WO2024061956A1 - Procédé de production de sels d'imide de sulfonyle alcalin - Google Patents

Procédé de production de sels d'imide de sulfonyle alcalin Download PDF

Info

Publication number
WO2024061956A1
WO2024061956A1 PCT/EP2023/075914 EP2023075914W WO2024061956A1 WO 2024061956 A1 WO2024061956 A1 WO 2024061956A1 EP 2023075914 W EP2023075914 W EP 2023075914W WO 2024061956 A1 WO2024061956 A1 WO 2024061956A1
Authority
WO
WIPO (PCT)
Prior art keywords
salt
solvent
csi
mixture
hcsi
Prior art date
Application number
PCT/EP2023/075914
Other languages
English (en)
Inventor
Elie Derrien
Etienne SCHMITT
Vincent Schanen
Original Assignee
Specialty Operations France
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.)
Filing date
Publication date
Application filed by Specialty Operations France filed Critical Specialty Operations France
Publication of WO2024061956A1 publication Critical patent/WO2024061956A1/fr

Links

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
    • C01B21/086—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
    • C01B21/093—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
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries

Definitions

  • the present invention relates to a method for producing a salt of bis(chloro sulfonyl)imide, which is economically feasible at industrial scale and which provides a high-purity product.
  • the present invention also provides a method for producing a lithium salt of bis(fluoro sulfonyl)imide (LiFSI), wherein said HCSI salt is used as an intermediate compound.
  • LiFSI bis(fluorosulfonyl)imide
  • HCSI bis(chlorosulfonyl)imide
  • HF hydrous hydrogen fluoride
  • KR 20190001092 (in the name of LIM KWANG MIN) discloses a method for manufacturing lithium bis(fluorosulfonyl)imide (LiFSI) comprising reacting a lithiation agent, a solvent and bis(chlorosulfonyl)imide (HCSI) and a fluorination reagent.
  • LiFSI lithium bis(fluorosulfonyl)imide
  • LiFSI LiFSI
  • HCSI bis(chlorosulfonyl)imide
  • HFSI bis(fluorosulfonyl)imide
  • a fluorination agent for example anhydrous hydrogen fluoride (HF)
  • HF anhydrous hydrogen fluoride
  • Another known two-step process for preparing LiFSI involves a first step of fluorination of bis(chlorosulfonyl)imide (HCSI) into ammonium bis(fluorosulfonyl)imide (NH4FSI) using NH4F(HF) X as a fluorinating agent, followed by a second step of lithiation of NH4FSI, leading then to the LiFSI product.
  • HCSI bis(chlorosulfonyl)imide
  • NH4FSI ammonium bis(fluorosulfonyl)imide
  • NH4FSI ammonium bis(fluorosulfonyl)imide
  • Another known two-step process for preparing LiFSI involves the lithiation of HCSI in a first step using a lithiation agent in order to prepare LiCSI as an intermediate product, and then the fluorination of LiCSI into LiFSI using a fluorination agent.
  • KR 20200049164 (in the name of CLS LABORATORIES INC.) discloses a LIFSI preparation method, comprising the reaction of HCSI with a lithiation reagent in an (S1) solvent to produce LiCSI as an intermediate product, which is not purified/separated but is rather directly reacted with an anhydrous fluorination reagent without purification. After lithium bis(fluorosulfonyl)imide is obtained, it is then filtered and concentrated, and then the solvent is completely removed using a thin film distiller at low temperature, thus obtaining a crystalline powder. In this method, the reaction is performed using a single solvent and no additional crystallisation or re-crystallization process is performed.
  • CN 103524387 discloses a preparation method for LiFSI comprising: (I) reacting sulfamic acid and chlorosulfonic acid in thionyl chloride solvent to prepare HCSI, (II) adding LiCI and remove the thionyl chloride solvent to obtain LiCSI, (III) add acetonitrile or butyl acetate and then add ZnF and filter to obtain a filtrate containing LiFSI salt, (IV) re-crystal I ize in methylene chloride to obtain a solid and drying.
  • the Applicant faced the technical problem of providing a method for manufacturing LiCSI having a low content of impurities such that it can be used for manufacturing LiFSI.
  • an element or component is said to be included in and/or selected from a list of recited elements or components, it should be understood that in related embodiments explicitly contemplated here, the element or component can also be any one of the individual recited elements or components, or can also be selected from a group consisting of any two or more of the explicitly listed elements or components; any element or component recited in a list of elements or components may be omitted from such list.
  • the present application relates to a method for the manufacture of a salt of bis(chloro sulfonyl)imide [CSI salt] in solid form, said method comprising:
  • M is selected from lithium, sodium, potassium and ammonium; x is 1 or 2; and
  • B is selected from Cl, COa 2 ' , SO4 2 ' , carboxylate; silicate, preferably metasilicate; borate, preferably tetraborate; and mixtures thereof; to provide a first mixture [mixture (M1)];
  • the expression “anti-solvent for the CSI salt” referred to the at least one second solvent (S2) is intended to indicate that the CSI salt shows a solubility below 2 wt.%, preferably below 1 wt.% into said at least one second solvent (S2).
  • the method of the present invention can be performed continuously or batch wise.
  • the method of the present invention can be stopped after step (II), to recover the CSI salt from mixture (M2).
  • the method of the present invention preferably comprises after step (II), a step (I l-b) of isolating the CSI salt from mixture (M2).
  • M is lithium
  • said compound is selected from those that do not generate water or soluble species over the course of the reaction.
  • M is lithium
  • said compound is selected from the group comprising: lithium chloride (LiCI), lithium carbonate (U2CO3), lithium sulphate (Li2SC>4), lithium carboxylate (Li n (RCO2) n ), Li2SiOs, I ⁇ B ⁇ and mixture thereof.
  • M is sodium.
  • Said compound is preferably selected in the group comprising: sodium chloride (NaCI), sodium carbonate (Na2COs), sodium sulphate (Na2SO4), and mixture thereof.
  • M is ammonium.
  • Said compound is preferably selected in the group comprising ammonium chloride (NH4CI), ammonium carbonate, and mixture thereof.
  • the molar ratio HCSI to the compound of formula (1) when M is lithium ranges from 1 :100 to 20:1 , in particular from 1 : 10 to 10:1 , more particularly from 1 :2 to 5:1 , even more particularly from 1 :1 to 1 :1.5.
  • the molar ratio of HCSI to U2CO3 is lower than 1 , i.e. that U2CO3 is in excess.
  • a molar ratio from 1 :2 to 1 :5 is even more preferred.
  • said compound of formula (1) is anhydrous lithium chloride (LiCI) in a solid form.
  • LiCI is used as the compound of formula (1) it is advantageous that the molar ratio of HCSI to LiCI is from 1 :1 to 1:1.5.
  • said solvent (S1) is selected in the group comprising: carbonates, such as dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC) ethylene carbonate (EC), propylene carbonate (PC); esters, such as ethyl acetate, n-butyl-acetate; ethers, such as tetrahydrofuran (THF), methyl tert-butyl ether (MTBE), methyl tetrahydrofuran (Me-THF). Carbonates are particularly preferred.
  • carbonates such as dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC) ethylene carbonate (EC), propylene carbonate (PC); esters, such as ethyl acetate, n-butyl-acetate; ethers, such as tetrahydrofuran (THF), methyl tert-butyl ether (MTBE),
  • solvent (S1) is different from thionyl chloride (SO2CI).
  • the HCSI provided in step (II) of the method of the present invention can be produced by a known method, for example by reacting:
  • CISO2NCO chlorosulfonyl isocyanate
  • CISO2OH chlorosulfonic acid
  • the HCSI is produced by reacting chlorosulfuric acid (CISO2OH) and chlorosulfonyl isocyanate (CISO2NCO).
  • step (i) consists in preparing a reaction mixture comprising a crude HCSI, heavy fractions and light fractions in a reactor, by reacting chlorosulfonyl isocyanate (CISO2NCO) with chlorosulfonic acid (CISO2OH).
  • the HCSI is produced by reacting sulfamic acid (NH2SO2OH), chlorosulfonic acid (CISO2OH) and thionyl chloride (SOCI2).
  • sulfamic acid NH2SO2OH
  • CISO2OH chlorosulfonic acid
  • SOCI2 thionyl chloride
  • the sulfamic acid to be applied may be ground to a certain particle size and dried under vacuum to decrease its water content and accelerate the kinetics of the transformation, which significantly reduces the reaction time.
  • the sulfamic acid employed can be optionally grinded and dried under vacuum, in order to decrease its water content and accelerate the kinetics of the transformation, hence reducing the reaction time significantly.
  • the HCSI is produced by reacting cyanogen chloride CNCI with sulfuric anhydride (SO3) and chlorosulfonic acid (CISO2OH).
  • the HCSI can be provided as a composition comprising HCSI in admixture with at least one other compound.
  • Such at least one other compound can be an undesired compound.
  • Said undesired compound can be selected for example from ions, solvent(s), water and/or reaction by-products.
  • the HCSI may be provided in a composition comprising from 80 to 99 wt.% of HCSI, preferably 85-98 wt.%, more preferably 90-97 wt.%, the remaining up to 100 wt.% being one or more other compound(s).
  • Such other compound(s) will be removed through the method of the present invention.
  • the HCSI is provided in step (II) in its molten form.
  • step (II) HCSI is heated at a temperature above its melting temperature (Trnncsi).
  • the melting temperature of of HCSI is influenced by the presence and amounts of impurities, it is preferred that the HCSI is heated at a temperature equal to or higher than 30°C, for example equal to or higher than 37°C, for example equal to or higher than 38°C, equal to or higher than 40°C, equal to or higher than 45°C or even equal to or higher than 50°C. In any case, the heating is performed at a temperature that is below the degradation temperature of HCSI.
  • step (II) is performed at a temperature from 15 to 60°C, more preferably from 20 to 35°C.
  • step (II) is performed at atmospheric pressure.
  • said at least one second solvent (S2) is selected in the group comprising: dioxane, chlorinated solvents such as dichloromethane (DCM), alkanes, toluene, xylenes.
  • dioxane is particularly preferred.
  • step (III) is performed at a temperature from 15 to 60°C, more preferably from 20 to 35°C.
  • step (III) is performed at atmospheric pressure.
  • the CSI salt in solid form obtained at the end of step (III) is in the form of a solvate with said at least one second solvent (S2).
  • the method according to the present invention comprises after step (III), at least one step (IV) of separating the CSI salt from impurities.
  • This separation step may be performed by any separation means known by the person skilled in the art.
  • the separation can be performed by filtration, more preferably under pressure and/or under vacuum, or decantation.
  • the mesh size of the filtration medium is preferably 100 pm or below, 50 pm or below, 10 pm or below, 2 pm or below, of 0.45 pm or below, or 0.22 pm or below.
  • the separated product(s) may be washed once or several times with appropriate solvent(s).
  • the separation step can be carried out one time or may be repeated twice or more. [0049] Some of the steps or all steps of the method according to the invention are advantageously carried out in equipment capable of withstanding the corrosion of the reaction medium.
  • materials are selected for the part in contact with the reaction medium that are corrosion-resistant, such as the alloys based on molybdenum, chromium, cobalt, iron, copper, manganese, titanium, zirconium, aluminium, carbon and tungsten, sold under the Hastelloy® brands or the alloys of nickel, chromium, iron and manganese to which copper and/or molybdenum are added, sold under the name Inconel® or MonelTM, and more particularly the Hastelloy C276 or Inconel 600, 625 or 718 alloys.
  • Stainless steels may also be selected, such as austenitic steels and more particularly the 304, 304L, 316 or 316L stainless steels.
  • the 304 and 304L steels have a nickel content that varies between 8 wt.% and 12 wt.%
  • the 316 and 316L steels have a nickel content that varies between 10 wt.% and 14 wt.%. More particularly, 316L steels are chosen. Use may also be made of equipment consisting of or coated with a polymeric compound resistant to the corrosion of the reaction medium.
  • PTFE polytetrafluoroethylene or Teflon
  • PFA perfluoroalkyl resins
  • Glass equipment such as glass-coated alloys, may also be used. It will not be outside the scope of the invention to use an equivalent material.
  • graphite derivatives materials capable of being suitable for contact with the reaction medium.
  • Materials for filtration have to be compatible with the medium used. Fluorinated polymers (PTFE, PFA), loaded fluorinated polymers (VitonTM), as well as polyesters (PET), polyurethanes, polypropylene, polyethylene, cotton, and other compatible materials can be used.
  • All raw materials used in the method according to the invention, including reactants, may preferably show very high purity criteria.
  • their content of metal components such as Na, K, Ca, Mg, Fe, Cu, Cr, Ni, Zn, is below 10 ppm, more preferably below 5 ppm, or below 2 ppm.
  • a pure or substantially pure salt of LiCSI is obtained as a solid.
  • the LiCSI salt may be used as such for other reactions, notably the preparation of LiFSI.
  • the present invention relates to a solid solvate complex [CSI solvate] comprising a solid lithium, sodium, potassium or ammonium salt of bis(chloro sulfonyl)imide and dioxane as the solvating solvent.
  • CSI solvate a solid lithium, sodium, potassium or ammonium salt of bis(chloro sulfonyl)imide and dioxane as the solvating solvent.
  • solvate is intended to indicate the solid lithium, sodium, potassium or ammonium salt of bis(chloro sulfonyl)imide, also referred to as CSI salt, which comprises molecules of said solvent (S2) attached to it via non-covalent bonds.
  • the weight ratio of CSI salt to solvent (S2), in the CSI solvate is in the range from 1:1 to 1:4, as measured on the dry powder.
  • said solvent (S2) in said CSI solvate is dioxane.
  • said CSI solvate is obtained at the end of step (III) or step (IV) of the method according to the present invention.
  • said CSI solvate is in the crystallised form.
  • the present invention relates to the use of the CSI solvate as obtained at the end of step (II) or step (IV) as defined above, for the manufacture of a salt of bis(fluorosulfonyl imide) [FSI salt].
  • the FSI salt is selected from: lithium, ammonium and sodium salt.
  • a further object of the present invention relates to a method for the manufacture of a salt of bis(fluoro sulfonyl) imide [FSI salt], said method comprising:
  • the fluorinating agent used in the method of the present invention is not limited.
  • it is anhydrous hydrogen fluoride (aHF).
  • aHF anhydrous hydrogen fluoride
  • Such aHF has advantageously a high purity, for example above 99.95 mol.%, with less than 1000 ppm of H2O, less than 10 ppm of SO2, less than 100 ppm of H2SO4, less than 20 ppm of FhSiFe and less than 25 ppm of As.
  • aHF used as a fluorinating agent in step (V)
  • it may be introduced in any form in the reaction mixture. It may be introduced as a liquid or it can be introduced as a gas in the reaction vessel.
  • step (V) can be performed by fluorinating the LiCSI using aHF gas in a fluidized bed.
  • the fluorinating agent is selected from the group comprising, preferably consisting of:
  • fluorinating agent (iv) examples include NH 4 F, NH 4 F.HF, NH 4 F.2HF, NH 4 F.3HF, and NH 4 F.4HF.
  • the preferred fluorinating agent is (iv) NH 4 F.
  • the fluorinating agent used in step (V) is preferably anhydrous.
  • Moisture content may be preferably below 100 ppm, below 50 ppm or even below 10 ppm.
  • the skilled person can determine the most suitable method to determine such moisture content. For example, such methods can include infrared techniques or Karl Fischer titration where applicable.
  • the stoichiometry amount (also called molar amount) of fluorinating agent to the CSI salt in solid form is from 0.1 :1 to 50:1 , for example from 1 :1 to 10:1 , or from 2:1 to 8:1.
  • the stoichiometry amount of fluorinating agent is not less than 2 equivalent per 1 mol of the CSI salt, preferably LiCSI, for example between 2 to 100 equivalents per 1 mol of CSI salt, preferably LiCSI.
  • the stoichiometry amount of fluorinating agent is between 2 to 80 equivalents per 1 mol of CSI salt, preferably LiCSI, or between 2 to 60 equivalents per 1 mol of CSI salt, preferably LiCSI. More preferably, the stoichiometry amount of fluorinating agent is between 2 to 50 equivalents per 1 mol of CSI salt, preferably LiCSI.
  • step (V) is performed in the presence of a solvent.
  • the CSI salt in solid form is the solvate with dioxane
  • said solvent is preferably dioxane
  • step (V) is performed at a temperature from 25 to 90°C, more preferably from 40 to 90°C.
  • step (V) is performed at a pressure from 1 to 2 bar.
  • the residual HF present in the final reaction crude may be eliminated using any relevant method such as vaporisation under vacuum or stripping using an inert gas or the combination thereof.
  • the LiFSI as obtained with the method of the present invention advantageously shows at least one or even more preferably all the following:
  • the LiFSI of the present invention advantageously shows at least one of the following features, and preferably all the following:
  • chloride (Cl’) content of below 100 ppm, preferably below 50 ppm, more preferably below 10 ppm, or more preferably below 2 ppm;
  • F fluoride
  • SC>4 2 ’ a sulfate (SC>4 2 ’) content of below 100 ppm, preferably below 50 ppm, more preferably below 10 ppm, or more preferably below 2 ppm.
  • Fluoride and chloride contents may be measured by means of titration by argentometry using ion selective electrodes (or ISE).
  • Sulfate content may be measured by ionic chrof the following features, and preferably all the following:
  • the lithium bis(fluorosulfonyl)imide (LiFSI) prepared according to the method of the present invention can be used in an electrolyte composition for an electrochemical cell.
  • the present invention to an electrolyte composition comprising the LiFSI as obtained with the method of the present invention.
  • said electrolyte composition is a non-aqueous electrolyte composition.
  • HCSI was prepared internally starting from chlorosulfonyl isocyanate and chlorosulfonic acid, and then used in its molten state.
  • a double-jacketed 100 mL glass reactor equipped with integrated baffles, a mechanical stirring, a condenser and connected to a 15 wt.% aqueous KOH scrubber was flushed with argon for 30 minutes.
  • the reactor vessel was loaded with 3.18 g anhydrous lithium chloride and 24.7 g carbon tetrachloride.
  • a dropping funnel was filled with 26 g of CCI4 and 20.0 g molten HCSI. The funnel was connected to the reactor.
  • the temperature setpoint of the condenser was fixed at 6°C and the stirring rate at 700 rpm before introducing the HCSI solution over 20 min.
  • the reaction medium was heated to reflux. After 5 hours of reflux, LiCI conversion was about 19% (estimated by KCI titration in the scrubber).
  • Example A2 Preparation of LiCSI solution via lithiation of HCSI using DEC as the solvent
  • a double-jacketed 250 mL glass reactor equipped with integrated baffles, a mechanical stirring, a condenser, a bottom valve and connected to a 15 wt.% aqueous KOH scrubber was flushed with nitrogen for 60 minutes.
  • the reactor vessel was loaded with 6.34 g anhydrous lithium chloride and 15.98 g diethyl carbonate (DEC).
  • the temperature setpoint of the condenser was fixed at 10°C, the reaction mixture at 25°C and the stirring rate at 400 rpm before introducing 47.84 g of the HCSI solution over 27 min.
  • reaction crude was diluted with 18.99 g DEC and withdrawn to a filter under controlled N2 atmosphere.
  • the solid residue containing the excess LiCI was washed with 2.00 g DEC and 79.25 g filtrate was recovered containing 36 wt. % LiCSI.
  • Example A3 Preparation of LiCSI solution via lithiation of HCSI using DEC as the solvent
  • a double-jacketed 500 mL glass reactor equipped with integrated baffles, a mechanical stirring, a condenser, a bottom valve and connected to a 15 wt.% aqueous KOH scrubber was flushed with nitrogen for 60 minutes.
  • the reactor vessel was loaded with 56.5 g anhydrous lithium chloride and 94.3 g DEC.
  • a dropping funnel was filled with 192.9 g molten HCSI (prepared from chlorosulfonyl isocyanate and chlorosulfonic acid) and 100.8 g DEC. The funnel was then connected to the reactor.
  • HCSI prepared from chlorosulfonyl isocyanate and chlorosulfonic acid
  • the temperature setpoint of the condenser is fixed at 13°C, the reaction mixture at 30°C and the stirring rate at 400 rpm before introducing the HCSI solution over 45 min. The stirring and temperature were maintained for 4.5 hours.
  • reaction crude was withdrawn and filtered inside a glovebox, 354 g transparent filtrates were isolated along with 18 g of solid residue.
  • the LiCSI recovery yield was 75%.
  • Example C1 Preparation of LiFSI starting from LiCSI. dioxane solvate in dioxane with aHF
  • dioxane solvate in dioxane with aHF
  • a preliminary thoroughly inerted C276 autoclave equipped with a magnetically coupled stirrer, a heating/cooling double-jacket, a temperature probe, a pressure sensor, a condenser and connected to a basic aqueous scrubber was introduced under N2 blanketing solid LiCSI.
  • Dioxane 23 g, Dioxane content 47 wt.% prepared following the procedure in Example B3.
  • reaction mixture was stripped with N2 for 12 h at 50 °C to evacuate most of HF excess.
  • Quantitative 19 F-NMR of the reaction mixture showed a mixture of LiFSI (7.2%) with important amounts of FSO3U, FSO2NH2 (or its lithium salt), residual HF and other unknown impurities.
  • the reactor vessel was loaded with 15.55 g diethyl carbonate and 7.74 g NH 4 F.
  • a 60 mL PP syringe was filled with 48 g LiCSI solution obtained by HCSI lithiation in DEC (37 wt.% LiCSI) and mounted on a syringe pump.
  • the temperature setpoint of the condenser was fixed at 10°C, the reaction mixture at 60°C and the stirring rate at 400 rpm before introducing 46.34 g of the LiCSI solution over 60 min.
  • the medium temperature was then set at 75-80°C for 10 hours. After cooling down to room temperature, the supernatant was sampled: the total chloride content was around 60% of its initial value (titration in aqueous solution) showing that LiCSI was not fully converted.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'un sel de bis(chlorosulfonyl)imide (sel de HCSI), qui est économiquement réalisable à l'échelle industrielle et qui fournit un produit de haute pureté. La présente invention concerne également un procédé de production d'un sel de lithium de bis(fluorosulfonyl)imide (LiFSI), ledit sel de HCSI étant utilisé en tant que composé intermédiaire.
PCT/EP2023/075914 2022-09-22 2023-09-20 Procédé de production de sels d'imide de sulfonyle alcalin WO2024061956A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22306391.8 2022-09-22
EP22306391 2022-09-22

Publications (1)

Publication Number Publication Date
WO2024061956A1 true WO2024061956A1 (fr) 2024-03-28

Family

ID=83689904

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2023/075914 WO2024061956A1 (fr) 2022-09-22 2023-09-20 Procédé de production de sels d'imide de sulfonyle alcalin

Country Status (1)

Country Link
WO (1) WO2024061956A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053494A1 (fr) 2000-12-29 2002-07-11 Hydro-Quebec Procede de fluoration d'un compose comprenant un groupe halosulfonyle ou dihalophosphonyle
CA2527802A1 (fr) 2005-12-12 2007-06-12 Christophe Michot Synthese de sels de lithium d'imides anhydres contenant un substituant fluorosulfonyle ou fluorophosphoryle
CN103524387A (zh) 2013-10-25 2014-01-22 中国海洋石油总公司 一种双氟磺酰亚胺锂盐的制备方法
KR20190001092A (ko) 2017-06-26 2019-01-04 임광민 매우 간단하고 효율적인 리튬 비스(플루오로술포닐)이미드의 새로운 제조방법
KR20200049164A (ko) 2018-10-31 2020-05-08 (주)씨엘에스 매우 효율적인 리튬 비스(플루오로술포닐)이미드의 새로운 제조방법
KR20200114963A (ko) * 2019-03-28 2020-10-07 주식회사 천보 불소 음이온의 함유량이 저감된 비스(플루오로설포닐)이미드 리튬염(LiFSI)의 제조 방법
WO2022128381A1 (fr) * 2020-12-16 2022-06-23 Rhodia Operations Procédé de production de sels d'onium de sulfonyl imide et de sels de métal alcalin de sulfonyl imide

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053494A1 (fr) 2000-12-29 2002-07-11 Hydro-Quebec Procede de fluoration d'un compose comprenant un groupe halosulfonyle ou dihalophosphonyle
CA2527802A1 (fr) 2005-12-12 2007-06-12 Christophe Michot Synthese de sels de lithium d'imides anhydres contenant un substituant fluorosulfonyle ou fluorophosphoryle
CN103524387A (zh) 2013-10-25 2014-01-22 中国海洋石油总公司 一种双氟磺酰亚胺锂盐的制备方法
KR20190001092A (ko) 2017-06-26 2019-01-04 임광민 매우 간단하고 효율적인 리튬 비스(플루오로술포닐)이미드의 새로운 제조방법
KR101955096B1 (ko) * 2017-06-26 2019-03-06 임광민 매우 간단하고 효율적인 리튬 비스(플루오로술포닐)이미드의 새로운 제조방법
KR20200049164A (ko) 2018-10-31 2020-05-08 (주)씨엘에스 매우 효율적인 리튬 비스(플루오로술포닐)이미드의 새로운 제조방법
KR20200114963A (ko) * 2019-03-28 2020-10-07 주식회사 천보 불소 음이온의 함유량이 저감된 비스(플루오로설포닐)이미드 리튬염(LiFSI)의 제조 방법
WO2022128381A1 (fr) * 2020-12-16 2022-06-23 Rhodia Operations Procédé de production de sels d'onium de sulfonyl imide et de sels de métal alcalin de sulfonyl imide

Similar Documents

Publication Publication Date Title
US8377406B1 (en) Synthesis of bis(fluorosulfonyl)imide
KR20160093670A (ko) 비스(플루오로설포닐)이미드산 및 이의 염을 제조하기 위한 방법
US20240132352A1 (en) Bis(fluorosulfonyl)imide salts and preparation method thereof
CA3200173A1 (fr) Procede de production de sels d'onium de sulfonyl imide et de sels de metal alcalin de sulfonyl imide
JP5471121B2 (ja) パーフルオロアルカンスルフィン酸塩の製造方法
RU2379286C2 (ru) Перфторалкансульфонат калия и способ его получения
JP5051568B2 (ja) ペルフルオロアルカンスルホン酸カリウムの製造方法
CN113979454A (zh) 一种氟磺酸碱金属盐的制备方法
KR20150036412A (ko) 설폰이미드 화합물 및 그 염의 제조 방법
WO2024061956A1 (fr) Procédé de production de sels d'imide de sulfonyle alcalin
KR20240127997A (ko) 비스(플루오로설포닐)이미드의 알칼리 염을 제조하기 위한 공정
WO2023169843A1 (fr) Procédé de production de sels de lithium fluorosulfonyl imide
WO2023169842A1 (fr) Procédé de production de sels sulfonyl imide alcalins
WO2023041519A1 (fr) Procédé sans solvant pour la préparation d'un sel de bis(fluorosulfonyl)imide
JP2024525134A (ja) ビス（フルオロスルホニル）イミドの塩を調製するための無溶媒方法
EP4347484A1 (fr) Méthode de production de sels de sulfonylimide alcalins
CN115140715A (zh) 一种双氟磺酰亚胺碱金属盐的制备方法
CN118843599A (zh) 用于生产氟磺酰基酰亚胺锂盐的方法
CN116670069A (zh) 用于生产磺酰亚胺鎓盐和磺酰亚胺碱金属盐的方法
CN118843600A (zh) 用于生产磺酰亚胺碱盐的方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23772888

Country of ref document: EP

Kind code of ref document: A1