Classifications

• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
  • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
  • C01B21/092—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more metal atoms
  • C01B21/0923—Metal imides or amides
  • C01B21/0926—Metal imides or amides of alkali metals
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
  • C01D15/00—Lithium compounds
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
  • C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
  • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
  • C01B21/092—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more metal atoms
  • C01B21/0923—Metal imides or amides
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
  • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
  • C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
  • C01B21/0935—Imidodisulfonic acid; Nitrilotrisulfonic acid; Salts thereof
• • 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
• • 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
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M2300/00—Electrolytes
  • H01M2300/0002—Aqueous electrolytes
  • H01M2300/0005—Acid electrolytes
• • 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

Definitions

• the present invention relates to a bis (fluorosulfonyl) imide lithium salt composition.
• Anions of sulfonylimide type by their very low basicity, are increasingly used in the field of energy storage in the form of inorganic salts in batteries, or organic salts in supercapacitors or in the field of liquids ionic.
• LiPF 6 LiPF 6
• this salt shows numerous disadvantages such as limited thermal stability, sensitivity to hydrolysis and therefore lower battery safety.
• new salts having the FSO 2 group have been studied and have demonstrated many advantages such as better ionic conductivity and resistance to hydrolysis.
• LiFSI LiN (FSO 2 ) 2
• LiFSI LiN (FSO 2 ) 2
• the present invention relates to a composition
• a composition comprising:
• lithium salt of bis (fluorosulfonyl) imide lithium, or lithium bis (fluorosulfonyl) imide.
• ppm or "part per million” means ppm by weight.
• the above-mentioned composition comprises at least 99.78%, preferably at least 99.80%, advantageously at least 99.85%, even more preferably at least 99.90% by weight of bis (fluorosulfonyl) lithium salt. imide, relative to the total weight of said composition.
• the composition comprises at least 99.95%, preferably at least 99.97%, advantageously at least 99.98%, even more preferably at least 99.99% by weight of bis (fluorosulfonyl) imide lithium salt. relative to the total weight of said composition.
• the mass content of acetic acid in the composition is less than or equal to 350 ppm, preferably less than or equal to 300 ppm, advantageously less than or equal to 250 ppm, even more advantageously less than or equal to 200 ppm, example less than or equal to 150 ppm. Even more preferably, the acetic acid content in the composition is less than or equal to 100 ppm, and in particular less than or equal to 50 ppm, relative to the total weight of the composition.
• the mass content of acetic acid in the composition is greater than or equal to 0.1 ppm, preferably greater than or equal to 1 ppm, advantageously greater than or equal to 10 ppm relative to the total weight of the composition. .
• the mass content of acetic acid in the composition ranges from 0.1 ppm to 300 ppm, preferably from 0.1 ppm to 200 ppm, advantageously from 0.1 ppm to 150 ppm, even more advantageously from 0.1 ppm to 100 ppm relative to the total weight of the composition.
• composition may also include:
• a content of Cl ions less than or equal to 20 ppm by weight, preferably less than or equal to 15 ppm, advantageously less than or equal to 10 ppm, by weight relative to the total weight of said composition;
• an H 2 O content less than or equal to 200 ppm, preferably less than or equal to 100 ppm, advantageously less than or equal to 50 ppm, still more preferably less than or equal to 30 ppm by weight relative to the total weight of said composition; and or
• a Na + content less than or equal to 200 ppm, preferably less than or equal to 100 ppm, advantageously less than or equal to 50 ppm, still more advantageously less than or equal to 20 ppm by weight relative to the total weight of said composition; and or
• a content of FSO 3 Li less than or equal to 500 ppm, preferably less than or equal to 300 ppm, advantageously less than or equal to 200 ppm, even more advantageously less than or equal to 100 ppm, and in particular less than or equal to 20 ppm by weight relative to the total weight of said composition; and or
• a content of FSO2NH2 less than or equal to 200 ppm preferably less than or equal to 100 ppm, advantageously less than or equal to 50 ppm, even more advantageously less than or equal to 20 ppm, and in particular less than or equal to 10 ppm by weight relative to the total weight of said composition.
• the composition comprises:
• an F content ranging from 0 to 200 ppm, preferably ranging from 0 to 50 ppm, advantageously ranging from 0 to 30 ppm by weight relative to the total weight of said composition;
• an H 2 O content ranging from 0 to 200 ppm, preferably ranging from 0 to 100 ppm, advantageously ranging from 0 to 50 ppm, still more advantageously ranging from 0 to 30 ppm by weight relative to the total weight of said composition; ; and or
• a content of SO 4 2 ranging from 0 to 300 ppm, preferably ranging from 0 to 200 ppm, advantageously ranging from 0 to 100 ppm, still more advantageously ranging from 0 to 50 ppm by weight relative to the total weight of said composition; ; and or
• a Na + content ranging from 0 to 200 ppm, preferably ranging from 0 to 100 ppm, advantageously ranging from 0 to 50 ppm, even more advantageously ranging from 0 to 20 ppm by weight relative to the total weight of said composition; and or
• a content of FSO 3 Li ranging from 0 to 500 ppm, preferably ranging from 0 to 300 ppm, advantageously ranging from 0 to 200 ppm, still more advantageously ranging from 0 to 100 ppm, and in particular ranging from 0 to 20 ppm; by weight relative to the total weight of said composition; and or
• a content of FSO 2 NH 2 ranging from 0 to 200 ppm, preferably ranging from 0 to 100 ppm, advantageously ranging from 0 to 50 ppm, still more advantageously ranging from 0 to 20 ppm, and in particular ranging from 0 to 10 ppm; ppm by weight relative to the total weight of said composition.
• the composition comprises:
• an F-content ranging from 0.1 to 200 ppm, preferably ranging from 0.1 to 50 ppm, advantageously ranging from 0.1 to 30 ppm by weight relative to the total weight of said composition;
• a content of H 2 O ranging from 0.1 to 200 ppm, preferably ranging from 0.1 to 100 ppm, advantageously ranging from 0.1 to 50 ppm, still more advantageously from 0.1 to 30 ppm by weight; relative to the total weight of said composition; and or
• a content of SO 4 2 ranging from 0.1 to 300 ppm, preferably ranging from 0.1 to 200 ppm, advantageously ranging from 0.1 to 100 ppm, still more advantageously ranging from 0.1 to 50 ppm by weight; relative to the total weight of said composition C; and or
• a Na + content ranging from 0.1 to 200 ppm, preferably ranging from 0.1 to 100 ppm, advantageously ranging from 0.1 to 50 ppm, still more advantageously ranging from 0.1 to 20 ppm by weight; relative to the total weight of said composition; and or
• a content of FS0 3 Li ranging from 0.1 to 500 ppm, preferably ranging from 0.1 to 300 ppm, advantageously ranging from 0.1 to 200 ppm, more advantageously from 0.1 to 100 ppm, and in particular ranging from 0.1 to 20 ppm by weight relative to the total weight of said composition; and or
• a content of FSO 2 NH 2 ranging from 0.1 to 200 ppm, preferably ranging from 0.1 to 100 ppm, advantageously ranging from 0.1 to 50 ppm, more advantageously from 0.1 to 20 ppm, and in particular ranging from 0.1 to 10 ppm by weight relative to the total weight of said composition.
• the composition may also comprise a butyl acetate content less than or equal to 2000 ppm, preferably less than or equal to 1500 ppm, preferably less than or equal to 1000 ppm, advantageously less than or equal to 500 ppm, even more advantageously lower or equal to 250 ppm, for example less than or equal to 150 ppm.
• the composition according to the invention is characterized in that the sum of the total contents of acetic acid and of butyl acetate is less than or equal to 2 200 ppm, preferably less than or equal to 1 700 ppm, advantageously less than or equal to at 1200 ppm based on the total weight of the composition.
• the composition is such that:
• the composition may also comprise a butanol content less than or equal to 500 ppm, preferably less than or equal to 300 ppm, preferably less than or equal to 200 ppm, advantageously less than or equal to 100 ppm, in particular less than or equal to 50 ppm by relative to the total weight of the composition.
• the composition may also comprise a content of crystallization solvent, preferably chosen from chlorinated solvents and aromatic solvents, less than or equal to 1000 ppm, preferably less than or equal to 800 ppm, preferably less than or equal to 500 ppm, advantageously less than or equal to 200 ppm, in particular less than or equal to 100 ppm relative to the total weight of the composition.
• a content of crystallization solvent preferably chosen from chlorinated solvents and aromatic solvents, less than or equal to 1000 ppm, preferably less than or equal to 800 ppm, preferably less than or equal to 500 ppm, advantageously less than or equal to 200 ppm, in particular less than or equal to 100 ppm relative to the total weight of the composition.
• crystallization solvent the solvent optionally used to crystallize the lithium salt of bis (fluorosulfonyl) imide.
• This solvent is preferably dichloromethane or toluene.
• the composition according to the invention is characterized in that the sum of the total contents of acetic acid and water is less than or equal to 400 ppm, preferably less than or equal to 300 ppm, advantageously less than or equal to 250 ppm by relative to the total weight of the composition.
• the composition is such that:
• the amount of acetic acid and / or butyl acetate and / or butanol and / or crystallization solvent is determined by proton NMR with an internal standard: trifluorotoluene.
• the composition according to the invention can be obtained by a process comprising the following steps:
• composition C1 comprising an organic solvent SOI, water and bis (fluorosulfonyl) imide salt, to produce a composition C2 comprising:
• said pre-concentration step being carried out at a temperature of less than or equal to 50 ° C;
• the bis (fluorosulfonyl) imide lithium salt of the composition C1 can be obtained by any known method for preparing said salt, for example as described in WO2015 / 158979 or WO2009 / 1233328.
• composition C1 may be obtained by any known method for preparing bis (fluorosulfonyl) imide lithium salt.
• composition C1 can also be obtained according to a process comprising the following steps:
• step ii) a step of contacting with an organic solvent SO 2 in the case where the LiFSI salt obtained in step i) is solid;
• composition C1 comprises:
• a mass content of water ranging from 0.1% to 10%, preferably from 1% to 10%, advantageously from 1.5% to 10% by weight relative to the total weight of said composition C1; and or a mass content of bis (fluorosulfonyl) imide salt ranging from 5% to 30%, preferably from 5% to 20% by weight relative to the total mass of the composition.
• the above-mentioned organic solvent SO 2 may be selected from the group consisting of esters, nitriles, ethers, chlorinated solvents, aromatic solvents, and mixtures thereof.
• the solvent SO 2 is chosen from dichloromethane, ethyl acetate, butyl acetate, tetrahydrofuran, acetonitrile, diethyl ether, and mixtures thereof.
• the organic solvent SO 2 is butyl acetate.
• the above-mentioned step iii) can be repeated at least once.
• the organic solvent SOI is selected from the group consisting of esters, nitriles, ethers, chlorinated solvents, aromatic solvents, and mixtures thereof.
• the SOI solvent is chosen from ethers, esters, and mixtures thereof.
• the solvent SOI is chosen from methyl-t-butyl ether, cyclopentyl methyl ether, ethyl acetate, propyl acetate and butyl acetate, and mixtures thereof, the organic solvent SO 2 being preferentially butyl acetate.
• Pre-concentration step a) is preferably carried out at a temperature of 25 ° C to 45 ° C, preferably 30 ° C to 40 ° C.
• the pre-concentration step a) is carried out under reduced pressure, for example at a pressure of less than or equal to 50 mbar abs, in particular at a pressure of less than or equal to 30 mbar abs.
• the pre-concentration step a) can be carried out by any means allowing the concentration, for example using an evaporator.
• the above-mentioned step b) is carried out in a short-path thin-film evaporator under the following conditions:
• the term “residence time” means the time elapsing between the entry of the lithium salt solution of bis (fluorosulfonyl) imide (in particular obtained at the end of step b) above) in the evaporator and the outlet of the first drop of the solution.
• the temperature of the condenser of the short-path thin-film evaporator is between -50 ° to 5 ° C., preferably between -35 ° C. and 5 ° C. In particular, the temperature of the condenser is -5 ° C.
• Short-path thin-film evaporators are also known under the name “Wiped film short path” (WFSP). They are typically so called because the vapors generated during evaporation make a “short trip" (short distance) before being condensed to the condenser.
• WFSP Wiped film short path
• evaporators marketed by the companies Buss SMS Ganzler ex Luwa AG, UIC Gmbh or VTA Process.
• short-path thin-film evaporators may include a solvent vapor condenser positioned within the apparatus itself (particularly in the center of the apparatus), unlike other types of film evaporators. thin (which are not short path) in which the condenser is located outside the device.
• the formation of a thin film of product to be distilled on the internal hot wall of the evaporator can typically be provided by continuously spreading on the evaporation surface by mechanical means. specified below.
• the evaporator may in particular be provided at its center, an axial rotor on which are mounted the mechanical means that allow the formation of the film on the wall.
• They may be rotors equipped with fixed blades: three-blade or four-blade lobed rotors in flexible or rigid materials, distributed over the entire height of the rotor or rotors equipped with moving blades, pallets, scrapers, guided rubbers.
• the rotor may be constituted by a succession of articulated pallets on pivot mounted on a shaft or axis via radial supports.
• Other rotors may be equipped with mobile rollers mounted on secondary axes and said rollers are pressed on the wall by centrifugation.
• the rotational speed of the rotor which depends on the size of the apparatus can be readily determined by those skilled in the art.
• the various mobiles can be made of various materials, for example metal, steel, alloy steel (stainless steel), aluminum, or polymers, for example polytetrafluoroethylene PTFE or glass materials (enamel); metallic materials coated with polymeric materials.
• the solution is introduced into the short-path thin film evaporator with a flow rate of between 700 g / h and 1200 g / h, preferably between 900 g / h and 1100 g / h for a evaporation surface of 0.04 m 2 .
• the aforementioned method further comprises a step c) of crystallization of the lithium salt of bis (fluorosulfonyl) imide obtained at the end of step b) mentioned above.
• the crystallization step may be carried out in an organic solvent ("crystallization solvent") chosen from chlorinated solvents, such as, for example, dichloromethane, and aromatic solvents, such as, for example, toluene.
• chlorinated solvents such as, for example, dichloromethane
• aromatic solvents such as, for example, toluene.
• the LiFSI composition obtained at the end of step c) is recovered by filtration.
• the crystallization is carried out at a temperature of less than or equal to 25 ° C., preferably less than or equal to 15 ° C.
• the ester solvents used to prepare the bis (fluorosulfonyl) imide lithium salt can be hydrolyzed (in the presence of water) to the decomposition products: acid and alcohol.
• Butyl acetate can in particular be hydrolyzed to acetic acid and butanol.
• the inventors have discovered that a high content of acetic acid can adversely affect the performance of the battery.
• the process according to the invention advantageously makes it possible to reduce or even avoid the partial decomposition of the organic solvents used, such as, for example, butyl acetate and acetic acid and / or butanol.
• composition according to the invention advantageously leads to improved performance in the batteries.
• composition according to the invention has at least one of the following advantages:
• the corrosion of the aluminum current collector is advantageously reduced and / or zero;
• the present invention also relates to the use of the composition according to the invention in batteries, in particular in Li-ion batteries.
• composition according to the invention can be used in Li-ion batteries of mobile devices (for example mobile phones, cameras, tablets or laptops), or electric vehicles, or storage vehicles. renewable energy (such as photovoltaic or wind energy).
• between x and y or “ranging from x to y” means an interval in which the terminals x and y are included.
• the temperature "between 30 and 100 ° C” includes in particular the values 30 ° C and 100 ° C. All the embodiments described above can be combined with each other.
• Residual solvent content Head space method or head space
• Butanol-1 0.01% by weight
• Acetic acid 5% by weight
• the limit of detection of acetic acid is particularly high.
• the H1 NMR analysis conditions are as follows:
• NMR spectra and quantification were performed on a Bruker AV 400 spectrometer, at 376.47 MHz for 19 F, on a 5 mm BBFO + probe.
• Absolute quantification by 19 F NMR and proton NMR is done by metered addition of ⁇ , ⁇ , ⁇ -trifluorotoluene (TFT), Aldrich into the tube containing the sample.
• TFT trifluorotoluene
• the signals of the fluorinated species to be assayed are integrated in comparison with that of the CF 3s of this internal standard, according to a method well known to those skilled in the art.
• proton NMR the quantification is done similarly to the aromatic proton signal of trifluorotoluene.
• the limit of quantification of a species is of the order of fifty ppm.
• LiFSI LiFSI in 823 g of butyl acetate
• the concentration of LiFSI is about 10% by weight and the water content of this solution is 3% by weight.
• the water content of this solution is greater than the solubility of water in butyl acetate due to the combination of lithium salt with water.
• a first concentration by evaporation of the solvent is carried out with a rotary evaporator at 40 ° C under reduced pressure (P ⁇ 30mbars).
• a solution is obtained whose dry extract is 42% and the water content measured by titration is 430 pppm.
• the last concentration is carried out on a film evaporation apparatus WFSP (Wiped Film Short Path) at the temperature of 80 ° C scus a vacuum of 0.5 mbar. This concentrate is taken up in dichloromethane. LiFSI crystallizes rapidly. After one hour of contact time, solid LiFSI is obtained which is recovered by filtration and which is dried under vacuum for at least 24 hours. The mass of solid LiFSI is 1 10 g, a yield of 82%.
• WFSP Wide Film Short Path
• the "head-space" measurement method by gas chromatography introduces a bias in the quantification of organic species because the measurement is directly related to the liquid / vapor equilibrium of the system (underestimated results).
• the NMR assay method is more reliable because it is a direct measurement of the composition, and has a lower detection limit than the head-space method.
• the electrolyte solutions No. 1 and No. 2 are made by dissolving the LiFSIs prepared according to Examples 1 and 2 above in a mixture of ethylene carbonate / ethylmethylcarbonate 3/7 by volume.
• the concentration of LiFSI is 0.8 mol / l.
• 2% by weight of fluroethylene carbonate is added to each electrolyte.
• Cyclic voltammetry test The cyclic volumetric tests are performed on button cells with a lithium metal anode and an aluminum cathode with the prepared electrolyte. The voltage is varied between 0 and 6V with a scanning speed of 1 mV / s over 3 cycles. The current obtained in the third cycle is noted, therefore, after formation of the optional passivation layer.
• the table below presents the results:
• electrolyte # 2 led to a running having a higher intensity than that obtained with the electrolyte 0 n 1.
• the current with a higher intensity indicates a higher corrosion of the aluminum.
• This test consists in imposing a constant voltage on a battery of the same type as that described for the cyclic voltametry test and for monitoring the intensity of current through the cell.
• the objective is to measure the leakage current, residual current of constant intensity, which accounts for the polarization of the battery and its lifetime. The higher the leakage current, the shorter the life of the battery.
• the test was performed at 4V.
• the leakage current is 3.1 mA.
• the leakage current for the cell manufactured with the LiFSI of Example 2 is 15 mA.

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