EP1501810A1 - Ionische fl ssigkeiten - Google Patents

Ionische fl ssigkeiten

Info

Publication number
EP1501810A1
EP1501810A1 EP03720488A EP03720488A EP1501810A1 EP 1501810 A1 EP1501810 A1 EP 1501810A1 EP 03720488 A EP03720488 A EP 03720488A EP 03720488 A EP03720488 A EP 03720488A EP 1501810 A1 EP1501810 A1 EP 1501810A1
Authority
EP
European Patent Office
Prior art keywords
nitrogen
ionic liquids
optionally substituted
optionally
carbon atoms
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Withdrawn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
EP03720488A
Other languages
German (de)
English (en)
French (fr)
Inventor
Hans Josef Laas
Reinhard Halpaap
Frank Richter
Jürgen Köcher
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP1501810A1 publication Critical patent/EP1501810A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2036—Heterocyclic amines; Salts thereof containing one heterocyclic ring having at least three nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only

Definitions

  • the invention relates to new ionic liquids, a process for their preparation and their use as solvents or catalysts for chemical reactions, in particular as catalysts for the oligomerization of isocyanates.
  • Ionic liquids are generally understood to be liquids which consist exclusively of ions
  • the ionic liquids known today are based on a relatively manageable number of different structural components.
  • the cations used are preferably tetraalkylammonium, tetraalkylphosphonium or N-alkylpyridinium or
  • 1,3-dialkylimidazolium ions which are usually combined with anions such as chloride, chloroaluminate, trifluoromethanesulfonate (triflate), toluenesulfonate (tosylate), tetrafluoroborate, hexafluorophosphate or hexafluoroantimonate ions.
  • anions such as chloride, chloroaluminate, trifluoromethanesulfonate (triflate), toluenesulfonate (tosylate), tetrafluoroborate, hexafluorophosphate or hexafluoroantimonate ions.
  • salts from special ammonium and phosphonium cations and deprotomeric five-membered nitrogen heteroaromatics also represent chemically stable ionic liquids as anions.
  • Ionic liquids with heterocyclic anions have hitherto not been known.
  • These new ionic liquids can not only be used as solvents for a large number of different (catalytic) reactions, but surprisingly, as such, are preferably also highly active and selective catalysts for the oligomerization of isocyanates.
  • the present invention relates to ionic liquids in general
  • Q A stands for a five-membered nitrogen heteroaromatic which is deprotonated, optionally substituted and / or fused to a ring nitrogen,
  • E represents a nitrogen or phosphorus atom
  • R 1 , R 2 , R 3 and R 4 stand for identical or different radicals and each a saturated or unsaturated aliphatic or cycloaliphatic, one optionally substituted aromatic or araliphatic radical which has up to 24 carbon atoms and. optionally contain up to 3 hetero atoms from the series oxygen, sulfur, nitrogen and can optionally be substituted by halogen atoms, with the proviso that at least one of the radicals R 1 to R 4 represents an aliphatic radical with at least 6 carbon atoms.
  • the invention also relates to a process for the preparation of these ionic liquids by deprotonation of a
  • X represents a halogen atom from the series chlorine, bromine, iodine, and
  • the invention also relates to the use of these ionic liquids as solvents and / or catalysts in chemical reactions, in particular as catalysts for the oligomerization of isocyanates.
  • Starting compounds A) for the preparation of the ionic liquids according to the invention are any five-membered nitrogen heteroaromatics containing a protonated ring nitrogen, which may optionally be substituted and / or fused and have a molecular weight of 67 to 800, preferably 67 to 650, particularly preferably 67 to 500 ,
  • R 5 to R 19 stand for identical or different radicals and each represent a hydrogen atom, a halogen atom from the series fluorine, chlorine or bromine or a nitro group, a saturated or unsaturated aliphatic or cycloaliphatic radical, an optionally substituted aromatic or araliphatic radical , which contain up to 20 carbon atoms and optionally up to 3 heteroatoms from the series oxygen, sulfur, nitrogen and can optionally be substituted by halogen atoms or nitro groups,
  • Suitable starting compounds A) are pyrrole, indole, 4-methylindole, 5-methylindole, 6-methylindole, 2,3-dimethylindole, 2,5-dimethylindole,
  • 5- and 6-chloroindole 4-fluoroindole, 5-fluoroindole, 6-fluoroindole, 4-nitroindole, 5-nitro-2-phenylindole, 4-benzyloxyindole, 4-methoxyindole, 5-methoxyindole, 5,6-dimethoxyindole , 5-ethyl indole, 7-ethyl indole, 2-ethyl-3-methylindole, 5,6- (methylenedioxy) indole, carbazole, 3-chlorocarbazole, carboline, 3,4: 5,6-dibenzocarbazole, pyrazole, 3-methylpyrazole , 4-methylpyrazole, 3,5-dimethylpyrazole, indazole, 3-methylindazole, 3-
  • Preferred starting compounds A) are those having an imidazole (formula V), 1,2,4-triazole (formula VI) or 1,2,3-triazole backbone (formula VII).
  • 1,2,4-Triazoles of the general formula (VI) are very particularly preferred.
  • Starting compounds B) for the preparation of the ionic liquids according to the invention are any quaternary ammonium or phosphonium halogens of the general formula (U) in which
  • X represents a halogen atom from the series chlorine, bromine, iodine,
  • E represents a nitrogen or phosphorus atom
  • R 1 , R 2 , R 3 and R 4 represent identical or different radicals and each represent a saturated or unsaturated aliphatic or cycloaliphatic radical, an optionally substituted aromatic or araliphatic radical which has up to 24 carbon atoms and optionally up to 3 heteroatoms from the Contain oxygen, sulfur, nitrogen and can optionally be substituted by halogen atoms, with the proviso that at least one of the radicals R 1 to R 4 is an aliphatic radical having 5 at least 6 carbon atoms.
  • Suitable ammonium and phosphonium halides are, for example, methyl trioctylammonium chloride, Ethymexadecyldimethylammoniumbromid, Benzyldime- thylhexadecylammoniumchlorid, benzyldimethylstearylammonium chloride, tetra-n-hexylammonium 0, tetraheptylammonium bromide, chloride Tetrahexylammoniumchlo-, dodecyltrimethylammonium bromide, benzyldimethyldodecylammonium bromide, hexadecyltrimethylammonium bromide, hexadecyltrimethylammonium chloride, benzyl zyldimethyltetradecylarnmoniumchlorid, tetra-n- octylammonium bromide, didecy
  • Preferred starting compounds B) are quaternary ammonium or phosphonium halogens of the general formula (II), in which
  • R 1 , R 2 , R 3 and R 4 represent the same or different radicals and each represent a saturated aliphatic radical which contains up to 18 carbon atoms and optionally up to 3 heteroatoms from the series oxygen, sulfur, nitrogen and optionally substituted by halogen atoms with the proviso that at least one of the radicals R 1 to R 4 represents an aliphatic radical having at least 6 carbon atoms.
  • R 1 , R 2 , R 3 and R 4 represent identical or different radicals and each represent a saturated aliphatic radical with up to 18 carbon atoms, with the proviso that at least two of the radicals R 1 to R 4 have at least 6 carbon atoms.
  • the process according to the invention is generally carried out in the presence of a suitable solvent.
  • suitable solvents are monohydric or polyhydric simple alcohols, such as. B. methanol, ethanol, n-propanol, Isopropanol, n-butanol, n-hexanol, 2-ethyl-l-hexanol, ethylene glycol, propylene glycol, the isomeric butanediols, 2-ethyl-l, 3-hexanediol or glycerin; Ether alcohols such as e.g. B.
  • ethyl ether diethylene glycol monobutyl ether, diethylene glycol or dipropylene glycol but also solvents such as hexane, toluene, xylene, chlorobenzene, ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, ethylene glycol ethyl or ethyl ether, ethyl acetate, methyl ethyl acetate, diethyl ether, - Propyl-2-acetate, 3-methoxy-n-butyl acetate, propylene glycol diacetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, N-methylpyrrolidone and N-methylcaprolactam or mixtures of such solvents.
  • Preferred solvents are simple monoalcohols of the type mentioned with 1 to 4 carbon atom
  • metal bases known from preparative organic chemistry preferably alkali or alkaline earth metal bases, such as e.g. Metal hydroxides, alcohols, amides or hydrides.
  • alkali or alkaline earth metal bases such as e.g. Metal hydroxides, alcohols, amides or hydrides.
  • bases are sodium methylate, sodium ethylate, potassium tert-butoxide, lithium diisopropylamide, sodium bis (trimethylsilyl) amide or sodium hydride.
  • Preferred metal bases are alkali metal alcoholates, which are generally used in solution in the corresponding alcohols.
  • the metal bases mentioned are generally used in the process according to the invention in an equimolar amount, based on the amount of five-membered heterocycles A) used.
  • the starting compounds A if appropriate under an inert gas atmosphere, are dissolved in a solvent of the type mentioned above by way of example and especially at a temperature of from -20 to + 80 ° C., preferably from -10 to + 60 ° C. preferably from 0 to
  • the frequently commercially available metal salts preferably alkali metal salts, such as, for example, Na salts
  • the starting compounds B preferably also in a form dissolved in the above-mentioned solvent, are then added while observing the above-mentioned temperature range, whereupon a metal / halide Exchange begins.
  • the metal halide which separates out is separated, for example by filtration, and the process product according to the invention is finally in a vacuum at a temperature of, for example, 20 to 120 ° C., preferably 30 to 100 ° C., particularly preferably 40 to 80 ° C., preferably in a Düm layer evaporator, freed from the solvent.
  • the ionic liquids according to the invention with residual organic solvent contents of less than 5% by weight, preferably less than 2% by weight, very particularly preferably less than 1% by weight, are obtained. They have melting points of less than 100 ° C., preferably less than 60 ° C., particularly preferably less than 40 ° C., and in the molten state viscosities of less than 3000 mPas, preferably less than 2000 mPas, particularly preferably less than 1000 mPas ,
  • the ionic liquids according to the invention are outstandingly suitable as solvents for a large number of different (catalytic) reactions. They are also highly active and selective catalysts for the oligomerization of isocyanates, in particular for the production of polyisocyanates with uretdione, isocyanurate and / or iminooxadiazinedione structure, and can advantageously be used as liquid compounds in solvent-free form. Examples
  • Methyltrioctylammonium-1,2,4-triazolate as a clear, almost colorless liquid with a viscosity of 670 mPas (23 ° C) and a refractive index n of 1.4751.
  • the residual methanol content is 0.3% by weight.
  • Example 1 180 g of a 30% strength methanolic sodium methanolate solution, corresponding to 1.0 mol of sodium methanolate, are dissolved in 200 with 69 g (1.0 mol) of 1,2,4-triazole ml methanol and 518 g (1.0 mol) trihexyltetradecylphosphonium chloride (CYPHOS ® 3653, Fa. Cytec Industries) dissolved in 60 g of methanol reacted. After filtration, thin-layer distillation at a temperature of 50 ° C.
  • Example 1 180 g of a 30% strength methanolic sodium methanolate solution, corresponding to 1.0 mol of sodium methanolate with 68 g (1.0 mol) of imidazole dissolved in 200 ml of methanol and 518 g ( 1.0 mol) trihexyltetradecylphosphonium chloride (CYPHOS ® 3653, Fa. Cytec Industries) dissolved in 60 g of methanol reacted. After filtration, thin-layer distillation at 50 ° C.
  • CYPHOS ® 3653, Fa. Cytec Industries trihexyltetradecylphosphonium chloride
  • the NCO content in the reaction mixture is 29.7%, corresponding to a degree of oligomerization of 21.4%.
  • 0.38 g (1.8 mmol) of dibutyl phosphate are added to stop the reaction and the excess monomeric diisocyanate is distilled off using a thin-film evaporator at a temperature of 160 ° C. and a pressure of 0.3 mbar.
  • a highly viscous, almost colorless uretdione polyisocyanate with a free NCO group content of 16.9% and a monomeric IPDI content of 0.3% is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (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)
  • Catalysts (AREA)
EP03720488A 2002-04-30 2003-04-17 Ionische fl ssigkeiten Withdrawn EP1501810A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10219227A DE10219227A1 (de) 2002-04-30 2002-04-30 Ionische Flüssigkeiten
DE10219227 2002-04-30
PCT/EP2003/004025 WO2003093246A1 (de) 2002-04-30 2003-04-17 Ionische flüssigkeiten

Publications (1)

Publication Number Publication Date
EP1501810A1 true EP1501810A1 (de) 2005-02-02

Family

ID=29224904

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03720488A Withdrawn EP1501810A1 (de) 2002-04-30 2003-04-17 Ionische fl ssigkeiten

Country Status (9)

Country Link
US (1) US20030204041A1 (es)
EP (1) EP1501810A1 (es)
JP (1) JP2005538944A (es)
CN (1) CN1665793A (es)
AU (1) AU2003224090A1 (es)
CA (1) CA2483829A1 (es)
DE (1) DE10219227A1 (es)
MX (1) MXPA04010788A (es)
WO (1) WO2003093246A1 (es)

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GB0407908D0 (en) * 2004-04-07 2004-05-12 Univ York Ionic liquids
US20050269001A1 (en) * 2004-04-22 2005-12-08 Liotta Charles L Ionic liquid energetic materials
EP1652814A1 (de) * 2004-10-27 2006-05-03 Solvay Fluor GmbH Verfahren zur Gastrennung
US7464580B2 (en) * 2005-09-26 2008-12-16 Oakland University Ionic liquid high temperature gas sensors
DE102005060828A1 (de) 2005-12-20 2007-06-28 Bayer Materialscience Ag Verfahren zur Herstellung von Polyadditionsverbindungen
WO2007088152A1 (de) * 2006-02-01 2007-08-09 Basf Se Verfahren zur herstellung von isocyanaten
US7886577B2 (en) 2006-03-30 2011-02-15 Oakland University Devices with surface bound ionic liquids and method of use thereof
US8375768B2 (en) * 2006-03-30 2013-02-19 Oakland University Ionic liquid thin layer sensor for electrochemical and/or piezoelectric measurements
TW200808656A (en) 2006-04-27 2008-02-16 Solvay Fluor Gmbh Reversible water-free process for the separation of acid-containing gas mixtures
WO2007138307A2 (en) * 2006-05-25 2007-12-06 The Queen's University Of Belfast Process for removing sulfur-containing acids from crude oil
US7807852B2 (en) * 2006-08-18 2010-10-05 The United States Of America As Represented By The Secretary Of The Navy Polymerizable sulfonate ionic liquids and liquid polymers therefrom
KR20110105386A (ko) * 2009-01-12 2011-09-26 브이티유 홀딩 게엠베하 담배 필터
US8623928B2 (en) 2009-11-12 2014-01-07 National Research Council Of Canada Polymers of intrinsic microporosity containing tetrazole groups
US8709544B2 (en) 2009-11-23 2014-04-29 Basf Se Catalysts for polyurethane coating compounds
CN102432813B (zh) * 2011-03-21 2014-04-30 江苏科泰绝热新材料有限公司 一种用离子液体催化制备pir材料的方法
CN102443135B (zh) * 2011-10-31 2014-05-07 西安邮电学院 一种低温解封单组份固化剂
EP2941446B1 (de) 2013-01-07 2018-10-10 Basf Se Katalysatoren für polyurethanbeschichtungsmassen
JP2018090527A (ja) * 2016-12-02 2018-06-14 大阪瓦斯株式会社 イオン液体製造方法
US11124692B2 (en) 2017-12-08 2021-09-21 Baker Hughes Holdings Llc Methods of using ionic liquid based asphaltene inhibitors
EA202091413A1 (ru) 2018-07-11 2020-09-24 Бейкер Хьюз Холдингз Ллк Скважинные ингибиторы асфальтенов на основе ионной жидкости и способы их применения

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Also Published As

Publication number Publication date
JP2005538944A (ja) 2005-12-22
US20030204041A1 (en) 2003-10-30
AU2003224090A1 (en) 2003-11-17
CN1665793A (zh) 2005-09-07
MXPA04010788A (es) 2005-03-07
CA2483829A1 (en) 2003-11-13
DE10219227A1 (de) 2003-11-13
WO2003093246A1 (de) 2003-11-13

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