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WO2009040242A1 - Procédé pour produire des sels d'imidazolium - Google Patents

Procédé pour produire des sels d'imidazolium Download PDF

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Publication number
WO2009040242A1
WO2009040242A1 PCT/EP2008/061906 EP2008061906W WO2009040242A1 WO 2009040242 A1 WO2009040242 A1 WO 2009040242A1 EP 2008061906 W EP2008061906 W EP 2008061906W WO 2009040242 A1 WO2009040242 A1 WO 2009040242A1
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WO
WIPO (PCT)
Prior art keywords
formula
weight
parts
methanol
reaction
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.)
Ceased
Application number
PCT/EP2008/061906
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German (de)
English (en)
Inventor
Georg Degen
Christoph Stock
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BASF SE
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BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP08803874A priority Critical patent/EP2203428A1/fr
Publication of WO2009040242A1 publication Critical patent/WO2009040242A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07D233/54—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
    • 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

Definitions

  • the invention relates to a process for the preparation of imidazolium salts of the formula I.
  • R 1 and R 3 independently of one another represent an organic radical having 1 to 20 C atoms
  • R 2 , R 4 and R 5 independently of one another are an H atom or an organic radical having up to 20 C atoms and
  • A- stands for an anion other than a carbonate anion, which is characterized in that
  • radicals R have the above meaning
  • RO- 1 C O wherein R 3 has the above meaning, is prepared and
  • the resulting imidazolium salts of the formula II are reacted with acids or salts which contain the anion A- to form the imidazolium salt I,
  • reaction takes place in both process steps in the presence of methanol and the content of methanol in the first process step at least 100 parts by weight of methanol and in the second process step at least 50 parts by weight, based in each case to 100 parts by weight of the sum of the first Process step used starting materials of formula III + IV is.
  • Imidazolium salts having a melting point of less than 200 ° C. have many uses as ionic liquids.
  • JP 2004-207451 discloses a corresponding implementation. It is called a variety of solvents, including methanol.
  • WO 2005/021484 describes a process for the preparation of imidazolium salts by anion exchange, starting, for. B. of imidazolium salts with alkyl carbonates as anion, the reaction of these salts with an acid.
  • DE-A 19 836 477 describes the preparation of an imidazolium carboxylate with the carboxylate group as substituent on the imidazole ring, corresponding to a compound of the above formula VI.
  • the reaction of 1-methylimidazole with dimethyl carbonate leads to the substituted imidazole carboxylate in high yields.
  • the reaction can be carried out in the presence or absence of solvent.
  • the high proportion of by-products is disadvantageous.
  • the object of the invention was therefore a process for the preparation of imidazolium salts of the formula I with as few by-products as possible, the process should be as simple and inexpensive as possible.
  • R 1 and R 3 independently of one another represent an organic radical having 1 to 20 C atoms
  • R 2 , R 4 and R 5 independently of one another are an H atom or an organic radical having up to 20 C atoms and A "is an anion.
  • R 1 and R 3 are preferably independently of one another an organic radical having 1 to 10 C atoms.
  • the organic radical may also contain further heteroatoms, in particular oxygen atoms, nitrogen, sulfur or phosphorus atoms or functional groups, for example hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • R 1 and R 3 are a hydrocarbon radical which, in addition to carbon and hydrogen, may at most also contain hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • R 1 and R 3 are particularly preferably independently of one another a hydrocarbon radical having 1 to 20 C atoms, in particular having 1 to 10 C atoms, which does not contain any other heteroatoms, eg. As oxygen or nitrogen.
  • the hydrocarbon radical may be aliphatic (which also includes unsaturated aliphatic groups) or aromatic, or may contain both aromatic and aliphatic groups.
  • R 1 and R 2 are an aliphatic hydrocarbon radical. Examples of hydrocarbon radicals which may be mentioned are the phenyl group, benzyl group, a phenyl group or benzyl group, alkyl groups and alkenyl groups substituted by one or more C1 to C4 alkyl groups, in particular the allyl group.
  • R 1 and R 3 are a C 1 to C 10 alkyl group.
  • a C1 to C6 alkyl group is particularly preferred, in a particular embodiment, the alkyl group is a C1 to C4 alkyl group.
  • R 1 and R 3 are each independently a methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl group, one wherein the methyl, ethyl, n-propyl and n-butyl group have special significance.
  • R 1 is a C 1 to C 6, especially a C 1 to C 4 alkyl group.
  • R 3 is a methyl group.
  • R 2 is preferably an H atom.
  • R 4 and R 5 are preferably, independently of one another, a hydrogen atom or an organic radical having 1 to 10 C atoms.
  • the organic radical may also contain further heteroatoms, in particular oxygen atoms, nitrogen, sulfur or phosphorus atoms or functional groups, for example hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • R4 and R5 stand for a hydrocarbon radical, which may contain, in addition to carbon and hydrogen, at most hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • R4 and R5 are particularly preferably independently of one another a hydrocarbon radical having 1 to 20 C atoms, in particular having 1 to 10 C atoms, no other heteroatoms, z. As oxygen or nitrogen.
  • the hydrocarbon radical may be aliphatic (including unsaturated aliphatic groups) or aromatic, or may contain both aromatic and aliphatic groups.
  • R 1 and R 2 are an aliphatic hydrocarbon radical.
  • hydrocarbon radicals which may be mentioned are the phenyl group, benzyl group, a phenyl group or benzyl group, alkyl groups and alkenyl groups, in particular the allyl group, substituted by one or more C1 to C4 alkyl groups.
  • R4 and R5 represent a hydrogen atom or a C1 to C10 alkyl group.
  • the alkyl group a C1 to C6 alkyl group is particularly preferred, in a particular embodiment, the alkyl group is a C1 to C4 alkyl group.
  • R 1 and R 3 independently represent a hydrogen atom or a methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl group, one wherein the methyl, Ethyl, n-propyl and n-butyl group have special significance.
  • R4 and R5 are each H atoms.
  • the anion A "in formula I, apart from a carbonate anion, may be any anion.
  • the anion is preferably selected so that the imidazolium salt of formula 1 has a melting point (at 1 bar) of less than 200 0 C, in particular 100 0 C, particularly preferably less than 50 ° C and has C most preferably less than 30 0, which is an ionic liquid is.
  • the imidazolium salt of the formula I is liquid at room temperature.
  • carboxylates compounds having a carboxylate group
  • carboxylates are suitable.
  • Preferred carboxylates are the anions of alkanecarboxylic acids, especially of C1 to C4 alkanecarboxylic acids, preferably the acetate anion.
  • Suitable anions may furthermore be selected from the following groups (listed polyvalent anions are the counter anions of a number corresponding to the valence imidazolium cations, R a and R b are independently an organic radical having preferably 1 to 20 C atoms, more preferably a hydrocarbon radical and very particularly preferably an aliphatic radical, in particular a C1 to C10 alkyl group):
  • SiO 4 4 " HSiO 4 3 -, H 2 SiO 4 2 -, H 3 SiO 4 -, R 3 SiO 4 3" , R 3 R b Si0 4 2 -, R 3 R b R c Si0 4 -, HR 3 SiO 4 2 " , H 2 R 3 SiO 4 " , HR 3 R b Si0 4 -;
  • Preferred anions are the above carboxylates, especially acetate, rhodanide (SCN), alkanesulfonates such as methanesulfonate, ethanesulfonate and bis (sulfonyl) imides, most preferably the above carboxylates, especially the acetate.
  • SCN rhodanide
  • alkanesulfonates such as methanesulfonate, ethanesulfonate and bis (sulfonyl) imides
  • radicals R have the above meaning, with an alkyl carbonate of formula IV
  • R 3 has the above meaning, prepared.
  • the alkyl carbonate is preferably dimethyl carbonate.
  • the molar ratio of the imidazole used to the alkyl carbonate can be chosen arbitrarily, for optimum yields and avoiding excessive excess of one of the two reactants are molar ratios of 1 mole of imidazole to 0.5 to 2 moles of alkyl carbonate, in particular from 1 mole of imidazole to 1, 2 bis 1, 6 moles of alkyl carbonate useful.
  • the reaction is preferably carried out at elevated pressures and temperatures.
  • the temperature is preferably 50 to 200 0 C, particularly preferably 80 to 200 0 C, most preferably 100 to 180 ° C.
  • the pressure may preferably be 2 to 50 bar, in particular 5 to 30 bar.
  • the reaction can be carried out in the presence or absence of a catalyst.
  • the reaction is carried out according to the invention in the presence of methanol.
  • the methanol content is preferably at least 125 parts by weight, in particular at least 150 parts by weight, more preferably at least 200 parts by weight and very particularly preferably at least 250 parts by weight per 100 parts by weight of the sum of the starting materials of the formula III ( Imidazole) and IV (dialkyl carbonate). More than 800 parts by weight of methanol, in particular more than 500 parts by weight of methanol are generally not used.
  • solvents can be used in the reaction.
  • Water, water-miscible organic solvents or water-immiscible organic solvents may be used.
  • the reaction can be carried out in the presence or absence of water.
  • the components III and IV can be used in equimolar amounts.
  • one of the components, more preferably the imidazole of formula III is used in deficit.
  • the first process step is preferably considered terminated when a conversion of more than 90%, in particular more than 95%, particularly preferably more than 98%, very particularly preferably more than 99%, based on the components III and IV (with equimolar starting amounts) or to the components used in deficit.
  • Solvent including methanol, may be used, for example. partially removed.
  • the reaction according to the invention is carried out in the presence of methanol.
  • the methanol content is preferably at least 75 parts by weight, in particular at least 100 parts by weight, particularly preferably at least 125 parts by weight and very particularly preferably at least 150 parts by weight, in a particular embodiment at least 200 or 250 parts by weight 100 parts by weight of the sum of the starting materials of the formula III (imidazole) and IV (dialkyl carbonate) in the first process step. More than 800 parts by weight of methanol, in particular more than 500 parts by weight of methanol are generally not used.
  • the methanol used in the first process step is not removed.
  • the solution obtained after the first process step is used without prior work-up or without removal (distillation) of individual constituents thereof.
  • an acid or salt containing the anion A is added to the solution
  • the acidity of the acid or salt should be such that the carbonate anion in formula II (preferably methylcarbonate anion) is converted to the corresponding alcohol (methanol) and In the presence of water, the hydroxycarbonate anion first forms from the carbonate anion by hydrolysis, so that the decomposition results in water (instead of alcohol) and carbon dioxide.
  • the anion A of the acid or salt then replaces the carbonate anion.
  • This implementation is z. As described in WO 2005/021484 (carbonate method).
  • Suitable acids for this purpose are hydrogen acids
  • suitable salts are those which contain hydrogen as a cation or in covalently bonded form.
  • acids and salts particular mention may be made of carboxylic acids or their salts or hydrogen acids or salts of the abovementioned anions.
  • the reaction can be carried out at atmospheric pressure. An overpressure is not necessary but not a hindrance.
  • Elevated temperatures can be helpful; Preference is given to temperatures of 20 to 100 ° C., in particular 30 to 70 ° C.
  • the acid or the salt which contains the anion A can be used in any desired amounts, depending on the desired conversion, Preferably, the acid or salt is used in excess or in stoichiometric amounts In particular, the desired or required amount can be obtained in advance be determined by titration.
  • solutions of the imidazolium salt of the formula I are preferably obtained in which the total by weight of the by-products of the formula V
  • the total weight of the three by-products of the formula V, VI and VII is particularly preferably less than 8 parts by weight, in particular less than 5 parts by weight, very preferably less than 2 parts by weight, in particular less than 1 part by weight and in one particular embodiment less than 0.5 or even less than 0.1 part by weight per 100 parts by weight of the imidazolium salt of the formula I.
  • the solution obtained initially has the above methanol content indicated for the second process step.
  • the methanol and other optional solvents may then be removed if desired.

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

Abstract

L'invention concerne un procédé servant à produire des sels d'imidazolium de formule (I) dans laquelle R1 et R3 représentent indépendamment l'un de l'autre un groupe organique ayant 1 à 20 atomes C, R2, R4 et R5 représentent indépendamment les uns des autres un atome H ou un groupe organique ayant jusqu'à 20 atomes C et A- représente un anion à l'exception d'un anion carbonate. Le procédé selon l'invention est caractérisé en ce que l'on produit, lors d'une première étape, un sel d'imidazolium de formule (Il) par réaction d'imidazoles de formule (III), dans laquelle les groupes R ont la signification précédente, avec un carbonate d'alkyle de formule (IV), dans laquelle R3 a la signification précédente, et en ce que l'on fait réagir, lors d'une deuxième étape, les sels d'imidazolium de formule (Il) obtenus avec des acides ou des sels qui contiennent l'anion A- pour obtenir le sel d'imidazolium (I). Dans ces deux étapes, la réaction se fait en présence de méthanol, la teneur en méthanol étant d'au moins 100 parties en poids de méthanol dans la première étape et d'au moins 50 parties en poids dans la deuxième étape, par rapport respectivement à 100 parties en poids de la somme des substances de formules (III) + (IV) mises en oeuvre dans la première étape.
PCT/EP2008/061906 2007-09-21 2008-09-09 Procédé pour produire des sels d'imidazolium Ceased WO2009040242A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08803874A EP2203428A1 (fr) 2007-09-21 2008-09-09 Procédé pour produire des sels d'imidazolium

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP07116953 2007-09-21
EP07116953.6 2007-09-21
EP08150996.0 2008-02-04
EP08150996 2008-02-04

Publications (1)

Publication Number Publication Date
WO2009040242A1 true WO2009040242A1 (fr) 2009-04-02

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PCT/EP2008/061906 Ceased WO2009040242A1 (fr) 2007-09-21 2008-09-09 Procédé pour produire des sels d'imidazolium

Country Status (2)

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EP (1) EP2203428A1 (fr)
WO (1) WO2009040242A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011061314A1 (fr) 2009-11-23 2011-05-26 Basf Se Catalyseurs pour des masses de revêtement à base de polyuréthane
EP2354121A1 (fr) 2010-02-05 2011-08-10 Philipps-Universität Marburg Carbonate organique à base d'hexa-organo-guanidine, sa fabrication et son utilisation
WO2013060579A1 (fr) 2011-10-25 2013-05-02 Basf Se Utilisation en tant que fluide de travail de compositions liquides contenant des sels d'imidazolium
DE102012006501A1 (de) 2012-03-29 2013-10-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Lignocellulose-Spinnlösung, Lignocellulose-Regeneratfaser sowie Verfahren zu deren Herstellung
CN103547584A (zh) * 2011-06-17 2014-01-29 流体公司 利用碳酸二烷基酯季铵化来合成杂离子化合物
US9963538B2 (en) 2013-01-07 2018-05-08 Basf Se Catalysts for polyurethane coating compounds
WO2018160678A1 (fr) 2017-02-28 2018-09-07 Basf Se Composition de matériau d'étanchéité durcissable
WO2018160691A1 (fr) 2017-02-28 2018-09-07 Basf Se Composition d'agent d'étanchéité durcissable
US11124692B2 (en) 2017-12-08 2021-09-21 Baker Hughes Holdings Llc Methods of using ionic liquid based asphaltene inhibitors
US11254881B2 (en) 2018-07-11 2022-02-22 Baker Hughes Holdings Llc Methods of using ionic liquids as demulsifiers

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19836477A1 (de) 1998-08-12 2000-02-17 Basf Ag Verfahren zur Herstellung von 1,3-Dimethyl-imidazolium-4carboxylat
EP1398318A1 (fr) 2002-09-07 2004-03-17 Basf Aktiengesellschaft Procédé pour la mise en oeuvre de réactions chimiques en phase liquide et en présence d'un catalyseur et un sel d'imidazolium
JP2004207451A (ja) 2002-12-25 2004-07-22 Sanyo Chem Ind Ltd 電解液
WO2005021484A2 (fr) 2003-08-27 2005-03-10 Proionic Production Of Ionic Substances Gmbh & Co Keg Procede pour produire des liquides ioniques, des solides ioniques ou leurs melanges

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005063661A1 (fr) * 2003-12-25 2005-07-14 Sumitomo Chemical Company, Limited Agent fluorant et procede de fabrication d'un compose contenant du fluor au moyen de cet agent
DE102004010662A1 (de) * 2004-03-04 2005-09-22 Basf Ag Verfahren zur Herstellung von Verbindungen mit quaternären sp2-hybridisierten Stickstoffatomen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19836477A1 (de) 1998-08-12 2000-02-17 Basf Ag Verfahren zur Herstellung von 1,3-Dimethyl-imidazolium-4carboxylat
EP1398318A1 (fr) 2002-09-07 2004-03-17 Basf Aktiengesellschaft Procédé pour la mise en oeuvre de réactions chimiques en phase liquide et en présence d'un catalyseur et un sel d'imidazolium
JP2004207451A (ja) 2002-12-25 2004-07-22 Sanyo Chem Ind Ltd 電解液
WO2005021484A2 (fr) 2003-08-27 2005-03-10 Proionic Production Of Ionic Substances Gmbh & Co Keg Procede pour produire des liquides ioniques, des solides ioniques ou leurs melanges

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2203428A1 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8709544B2 (en) 2009-11-23 2014-04-29 Basf Se Catalysts for polyurethane coating compounds
WO2011061314A1 (fr) 2009-11-23 2011-05-26 Basf Se Catalyseurs pour des masses de revêtement à base de polyuréthane
EP2354121A1 (fr) 2010-02-05 2011-08-10 Philipps-Universität Marburg Carbonate organique à base d'hexa-organo-guanidine, sa fabrication et son utilisation
WO2011095428A1 (fr) 2010-02-05 2011-08-11 Philipps-Universität Marburg Organocarbonate d'hexaorganoguanidinium, leur production et leur utilisation
CN103547584B (zh) * 2011-06-17 2017-02-15 流体公司 利用碳酸二烷基酯季铵化来合成杂离子化合物
CN103547584A (zh) * 2011-06-17 2014-01-29 流体公司 利用碳酸二烷基酯季铵化来合成杂离子化合物
WO2013060579A1 (fr) 2011-10-25 2013-05-02 Basf Se Utilisation en tant que fluide de travail de compositions liquides contenant des sels d'imidazolium
DE102012006501A1 (de) 2012-03-29 2013-10-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Lignocellulose-Spinnlösung, Lignocellulose-Regeneratfaser sowie Verfahren zu deren Herstellung
US9963538B2 (en) 2013-01-07 2018-05-08 Basf Se Catalysts for polyurethane coating compounds
WO2018160678A1 (fr) 2017-02-28 2018-09-07 Basf Se Composition de matériau d'étanchéité durcissable
WO2018160691A1 (fr) 2017-02-28 2018-09-07 Basf Se Composition d'agent d'étanchéité durcissable
US11124692B2 (en) 2017-12-08 2021-09-21 Baker Hughes Holdings Llc Methods of using ionic liquid based asphaltene inhibitors
US11254881B2 (en) 2018-07-11 2022-02-22 Baker Hughes Holdings Llc Methods of using ionic liquids as demulsifiers
US12180428B2 (en) 2018-07-11 2024-12-31 Baker Hughes Holdings, LLC Methods of using ionic liquids as paraffin inhibitors, pour point depressants and cold flow improvers

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