WO2007006389A1 - Melange d'alkylsulfonates d'onium et d'alkylsulfites d'onium - Google Patents

Melange d'alkylsulfonates d'onium et d'alkylsulfites d'onium Download PDF

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Publication number
WO2007006389A1
WO2007006389A1 PCT/EP2006/005743 EP2006005743W WO2007006389A1 WO 2007006389 A1 WO2007006389 A1 WO 2007006389A1 EP 2006005743 W EP2006005743 W EP 2006005743W WO 2007006389 A1 WO2007006389 A1 WO 2007006389A1
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atoms
substituted
alkyl
substituents
partially
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PCT/EP2006/005743
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German (de)
English (en)
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Nikolai Ignatyev (Mykola)
Urs Welz-Biermann
Andriy Kucheryna
Helge Willner
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Merck Patent Gmbh
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    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

Definitions

  • the invention relates to a process for the preparation of mixtures of onium alkyl sulfonates and onium alkyl sulfites by reacting an onium halide or carboxylate with a symmetrically substituted one
  • Ionic liquids A large number of onium salts, for example alkyl sulfates, are ionic liquids. Ionic liquids, through their properties in modern research, are an effective alternative to traditional volatile organic solvents for organic synthesis. The use of ionic liquids as a novel reaction medium could continue to be a practical solution for both solvent emission and reprocessing problems Catalysts (R. Sheldon, Chem. Commun., 2001, pp. 2399-2407). Ionic liquids or liquid salts are ionic species consisting of an organic cation and a generally inorganic anion. They contain no neutral molecules and usually have melting points less than 373 K. However, the melting point may also be higher without restricting the applicability of the salts in all fields of application. Examples of organic cations include tetraalkylammonium, tetraalkylphosphonium, N-
  • Alkylpyridinium, 1, 3-dialkylimidazolium or trialkylsulfonium are, for example, BF 4 “ , PFe “ , SbF 6 “ , NO 3 “ , CF 3 SO 3 “ , (CF 3 SO 2 J 2 N “ , alkylSO 3 ' , arylSO 3 “ , CF 3 CO 2 “ , CH 3 CO 2 “ or AI 2 CI 7 " to call.
  • mixtures of two or more components e.g. Salts
  • Such mixtures are also referred to as eutectic mixtures.
  • Such mixtures are widely used, e.g. in metallurgy, for example in the production of aluminum.
  • the formation of eutectic mixtures is also conceivable for ionic liquids, but so far has not been used, since so far each individual component must be prepared in separate synthesis steps on different reaction routes. This makes a mix more expensive and thus more impractical than a system based on a single component.
  • the object is achieved by the method according to the invention.
  • the invention therefore provides a process for preparing mixtures of onium alkyl sulfonates and onium alkyl sulfites by reacting an onium halide or onium carboxylate with a symmetrically substituted dialkyl sulfite or with an unsymmetrically substituted dialkyl sulfite at temperatures of 50 to 120 ° C.
  • the inventive method has the advantage that no alkyl group of the sulfite used is transferred to the cation and thus the substitution pattern in the cation of the choice of Alkansulfonatanions or Alkylsulfitanions is independent.
  • dialkyl sulfites used are less toxic than alkyl sulfate esters.
  • alkyl halides or esters are obtained, which in turn can be used as valuable reagents.
  • the alkyl halides which are by-produced when using onium halides are generally gases or volatile compounds which can be removed from the reaction mixture without great expense in terms of process engineering
  • the mixture provided by the method according to the invention represents a new type of ionic liquids.
  • the mixture according to the invention can not only be used for a number of fields of application, in particular as an ionic liquid, but can also be used as a reactive ionic liquid the onium alkyl sulfonate acts as an inert solvent and the onium alkyl sulfite, for example, as a reducing reagent or as an antioxidant.
  • the composition of the mixture can be controlled in a simple manner by varying the starting compounds and by adjusting the process parameters.
  • Onium halides suitable for the process according to the invention are ammonium halides, phosphonium halides, thiouronium halides, guanidinium halides or heterocyclic cation halides, where the halides can be selected from the group of chlorides or bromides. Preference is given in the process according to the invention
  • Onium carboxylates suitable for the process according to the invention are ammonium carboxylates, phosphonium carboxylates, thiouronium carboxylates, guanidinium carboxylates or carboxylates with a heterocyclic cation, where the carboxylates are selected from the group consisting of carbonates, formates, acetates,
  • Propylates or butylates can be selected.
  • Onium halides are preferably used in the process according to the invention.
  • the onium halides or carboxylates are usually commercially available or can be prepared by synthetic methods as known from the literature, e.g. in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart or Richard C. Larock, Comprehensive Organic Transformations, 2nd Edition, Wiley-VCH, New York, 1999. One can also make use of known per se, not mentioned here variants.
  • Ammonium or phosphonium halides can be described, for example, by the formula (1)
  • Hal is Cl or Br and R are each independently
  • substituents R may be H at the same time, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or completely unsaturated cycloalkyl having 3-7 C
  • Atoms which may be substituted by alkyl groups having 1-6 C atoms, wherein one or more R partially with Cl, Br and / or CN or partially or completely with -F or F and Cl, or F and Br, or F Cl and Br may be substituted, but not all four or three R may be fully substituted with halogens, and one or two non-adjacent and not ⁇ - or ⁇ z -containing
  • Carbon atoms of R by atoms and / or atomic groups selected from the group -O-, -C (O) -, -S-, -S (O) - or -SO 2 - may be replaced.
  • Guanidinium halides can be described, for example, by the formula (2), [C (NR 1 R 2 ) (NR 3 R 4 ) (NR 5 R 6 )] + Hal ' (2), wherein
  • R 1 to R 6 are each independently
  • Thiouronium halides can be exemplified by the formula (3)
  • R 1 to R 4 and R 7 are each independently hydrogen or CN, wherein hydrogen is excluded for R 7 , straight-chain or branched alkyl having 1 to 20 C-atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or a plurality of double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or completely unsaturated cycloalkyl having 3-7 C
  • Atoms which may be substituted by alkyl groups having 1-6 C atoms, wherein one or more of the substituents R 1 to R 4 and R 7 partially or completely with F, Cl and / or Br, in particular -F and / or -Cl, or may be partially substituted with CN, but not all
  • Substituents may be substituted on an N atom completely with halogens, wherein the substituents R 1 to R 7 and may be connected in pairs by single or double bond and wherein one or two non-adjacent, not directly bonded to the heteroatom and not ⁇ -permanent Carbon atoms of the substituents R 1 to and R 7 by atoms and / or atomic groups selected from the group -O-, -C (O) -, -S-,
  • Halides with a heterocyclic cation can be obtained, for example, by the
  • R 1 'to R 4 ' are each independently
  • Hydrogen or CN straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds,
  • Heteroatom of the heterocycle is present, saturated, partially or completely unsaturated cycloalkyl having 3-7 C
  • Atoms which may be substituted by alkyl groups having 1-6 C atoms or aryl-CrC 6 alkyl, wherein the substituents R 1 'and R 4 ' partially or completely with F, Cl and / or Br, in particular -F and / or -Cl may be substituted, but not simultaneously R 1 ' and R 4' are CN or may be completely substituted with F or other halogens, wherein the substituents R 2 and R 3 may be partially or completely substituted by F, Cl and / or Br, in particular -F and / or -Cl, or partially substituted by NO 2 or CN and wherein one or two non-adjacent, not directly on Heteroatom bound and not Carbon atoms of the substituents R 1 'to R 4 ', by atoms and / or atomic groups selected from the group -O-, -C (O) -, -S-, -S (O) - or -SO 2 - may be replaced
  • the C 1 -C 20 -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, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl or tetradecyl.
  • fluorinated alkyl groups for example difluoromethyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl.
  • a straight-chain or branched alkenyl having 2 to 20 C atoms, wherein several double bonds may also be present, is, for example, vinyl, allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore 4-pentenyl, iso-pentenyl, Hexenyl, heptenyl, octenyl, -C 9 Hi 7 , -CioH 19 to -C 20 H 39 ; preferably vinyl, allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore preferred is 4-pentenyl, iso-pentenyl or hexenyl.
  • a straight-chain or branched alkynyl having 2 to 20 C atoms, wherein a plurality of triple bonds may also be present, is, for example, ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl, Heptynyl, octynyl, -C 9 H 15 , -C 10 Hi 7 to -C 20 H 3 7, preferably ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, 4-pentynyl, 3-pentynyl or hexynyl.
  • completely unsaturated cycloalkyl also means aromatic substituents.
  • Unsubstituted saturated or partially or fully unsaturated cycloalkyl groups having 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 may be substituted by Cr to C 6 alkyl groups, in turn, the cycloalkyl group or with the Cr to C 6 - Alkyl-substituted cycloalkyl group may also be substituted by F or F and Cl.
  • the cycloalkyl groups may likewise be substituted by further functional groups, for example by CN, SO 2 R ', SO 2 OR', SO 2 NH 2, C (O) NH 2 or C (O) OR '.
  • R ' has a meaning defined below.
  • ArylCrC 6 -alkyl is, for example, benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, where both the phenyl ring and the alkylene chain, as described above, may be partially or completely substituted by -F, or F and Cl, more preferably benzyl or phenylpropyl.
  • the phenyl ring or the alkylene chain can likewise be substituted by further functional groups, for example by CN, SO 2 R ', SO 2 OR', SO 2 NH 2 , C (O) NH 2 or C (O) OR '.
  • R 'does not mean partially or perfluorinated C 1 to C 6 alkyl, C 3 to C 7 cycloalkyl, unsubstituted or substituted phenyl.
  • C 3 - to C 7 - cycloalkyl is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
  • R ' is phenyl substituted by C 1 - to C 6 -alkyl, d- to C 6 - alkenyl, NO 2, F, Cl, Br, I, -C 6 alkoxy, SCF 3, SO 2 CF 3, SO 2 CH 3 , COOR ", SO 2 X ', SO 2 NR" 2 or SO 3 R "substituted phenyl, wherein X' is F, Cl or Br and R" is an unfluorinated or partially fluorinated C 1 to C 6 alkyl or C 3 - to C 7 - Cycloalkyl as defined for R ', for example, o-, m- or p-methylphenyl, o-, m- or p-ethylphenyl, o-, m- or p-propylphenyl, o-, m- or p-isopropylphenyl, o-, m- or p-nitrophenyl, o-,
  • R 1 to R 7 or R 1 ' to R 4 also one or two non-adjacent, not directly bonded to the heteroatom and not ⁇ -standing carbon atoms, by atoms and / or atomic groups selected from the group -O- , -C (O) -S-, -S (O) - or -SO 2 - be replaced.
  • the substituents R 1 to R 7 are each, independently of one another, preferably a straight-chain or branched alkyl group having 1 to 10 C atoms.
  • the substituents R 1 and R 2 , R 3 and R 4 and R 5 and R 6 in compounds of the formulas (2) and (3) may be the same or different.
  • R 1 to R 7 are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, phenyl or cyclohexyl, most preferably methyl, ethyl, n-propyl, isopropyl or n-butyl ,
  • the substituents R and R 1 to R 7 may also be substituted by further functional groups, for example by
  • substituents R 1 to R 4 of compounds of the formula (4) are according to the invention, besides hydrogen, preferably: CN, d- to C 20 -, in particular Cr to C 2 alkyl groups, and saturated or unsaturated, ie also aromatic, C 3 - to C 7 -cycloalkyl groups which may be substituted by Cr to C ⁇ -alkyl groups, in particular phenyl or aryl-Ci-C 6 -alkyl.
  • the substituents R 1 and R 4 are each, in each case independently of one another, more preferably CN, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl, pentyl, hexyl, octyl, decyl, cyclohexyl, phenyl, phenylpropyl or benzyl. They are very particularly preferably methyl, CN, ethyl, n-butyl or hexyl. In pyrrolidinium or piperidinium compounds, the two substituents R 1 and R 4 are preferably different.
  • the substituent R 2 or R 3 is, in each case independently of one another, in particular hydrogen, dimethylamino, diethylamino, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl, cyclohexyl, phenyl or benzyl.
  • R 2 is particularly preferably hydrogen, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or dimethylamino. Most preferably, R 2 and R 3 'are hydrogen.
  • the alkyl groups as substituents R and R 1 to R 6 and R 1 and R 4 of the heterocyclic cations of formula (4) are different from the alkyl group of the anion in onium alkyl sulfite.
  • the onium alkyl sulfite prepared according to the invention may also have alkyl groups in the cation which are the same as the alkyl group in the anion, but which have not been introduced by alkylation according to the invention.
  • Substituents R 1 , R 3 and R 7 may have a previously given or particularly preferred meaning.
  • the carbocycles or heterocycles of the above-mentioned thiouronium cations can still by Cr to C ⁇ -alkyl, Ci to Ce alkenyl, NO 2 , F, Cl, Br, I 1 Ci-C 6 alkoxy, SCF 3 , SO 2 CF 3 , SO 2 CH 3 , COOR ", SO 2 NR" 2 , SO 2 X 'or SO 3 R ", where X' is F, Cl or Br and R" is a non, partially or perfluorinated C r to C 6 -alkyl or C 3 - to C 7 -cycloalkyl as defined for R 'or substituted by substituted or unsubstituiert.es phenyl.
  • substituents R 1 to R 4 may likewise be substituted by further functional groups, for example by CN, SO 2 R ',
  • HetN + of the formula (4) is preferable Pyridinium Pyrimidinium
  • HetN + is particularly preferably imidazolium, pyrrolidinium or pyridinium, as defined above, wherein the substituents R 1 ' to R 4' each independently have a meaning as described above.
  • Hal can be replaced by carboxylates according to the invention, as defined above.
  • the choice of anion does not limit the choice of cation.
  • the symmetrically substituted dialkyl sulfite used in the process according to the invention is preferably a dialkyl sulfite having a straight-chain or branched alkyl group having 1-10 C atoms, preferably having 1-4 C atoms, particularly preferably having 1-2 C atoms.
  • the alkyl group is preferably a straight-chain or branched alkyl group having 1-4 C atoms, such as, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl.
  • the alkyl group is methyl or ethyl.
  • Examples of symmetrically substituted dialkyl sulfites are dimethyl sulfite, diethyl sulfite, di- (n-propyl) sulfite, di- (iso-propyl) sulfite, di- (n-butyl) sulfite or Di- (sec-butyl) sulfite. Preference is given to using dimethyl sulfite or diethyl sulfite.
  • the symmetrical dialkyl sulfites used are usually commercially available or can be prepared by synthetic methods as known from the literature, e.g. in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart or Richard C. Larock, Comprehensive Organic Transformations, 2nd Edition, Wiley-VCH, New York, 1999, or from the article by W. Voss and E. Blanke, Justus Liebigs Ann. Chem., 485 (1931), pp. 258-279.
  • dialkyl sulfite is preferably a dialkyl sulfite having a straight-chain or branched alkyl group having 1 to 10 carbon atoms and a methyl or ethyl group as the second alkyl group, preferably having an alkyl group having 3-8 carbon atoms used.
  • Examples of asymmetrically substituted dialkyl sulfites are methyl propyl sulfite, methyl butyl sulfite, ethyl butyl sulfite, methyl pentyl sulfite, ethyl pentyl sulfite, methyl hexyl sulfite, ethyl hexyl sulfite, methyl heptyl sulfite, ethyl heptyl sulfite, methyl octyl sulfite or ethyl octyl sulfite.
  • the unsymmetrical dialkyl sulfites used can be prepared by synthesis processes as described in the literature, for example in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart or Richard C. Larock, Comprehensive Organic Transformations, 2nd Edition, Wiley-VCH, New York, 1999, or from the article by W. Voss and E. Blanke, Justus Liebigs Ann. Chem., 485 (1931), pp. 258-279, or VM Pavlov, J. Gen. Chem. Chem. USSR (Eng. Transl.), 41 (1971), pp. 2559-2561.
  • a general scheme summarizes the process according to the invention, wherein the arrow in the resulting alkyl halogen compound is a symbol for the volatility of the compound:
  • the reaction with dialkyl sulfites is carried out at temperatures between 50 and 120 0 C, preferably at temperatures between 70 and 100 ° C.
  • the choice of the optimum reaction temperature depends on the amount of excess of the dialkyl sulfite and on the nature of the halide and the dialkyl sulfite used.
  • solvents for example dimethoxyethane, acetonitrile, acetone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, dioxane, propionitrile, dichloromethane or mixtures with one another.
  • the reaction is carried out with an excess or equimolar amount of dialkyl sulfite, preferably with a slight excess of dialkyl sulfite.
  • mixtures of the formula (9) according to the invention as a solvent, solvent additive, heat transfer, reducing agent, antioxidant, phase transfer catalyst, as extractant, as an additive, as a surfactant, as an electrolyte in galvanic cells, as a modifier or as a plasticizer is also the subject of present invention.
  • the mixtures of formula (9) are also suitable as starting material for the synthesis of mixtures of onium salts with alkyl sulfonate and alkyl sulfate anions by oxidation.
  • Suitable oxidizing agents in this reaction are all oxidizing agents known to those skilled in the art, for example oxygen.
  • the mixtures according to the invention in any known to those skilled in the type of reaction, for example, transition metal, enzyme, or with other biocatalysts catalyzed reactions, such as
  • the NMR spectra were measured on solutions in deuterated solvents at 20 ° C. on a Bruker ARX 400 spectrometer with a 5 mm 1 H / BB broadband head with deuterium lock, unless indicated in the examples.
  • the measurement frequencies of the different cores are: 1 H: 400.13 MHz and 31 P .161.98 MHz.
  • the referencing method is specified separately for each spectrum or for each data record.
  • Example 1 Mixture of 1-butyl-3-methylimidazoliummethylsulfite and 1-butyl-3-methylimidazolium methanesulfonate
  • a mixture of 3:51 g (20.1 mmol) of 1-butyl-3-methylimidazolium chloride and 3:06 g (22.1 mmol) diethyl sulfite is at 120 0 C (temperature of oil bath) for 19 hours under an inert atmosphere (nitrogen) in a closed reaction vessel equipped with a pressure valve for 1- 1.5 bar overpressure stirred. The end of the reaction is determined by NMR measurement. The product is pumped off in vacuo at 13.3 Pa and 100 ° C (temperature of the oil bath) within 1 hour.
  • Example 3 Mixture of 1-hexyl-3-methylimidazoliumethylsulfite and 1-hexyl-3-methylimidazoliumethanesulfonate
  • a mixture of 10.58 g (52.2 mmol) of 1-hexyl-3-methylimidazolium- chloride and 7.58 g (54.9 mmol) Diethylsulfit is at 120 0 C (temperature of the oil bath) for 19 hours under inert gas atmosphere (nitrogen) in a closed reaction vessel with pressure valve for Stirred at 1-1.5 bar overpressure. The end of the reaction is determined by NMR measurement. The product is pumped off in vacuo at 13.3 Pa and 100 0 C (temperature of the oil bath) within 1 hour.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé pour préparer des mélanges d'alkylsulfonates d'onium et d'alkylsulfites d'onium, par conversion d'un halogénure d'onium ou d'un carboxylate d'onium avec un dialkylsulfite substitué de façon symétrique ou un dialkylsulfite substitué de façon asymétrique, à des températures de 50 à 120°C, ainsi que des mélanges préparés à l'aide de ce procédé.
PCT/EP2006/005743 2005-07-14 2006-06-14 Melange d'alkylsulfonates d'onium et d'alkylsulfites d'onium WO2007006389A1 (fr)

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DE102005032838.5 2005-07-14
DE200510032838 DE102005032838A1 (de) 2005-07-14 2005-07-14 Mischung von Onium-Alkylsulfonaten und Onium-Alkylsulfiten

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9260397B2 (en) 2008-01-30 2016-02-16 Technische Universitaet Dresden Salts comprising aryl-alkyl-substituted imidazolium and triazolium cations and the use thereof
AU2016209321B2 (en) * 2015-01-20 2019-05-09 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic compounds, compositions and method of using thereof

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DE228247C (fr) *
JPS63262830A (ja) * 1987-04-21 1988-10-31 三菱油化株式会社 コンデンサ用電解液
WO2002034722A1 (fr) * 2000-10-27 2002-05-02 Centre National De La Recherche Scientifique (C.N.R.S.) Sels d'imidazolium et utilisation de ces liquides ioniques comme solvant
WO2004106288A2 (fr) * 2003-06-02 2004-12-09 Merck Patent Gmbh Liquides ioniques contenant des cations de guanidine
WO2006021303A1 (fr) * 2004-08-24 2006-03-02 Basf Aktiengesellschaft Sulfites d'imidazolium-methyle utilises comme composes de depart ausgangsverbindungen pour la production de liquides ioniques
WO2006021304A1 (fr) * 2004-08-24 2006-03-02 Basf Aktiengesellschaft Procede de production de composes d'ammonium quaternaires de grande purete

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE228247C (fr) *
JPS63262830A (ja) * 1987-04-21 1988-10-31 三菱油化株式会社 コンデンサ用電解液
WO2002034722A1 (fr) * 2000-10-27 2002-05-02 Centre National De La Recherche Scientifique (C.N.R.S.) Sels d'imidazolium et utilisation de ces liquides ioniques comme solvant
WO2004106288A2 (fr) * 2003-06-02 2004-12-09 Merck Patent Gmbh Liquides ioniques contenant des cations de guanidine
WO2006021303A1 (fr) * 2004-08-24 2006-03-02 Basf Aktiengesellschaft Sulfites d'imidazolium-methyle utilises comme composes de depart ausgangsverbindungen pour la production de liquides ioniques
WO2006021304A1 (fr) * 2004-08-24 2006-03-02 Basf Aktiengesellschaft Procede de production de composes d'ammonium quaternaires de grande purete

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9260397B2 (en) 2008-01-30 2016-02-16 Technische Universitaet Dresden Salts comprising aryl-alkyl-substituted imidazolium and triazolium cations and the use thereof
AU2016209321B2 (en) * 2015-01-20 2019-05-09 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic compounds, compositions and method of using thereof

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