EP1636173A2 - Liquides ioniques contenant des cations de guanidine - Google Patents

Liquides ioniques contenant des cations de guanidine

Info

Publication number
EP1636173A2
EP1636173A2 EP04724995A EP04724995A EP1636173A2 EP 1636173 A2 EP1636173 A2 EP 1636173A2 EP 04724995 A EP04724995 A EP 04724995A EP 04724995 A EP04724995 A EP 04724995A EP 1636173 A2 EP1636173 A2 EP 1636173A2
Authority
EP
European Patent Office
Prior art keywords
atoms
perfluorinated
substituted
guanidinium
salt
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04724995A
Other languages
German (de)
English (en)
Inventor
Urs Welz-Biermann
Nikolai Ignatyev (Mykola)
Helge Willner
German Bissky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP1636173A2 publication Critical patent/EP1636173A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/02—Guanidine; Salts, complexes or addition compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds

Definitions

  • the present invention relates to salts containing guanidinium cations and various anions, processes for the preparation of these salts and their use as ionic liquids.
  • Ionic liquids or liquid salts are ionic species that consist of an organic cation and a generally inorganic anion. They contain no neutral molecules and mostly have melting points below 373 K. A large number of compounds which are used as ionic liquids are known in the prior art. In particular, they are also the subject of a number of patents and patent applications. For example, solvent-free ionic liquids were first disclosed by Hurley and Wier in a number of US patents (US 2,446,331, US 2,446,339 and US 2,446,350).
  • ionic liquids e.g. melting point, thermal and electrochemical stability, viscosity
  • properties of ionic liquids are strongly influenced by the nature of the Anions influenced.
  • the polarity and the hydrophilicity or lipophilicity can be varied by the suitable choice of the cation / anion pair.
  • the object of the present invention is to provide new, stable, low viscosity, salt-like compounds which can be used as ionic liquids, and to provide a process for their preparation.
  • Nitrogen atoms are delocalized in combination with selected anions according to claim 1.
  • EP 1 363 345 explicitly discloses the compound tetramethylguanidinium bis (trifluoromethanesulfonyl) imide and its use as an electrolyte.
  • EP 1 363 345 was published after the priority application DE 10325051 was submitted.
  • Guanidinium cations are understood in the sense that not all three nitrogen atoms may be substituted identically. However, alicyclic and aromatic groups can also be substituents of a proton or some protons of guanidinium, in particular which form a mono-, bi- or tricyclic ring. 1-methyl-7-n-propyl-1,5,7-triazabicysclo [4.4.0] dec-5-enium is given as an example of this.
  • Suitable anions include not only bis (trifluoromethanesulfonyl) imide also hexafluorophosphate, tetrafluoroborate and trifluoromethanesulfonate (triflate) or Trifluormethansulfonyltrifluoracetylimid, Trifluormethansulfonylpentafluorethansulfonylimid or Closocarborate as B 9 H 9 CH “B- ⁇ H 22 CH ', Closoborate such as B 10 H 10 2" and B ⁇ 2 H ⁇ 2 2 " and their halogenated derivatives, AsF 6 " , SbF 6 " , CIO4 “ , O 2 " , AICI 4 " , GaCI 4 " , C (SO 2 CF 3 ) 3 " , SCN-, C 6 F 5 S0 3 " , O2CCF3 “ , SO 6 F and B (C 6 H 5 ) 4 " .
  • the object is to obtain stable, low viscosity, salt-like compounds which can be used as ionic liquids from salts with guanidinium cations, in which the positive charge is delocalized over several nitrogen atoms, according to the general formula (1)
  • the groups R have the meaning of
  • R can be partially or completely substituted with halogens, in particular -F and / or -Cl, or partially with -CN or -N0 2l
  • a ⁇ is selected from the group consisting of: [(FSO 2 ) 2 N] ⁇ [R F CF 2 SO 3 ] ⁇ , [(R p SO 2 ) 2 N] -, [(R p SO 2 ) 3 C] ⁇ [(FS0 2 ) 3 C] - [R F CF 2 C (O) O] - [P (C n F 2n + 1-rn H m ) y F 6 - y ] " [P (C 6 F 5 ) y F 6-y ] " [R F 2 P (O) O] ⁇
  • R F perfluorinated and straight-chain or branched alkyl
  • R F can each be the same or different
  • R F can be connected in pairs by single or double bond
  • R F perfluorinated straight-chain or branched alkyl with 2-20 C atoms, perfluorinated and straight-chain or branched alkenyl with 2-20 C-atoms and one or more double bonds perfluorinated and straight-chain or branched alkynyl with 2-20 C-atoms and one or more triple bonds perfluorinated and saturated, partially or completely unsaturated cycloalkyl with 3-7 C Atoms, especially phenyl, which can be substituted with perfluoroalkyl groups,
  • R F can each be the same or different
  • R F can be connected in pairs by single or double bond
  • the compounds according to the invention are distinguished in particular by very stable cations.
  • the compounds according to the invention are accordingly salts which have an optionally substituted guanidinium cation.
  • the substituents R of the guanidinium cation which can be used according to the invention are: C 1 -C 2 -o, in particular C to C1.2-alkyl groups, and saturated or unsaturated, ie also aromatic, C 3 -C -cycloalkyl groups, which can be substituted with Cr to C 6 alkyl groups, especially phenyl.
  • the six substituents R of the guanidinium cation according to the invention can be the same or different.
  • the CrCe alkyl group is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, and also pentyl, 1-, 2- or 3-methylbutyl, 1, 1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl or hexyl. If necessary, difluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
  • Unsubstituted saturated or partially or completely unsaturated cycloalkyl groups with 3-7 C atoms are therefore cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclopenta-1, 3-dienyl, cyclohexenyl, cyclohexa-1, 3-dienyl, cyclohexa-1 , 4-dienyl, phenyl, cycloheptenyl, cyclohepta-1, 3-dienyl, cyclohepta-1, 4-dienyl or cyclohepta-1, 5-dienyl, which can be substituted by C to C 6 alkyl groups, again the cycloalkyl group or the cycloalkyl group substituted by C to C 6 alkyl groups can also be substituted by halogen atoms such as F, Cl, Br or I, in particular F or Cl,
  • the substituents R can be partially or completely substituted with halogen atoms, in particular with F and / or Cl, or partially with CN or NO 2 .
  • R ' is C 3 - to C 7 -cycloalkyl, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
  • R 'substituted phenyl means by C to C 6 alkyl, d to C 6 alkenyl, NO 2 , F, Cl, Br, I, OH, CrC 6 alkoxy, CN, SCN, SCF 3 , SO 2 CF 3 , C (O) 0-CrC 6 alkyl, NH 2 , CrC 6 alkylamino or CrC 6 dialkylamino, COOH, C (O) NR " 2 , SO 2 OR", S0 2 X ', SO 2 NR " 2 , SO 3 H or NHC (O) R" substituted phenyl, where X 'F, Cl or Br and R "is a non, partially or perfluorinated Cr to C 6 alkyl or C
  • the heterocycle is understood to mean a saturated or unsaturated mono- or bicyclic heterocyclic radical with 5 to 13 ring members, where 1, 2 or 3 N and / or 1 or 2 S or O atoms can be present and the heterocyclic radical is one - or several times by Cr to Cö-alkyl, Cr to Ce-alkenyl, NO 2 , F, Cl, Br, I, OH, -C-C 6 alkoxy, CN, SCN, SCF 3 , SO 2 CF 3 , C ( O) O-Cr Ce alkyl, NH 2 , CrC 6 alkylamino or CrC 6 dialkylamino, COOH, C (O) NR " 2 , SO 2 OR", SO 2 X ', SO 2 NR " 2 , SO 3 H or NHC (0) R "can be substituted, where X 'and R" have a meaning given above.
  • the heterocyclic radical is preferably substituted or unsubstituted.
  • Benzopyrazolyl 2-, 4-, 5-, 6- or 7-benzoxazolyl, 3-, 4-, 5-, 6- or 7-benzisoxazolyl, 2-, 4-, 5-, 6- or 7-benzthiazolyl, 2-, 4-, 5-, 6- or 7-benzisothiazolyl, 4-, 5-, 6- or 7-benz-2,1, 3-oxadiazolyl, 1-, 2-, 3-, 4-, 5 -, 6-, 7- or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolinyl, 1-, 2-, 3-, 4- or 9-carbazolyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-acridinyl, 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl, 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl or 1-, 2- or 3-pyrrolidinyl.
  • substituents R can also be linked in pairs in such a way that mono-, bi- or polycyclic cations are formed.
  • the substituents R can have a previously specified or particularly preferred meaning.
  • the carbocycles or heterocycles of the guanidinium cations given above can also be substituted by C to Ce alkyl, Cr to Ce alkenyl, NO 2 , F, Cl, Br, I, OH, CrC 6 alkoxy, CN, SCN, SCF 3 , SO 2 CF 3 ,
  • the anion A of the salts according to the invention is selected from [(FSO 2 ) 2 N] ⁇ [R F CF 2 SO 3 ] -, [(R P SO 2 ) 2 N] - [(R F SO 2 ) 3 C] " , [(FSO 2 ) 3 C] -, [R F CF 2 C (O) O] -, [P (C n F 2n + 1.
  • the organic groups R F and and R F of the anion which can be used according to the invention are: Cr or C 2 - to C 2 o-, in particular Cr or C 2 - to C 2 -alkyl groups, C 2 - to C 2 o -, In particular C 2 - to C ⁇ . 2 -, alkenyl or alkynyl groups and saturated or unsaturated, ie also aromatic, C 3 - to C 7 -cycloalkyl groups, which can be substituted by Cr to C 6 -alkyl groups 0, in particular phenyl, with all the groups listed being perfluorinated.
  • a straight-chain or branched alkenyl with 2 to 20 C atoms it also being possible for several double bonds to be present, for example allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore 4-pentenyl, isopentenyl, hexenyl, Heptenyl, octenyl, -C 9 H 17 , -C 10 H - ⁇ to -C 2 oH 3 g; preferably allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, further preferred is 4-pentenyl, isopentyl or hexenyl.
  • R F or R F are present in one anion, these can also be connected in pairs by single or double bonds in such a way that bi- or polycyclic anions are formed.
  • R F is preferably pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
  • R F is preferably trifluoromethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
  • [P (C ⁇ F 5 ) 2F 4 ] " [(CF 3 ) 2 P (O) O] -, [(C 4 F ⁇ ) 2 P (0) 0] -, [CF 3 P (O) ⁇ 2J ⁇ 2 ⁇ - ⁇ , [BF 3 (CF 3 )], [BF 2 (C 2 F 5 ) 2 ] - [BF 3 (C 2 F 5 )] -, [BF 2 (CF 3 ) 2 j-, [B ( C 2 F 5 ) 4 ] ⁇ [BF 3 (CN)] - [BF 2 (CN) 2 ] -, [B (CN) 4 ] - [B (CF 3 ) 4 ] - [N (CF 3 ) 2 ] -, [N (CN 2 ) 2 ] -, [C (CN) 3 r,
  • Very preferred anions of this group are [P (CnF 2n + 1-m Hm) y F 6-y ] " , [BF Z R F 4-Z ] ⁇ or [BF Z (CN) 4 -Z ] ⁇ , where n , m, y and z have one of the abovementioned meanings, for example [B (CN) 4 ] " , [(C 2 F 5 ) 3 PF 3 j ⁇ , [(C 2 F 5 ) 2 PF 4 ] ⁇ , [( C 4 F 9 ) 3 PF 3 ] " , [(C 3 F 7 ) 3 PF 3 ] - [B (C 2 F 5 ) F 3 ] ' or [B (CF 3 ) 4 ] " .
  • Very particularly preferred anions of this group are [B (CN) 4 ] " , [(C 2 F 5 ) 3 PF 3 ] ⁇ or
  • a group of salts of the formula (1) is preferred, the substituents R of the guanidinium cation being hydrogen or a straight-chain or branched alkyl group having 1-12 C atoms, in particular having 1-4 C atoms, and A " a Formula (1) or has a meaning given as preferred or particularly preferred.
  • a group of salts of the formula (1) is preferred, the substituents R of the guanidinium cation from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, phenyl and Cyclohexyl are selected and A "has a meaning given in formula (1) or a preferred or particularly preferred meaning.
  • a group of salts of the formula (1) is preferred in which at least two substituents R are bonded to one another by single or double bonds, so that a monocyclic cation is formed and A "is a preferred or particularly preferred formula (1) Has meaning.
  • a group of salts is particularly preferred, the substituents R each independently signifying hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl or i-butyl or two substituents R being linked to one another in such a way that an imidazolidinium cation arises and A "has a meaning given in formula (1) or a preferred or particularly preferred meaning.
  • the present invention also relates to a process for the preparation of the salts according to the invention with guanidinium cations according to the general formula (1).
  • the anion X ⁇ of the reacting guanidinium salt is selected from the group F “ , Cl “ Br “ I " [HF 2 ] “ , [CN] ⁇ , [SCN] “ , [CH 3 COO] “ , [CF 3 COO] -, [CF3SO3] -, [CH3OSO 3 ] - [SiFe] 2 " , [BF 4 ] -, [SO 4 ] 2 ' [N0 3 ] " , [C 2 H 5 OSO3] " , tosylates, malonates Malonates and [CO 3 ] ⁇ .
  • the groups or substituents A and R are defined like those of the general formula (1) and Kt is an alkali or alkaline earth metal, it being the case for the esters AR that for the meaning of the substituents R perhalogenated alkyl groups with 1-20 C- Atoms, cycloalkyl groups with 3- 7 C atoms, alkenyl groups with 2-20 C atoms and alkynyl groups with 2- 20 C atoms are excluded.
  • the reaction is preferably carried out at a temperature at which at least one of the components is liquid. Particularly preferred the reaction is carried out in a temperature range at which the reaction mixture is liquid.
  • reaction of the guanidine or the guanidinium salt with an acid AH or a salt Kt + A " can be carried out in polar inorganic or organic solvents, for example water, acetonitrile, dimethoxyethane, methanol, dimethylformamide, propionitrile or dichloromethane.
  • polar inorganic or organic solvents for example water, acetonitrile, dimethoxyethane, methanol, dimethylformamide, propionitrile or dichloromethane.
  • nonpolar organic solvents as a diluent , for example hexane or pentane, or without a solvent, for example in the molten salt
  • the reaction can be carried out with an ester, an acid or a salt
  • the alkylation of the guanidine with an ester can be carried out in a non-basic solvent, preferably hexane, pentane or
  • solvent mixtures can also be used instead of pure solvents.
  • the reagents can be reacted in an amount of up to five times excess of one of the reactants, in particular the alkylating agent, in the alkylation.
  • the reactants are preferably used in an equimolar amount.
  • the salts according to the invention can be isolated in very good yields, generally over 80%, preferably over 90%.
  • Another object of the present invention is a process for the preparation of a salt with a guanidinium cation according to the general formula (1) and a [BF 4 ] ⁇ anion, where R has a meaning given or preferred given in formula (1), which can further be used for the preparation of the guanidinium salts according to the invention.
  • This is a guanidinium chloride
  • guanidinium tetrafluoroborates with a reduced amount of chloride ions i.e. the proportion of chloride ions is ⁇ 100 ppm, preferably ⁇ 50 ppm.
  • the anhydrous hydrofluoric acid acts both as a solvent and as a reagent.
  • the reaction is preferably carried out at a temperature at which at least one of the components is liquid.
  • the reaction is particularly preferably carried out in a temperature range at which the reaction mixture is liquid.
  • the boron trifluoride etherate can be used in excess of up to 10% in relation to the guanidinium salt.
  • the reactants are preferably used in an equimolar amount.
  • All compounds according to the invention have a salt-like character, relatively low melting points (mostly below 100 ⁇ C) and can be used as ionic liquids. In particular, as described above, they have particularly low viscosities.
  • the salts according to the invention can be used as solvents for many synthetic or catalytic reactions, for example Friedel-Crafts acylation and alkylation, Diels-Alder cycloadditions, hydrogenation and oxidation reactions or Heck reactions. It is also possible to use the compounds according to the invention as a non-aqueous electrolyte, optionally in combination with other electrolytes known to the person skilled in the art.
  • salts according to the invention can be used as non-aqueous polar
  • Substances can be used in suitable reactions as a phase transfer catalyst, as a manufacturer (surface active agent) or as a medium for the heterogenization of homogeneous catalysts.
  • the NMR spectra were measured on solutions in deuterated solvents at 20 ° C. on a Bruker Avance 300 spectrometer with a 5 mm broadband head 1 H / BB with deuterium lock, unless stated in the examples.
  • the measuring frequencies of the different cores are: 1 H: 300.13 MHz, 11 B: 96.92 MHz, 19 F: 282.41 MHz and 31 P: 121, 49 MHz.
  • the referencing method is specified separately for each spectrum or for each data set.
  • Example 1 Hexamethylguanidinium triflate
  • the yield at N, N, N ' , N ' , N " -pentamethyl-N " - / - propylguanidinium tris (pentafluoroethyl) trifluorophosphate is 94.0% based on N, N, N ', N', N ' pentamethyl-N " - / - propylguanidinium triflate.
  • Tris (pentafluoroethyl) trifluorophosphoric acid pentahydrate added at room temperature.
  • the flask with the reaction mixture is cooled with ice, the lower phase is separated and washed twice with 30 cm 3 of ice water.
  • the yield of guanidinium tris (pentafluoroethyl) trifluorophosphate is 89.0%.
  • the material is characterized by 19 F and 1 H NMR spectroscopy, 5 which show the formation of two isomers of N, N, N ', N'-tetramethyl-N "-ethylguanidinium triflate.
  • reaction mixture is then stirred at room temperature overnight.
  • the solvent is removed in vacuo.
  • the residue is washed twice with 30 cm 3 of hexane and in vacuo for one hour
  • Tris (pentafluoroethyl) trifluorophosphate is 97.8% based on 1,3-dimethyl-2-diethylaminoimidazolidinium chloride.
  • Hexamethylguanidinium pentafluoroethyl trifluoroborate is 93.5% based on hexamethylguanidinium chloride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne des sels comprenant des cations de guanidine, un procédé pour les préparer et leur utilisation en tant que liquides ioniques.
EP04724995A 2003-06-02 2004-04-01 Liquides ioniques contenant des cations de guanidine Withdrawn EP1636173A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10325051A DE10325051A1 (de) 2003-06-02 2003-06-02 Ionische Flüssigkeiten mit Guanidinium-Kationen
PCT/EP2004/003459 WO2004106288A2 (fr) 2003-06-02 2004-04-01 Liquides ioniques contenant des cations de guanidine

Publications (1)

Publication Number Publication Date
EP1636173A2 true EP1636173A2 (fr) 2006-03-22

Family

ID=33482435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04724995A Withdrawn EP1636173A2 (fr) 2003-06-02 2004-04-01 Liquides ioniques contenant des cations de guanidine

Country Status (4)

Country Link
US (1) US7709656B2 (fr)
EP (1) EP1636173A2 (fr)
DE (1) DE10325051A1 (fr)
WO (1) WO2004106288A2 (fr)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10325051A1 (de) 2003-06-02 2004-12-23 Merck Patent Gmbh Ionische Flüssigkeiten mit Guanidinium-Kationen
DE102004060076A1 (de) * 2004-12-14 2006-07-06 Merck Patent Gmbh Verfahren zur Herstellung von Onium-Salzen mit Alkyl- oder Arylsulfonat-Anionen oder Alkyl- oder Arylcarboxylat-Anionen mit geringem Halogenid-Gehalt
DE102004060075A1 (de) * 2004-12-14 2006-07-06 Merck Patent Gmbh Verfahren zur Herstellung von Onium-Salzen mit Dialkylphosphat-, Dialkylphosphinat oder (O-Alkyl)-alkyl- oder Alkyl-phosphonat-Anionen mit geringem Halogenid-Gehalt
US8247117B2 (en) 2004-12-27 2012-08-21 National Institute Of Advanced Industrial Science And Technology Ionic liquid
DE102005025315A1 (de) * 2005-06-02 2006-12-14 Merck Patent Gmbh Ionische Flüssigkeiten mit niedriger Viskosität
DE102005032838A1 (de) * 2005-07-14 2007-02-08 Merck Patent Gmbh Mischung von Onium-Alkylsulfonaten und Onium-Alkylsulfiten
JP2009502738A (ja) * 2005-07-27 2009-01-29 株式会社日本触媒 反応用溶媒及びそれを用いた製造方法
CA2527144C (fr) * 2005-11-15 2014-04-29 Queen's University At Kingston Surfactants reversibles, et methodes d'utilisation
EP1819005A1 (fr) 2006-02-13 2007-08-15 Ecole Polytechnique Fédérale de Lausanne (EPFL) Electrolyte composé d'un liquide ionique
EP2279192B1 (fr) * 2008-05-28 2013-10-30 Merck Patent GmbH Liquides ioniques
DE102009003466A1 (de) * 2009-02-11 2010-08-19 Karlsruher Institut für Technologie Hexaalkylguanidiniumsalze
CA2683660C (fr) 2009-10-28 2017-07-04 Queen's University At Kingston Solvants a hydrophilicite modifiable et methodes d'utilisation
EP2534106B1 (fr) 2010-02-10 2019-10-16 Queen's University At Kingston Methode de modification de la force ionique
DE102010048614B4 (de) * 2010-10-15 2015-01-15 Bayer Intellectual Property Gmbh Verfahren zur Gewinnung von Lignin, Tannin, Cellulose und Hemicellulose aus biogenem Material
AU2011342287B2 (en) 2010-12-15 2015-09-17 Greencentre Canada Systems and methods for use of water with switchable ionic strength
DE102013202254A1 (de) * 2013-02-12 2014-08-14 Siemens Aktiengesellschaft Verfahren zur Herstellung von Hochenergiemagneten
WO2015049239A1 (fr) 2013-10-04 2015-04-09 Solvay Specialty Polymers Italy S.P.A. Procédé de synthèse de sels de sulfonate de fluoralkyle
CN104447418B (zh) * 2014-12-16 2016-07-20 四川大学 一种胍类磁性离子液体及其去除非极性溶液中含硫有机物的用途
JP6576656B2 (ja) * 2015-03-13 2019-09-18 デクセリアルズ株式会社 イオン液体、潤滑剤及び磁気記録媒体
DE102015006926B4 (de) 2015-05-29 2022-09-22 Willi Kantlehner Neuartiges durch RIBIL' s katalysiertes Verfahren zur Fraktionierung von Lignocellulose-haltiger Biomasse

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446331A (en) 1944-02-14 1948-08-03 William Marsh Rice Inst For Th Electrodeposition of aluminum
US2446350A (en) 1944-02-29 1948-08-03 William Marsh Rice Inst For Th Electrodeposition of aluminum
US2446339A (en) 1946-02-09 1948-08-03 George M Holley Speed density carburetor
JP3194780B2 (ja) * 1992-04-09 2001-08-06 森田化学工業株式会社 ４級アルキルアンモニウムテトラフルオロボレート類の製造法
US5827602A (en) * 1995-06-30 1998-10-27 Covalent Associates Incorporated Hydrophobic ionic liquids
WO1998050153A1 (fr) * 1997-05-01 1998-11-12 Akzo Nobel N.V. Formation in-situ de catalyseur liquide ionique pour une reaction chimique catalysee liquide ionique
JPH11310555A (ja) * 1998-04-30 1999-11-09 Mitsui Chem Inc ４級アルキルアンモニウムテトラフルオロボレート類の製造方法
GB9928290D0 (en) * 1999-12-01 2000-01-26 Univ Belfast Process for preparing ambient temperature ionic liquids
DE10027995A1 (de) 2000-06-09 2001-12-13 Merck Patent Gmbh Ionische Flüssigkeiten II
DE10038858A1 (de) * 2000-08-04 2002-02-14 Merck Patent Gmbh Fluoralkylphosphate zur Anwendung in elektrochemischen Zellen
JP4240263B2 (ja) * 2000-12-22 2009-03-18 富士フイルム株式会社 電解質組成物及び非水電解質二次電池
CA2445459A1 (fr) 2001-05-17 2002-11-21 Maxime Garayt Utilisation d'une composition de nature ionique comme reactif de substitution, composition constituant un reactif de fluoration et procede l'utilisant
JP2004253357A (ja) 2002-05-09 2004-09-09 Wilson Greatbatch Technologies Inc 電気化学電源における常温溶融塩のためのカチオンとしてのグアニジン誘導体
DE10325051A1 (de) 2003-06-02 2004-12-23 Merck Patent Gmbh Ionische Flüssigkeiten mit Guanidinium-Kationen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004106288A2 *

Also Published As

Publication number Publication date
DE10325051A1 (de) 2004-12-23
US7709656B2 (en) 2010-05-04
WO2004106288A2 (fr) 2004-12-09
US20070265453A1 (en) 2007-11-15
WO2004106288A3 (fr) 2005-03-17

Similar Documents

Publication Publication Date Title
WO2004106288A2 (fr) Liquides ioniques contenant des cations de guanidine
EP1711458B1 (fr) Procede de production de sels de guanidinium
EP1592696B1 (fr) Sels a base d'anions cyanoborates
US8859813B2 (en) Ionic liquids having uronium cations and a process for making same
US8106217B2 (en) Ionic liquids with bis[bis(pentafluoroalkyl)phosphinyl]imides
EP1768962B1 (fr) Procede pour produire des sels d'onium a faible teneur en chlorure
WO2008092489A1 (fr) Composé contenant des ions fluorochlorophosphatane organiques
EP1979361B1 (fr) Sels d'oxonium et de sulfonium
EP1773848B1 (fr) Sels a anions d'alcoxytris (fluoroalkyl) borate
DE10325050A1 (de) Ionische Flüssigkeiten mit Uronium-Kationen
EP2279192B1 (fr) Liquides ioniques
EP1685095B1 (fr) Procede de preparation de sels organiques contenant des anions de bis(perfluoralkyl)phosphinate
US8101749B2 (en) Process for the preparation of onium salts with a tetrafluoroborate anion having a reduced halide content
DE10324891A1 (de) Ionische Flüssigkeiten mit Thiouronium-Kationen
DE102016010488A1 (de) Verbindungen mit ein-, bis- und mehrfach geladenen schwach koordinierenden Anionen
DE102004036299A1 (de) Salze mit Alkoxytris(fluoralkyl)borat-Anionen
DE102009058969A1 (de) Verbindung mit (Perfluoralkyl)fluorohydrogenphosphat - Anionen

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20051018

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20071221

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20111102