  • Ionic liquids or liquid salts are ionic species consisting of an organic cation and a generally inorganic anion. They contain no neutral molecules and usually have melting points less than 373 K.
  • reactive ionic liquids ionic liquids which have electrochemically reduction-susceptible groups or substituents on the organic cation, such as cyano groups, ester groups, carbonate groups or side chains with double bonds.
  • ionic liquids have gained more and more interest, and a variety of review articles have described unique properties of ionic fluids (ionic liquids, lonic liquids, or "ILs" for short) and demonstrated various potential uses.
  • ionic liquids appear promising for use in energy storage media such as double layer capacitors and batteries with a particular focus on electric and hybrid vehicles.
  • Outstanding properties of ionic liquids include: • A practical non-existent volatility and therefore very high flashpoints • A very large liquid area over several 100K in some cases
  • Tetrafluoroborate (EMIBF 4 ) are already used commercially in double-layer capacitors (super or ultracaps), the use of batteries in particular lithium-ion batteries continues to be difficult. 0
  • AICI4-based ionic liquids are extremely sensitive to hydrolysis and react with water to release hydrochloric acid HCl.
  • the development for battery systems has been discontinued due to this.
  • Imidazolium-based ILs show inadequate reductive stability and are therefore not considered to be promising for commercial use in high energy batteries.
  • Ionic liquids with inorganic anions, especially with BF4- cause, especially in the first charge / discharge cycles, a significant capacity drop.
  • the ionic liquids currently best suited for Li-ion batteries use N 1 N di-alkyl pyrollidinium in combination with bis (trifluoromethyl) imides (see, eg, JP 2006-260952). However, even these ionic liquids still cause a significant decrease in the power densities of lithium-ion batteries.
  • the object of the present invention was therefore to develop ionic liquids which have a high thermal stability, very good Have oxidation stability and low corrosivity and cost synthesized anions and do not have the above-mentioned disadvantages.
  • K + is a cation, preferably stable to reduction, selected from the group of the general formulas II to IX
  • Ri to R 4 halogen, in particular F, and / or a fluorinated or not
  • OU is fluorinated alkoxy or carboxy radical.
  • the reactive ionic liquids according to the invention are distinguished by the fact that they are susceptible to electrochemical reduction in the organic cation
  • the reactive ionic liquids according to the invention significantly form a passivating outer layer rather than ethylene carbonate (0.7 to 0.8 V versus Li / Li + ).
  • This cover layer is electronically passivating, but permeable to lithium ions.
  • Another advantage is the excellent oxidation stability with> 5 V versus Li / Li + .
  • the reactive ionic liquids of this invention are nonvolatile and have no measurable vapor pressure.
  • the cations K + of the ionic liquids according to the invention are cations selected from the general formula IV
  • X is CH 2 , O, S or NR ' R ' - (CH 2 ) n -CN, methyl, ethyl, propyl, butyl, HRH, methyl, ethyl, propyl, butyl
  • electrolyte comprising at least one conducting salt, an aprotic solvent or solvent mixture, at least one ionic liquid of the abovementioned formula I according to the invention and optionally further additives.
  • the conductive salt is a lithium secondary salt such as LiPF 6 , LiN (SO 2 CF 3 ) 2 , LiN (SO 2 C 2 Fs) 2 , LiF 3 P ( C 2 Fs) 3 , LiF 3 P (C 4 Fg) 3 , LiB (C 2 O 4 ) 2 or LiF 2 B (C 2 O 4 ) 2.
  • the conductive salt is a compound from the group N (C 2 Hs) 4 BF 4 N (C 2 Hs) 4 PF 6 , N (C 2 Hs) 3 (CH 3 ) BF 4 , N (C 2 Hs) 3 (CH 3 ) PF 6 , N (C 2 H 5 ) 4 N (SO 2 CF 3 ) 2 , N (C 2 Hs) 3 (CH 3 ) N (SO 2 CF 3 ) ,
  • the aprotic solvent of the electrolyte consists of organic open-chain or cyclic carbonates, carboxylic acid esters, nitriles, ethers or lactones or a mixture thereof.
  • Nitriles, in particular acetonitrile, are preferably used as solvents in double-layer capacitors.
  • Another object of the present invention is a process for the preparation of ionic liquids of the formula I.
  • Halogencarbonates, halogenated alkylnitriles or alkyl halides by conventional wet-chemical methods.
  • the anions according to the invention are stable to oxidation, as can be seen from Tables 1.1 to 1.3.
  • Table i.1 Electrochemical stability of reactive ionic liquids with tris (pentafluoroethyl) trifluorophosphate anion (FAP anion) and bis (pentafluoroethyl) phosphinate anion, (C 2 F 5 JaP (O) O " , in comparison to similar ionic liquids with Triflate and tetrafluoroborate anions
  • the preparation of the fluoroalkyl phosphate-based reactive ionic liquids is effected by reacting the corresponding cationic onium chlorides or onium bromides with the corresponding potassium or sodium fluoroalkyl phosphates or fluoroalkylphosphoric acid (HFAP) in an aqueous medium.
  • HFAP fluoroalkylphosphoric acid
  • the preparation of the imide and methide-based ionic liquids is carried out by reacting the corresponding, cationic onium chlorides or onium bromides with the corresponding lithium salts in an aqueous medium.
  • the preparation of the trifluoroacetate and triflate-based ionic liquids is accomplished by three different methods:
  • the preparation of the trifluoroacetate and triflate-based ionic liquids is via the triflic acid or trifluoroacetic acid and / or methyl or ethyl triflates or trifluoroacetates or trimethylsilyl triflates,
  • Triflic anhydride or trifluoroacet-anhydride method preferred.
  • the borate, phosphate or aluminate-based reactive ionic liquids are prepared by reacting the corresponding cationic onium chlorides or onium bromides with the corresponding anionic potassium or lithium borates, phosphates or aluminates in an aqueous or organic medium ,
  • reaction of the cations according to the invention with the anions to the end product can be carried out at temperatures of 0 to 150 0 C, preferably at 0 to 5O 0 C and in particular at room temperature.
  • Suitable solvents or solvent mixtures are water or deionized water, alcohols, dioxane, acetonitrile and acetone.
  • the alcohol used is preferably methanol and isopropanol.
  • methyl phosphinates usually no solvent is needed.
  • Another object of the present invention is an electrochemical and / or electro-optical device containing at least one electrolyte which contains at least one ionic liquid of the general formula I.
  • the device may be a solar cell, lithium or lithium ion battery
  • Double-layer and supercapacitor, lithium capacitor, a light-emitting device, an electrochemical sensor and / or biosensor Double-layer and supercapacitor, lithium capacitor, a light-emitting device, an electrochemical sensor and / or biosensor.
  • the present invention relates to the use of said reactive ionic liquids according to the general formula I as conductive salt or additive in electrolytes for electrochemical or electro-optical cells.
  • the reactive ionic liquids according to the invention are used as electrolyte salt or additive in batteries for batteries, secondary lithium batteries, double-layer and supercapacitors or lithium capacitors.
  • the subject of the present invention is the use of the electrolytes according to the invention in electrochemical and / or electro-optical devices.
  • these devices are lithium or lithium ion batteries as well as double-layer and supercapacitors or lithium capacitors.
  • Halogencarboxylats or, carbonate preferably Bromcarboxylat or - carbonate
  • the reaction mixture was allowed to continue to react for 0.5 to 48 hours at this temperature and stirred into 1 L of ethyl acetate, whereby the product precipitates as a white solid.
  • the product is filtered off, washed with ethyl acetate and dried (rotary evaporator at about 30 0 C water bath). The yield is between 90 and 95%
  • Onium chloride (from the examples described above) dissolved in 200 ml of deionized water and then slowly added with 1 mole of the corresponding bis (fluoroalkyl) phosphinic acid.
  • reaction mixture is stirred for a further 1 h at room temperature and water is distilled off together with the resulting hydrochloric acid.
  • water is distilled off together with the resulting hydrochloric acid.
  • Example 5.2 Preparation of bis (fluoroalkyl) phosphinate-based reactive ionic liquids via the corresponding potassium salts
  • Onium chloride (from the examples previously described) in / so-propanol (or methanol, or acetonitrile) dissolved and then slowly with 1
  • reaction mixture is stirred for 1 to 20 h at room temperature or heating to 100 ° C and resulting CH 3 Cl (or CH 3 Br) and excess of methyl bis (fluoroalkyl) phosphinate removed in vacuo.
  • Bis (fluoroalkyl) phosphinates form in near quantitative yield.
  • the organic solution is mixed with 10 g of Al 2 O 3 and 1, 4 g of activated charcoal and filtered again after about 1 h and concentrated on a rotary evaporator in a water bath of about 80 0 C.
  • Onium chloride (from the previously described examples) in 200-500 ml
  • reaction mixture is stirred for a further 1 h at room temperature and water is distilled off together with the resulting HCl.
  • Onium chloride (from the examples described above) dissolved in / so-propanol (or methanol or acetonitrile) and then slowly added with 1 mol of the corresponding potassium (or lithium) trifluoroacetates or triflates.
  • reaction mixture is stirred for a further 1 h at room temperature and the resulting KCl (or LiCl) is filtered off. After removal of isopropanol (or methanol or acetonitrile) in vacuo with
  • Rotary evaporator gives the trifluoroacetates or triflates in near quantitative yield.
  • Triflates Triflates, trimethylsilyl triflates, triflic anhydrides or trifluoroacetate anhydrides
  • the reaction mixture is stirred for 1 to 48 h at room temperature or at heating to 100 ° C and arising CH 3 CI (or CH 3 Br, or (CH 3) 3 SiCl or CF 3 SO 2 CI or CF 3 COCI or CF 3 COBr ) and Excess of methyl or trimethylsilyl triflates or anhydrides removed in vacuo. Trifluoroacetates or triflates form in close to quantitative yield.
  • Example 7 Preparation of borate, phosphate and aluminate-based ionic liquids
  • the n-heptane phase with the ionic liquid was separated overnight and concentrated on a rotary evaporator in a water bath of 60 to 70 0 C.
  • lithium counter electrode and lithium reference electrode are each 5
  • Cyclic voltammograms taken in succession. For this purpose, starting from the rest potential, the potential is first lowered to 0 V with respect to Li / Li "1" at a feed rate of 0.1 mV / s and then returned to the rest potential in the further course.
  • the electrolyte used is 1M LiPF 6 in ethylene carbonate: diethylene carbonate (ratio 3: 7), to which in each case between about 2% of a reactive ionic liquid selected from Table 7 is added.
  • the reactive ionic liquid forms a passivating surface layer at potentials between approx. 2 V and 0.9 V versus Li / Li + . From the second cycle, a 95% yield ( ⁇ 5% measurement tolerance) of the incorporation and removal of lithium ions into the graphite is achieved. Co-intercalation of the reactive ionic liquid selected from Table 15 into the graphite can not be observed.
  • lithium counterelectrode and lithium reference electrode 5 Zyklovoltammog ramme are added in succession.
  • the potential is first lowered to 0 V with respect to Li / Li + at a feed rate of 0.1 mV / s and then driven back to the rest potential in the further course.
  • the electrolyte used is 1 M LiPF 6 in EC: DEC (3: 7), to which in each case between about 10% of a reactive ionic liquid selected from Table 8 is added.
  • the reactive ionic liquid forms a passivating surface layer at potentials between about 2 V and 0.9 V versus Li / Li + . From the second cycle on, a more than 90% yield of the incorporation and removal of lithium ions into the graphite is achieved.
  • the electrolyte used is 1M LiPF 6 in EC: DEC (3: 7), to which in each case between about 2% of a reactive ionic liquid selected from Table 17 is added.
  • the oxidation potential is determined to be> 5V versus Li / Li + . In none of the investigated systems is a signal found that is below the oxidation stability of the reference electrolyte.

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EP2274291B1 (de) 2016-06-01
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JP5778575B2 (ja) 2015-09-16
DE102008021271A1 (de) 2010-01-28
US20150152045A1 (en) 2015-06-04
US20110045359A1 (en) 2011-02-24
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EP2274291A2 (de) 2011-01-19

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