WO2007104144A1 - Compounds, ionic liquids, molten salts and uses thereof - Google Patents

Compounds, ionic liquids, molten salts and uses thereof Download PDF

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Publication number
WO2007104144A1
WO2007104144A1 PCT/CA2007/000390 CA2007000390W WO2007104144A1 WO 2007104144 A1 WO2007104144 A1 WO 2007104144A1 CA 2007000390 W CA2007000390 W CA 2007000390W WO 2007104144 A1 WO2007104144 A1 WO 2007104144A1
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compound
alkyl
linear
formula
branched
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PCT/CA2007/000390
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French (fr)
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Amer Hammami
Benoît MARSAN
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Transfert Plus, S.E.C.
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Priority to US12/282,198 priority Critical patent/US20090045373A1/en
Publication of WO2007104144A1 publication Critical patent/WO2007104144A1/en

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/122—Ionic conductors
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/022—Electrolytes; Absorbents
    • H01G9/035—Liquid electrolytes, e.g. impregnating materials
    • 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
    • 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
    • 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 document relates to the field of electrochemistry.
  • it relates to compounds that are useful as electrolytes such as molten salts or ionic liquids.
  • An electrolyte in an electrochemical cell may conduct electricity through the movement of ions, charged species, towards an electrode having opposite electrical charge to the ions.
  • the electrolytes consist of a salt, dissolved in a solvent, which may be water (aqueous solution) or one or more organic compounds (non-aqueous solution).
  • a solvent which may be water (aqueous solution) or one or more organic compounds (non-aqueous solution).
  • molten salts or ionic liquids, or room temperature molten salts materials and mixtures which consist of an ionically bound liquid at ambient temperatures
  • WO 2005/089390 describes methyl-propyl-imidazolium-bis-fluoro- sulfonylimide (MPI-FSI) and ethyl-1-methyl-3-imidazolium-bis-fluoro- sulfonylimide (EMI-FSI) as suitable molten salt electrolytes.
  • MPI-FSI methyl-propyl-imidazolium-bis-fluoro- sulfonylimide
  • EMI-FSI ethyl-1-methyl-3-imidazolium-bis-fluoro- sulfonylimide
  • each of the Ri is independently F, Cl, -N(Rs ⁇ , or -CN; Q + is chosen from
  • R 2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C-1-C12 heterocyclyl, C2-C20 alkenyl, C 2 -C 2 O alkynyl, C 6 -Ci 2 aryl, C 6 -C 2 O aralkyl, C 6 -C 20 alkylaryl, and Ci-Ci 2 heteroaryl;
  • R 3 is a hydrogen atom, a CrC 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, Ci-Ci 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 2 O alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and Ci-Ci 2 heteroaryl;
  • R 4 is a hydrogen atom, a Ci-C 2 o alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, CrCi 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl; and
  • R 5 is a hydrogen atom, a Ci-C 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, CrCi 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl, an effective protecting group for an amino group,
  • the heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from of -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH, - OMe, -OCH 2 Ph, -SMe, -SPh, -SCH 2 Ph, -COOH, -COOR 4 , -NH 2 , C 2 -C 20 alkenyl, CrC 20 alkoxy, CrC 20 alkyl, C 2 -C 20 alkynyl, C 6 -C 20 aralkyl, C 6 -Ci 2 aryl, C 3 -C 8 cycloalkyl, CrC 20 aminoalkyl, CrC 6 hydroxyalkyl, C 2 -Ci 2 heteroaryl, CrCi 2 , vinyl, C 4 -C 20 alkylvinyl, C 4 -C 20 vinylalkyl, and C 3 -C 20 expoxyalkyl,
  • each of the Ri is independently F 1 CI, -N(Rs) 2 , or -CN,
  • R2 is a hydrogen atom, a C1-C2 0 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C2 0 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
  • R3 is a hydrogen atom, a Ci-C 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C12 heterocyclyl, C 2 -C 2 O alkenyl, C2-C20 alkynyl, C 6 -Ci 2 aryl, C6-C20 aralkyl, C 6 -C 2 O alkylaryl, and C1-C12 heteroaryl;
  • R 4 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C12 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl; and
  • R5 is a hydrogen atom, a CrC 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C 1 -C 12 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 2 O aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl, an effective protecting group for an amino group,
  • heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH,
  • Ri and Q are as previously defined; M + is chosen from Li + , Na + , K + , and Cs +
  • X ' is chosen from P 1 Cl “ , Br “ , I “ , CH 3 COO-, PhCH 2 COO-, CN “ , CF 3 COO-, SO 4 2" , CF 3 SO 3 -, BF 4 " , PF 6 ' , NO 3 ' , CIO 4 “ , SbF 6 “ , and RuO 4 " .
  • R 2 is a hydrogen atom, a C 1 -C 20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C 6 -Ci 2 aryl, C6-C 2 0 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
  • R3 is a hydrogen atom, a C1-C 20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C 2 -C 2 O alkynyl, C6-C1 2 aryl, C6-C 2 0 aralkyl, C6-C 2 0 alkylaryl, and C1-C12 heteroaryl; and
  • R 4 is a hydrogen atom, a C 1 -C 2 O alkyl which is linear or branched, C3-C12 cycloalkyl, C 1 -C 12 heterocyclyl, C 2 -C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C ⁇ -C ⁇ o alkylaryl, and C1-C12 heteroaryl, the heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH,
  • each of Re is independently H, Li, Na, K, Cs 1 or (R 7 ) 3 Si-, each of the R 7 being independently a C1-C12 alkyl.
  • R 2 is a hydrogen atom, a C 1 -C 20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C 6 -C ⁇ aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C- 1 -C12 heteroaryl;
  • R 3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 2 O aralkyl, C 6 -C 2 O alkylaryl, and Ci-C-
  • R 4 is a hydrogen atom, a Ci-C 2O alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C12 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, Ce-C 20 alkylaryl, and CrCi 2 heteroaryl, the heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH, -OMe, -OCH 2 Ph, -SMe, -SPh, -SCH 2 Ph, -COOH, -COOR 4 , -NH 2 , C 2 -C 20 aikenyl, d- C 20 alkoxy, Ci-C 2 o alkyl, C 2 -C 2 O alky
  • CH 2 CHC 6 H 5 -
  • CH 2 CHC 6 H 4 CpH 2P+ I-
  • CH 2 CHC p H 2p C 6 H 4 - ⁇ -C p H 2p - , where (1 ⁇ n, p ⁇ 48),
  • each of the R 6 is independently H, Li, Na, K, Cs, or (Rr) 3 Si-, each of the R 7 being independently a Ci-Ci 2 alkyl so as to obtain a compound of formula (Ic);
  • R 2 is a hydrogen atom, a C1-C 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C12 heterocyclyl, C2-C2 0 alkenyl, C2-C2 0 alkynyl, C 6 -Ci 2 aryl, C6-C20 aralkyl, C 6 -C 2 O alkylaryl, and C1-C12 heteroaryl;
  • R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, Ci-Ci 2 heterocyclyl, C 2 -C 2O alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 2 O aralkyl, C 6 -C2o alkylaryl, and CrCi 2 heteroaryl; and
  • R 4 is a hydrogen atom, a Ci-C 20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C2 0 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and C 1 -C1 2 heteroaryl, the heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH, - OMe, -OCH 2 Ph, -SMe, -SPh, -SCH 2 Ph, -COOH, -COOR 4 , -NH 2 , C 2 -C 20 alkenyl, CrC 20 alkoxy, CrC 20 alkyl, C 2 -C 20 alkynyl, Ce-C
  • each of the R 9 is independently Cl, Br, or I
  • T + is Li + , Na + , K + ,Cs + or H + and
  • each of the R 6 is independently H, Li, Na, K, Cs, or (RrbSi-, each of the R ⁇ being independently a C1-C12 alkyl.
  • each of the Rg is as previously defined for formula (Ha);
  • T + is as previously defined for formula (Ilia).
  • alkyl refers to linear or branched radicals. Examples of such radicals include, but are not limited to, methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like.
  • the alkyl can be a methyl.
  • aryl has used herein refers to a cyclic or polycyclic aromatic ring.
  • the aryl group can be a phenyl or napthyl.
  • heteroaryl refers to an aromatic cyclic or fused polycyclic ring system having at least one heteroatom chosen from N, O, and S.
  • the heteroaryl groups include, but are not limited to, furyl, thienyl, pyridyl, quinolinyl, isoquinolinyl, indolyl, isoindolyl, triazolyl, pyrrolyl, tetrazolyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothiophenyl, carbazolyl, benzoxazolyl, pyrimidinyl, benzimidazolyl, quinoxalinyl, benzothiazolyl, naphthyridinyl, isoxazolyl, isothiazolyl, purinyl, quinazolinyl, among others.
  • heterocyclyl includes non-aromatic rings or ring systems that contain at least one ring having at least one hetero atom (such as nitrogen, oxygen or sulfur).
  • this term can include all of the fully saturated and partially unsaturated derivatives of the above mentioned heteroaryl groups.
  • heterocyclic groups include, without limitation, pyrrolidinyl, tetrahydrofuranyl, morpholinyl, thiomorpholinyl, piperidinyl, piperazinyl, thiazolidinyl, isothiazolidinyl, and imidazolidinyl.
  • Q + can be chosen from
  • Q + can be chosen from:
  • Q + can be chosen from
  • R 2 can be a C 1 -C 20 alkyl which is linear or branched or a C3-C12 cycloalkyl.
  • R2 can be a C1-C20 alkyl which is linear or branched.
  • R 2 can be a C-i-C ⁇ alkyl which is linear.
  • R 3 can be a C1-C20 alkyl which is linear or branched or a C 3 -Ci 2 cycloalkyl.
  • R 3 can be a C1-C20 alkyl which is linear or branched .
  • R 3 is a CrC 8 alkyl which is linear.
  • R 4 can be a C1-C2 0 alkyl which is linear or branched or a C3-C12 cycloalkyl.
  • R 4 can be a C1-C20 alkyl which is linear or branched.
  • R 4 can be a Ci-Ce alkyl which is linear.
  • R 4 can be a CrC 4 alkyl which is linear.
  • the compounds previously presented can have a conductivity of at least 0.0001 mS cm "1 .
  • the conductivity can be of at least 1 mS cm “1 , or of at least 10 mS cm “1 .
  • they can have a conductivity of about 0.0001 to about 100 mS cm “1 .
  • the compounds can have a melting point below 100 ° C.
  • the melting point can be below 40 ° C, or below 25 ° C.
  • the compounds can have a melting point of about 0 0 C to about 100 ° C.
  • the Ri group can be a halogen atom.
  • Ri is F or Cl.
  • Ri is F.
  • the compounds previously presented can be used as a molten salt, an ionic liquid or an electrolyte. These compounds can also be used in an electrochemical device such as a battery.
  • the reaction can be carried out in water so that the so-obtained product of formula (I) precipitates and the so-formed byproduct of formula M + X " is at least substantially soluble.
  • M + can be K + .
  • X " can be F “ , Cl “ , Br “ , or I " .
  • X " is Cl “ , or Br " .
  • Each of the Ri can be a halogen atom.
  • Ri can be Cl “ or F " .
  • Ri can be F " .
  • the compound of formula (III) can be a compound of formula (IV):
  • each of the R 7 is independently a C1-C12 alkyl.
  • each of the R 7 can be the same.
  • R 7 can be methyl.
  • the compounds of formulas (II) and (III) can be reacted together at a temperature of about -78 to about 110 ° C.The temperature can be for example about -5 to about 25 ° C, or about 15 to about 25 0 C.
  • Ri can be F or Cl. According to one example, Ri can be F.
  • step (a) can be carried out at a temperature of about -78 to about 110 ° C.
  • the temperature can be about -5 to about 25 ° C or about 15 to about 25 0 C.
  • Step (b) can be carried out in the presence of an aprotic solvent.
  • the aprotic solvent can be a polar solvent such as nitromethane or acetonitrile.
  • the compound of formula (III) can be a compound of formula (IV):
  • each of the R 7 is independently a C1-C12 alkyl.
  • R 7 can be the same.
  • R 7 can be a methyl.
  • the compound of formula (Ilia) can be a compound of formula (IVa):
  • T + is as previously defined in formula (Ilia).
  • each of the R 7 is independently a C 1 -C 12 alkyl.
  • each of the R 7 can be the same.For example, each of the R 7 can be a methyl.
  • molten salt comprising a compound as defined in the present invention.
  • an ionic liquid comprising a compound as defined in the present invention.
  • an electrolyte comprising a compound as defined in the present invention.
  • an electrochemical device comprising a compound as defined in the present invention.
  • a battery comprising a compound as defined in the present invention.
  • a method of using a compound as previously defined which comprises contacting the compound with electrodes and using it as an electrolyte.
  • a method of using a compound as previously defined which comprises introducing the compound in the manufacture of a proton exchange membrane.
  • the compounds previously described can be used in many applications. For example, they can be used as solvents for organic and organometallic syntheses and catalysis. They can also be used as electrolytes (for example in electrochemistry or in fuel and solar cells), as lubricants, as a stationary phase for chromatography, as matrices for mass spectrometry, supports for the immobilization of enzymes, in separation technologies, as liquid crystals, templates for the synthesis of mesoporous, nano-materials and ordered films, materials for embalming and tissue preservation, etc.
  • the compounds previously mentioned can be used in various solutions (dry cleaning, metal extraction, personal care, embalming, household products, coatings, etc.) and in electrochemistry ( batteries, solar panel, ion propulsion, fuel cells, electro-optics, etc.).
  • The can also be used in view of their various interesting properties for heat transfer or as lubricants. They can also be used in drug delivery, biomass processing, biocides etc.
  • compositions for lithium-ions batteries comprising a compound of formula (I) and a compound of formula (VIII):
  • D is chosen from CF 3 SO 3 -, (FSO 2 ) 2 N- ,(CF 3 SO 2 )2N-, (CF 3 CF 2 SO 2 ) 2 N-, (CF 3 SO 2 ) 3 C-, PF 6 “ , CF 3 COO-, AsF 6 " , CH 3 COO “ , (CN) 2 N “ , NO 3 " , BF 4 " , CIO 4 “ , (C 8 H 16 SO 2 ) 2 N “ , and C 3 H 3 N 2 "
  • R 2 is a hydrogen atom, a C 1 -C2 0 alkyl which is linear or branched, C 3 - Ci 2 cycloalkyl, Ci-Ci 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and Ci-Ci 2 heteroaryl;
  • R 3 is a hydrogen atom, a CrC 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, CrCi 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and C1-C12 heteroaryl;
  • R 4 is a hydrogen atom, a CrC 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C1 2 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl; and
  • R 5 is a hydrogen atom, a CrC 20 alkyl which is linear or branched, C 3 -Ci 2 cycloalkyl, C1-C12 heterocyclyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 6 -Ci 2 aryl, C 6 -C 20 aralkyl, C 6 -C 20 alkylaryl, and CrCi 2 heteroaryl, an effective protecting group for an amino group,
  • the heterocycles represented by Q + are as previously presented or substituted with 1 to 3 substituents chosen from of -NO 2 , -CN -OH, -CF 3 -COR 4 , -SH, - OMe, -OCH 2 Ph, -SMe, -SPh, -SCH 2 Ph, -COOH, -COOR 4 , -NH 2 , C 2 -C 20 alkenyl, CrC 20 alkoxy, CrC 20 alkyl, C 2 -C 20 alkynyl, C 6 -C 20 aralkyl, C 6 -Ci 2 aryl, C 3 -Ce cycloalkyl, CrC 20 aminoalkyl, CrC 6 hydroxyalkyl, C 2 -Ci 2 heteroaryl, CrCi 2 , vinyl, C 4 -C 20 alkylvinyl, C 4 -C 20 vinylalkyl, and C 3 -C 20 expoxyalkyl,
  • CH 2 CHC 6 H 5 -
  • CH 2 CHC 6 H 4 CpH 2P+1 -
  • CH 2 CHC p H 2p C 6 H 4 - ⁇ C p H 2p -
  • a method of using a compound as previously defined which comprises mixing the compound with a compound of formula (VIII) so as to obtain a mixture and using said mixture as an electrolyte, for example in a lithium-ion battery.
  • the reaction mixture is heated and stirred over 12h. Then, the solid particles are filtered- out and the solvent is removed under vacuum and replaced by 100 mL of distilled water.
  • the aqueous solution is charged into a 500 ml_ flask and mixed with 100 ml_ of an aqueous solution of 1.68 g (7.4 mM) of N 1 N- dimethyl-pyrrolidinium iodide. The resulting compound 1 is then extracted by dichloromethane and isolated in pure form.
  • Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.41 g (10 mM) of N.N-ethylmethylpyrrolidinium iodide is dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N,N-ethylmethylpyrrolidinium iodide exchanges anions with KFSI in water. The Potassium iodide stays in the aqueous phase and the desired molten salt 2 is decanted.
  • Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.37 g (10 mM) of N,N-ethylmethylpyrrolium iodide was dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N,N-ethylmethylpyrrolium iodide exchanges anions with KFSI in water. The potassium iodide stays in the aqueous phase and the desired molten salt 3 is decanted.
  • the organic layer was decanted, extracted with 40 mL of CH 2 CI 2 and then washed with 80 mL of distilled H 2 O and dried over anhydrous MgSO 4 . After concentration with a rotative evaporator, the translucent ionic liquid obtained is dried under vacuum at 60 0 C for 3 hours. Its purity is confirmed by NMR (1 H, 13C, 19F) and cyclic voltammetry.
  • Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.13 g (10 mM) of, N-methyloxazolinium iodide is dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N-methyloxazolinium iodide exchanges anions with KFSI in water. The potassium iodide stays in the aqueous phase and the desired molten salt 4 is decanted.
  • the organic layer is decanted, extracted with 60 mL of CH2CI2 and then washed with 100 mL of distilled H2O and dried over anhydrous MgSO 4 . After concentration with a rotative evaporator, the translucent ionic liquid obtained is dried under vacuum at 60 0 C for 3 hours. Its purity is confirmed by NMR ( 1 H, 13 C, 19 F) and cyclic voltammetry.

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Abstract

There are provided compounds represented by formula (I): in which R1 is F, CI, -N(R5)2 or -CN and Q+ is selected among various organic cations that include an heterocyle. These compounds are useful as electrolytes, ionic liquids or molten salts.

Description

COMPOUNDS, IONIC LIQUIDS, MOLTEN SALTS AND USES THEREOF
FIELD OF THE INVENTION
The present document relates to the field of electrochemistry. In particular, it relates to compounds that are useful as electrolytes such as molten salts or ionic liquids.
BACKGROUND OF THE INVENTION
An electrolyte in an electrochemical cell may conduct electricity through the movement of ions, charged species, towards an electrode having opposite electrical charge to the ions. Typically, the electrolytes consist of a salt, dissolved in a solvent, which may be water (aqueous solution) or one or more organic compounds (non-aqueous solution). Alternatively, molten salts or ionic liquids, or room temperature molten salts (materials and mixtures which consist of an ionically bound liquid at ambient temperatures) may be used.
In recent years, highly conductive electrolyte salts that are molten at room temperature have been developed for electrochromic windows, variable reflectance mirrors, batteries, capacitors, and other important devices.
US 6,853,472 describes molten salts including lithium or quarternary ammonium cations, and perfluorinated anions selected from the group consisting of trifluoromethylsulfonate (CF3SO3 ), bis(trifluoromethylsulfonyl)imide ((CF3SO2^N"), bis(perfluoroethylsulfonyl)imide ((CF3CF2SO2^N") and tris(trifluoromethylsulfonyl)methide ((CF3SO2)3C").
WO 2005/089390 describes methyl-propyl-imidazolium-bis-fluoro- sulfonylimide (MPI-FSI) and ethyl-1-methyl-3-imidazolium-bis-fluoro- sulfonylimide (EMI-FSI) as suitable molten salt electrolytes.
It would therefore be highly desirable to be provided with compounds that would represent an alternative to the compounds previously mentioned. SUMMARY OF THE INVENTION
In accordance with one aspect there is provided a compound of formula (I):
Figure imgf000003_0001
wherein each of the Ri is independently F, Cl, -N(Rs^, or -CN; Q+ is chosen from
Figure imgf000003_0002
wherein R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C-1-C12 heterocyclyl, C2-C20 alkenyl, C2-C2O alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C20 alkylaryl, and Ci-Ci2 heteroaryl;
R3 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, Ci-Ci2 heterocyclyl, C2-C20 alkenyl, C2-C2O alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and Ci-Ci2 heteroaryl;
R4 is a hydrogen atom, a Ci-C2o alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl; and
R5 is a hydrogen atom, a Ci-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl, an effective protecting group for an amino group,
the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from of -NO2, -CN -OH, -CF3 -COR4, -SH, - OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6-Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+iC6H4— , CpH2p+iC6H4CnH2n— , CH2=CHCpH2P-, CH2=CHC6H5-, CH2=CHC6H4CpH2P+I- and CH2=CHCpH2pC6H4- where (1 < n, p < 48),
Figure imgf000005_0001
with the proviso that the compound of formula (I) is different than 1-methyl-1-propylpyrrolidinium imidosulfuryl fluoride.
The compounds previously presented represent a very interesting alternative to the compounds previously proposed in the prior art. In fact, these compounds can be simply and rapidly prepared at low costs.
In accordance with another aspect there is provided a process for preparing a compound of formula (I):
Figure imgf000005_0002
wherein each of the Ri is independently F1 CI, -N(Rs)2, or -CN,
Q+ is chosen from
Figure imgf000006_0001
Figure imgf000006_0002
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
R3 is a hydrogen atom, a Ci-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C2O alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C2O alkylaryl, and C1-C12 heteroaryl;
R4 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl; and
R5 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl, an effective protecting group for an amino group,
the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH,
-OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6-Ci2 aryl, C3-Cs cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I, OH, a d-C6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ', CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, CeHsCpH2P-, CpH2p+iC6H4— , CpH2p+iC6H4CnH2n— ,
Figure imgf000007_0001
CH2=CHC6H5-, CH2=CHC6H4CpH2P+I- and CH2=CHCpH2pC6H4- __CpH2p- , where (1 < n, p < 48),
comprising the step of reacting together a compound of formula (V) and a compound of formula (VI) :
Figure imgf000007_0002
wherein
Ri and Q are as previously defined; M+ is chosen from Li+, Na+, K+, and Cs+
X' is chosen from P1 Cl", Br", I", CH3COO-, PhCH2COO-, CN", CF3COO-, SO4 2", CF3SO3-, BF4 ", PF6 ', NO3 ', CIO4 ", SbF6 ", and RuO4 ".
Such a process is useful and efficient to prepare, at low costs, compounds of general formula (I). This process is simple and can easily be carried out.
According to another aspect, there is provided a process for preparing a compound of formula (Ia):
Figure imgf000008_0001
wherein each of the Ri is independently F or Cl, Q+ is chosen from
Figure imgf000009_0001
Figure imgf000009_0002
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C2O alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl; and
R4 is a hydrogen atom, a C1-C2O alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, Cβ-C∑o alkylaryl, and C1-C12 heteroaryl, the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH,
-OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, Ce-C20 aralkyl, C6-Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I, OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+1, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, CeHsCpH2P-, CpH2p+i C6H4-, CpH2P+IC6H4CnH2n-, CH2=CHCpH2p-,
CH2=CHC6Hs-, CH2=CHC6H4CpH2p+i—, and CH2=CHCpH2pCeH4— v-7^CpHa,- , where (1 < n, p < 48), O F F
comprising the step of reacting a compound of formula (II):
O
R1 S Ri
O (II) wherein each of the Ri is as previously defined,
with a compound of formula (III):
Figure imgf000010_0001
(III) wherein
Q+ is as previously defined for formula (Ia); and
each of Re is independently H, Li, Na, K, Cs1 or (R7)3Si-, each of the R7 being independently a C1-C12 alkyl.
According to another aspect, there is provided a process for preparing a compound of formula (Ib):
Figure imgf000011_0001
wherein
Rs is F; and
Q+ is chosen from
Figure imgf000012_0001
Figure imgf000012_0002
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C^ aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C-1-C12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C2O alkylaryl, and Ci-C-|2 heteroaryl; and
R4 is a hydrogen atom, a Ci-C2O alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, Ce-C20 alkylaryl, and CrCi2 heteroaryl, the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 aikenyl, d- C20 alkoxy, Ci-C2o alkyl, C2-C2O alkynyl, C6-C20 aralkyl, C6-Ci2 aryl, C3-C8 cycloalkyl, C1-C20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, Ci-Ci2 vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, aikenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I, OH, a C1-C6 alkoxy, a C1-C6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+-!, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+i, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6H5CpH2p— , CpH2p+i C6H4-, CpH2p+iC6H4CnH2n— , CH2 =CHCpH2p— ,
CH2=CHC6H5-, CH2=CHC6H4CpH2P+I-, and CH2=CHCpH2pC6H4- ^-CpH2p- , where (1 < n, p < 48),
comprising the steps of :
a) reacting SO2CI2 with a compound of formula (III):
R6. -R6
•N'
(III)
wherein
Q+ is as previously defined for formula (Ib); and
each of the R6 is independently H, Li, Na, K, Cs, or (Rr)3Si-, each of the R7 being independently a Ci-Ci2 alkyl so as to obtain a compound of formula (Ic);
O o
Cl- -N- -Cl
I l
O (Ic)
wherein
Q+ is as previously defined for formula (Ib); and
b) reacting the compound of formula (Ic) with a compound of formula MF, wherein M is Li, Na, K, or Cs, so as to obtain the compound of formula (Ib).
According to another aspect, there is provided a process for preparing a compound of formula (Ib):
o o
r\g O IN O r\g
0 Q ° (Ib)
wherein
Re is F; and
Q+ is chosen from
Figure imgf000015_0001
Figure imgf000015_0002
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C2O alkylaryl, and C1-C12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, Ci-Ci2 heterocyclyl, C2-C2O alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C2o alkylaryl, and CrCi2 heteroaryl; and
R4 is a hydrogen atom, a Ci-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl, the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, - OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, Ce-C20 aralkyl, Ce-Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, C1-C6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+i C6H4-, CpH2p+iC6H4CnH2n— , CH2=CHCpH2p— ,
CH2=CHC6Hs-, CH2 =CHC6H4CpH2p+i— , and CH2=CHCpH2pC6H4— , ^7-CpH2P- , where: (1 < n, p < 48),
comprising the steps of :
a) reacting a compound of formula (Ha):
Figure imgf000016_0001
wherein
each of the R9 is independently Cl, Br, or I
with a compound of formula (Ilia): R16 v Θ ^^6
(Ilia)
wherein
T+ is Li+, Na+, K+ ,Cs+ or H+ and
each of the R6 is independently H, Li, Na, K, Cs, or (RrbSi-, each of the Rγ being independently a C1-C12 alkyl.
so as to obtain a compound of formula (VII);
Figure imgf000017_0001
wherein
each of the Rg is as previously defined for formula (Ha); and
T+ is as previously defined for formula (Ilia); and
b) reacting the compound of formula (VII) with a compound of formula Q-Rs, wherein Q and R8 are as previously defined in formula (Ib), so as to obtain the compound of formula (Ib). The term "alkyl" as used herein refers to linear or branched radicals. Examples of such radicals include, but are not limited to, methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. For example, the alkyl can be a methyl.
The term "aryl" has used herein refers to a cyclic or polycyclic aromatic ring. The aryl group can be a phenyl or napthyl.
The term "heteroaryl" has used herein refers to an aromatic cyclic or fused polycyclic ring system having at least one heteroatom chosen from N, O, and S. For example, the heteroaryl groups include, but are not limited to, furyl, thienyl, pyridyl, quinolinyl, isoquinolinyl, indolyl, isoindolyl, triazolyl, pyrrolyl, tetrazolyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothiophenyl, carbazolyl, benzoxazolyl, pyrimidinyl, benzimidazolyl, quinoxalinyl, benzothiazolyl, naphthyridinyl, isoxazolyl, isothiazolyl, purinyl, quinazolinyl, among others.
The term "heterocyclyl" includes non-aromatic rings or ring systems that contain at least one ring having at least one hetero atom (such as nitrogen, oxygen or sulfur). For example, this term can include all of the fully saturated and partially unsaturated derivatives of the above mentioned heteroaryl groups. Examples of heterocyclic groups include, without limitation, pyrrolidinyl, tetrahydrofuranyl, morpholinyl, thiomorpholinyl, piperidinyl, piperazinyl, thiazolidinyl, isothiazolidinyl, and imidazolidinyl.
In the compounds and processes previously presented, Q+ can be chosen from
Figure imgf000019_0001
R2 R?
Θ/ ®/
// Λ and fl
O
Alternatively, Q+ can be chosen from:
Figure imgf000019_0002
R2 XR3 R2 NR3 R2 R3
Figure imgf000019_0003
According to another example Q+ can be chosen from
Figure imgf000019_0004
R2 can be a C1-C20 alkyl which is linear or branched or a C3-C12 cycloalkyl. According to one example, R2 can be a C1-C20 alkyl which is linear or branched. According to another example, R2 can be a C-i-Cβ alkyl which is linear. R3 can be a C1-C20 alkyl which is linear or branched or a C3-Ci2 cycloalkyl. According to one example, R3 can be a C1-C20 alkyl which is linear or branched .Accord ing to another example, R3 is a CrC8 alkyl which is linear. R4 can be a C1-C20 alkyl which is linear or branched or a C3-C12 cycloalkyl.According to one example, R4 can be a C1-C20 alkyl which is linear or branched.According to another example, R4 can be a Ci-Ce alkyl which is linear. According to a further example, R4 can be a CrC4 alkyl which is linear.
The compounds previously presented can have a conductivity of at least 0.0001 mS cm"1. For example, the conductivity can be of at least 1 mS cm"1, or of at least 10 mS cm"1. Alternatively, they can have a conductivity of about 0.0001 to about 100 mS cm"1. The compounds can have a melting point below 100 ° C. For example, the melting point can be below 40 ° C, or below 25 ° C. Alternatively, the compounds can have a melting point of about 0 0 C to about 100 ° C. For example, the Ri group can be a halogen atom. According to one example, Ri is F or Cl. According to another example, Ri is F.
The compounds previously presented can be used as a molten salt, an ionic liquid or an electrolyte. These compounds can also be used in an electrochemical device such as a battery.
In the process for preparing the compounds represented by formula (I), the reaction can be carried out in water so that the so-obtained product of formula (I) precipitates and the so-formed byproduct of formula M+X" is at least substantially soluble. For example, M+ can be K+. For example, X" can be F", Cl", Br", or I". According to another example, X" is Cl", or Br". Each of the Ri can be a halogen atom. According to another example, Ri can be Cl" or F". According to another example, Ri can be F".
In the process for preparing compounds represented by formula (Ia), the compound of formula (III) can be a compound of formula (IV):
Figure imgf000021_0001
wherein
Q+ is as previously defined in formula (I); and
each of the R7 is independently a C1-C12 alkyl.
For example, each of the R7 can be the same. According to one example, R7 can be methyl. The compounds of formulas (II) and (III) can be reacted together at a temperature of about -78 to about 110 ° C.The temperature can be for example about -5 to about 25 ° C, or about 15 to about 25 0C. Ri can be F or Cl. According to one example, Ri can be F.
In the process for preparing compounds represented by formula (Ib), step (a) can be carried out at a temperature of about -78 to about 110 ° C. For example, the temperature can be about -5 to about 25 ° C or about 15 to about 25 0C. Step (b) can be carried out in the presence of an aprotic solvent. For example, the aprotic solvent can be a polar solvent such as nitromethane or acetonitrile. According to one example, the compound of formula (III) can be a compound of formula (IV):
Figure imgf000021_0002
wherein
Q+ is as previously defined in formula (Ib); and
each of the R7 is independently a C1-C12 alkyl.
Each of the R7 can be the same. For example, R7 can be a methyl.
In the process for preparing compounds represented by formula (Ib), the compound of formula (Ilia) can be a compound of formula (IVa):
Figure imgf000022_0001
wherein
T+ is as previously defined in formula (Ilia); and
each of the R7 is independently a C1-C12 alkyl.
Each of the R7 can be the same.For example, each of the R7 can be a methyl.
In accordance with another aspect there is provided a molten salt comprising a compound as defined in the present invention.
In accordance with another aspect there is provided an ionic liquid comprising a compound as defined in the present invention. In accordance with another aspect, there is provided an electrolyte comprising a compound as defined in the present invention.
In accordance with another aspect, there is provided an electrochemical device comprising a compound as defined in the present invention.
In accordance with another aspect, there is provided a battery comprising a compound as defined in the present invention.
In accordance with another aspect, there is provided a method of using a compound as previously defined, which comprises contacting the compound with electrodes and using it as an electrolyte.
In accordance with another aspect, there is provided a method of using a compound as previously defined, which comprises introducing the compound in the manufacture of a proton exchange membrane.
The compounds previously described can be used in many applications. For example, they can be used as solvents for organic and organometallic syntheses and catalysis. They can also be used as electrolytes (for example in electrochemistry or in fuel and solar cells), as lubricants, as a stationary phase for chromatography, as matrices for mass spectrometry, supports for the immobilization of enzymes, in separation technologies, as liquid crystals, templates for the synthesis of mesoporous, nano-materials and ordered films, materials for embalming and tissue preservation, etc.
The compounds previously mentioned can be used in various solutions (dry cleaning, metal extraction, personal care, embalming, household products, coatings, etc.) and in electrochemistry ( batteries, solar panel, ion propulsion, fuel cells, electro-optics, etc.). The can also be used in view of their various interesting properties for heat transfer or as lubricants. They can also be used in drug delivery, biomass processing, biocides etc.
The compounds previously mentioned can also be useful for preparing compositions for lithium-ions batteries. In accordance with another aspect there is provided a composition comprising a compound of formula (I) and a compound of formula (VIII):
Figure imgf000024_0001
(I) wherein each of the Ri is independently F, Cl, -N(Rs^, or -CN; Q+ is chosen from
Figure imgf000024_0002
Figure imgf000024_0003
wherein D is chosen from CF3SO3-, (FSO2)2N- ,(CF3SO2)2N-, (CF3CF2SO2)2N-, (CF3SO2)3C-, PF6 ", CF3COO-, AsF6 ", CH3COO", (CN)2N", NO3 ", BF4 ", CIO4 ", (C8H16SO2)2N", and C3H3N2 "
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3- Ci2 cycloalkyl, Ci-Ci2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and Ci-Ci2 heteroaryl;
R3 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
R4 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl; and
R5 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl, an effective protecting group for an amino group,
the heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from of -NO2, -CN -OH, -CF3 -COR4, -SH, - OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2, C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6-Ci2 aryl, C3-Ce cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, CeHsCpH2P-, CpH2p+iC6H4— , CpH2P+ICeH4CnH2n-, CH2=CHCpH2p— ,
CH2=CHC6H5-, CH2=CHC6H4CpH2P+1-, and CH2=CHCpH2pC6H4- ^^CpH2p- where (1 < n, p < 48),
In accordance with another aspect, there is provided a method of using a compound as previously defined, which comprises mixing the compound with a compound of formula (VIII) so as to obtain a mixture and using said mixture as an electrolyte, for example in a lithium-ion battery.
DETAILED DESCRIPTION OF OF THE INVENTION
The following examples are given in a non-limitative manner.
EXAMPLE 1
O
H3C^CH3
Figure imgf000026_0001
Compound 1
2 g (14.81 mM) of sulfuryl chloride are charged under argon into a 500 ml_ flask and mixed with 50 ml_ of anhydrous acetonitrile. Then, the mixture is cooled at -200C. 14.81 ml_ of a potassium hexamethyldisilazane (KHMDS) solution (0.5 M in toulene) is added dropwise over 5 minutes at -200C under argon. The mixture is stirred at room temperature for 12h. Then, the solvent is removed under vacuum and the resulting brown crude is dissolved in 100 mL acetonitrile and mixed with 1.72 g (29.08 mM) of anhydrous KF. The reaction mixture is heated and stirred over 12h. Then, the solid particles are filtered- out and the solvent is removed under vacuum and replaced by 100 mL of distilled water. The aqueous solution is charged into a 500 ml_ flask and mixed with 100 ml_ of an aqueous solution of 1.68 g (7.4 mM) of N1N- dimethyl-pyrrolidinium iodide. The resulting compound 1 is then extracted by dichloromethane and isolated in pure form.
EXAMPLE 2
Figure imgf000027_0001
O Q O
I l ^ I l
F-S-N-S-F
Il Il
O O
Compound 2
Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.41 g (10 mM) of N.N-ethylmethylpyrrolidinium iodide is dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N,N-ethylmethylpyrrolidinium iodide exchanges anions with KFSI in water. The Potassium iodide stays in the aqueous phase and the desired molten salt 2 is decanted. The organic layer is decanted, extracted with 40 mL of CH2CI2 and then washed with 80 mL of distilled H2O and dried over anhydrous MgSO4. After concentration with a rotative evaporator, the translucent ionic liquid obtained is dried under vacuum at 60 0C for 3 hours. Its purity is confirmed by NMR (1H, 13C, 19F) and cyclic voltammetry. EXAMPLE 3
Figure imgf000028_0001
O Q O
I l V-^ I l
F-S-N-S-F
Il Il
O O
Compound 3
Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.37 g (10 mM) of N,N-ethylmethylpyrrolium iodide was dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N,N-ethylmethylpyrrolium iodide exchanges anions with KFSI in water. The potassium iodide stays in the aqueous phase and the desired molten salt 3 is decanted. The organic layer was decanted, extracted with 40 mL of CH2CI2 and then washed with 80 mL of distilled H2O and dried over anhydrous MgSO4. After concentration with a rotative evaporator, the translucent ionic liquid obtained is dried under vacuum at 60 0C for 3 hours. Its purity is confirmed by NMR (1 H, 13C, 19F) and cyclic voltammetry.
EXAMPLE 4
CH3
@/
N
W
O O I l Q w O I l
F-S-N-S-F
Il I l
O O
Compound 4
Potassium bis(fluoromethanesulfonimide) KFSI is prepared as previously described and 2.2 g (10 mM) of this compound are used to prepare an aqueous solution by charging it into a 500 ml_ flask and dissolving it into 50 mL of distilled water. 2.13 g (10 mM) of, N-methyloxazolinium iodide is dissolved into 50 mL of distilled water and then mixed with KFSI solution. The N-methyloxazolinium iodide exchanges anions with KFSI in water. The potassium iodide stays in the aqueous phase and the desired molten salt 4 is decanted. The organic layer is decanted, extracted with 60 mL of CH2CI2 and then washed with 100 mL of distilled H2O and dried over anhydrous MgSO4. After concentration with a rotative evaporator, the translucent ionic liquid obtained is dried under vacuum at 60 0C for 3 hours. Its purity is confirmed by NMR (1H, 13C, 19F) and cyclic voltammetry.
The person skilled in the art would clearly recognize that all the references cited in this application are hereby incorporated by references. The person skilled in the art would also recognize that various modifications, adaptations, and variations may be brought to the previously presented preferred embodiments without departing from the scope of the following claims.

Claims

CLAIMS:
1. A compound of formula (I):
Figure imgf000030_0001
wherein each of the Ri is independently F, Cl, -N(R5)2, or -CN, Q+ is selected from the group consisting of
Figure imgf000030_0002
wherein R2 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrC12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrC12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl;
R4 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-Ci2 heteroaryl; and
R5 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl, an effective protecting group for an amino group,
said heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2,
C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6- C12 aryl, C3-Ce cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+1, C1-C12 alkyl which is linear or branched, C6-C12 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+i C6H4-, CpH2P+IC6H4CnH2n-, CH2 =CHCpH2p— , CH2=CHC6H5-, CH2=CHC6H4CpH2P+I-, and CH2=CHCpH2PC6H4- ^-^-CpH2p- , where (1 < n, p < 48),
with the proviso that said compound of formula (I) is different than 1-methyl-1-propylpyrrolidinium imidosulfuryl fluoride.
2. The compound of claim 1 , wherein each of said Ri is F or Cl.
3. The compound of claim 1 , wherein each of said Ri is F.
4. The compound of any one of claims 1 to 3, wherein Q+ is chosen from
R2 R3 R2 R3 R2 R3 °2 R3
Figure imgf000032_0001
5. The compound of any one of claims 1 to 3, wherein Q+ is chosen from
R2 R3 R2 R3 R2 R3
Figure imgf000032_0002
6. The compound of any one of claims 1 to 3, wherein Q+ is chosen from
Figure imgf000033_0001
7. The compound of any one of claims 1 to 3, wherein Q+ is chosen from
Figure imgf000033_0002
8. The compound of any one of claims 1 to 3, wherein Q+ is
R2 VR3
9. The compound of any one of claims 1 to 8, wherein R2 is a C1-C20 alkyl which is linear or branched or a C3-C12 cycloalkyl.
10. The compound of claim 9, wherein R2 is a Ci-C20 alkyl which is linear or branched.
11. The compound of claim 10, wherein R2 is a Ci-Cs alkyl which is linear.
12. The compound of any one of claims 1 to 11 , wherein R3 is a Ci-C20 alkyl which is linear or branched or a C3-Ci2 cycloalkyl.
13. The compound of claim 12, wherein R3 is a C1-C20 alkyl which is linear or branched.
14. The compound of claim 13, wherein R3 is a CrCs alkyl which is linear.
15. The compound of any one of claims 1 to 4, wherein R4 is a Ci-C2o alkyl which is linear or branched or a C3-Ci2 cycloalkyl.
16. The compound of claim 15, wherein R4 is a C1-C20 alkyl which is linear or branched.
17. The compound of claim 16, wherein R4 is a Ci-Ce alkyl which is linear.
18. The compound of claim 17, wherein R4 is a CrC4 alkyl which is linear.
19. The compound of any one of claims 1 to 18, wherein said compound has a conductivity of at least 0.0001 mS cm'1.
20. The compound of any one of claims 1 to 18, wherein said compound has a conductivity of at least 1 mS cm"1.
21. The compound of any one of claims 1 to 18, wherein said compound has a conductivity of at least 10 mS cm"1.
22. The compound of any one of claims 1 to 18, wherein said compound has a conductivity of about 0.0001 to about 100 mS cm"1.
23. The compound of any one of claims 1 to 22, wherein said compound has a melting point below 100 0 C.
24. The compound of any one of claims 1 to 22, wherein said compound has a melting point below 40 ° C.
25. The compound of any one of claims 1 to 22, wherein said compound has a melting point below 25 ° C.
26. The compound of any one of claims 1 to 22, wherein said compound has a melting point of about 0 ° C to about 100 ° C.
27. A molten salt comprising at least one compound as defined in any one of claims 1 to 22.
28. An ionic liquid comprising at least one compound as defined in any one of claims 1 to 22.
29. An electrolyte comprising a compound as defined in any one of claims 1 to 26.
30. An electrochemical device comprising a compound as defined in any one of claims 1 to 26.
31. A battery comprising an anode, a cathode and a compound as defined in any one of claims 1 to 26.
32. Use of a compound as defined in any one of claims 1 to 22, as a molten salt.
33. Use of a compound as defined in any one of claims 1 to 22, as a solvent.
34. Use of a compound as defined in any one of claims 1 to 22, as an ionic liquid.
35. Use of a compound as defined in any one of claims 1 to 26, as an electrolyte.
36. Use of a compound as defined in any one of claims 1 to 26 in an electrochemical device.
37. Use of a compound as defined in any one of claims 1 to 26 in a battery.
38. A method of using a compound as defined in any one of claims 1 to 26, comprising contacting said compound with electrodes and using it as an electrolyte.
39. A method of using a compound as defined in any one of claims 1 to 26, comprising introducing said compound in the manufacture of a proton exchange membrane.
40. A method of using a compound as defined in any one of claims 1 to 26, comprising mixing said compound with a compound of formula (VIII) LiD
(VIII)
wherein
D is chosen from CF3SO3-, (FSO2)2N-, (CF3SOa)2N-, (CF3CF2SO2)2N-, (CF3SO2)3C-, PF6 ", CF3COO-, AsF6 ", CH3COO-, (CN)2N-, NO3-, BF4-, CIO4-, (C8Hi6SOz)2N-, and C3H3N2 ",
so as to obtain a mixture and using said mixture as an electrolyte.
41. The method of claim 40, further comprising using said electrolyte in a lithium-ion battery.
42. A process for preparing a compound of formula (Ia):
Figure imgf000036_0001
wherein each of said Ri is independently F or Cl, Q+ is chosen from
Figure imgf000037_0001
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C2O alkylaryl, and C1-C12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2o aralkyl, C6-C2o alkylaryl, and C1-C12 heteroaryl; and
R4 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C2O alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C2o alkylaryl, and C1-C12 heteroaryl, said heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2,
C2-C20 alkenyl, CrC20 alkoxy, Ci-C20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6- Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, C1-C12, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I, OH, a CrC6 alkoxy, a Ci-C6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, Ci-Ci2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+iC6H4— , CpH2p+iC6H4CnH2n— , CH2=CHCpH2p— ,
CH2=CHC6Hs-,
Figure imgf000038_0001
and CH2 =CHCpH2pC6H4— -CpH2P- , where: (1 < n, p < 48),
O
comprising the step of reacting a compound of formula (II):
Figure imgf000038_0002
wherein each of said Ri is as previously defined,
with a compound of formula (III):
R6 ^ ^ R6
Q (HI) wherein
Q+ is as previously defined for formula (Ia); and
each of said R6 is independently H, Li, Na, K, Cs, or (R7)3Si-, each of said R7 being independently a C1-C12 alkyl.
43. The process of claim 42, wherein said compound of formula (III) is a compound of formula (IV):
Figure imgf000039_0001
wherein
Q+ is as previously defined in formula (I); and
each of said R7 is independently a C1-C12 alkyl.
44. The process of claim 43, wherein each of said R7 is the same.
45. The process of claim 43, wherein each of said R7 is methyl.
46. The process of any one of claims 42 to 45, wherein said compounds of formulas (II) and (III) are reacted together at a temperature of about -78 to about 110 0 C.
47. The process of claim 46, wherein said temperature is about -5 to about 25 0 C.
48. The process of claim 46, wherein said temperature is about 15 to about 25 0C.
49. The process of any one of claims 42 to 48, wherein each of said Ri is F.
50. The process of any one of claims 42 to 48, wherein each of said Ri is Cl.
51. A process for preparing a compound of formula (Ib):
Figure imgf000040_0001
wherein
Rs is F; and
Q+ is chosen from
Figure imgf000041_0001
Figure imgf000041_0002
R4 R2
-N. A^ tf^N ri^ N-^N
C *eN)' ; (Θ N;D' ; Ψ I ■ h I » and ψ I
R^ ^R3 R2 R2 R2
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl;
R3 is a hydrogen atom, a CrC20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, Ci-Ci2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl; and
R4 is a hydrogen atom, a Ci-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl, said heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2,
C2-C2O alkenyl, C1-C20 alkoxy, C1-C20 alkyl, C2-C2O alkynyl, C6-C2o aralkyl, C6- Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, C1-C6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2 vinyl, C4-C2O alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a Ci-C6 alkoxy, a d-C6 hydroxy alkyl, NO2, CN1 CF3, SO3 ", CnF2n+I, Ci-Ci2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+iC6H4— , CpH2p+iC6H4CnH2n— , CH2=CHCpH2p— ,
CH2=CHC6Hs-, CH2=CHC6H4CpH2p+i—, and CH2=CHCpH2pC6H4— ^-^CpH2p- , where: (1 < n, p < 48),
comprising the steps of :
a) reacting SO2CI2 with a compound of formula (III):
Figure imgf000042_0001
Q (III)
wherein
Q+ is as previously defined for formula (Ib); and each of said R6 is independently H, Li, Na, K, Cs, or (R7)3Si-, each of said R7 being independently a C-1-C12 alkyl
so as to obtain a compound of formula (Ic);
O O
Cl- -N- -Cl
o Q o (Ic)
wherein
Q+ is as previously defined for formula (Ia); and
b) reacting said compound of formula (Ic) with a compound of formula MF, wherein M is Li, Na, K, or Cs, so as to obtain said compound of formula (Ib).
52. The process of claim 51 , wherein said step (a) is carried out at a temperature of about -78 to about 11O 0 C.
53. The process of claim 52, wherein said temperature is about -5 to about 25 0 C.
54. The process of any one of claims 51 to 53, wherein said step (b) is carried out in the presence of an aprotic solvent.
55. The process of claim 54, wherein said aprotic solvent is a polar solvent.
56. The process of claim 54 or 55, wherein said aprotic solvent is nitromethane or acetonitrile.
57. The process of any one of claims 51 to 56, wherein said aprotic solvent is acetonitrile.
58. The process of any one of claims 51 to 57, wherein said compound of formula (III) is a compound of formula (IV):
Figure imgf000044_0001
wherein
Q+ is as previously defined in formula (Ib); and
each of said R7 is independently a C1-C-12 alkyl.
59. The process of claim 58, wherein each of said R7 is the same.
60. The process of claim 59, wherein each of said R7 is methyl.
61. A process for preparing a compound of formula (I):
Figure imgf000044_0002
wherein each of said Ri is independently F, Cl, -N(R5^ or -CN; Q+ is chosen from
Figure imgf000045_0001
Figure imgf000045_0002
wherein
R2 is a hydrogen atom, a Ci-C2O alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and CrCi2 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, CrCi2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-Ci2 heteroaryl;
R4 is a hydrogen atom, a Ci-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, Ce-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl; and
R5 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-Ci2 cycloalkyl, C1-Ci2 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C2O alkylaryl, and CrCi2 heteroaryl, an effective protecting group for an amino group,
said heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2,
C2-C20 alkenyl, CrC20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, C6-C20 aralkyl, C6- Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, CrCi2 vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl,
said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I, OH, a C1-C6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+I, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+iC6H4— , CpH2P+IC6H4CnH2n-, CH2=CHCpH2p— ,
CH2=CHC6Hs-, CH2=CHC6H4CpH2P+I-, and CH2=CHCpH2pC6H4— , ^-^^CpH2p- , where: (1 < n, p < 48),
comprising the step of reacting together a compound of formula (V) and a compound of formula (VI) :
Figure imgf000046_0001
wherein Ri and Q are as previously defined;
M+ is chosen from Li+, Na+, K+, and Cs+
X- is chosen from F1 Cl", Br, I", CH3COO-, PhCH2COO", CN', CF3COO-, SO4 2", CF3SO3-, BF4-, PF6 ", NO3 ", CIO4 ", SbF6 ", and RuO4 ".
62. The process of claim 61 , wherein said reaction is carried out in water so that the so-obtained product of formula (I) precipitates and the so-formed by product of formula M+X" is at least substantially soluble.
63. The process of claim 61 or 62, wherein M+ is K+.
64. The process of any one of claims 61 to 63, wherein X" is F", Cl", Br", or I".
65. The process of any one of claims 61 to 63, wherein X" is Cl", or Br".
66. The process of any one of claims 61 to 65, wherein each of said Ri is Cl or F.
67. The process of any one of claims 61 to 65, wherein each of said Ri is F.
68. The process of any one of claims 61 to 65, wherein each of said Ri is Cl.
69. A process for preparing a compound of formula (Ib):
Figure imgf000047_0001
wherein
Re is F; and
Q+ is chosen from
Figure imgf000048_0001
Figure imgf000048_0002
wherein
R2 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C12 aryl, C6-C20 aralkyl, C6-C2O alkylaryl, and C1-C12 heteroaryl;
R3 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-Ci2 aryl, C6-C2O aralkyl, C6-C2o alkylaryl, and C1-C12 heteroaryl; and
R4 is a hydrogen atom, a C1-C20 alkyl which is linear or branched, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-CI2 aryl, C6-C20 aralkyl, C6-C20 alkylaryl, and C1-C12 heteroaryl, said heterocycles represented by Q+ are as previously presented or substituted with 1 to 3 substituents chosen from -NO2, -CN -OH, -CF3 -COR4, -SH, -OMe, -OCH2Ph, -SMe, -SPh, -SCH2Ph, -COOH, -COOR4, -NH2,
C2-C20 alkenyl, Ci-C20 alkoxy, CrC20 alkyl, C2-C20 alkynyl, Ce-C20 aralkyl, C6- Ci2 aryl, C3-C8 cycloalkyl, CrC20 aminoalkyl, CrC6 hydroxyalkyl, C2-Ci2 heteroaryl, C1-C12, vinyl, C4-C20 alkylvinyl, C4-C20 vinylalkyl, and C3-C20 expoxyalkyl;
said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, and heteroaryl being unsubstituted or substituted with 1 to 3 substituents chosen from F, Cl, Br, I1 OH, a CrC6 alkoxy, a CrC6 hydroxy alkyl, NO2, CN, CF3, SO3 ", CnF2n+I, CrCi2 alkyl which is linear or branched, C6-Ci2 aryl, CnH2n+i, Ph2P(O)-, Ph2P-, Me2P(O)-, Me2P, Ph2P(S), Me2P(S), Ph3P=N-, Me3P=N-, C6HsCpH2P-, CpH2p+iC6H4— , CpH2p+iC6H4CnH2n— , CH2 =CHCpH2p— ,
CH2=CHC6H5-, CH2=CHC6H4CpH2P+I-, and CH2=CHCpH2pC6H4- , ^-^-CpH2p- , where: (1 < n, p < 48),
comprising the steps of :
a) reacting a compound of formula (Ha):
Rg ^~~ " S ^~^~ Rg
(Ha)
wherein each of said Rg is independently Cl, Br, or I
with a compound of formula (Ilia):
Figure imgf000050_0001
(Ilia)
wherein
T+ is Li+, Na+, K+ ,Cs+ or H+ and
each of said Re is independently H, Li, Na, K, Cs, or (R7)3Si-, each of said R7 being independently a C1-C12 alkyl.
so as to obtain a compound of formula (VII);
Figure imgf000050_0002
wherein
each of said Rg is as previously defined for formula (Ha); and
T+ is as previously defined for formula (Ilia); and b) reacting said compound of formula (VII) with a compound of formula Q-Rs1 wherein Q and R8 are as previously defined in formula (Ib), so as to obtain said compound of formula (Ib).
70. The process of claim 69, wherein said step (a) is carried out at a temperature of about -78 to about 11O 0 C.
71. The process of claim 70, wherein said temperature is about -5 to about 25 0 C.
72. The process of any one of claims 69 to 71 , wherein said step (b) is carried out in the presence of an aprotic solvent.
73. The process of claim 72, wherein said aprotic solvent is a polar solvent.
74. The process of claim 72 or 73, wherein said aprotic solvent is nitromethane or acetonitrile.
75. The process of claim 72 or 73, wherein said aprotic solvent is acetonitrile.
76. The process of any one of claims 69 to 75, wherein said compound of formula (Ilia) is a compound of formula (IVa):
Figure imgf000051_0001
(IVa)
wherein T+ is as previously defined in formula (Ilia); and
each of said R7 is independently a C1-C12 alkyl.
77. The process of claim 76, wherein each of said R7 is the same.
78. The process of claim 76, wherein each of said R7 is methyl.
79. The process of any one of claims 42 to 78, wherein Q+ is chosen from
Figure imgf000052_0001
80. The process of any one of claims 42 to 78, wherein Q+ is chosen from
Figure imgf000052_0002
81. The process of any one of claims 42 to 78, wherein Q+ is chosen from
Figure imgf000053_0001
82. The process of any one of claims 42 to 78, wherein Q+ is chosen from
83. The process of any one of claims 42 to 78, wherein Q+ is chosen from
R2 R3
84. The process of any one of claims 42 to 83, wherein R2 is a C1-C20 alkyl which is linear or branched or a C3-C12 cycloalkyl.
85. The process of claim 84, wherein R2 is a C1-C20 alkyl which is linear or branched.
86. The process of claim 85, wherein R2 is a CrCs alkyl which is linear.
87. The process of any one of claims 42 to 86, wherein R3 is a C1-C20 alkyl which is linear or branched or a C3-C12 cycloalkyl.
88. The process of claim 87, wherein R3 is a C1-C20 alkyl which is linear or branched.
89. The process of claim 84, wherein R3 is a Ci-Cs alkyl which is linear.
90. The process of any one of claims 42 to 79, wherein R4 is a C1-C20 alkyl which is linear or branched or a C3-Ci2 cycloalkyl.
91. The process of claim 90, wherein R4 is a C1-C20 alkyl which is linear or branched.
92. The process of claim 90, wherein R4 is a CrC8 alkyl which is linear.
93. A composition comprising a compound as defined in any one of claims 1 to 26 and a compound of formula (VIII):
LiD
(VIII)
wherein
D is chosen from CF3SO3-, (FSO2)2N-, (CF3SO2^N-, (CF3CF2SO2)2N-, (CF3SO2)3C-, PF6 ", CF3COO", AsF6-, CH3COO-, (CN)2N-, NO3-, BF4 ", CIO4 ", (C8H16SO2)2N-, and C3H3N2 '.
94. Use of a composition as defined in claim 93 as an electrolyte.
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