WO1996018459A1 - Ionic liquids - Google Patents

Ionic liquids Download PDF

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Publication number
WO1996018459A1
WO1996018459A1 PCT/GB1995/002781 GB9502781W WO9618459A1 WO 1996018459 A1 WO1996018459 A1 WO 1996018459A1 GB 9502781 W GB9502781 W GB 9502781W WO 9618459 A1 WO9618459 A1 WO 9618459A1
Authority
WO
WIPO (PCT)
Prior art keywords
process according
solution
ionic liquid
alkyl
lead
Prior art date
Application number
PCT/GB1995/002781
Other languages
French (fr)
Inventor
Brian Ellis
Original Assignee
Bp Chemicals Limited
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 Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to JP8518427A priority Critical patent/JPH09509888A/en
Priority to AU39864/95A priority patent/AU3986495A/en
Priority to EP95938493A priority patent/EP0743878A1/en
Publication of WO1996018459A1 publication Critical patent/WO1996018459A1/en
Priority to NO963294A priority patent/NO963294L/en
Priority to FI963134A priority patent/FI963134A/en

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0287—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing atoms other than nitrogen as cationic centre
    • B01J31/0288—Phosphorus
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/52—Isomerisation reactions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/077—Ionic Liquids

Definitions

  • This invention relates to a method of making ionic liquids using relatively inexpensive reactants.
  • Ionic liquids are primarily salts or mixtures of salts which melt below room temperature. Such salts or mixtures comprise a cation and an anion and the anion itself may be a salt such as eg haloaluminate.
  • ionic liquids include in various combinations one or more anions such as eg haloaluminates, nitrates, sulphates, fluoroborates and acetates in combination with one or more cations such as imidazolium, pyridinium and phosphonium cations each of which may carry hydrocarbyl substituents.
  • Examples of the source of cations include one or more of l-methyl-3 -butyl imidazolium halides, 1 -butyl pyridinium halide and tetrabutyl phosphonium halides.
  • the present invention is a method for making ionic liquids said process comprising reacting a solution of a lead salt of an anion desired in the ionic liquid with a solution of a halide of a cation desired in said ionic liquid, separating the precipitate of the lead halide so formed to leave behind a solution of the desired ionic liquid.
  • the lead salt used to make the desired ionic liquid may be selected from the group comprising acetate, fluoroborate, nitrate and sulphate.
  • the salt of the cation reacted with the lead salt may be selected from the group comprising an imidazolium chloride, a pyridinium chloride, a phosphonium chloride, and hydrocarbyl substituted derivatives of such cations. Examples of such cations include H-pyridinium; alkyl pyridinium; alkyl, alkyl imidazolium; trialkyl, alkyl phosphonium; and trialkyl, alkyl ammonium.
  • Each of the hydrocarbyl groups such as alkyl groups in such cations may contain 2-20 carbon atoms.
  • the two salts are suitably reacted together in the form of their respective solutions, suitably an aqueous alcoholic solutions eg in aqueous methanol.
  • the aqueous alcoholic solution suitably contains alcohol and water in a volume ratio of about 4: 1.
  • the reaction can be carried out at ambient temperature and the resultant precipitate of lead chloride can be separated from the solution by filtration. In order to enable completion of the reaction, it is preferable to allow the filtrate resulting from separation of the initial deposit of lead chloride precipitate to stand for a further period of time.
  • the method described above can be used to make ionic liquids from any cations derivable from a cation selected from imidazolium, pyridinium or phosphonium halides or the hydrocarbyl substituted derivatives thereof, especially those cations which include H-pyridinium; alkyl pyridinium; alkyl, alkyl imidazolium; trialkyl, alkyl phosphonium; and trialkyl, alkyl ammonium.
  • Ionic liquids made by the method of the present invention can be used in all known reactions where such ionic liquids function as catalysts such as eg oligomerization, polymerization and alkylation reactions.
  • Lead nitrate (0.2 M) was dissolved in a solution (400 ml) of methanol in water (4:1 v/v). Not all the solid dissolved so a further 100 ml of distilled water was added and the solution refluxed until all the white solid had dissolved. Butyl, methyl imidazolium chloride (0.2 M) was also dissolved in a solution (100 ml) of methanol in water (4:1 v/v) and then added to the lead nitrate solution. A white precipitate was formed. The mixture was then refluxed at 70-100°C approximately for 30 minutes and then left to cool to ambient temperature.
  • the cooled solution was filtered to separate the precipitate and the filtrate was then left in a refrigerator to allow further precipitation of any dissolved lead chloride. This was then filtered again and the filtrate recovered.
  • the aqueous methanol solvent was removed from the second filtrate by evaporation under vacuum at about 100°C for approximately 90 minutes.
  • a yellow ionic liquid comprising 1 -butyl, 3-methyl imidazolium nitrate substantially free of solvent was recovered.

Abstract

This invention relates to a process for making ionic liquids by reacting a solution of a lead salt of an anion desired in the ionic liquid with a solution of a halide of a cation desired in said ionic liquid, separating the precipitate of the lead halide so formed to leave behind a solution of the desired ionic liquid. Ionic liquids are versatile and can be used as catalysts in a number of hydrocarbon conversion reaction such as e.g. alkylation, oligomerisation, isomerisation and polymerisation.

Description

IONIC LIQUIDS
This invention relates to a method of making ionic liquids using relatively inexpensive reactants.
Ionic liquids are primarily salts or mixtures of salts which melt below room temperature. Such salts or mixtures comprise a cation and an anion and the anion itself may be a salt such as eg haloaluminate. Thus, ionic liquids include in various combinations one or more anions such as eg haloaluminates, nitrates, sulphates, fluoroborates and acetates in combination with one or more cations such as imidazolium, pyridinium and phosphonium cations each of which may carry hydrocarbyl substituents. Examples of the source of cations include one or more of l-methyl-3 -butyl imidazolium halides, 1 -butyl pyridinium halide and tetrabutyl phosphonium halides.
It is known to prepare such ionic liquids by various methods. For instance, in J Chem. Soc. Chem. Comm. 965 (1992), Wilkes et al describe a method of preparing ionic liquids which involves: (i) mixing a methanol- water solution of a silver salt of an anion such as the acetate, tetrafluoroborate, nitrate or sulphate with a methanol-water solution of an equimolar amount of 1 -ethyl, 3-methyI-imidazolium chloride, (ii) filtering off the resultant precipitate of silver chloride and (iii) evaporating the solvent to leave behind the ionic liquid so formed. Whilst the process is very efficient, it is relatively uneconomic in that silver salts are relatively expensive. It has now been found that such ionic liquids can be prepared by using relatively inexpensive raw materials.
Accordingly, the present invention is a method for making ionic liquids said process comprising reacting a solution of a lead salt of an anion desired in the ionic liquid with a solution of a halide of a cation desired in said ionic liquid, separating the precipitate of the lead halide so formed to leave behind a solution of the desired ionic liquid.
The lead salt used to make the desired ionic liquid may be selected from the group comprising acetate, fluoroborate, nitrate and sulphate. The salt of the cation reacted with the lead salt may be selected from the group comprising an imidazolium chloride, a pyridinium chloride, a phosphonium chloride, and hydrocarbyl substituted derivatives of such cations. Examples of such cations include H-pyridinium; alkyl pyridinium; alkyl, alkyl imidazolium; trialkyl, alkyl phosphonium; and trialkyl, alkyl ammonium. Each of the hydrocarbyl groups such as alkyl groups in such cations may contain 2-20 carbon atoms.
The two salts, suitably in equimolar proportions, are suitably reacted together in the form of their respective solutions, suitably an aqueous alcoholic solutions eg in aqueous methanol. The aqueous alcoholic solution suitably contains alcohol and water in a volume ratio of about 4: 1. The reaction can be carried out at ambient temperature and the resultant precipitate of lead chloride can be separated from the solution by filtration. In order to enable completion of the reaction, it is preferable to allow the filtrate resulting from separation of the initial deposit of lead chloride precipitate to stand for a further period of time. This is suitably carried out by leaving the solution to stand overnight in a cool place such as eg a refrigerator so that any lead chloride (which has a small solubility in water at ambient temperature) remaining in solution can separate out and is removed by a further filtration. Thereafter, the solvent component of the filtrate can be removed by conventional methods such as eg distillation or rotary evaporation to leave behind the desired ionic liquid. The method described above can be used to make ionic liquids from any cations derivable from a cation selected from imidazolium, pyridinium or phosphonium halides or the hydrocarbyl substituted derivatives thereof, especially those cations which include H-pyridinium; alkyl pyridinium; alkyl, alkyl imidazolium; trialkyl, alkyl phosphonium; and trialkyl, alkyl ammonium. Ionic liquids made by the method of the present invention can be used in all known reactions where such ionic liquids function as catalysts such as eg oligomerization, polymerization and alkylation reactions.
The present invention is further illustrated with reference to the following Examples. EXAMPLE 1:
Preparation of 1 -Butyl, 3-methyIimidazolium nitrate:
Lead nitrate (0.2 M) was dissolved in a solution (400 ml) of methanol in water (4:1 v/v). Not all the solid dissolved so a further 100 ml of distilled water was added and the solution refluxed until all the white solid had dissolved. Butyl, methyl imidazolium chloride (0.2 M) was also dissolved in a solution (100 ml) of methanol in water (4:1 v/v) and then added to the lead nitrate solution. A white precipitate was formed. The mixture was then refluxed at 70-100°C approximately for 30 minutes and then left to cool to ambient temperature. The cooled solution was filtered to separate the precipitate and the filtrate was then left in a refrigerator to allow further precipitation of any dissolved lead chloride. This was then filtered again and the filtrate recovered. The aqueous methanol solvent was removed from the second filtrate by evaporation under vacuum at about 100°C for approximately 90 minutes. A yellow ionic liquid comprising 1 -butyl, 3-methyl imidazolium nitrate substantially free of solvent was recovered.

Claims

Claims:
1. A process for making ionic liquids said process comprising reacting a solution of a lead salt of an anion desired in the ionic liquid with a solution of a halide of a cation desired in said ionic liquid, separating the precipitate of the lead halide so formed to leave behind a solution of the desired ionic liquid.
2. A process according to Claim 1 wherein the lead salt used to make the desired ionic liquid is selected from the acetate, fluoroborate, nitrate and sulphate.
3. A process according to Claim 1 or 2 wherein the salt of the cation reacted with the lead salt is selected from an imidazolium chloride, a pyridinium chloride, a phosphonium chloride and the hydrocarbyl substituted derivatives of such cations.
4. A process according to any one of the preceding Claims wherein the cation reacted with the lead salt is selected from the group: H-pyridinium; alkyl pyridinium; alkyl, alkyl imidazolium; trialkyl, alkyl phosphonium; and trialkyl, alkyl ammonium.
5. A process according to Claim 3 or 4 wherein each of the hydrocarbyl groups in the cations contain from 2-20 carbon atoms.
6. A process according to any one of the preceding Claims wherein the lead salt and the salt of the cation are reacted together in equimolar proportions in the form of their respective solutions.
7. A process according to Claim 6 wherein the salts are in the form of their aqueous alcoholic solutions.
8. A process according to Claim 6 wherein the aqueous alcoholic solutions contain the alcohol and water in a volume ratio of about 4: 1.
9. A process according to any one of the preceding Claims 6-8 wherein the reaction is carried out at ambient temperature and the resultant precipitate of lead chloride can be separated from the solution by filtration.
10. A process for producing ionic liquid according to any one of the preceding Claims and as hereinbefore described with reference to the Examples.
PCT/GB1995/002781 1994-12-13 1995-11-28 Ionic liquids WO1996018459A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP8518427A JPH09509888A (en) 1994-12-13 1995-11-28 Ionic liquid
AU39864/95A AU3986495A (en) 1994-12-13 1995-11-28 Ionic liquids
EP95938493A EP0743878A1 (en) 1994-12-13 1995-11-28 Ionic liquids
NO963294A NO963294L (en) 1994-12-13 1996-08-07 Ionic liquids
FI963134A FI963134A (en) 1994-12-13 1996-08-09 Jonvätskor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9425105.5 1994-12-13
GBGB9425105.5A GB9425105D0 (en) 1994-12-13 1994-12-13 Ionic liquids

Publications (1)

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WO1996018459A1 true WO1996018459A1 (en) 1996-06-20

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Application Number Title Priority Date Filing Date
PCT/GB1995/002781 WO1996018459A1 (en) 1994-12-13 1995-11-28 Ionic liquids

Country Status (10)

Country Link
EP (1) EP0743878A1 (en)
JP (1) JPH09509888A (en)
CN (1) CN1140422A (en)
AU (1) AU3986495A (en)
CA (1) CA2182894A1 (en)
FI (1) FI963134A (en)
GB (1) GB9425105D0 (en)
NO (1) NO963294L (en)
WO (1) WO1996018459A1 (en)
ZA (1) ZA9510411B (en)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998006106A2 (en) * 1996-08-02 1998-02-12 British Nuclear Fuels Plc Ionic liquids as solvents
WO1999041752A1 (en) * 1998-02-11 1999-08-19 British Nuclear Fuels Plc Nuclear fuel reprocessing
WO2000016902A1 (en) * 1998-09-24 2000-03-30 Bp Chemicals Limited Ionic liquids
WO2000020115A1 (en) * 1998-10-06 2000-04-13 Bp Chemicals Limited Ionic salts
WO2001077081A1 (en) * 2000-04-07 2001-10-18 The Queen's University Of Belfast Imidazole carbenes
GB2371805A (en) * 2000-06-20 2002-08-07 Chevron Usa Inc Separation of olefins from paraffins
WO2005030392A1 (en) 2003-09-29 2005-04-07 Total Petrochemicals Research Feluy Ionic liquids as supports
US6881698B2 (en) 2000-04-26 2005-04-19 Atofina Ion liquids derived from Lewis acid based on titanium, niobium, tantalum, tin or antimony, and uses thereof
WO2005085305A1 (en) 2004-03-02 2005-09-15 Total Petrochemicals Research Feluy Ionic liquids for heterogenising metallocene catalysts
US6998152B2 (en) 1999-12-20 2006-02-14 Micron Technology, Inc. Chemical vapor deposition methods utilizing ionic liquids
US7053261B2 (en) 2002-03-22 2006-05-30 Haldor Topsoe A/S Process for paraffin hydrocarbon isomerization and composite catalyst therefore
EP1707265A1 (en) * 2005-03-29 2006-10-04 Dai-Ichi Kogyo Seiyaku Co., Ltd. Superhigh purity ionic liquid
WO2007006388A1 (en) * 2005-07-14 2007-01-18 Merck Patent Gmbh Method for the production of onium alkyl sulfites
CN100443157C (en) * 2006-11-16 2008-12-17 中国科学院长春应用化学研究所 Application of continuous microwave reactor
US7501522B2 (en) 2003-07-21 2009-03-10 Basf Aktiengesellschaft Method for the production of purified 1,3-substituted imidazolium salts
DE102008059702A1 (en) 2008-12-01 2010-06-02 Byk-Chemie Gmbh Process for the preparation of rheologically active urea urethanes in organic salts
US7732651B2 (en) 2006-06-01 2010-06-08 Chevron Oronite Company, Llc Method of making an alkylated aromoatic using acidic ionic liquid catalyst
WO2010094640A1 (en) * 2009-02-23 2010-08-26 Basf Se Distillation of ionic liquids using an auxiliary distillation agent
US7999111B2 (en) 2005-07-14 2011-08-16 Merck Patent Gesellschaft Mit Beschrankter Haftung Process for the preparation of onium alkylsulfonates
WO2013079617A1 (en) 2011-11-29 2013-06-06 Total Research & Technology Feluy Planar chromatography with an inverse gradient elution
CN103934023A (en) * 2014-04-25 2014-07-23 中国石油大学(华东) Ionic liquid catalyst for C5/C6 alkane isomerization and preparation and using method of catalyst
DE10336001B4 (en) * 2002-08-05 2017-02-09 IFP Energies Nouvelles Process for the isomerization of olefins
KR20230129782A (en) 2022-03-02 2023-09-11 엠파오 랩 더블유.엘.엘 Method for preparing olefin-based polymer using metal-containing ionic liquid catalyst

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100424259C (en) * 2002-12-12 2008-10-08 中国科学院化学研究所 Room temperature ionic liquid containing unsaturated double bond and its prepn and application
CN100344380C (en) * 2004-12-08 2007-10-24 北京化工大学 Room temperature ionic liquid and its preparation method
CN101230041B (en) * 2006-09-29 2013-04-17 亚申科技研发中心（上海）有限公司 Process and system of preparing ultra pure ionic liquids
CN101337938B (en) * 2007-07-04 2012-03-21 中国纺织科学研究院 Method for synthesizing acetate ionic liquid
US8540871B2 (en) * 2010-07-30 2013-09-24 Chevron U.S.A. Inc. Denitrification of a hydrocarbon feed
CN105203372A (en) * 2014-05-26 2015-12-30 中国科学院大连化学物理研究所 Method for removing ionic liquid in sample solution
CN105552235B (en) * 2015-12-24 2017-11-03 上海博暄能源科技有限公司 A kind of method for improving perovskite solar battery efficiency
CN110646272B (en) * 2019-09-26 2022-04-12 武汉海关技术中心 Method for purifying hydrophilic ionic liquid

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1318190A (en) * 1961-03-24 1963-02-15 Armour & Co Process for the preparation of quaternary ammonium nitrates
EP0101239A2 (en) * 1982-08-09 1984-02-22 Kabushiki Kaisha Meidensha Meidensha Electric Mfg. Co., Ltd. Zinc dendrite inhibitor
FR2626572A1 (en) * 1988-02-02 1989-08-04 Inst Francais Du Petrole Process for alkylating aliphatic hydrocarbons
EP0443167A1 (en) * 1990-02-23 1991-08-28 Bayer Ag Trimerization-catalysts, method for their preparation and their use in producing of isocyanate groups containing polyisocyanates
EP0448445A2 (en) * 1990-03-20 1991-09-25 Institut Français du Pétrole Liquid non-aqueous composition with an ionic character and its use as a solvent
EP0558187A1 (en) * 1992-02-19 1993-09-01 BP Chemicals Limited Butene polymers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1318190A (en) * 1961-03-24 1963-02-15 Armour & Co Process for the preparation of quaternary ammonium nitrates
EP0101239A2 (en) * 1982-08-09 1984-02-22 Kabushiki Kaisha Meidensha Meidensha Electric Mfg. Co., Ltd. Zinc dendrite inhibitor
FR2626572A1 (en) * 1988-02-02 1989-08-04 Inst Francais Du Petrole Process for alkylating aliphatic hydrocarbons
EP0443167A1 (en) * 1990-02-23 1991-08-28 Bayer Ag Trimerization-catalysts, method for their preparation and their use in producing of isocyanate groups containing polyisocyanates
EP0448445A2 (en) * 1990-03-20 1991-09-25 Institut Français du Pétrole Liquid non-aqueous composition with an ionic character and its use as a solvent
EP0558187A1 (en) * 1992-02-19 1993-09-01 BP Chemicals Limited Butene polymers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WILKES J S ET AL.: "Air and Water Stable 1-Ethyl-3-methylimidazolium Based Ionic Liquids", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, LETCHWORTH GB, pages 965 - 967 *

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998006106A3 (en) * 1996-08-02 1998-05-22 British Nuclear Fuels Plc Ionic liquids as solvents
US6379634B1 (en) 1996-08-02 2002-04-30 British Nuclear Fuels Plc Ionic liquids as solvents
WO1998006106A2 (en) * 1996-08-02 1998-02-12 British Nuclear Fuels Plc Ionic liquids as solvents
WO1999041752A1 (en) * 1998-02-11 1999-08-19 British Nuclear Fuels Plc Nuclear fuel reprocessing
WO2000016902A1 (en) * 1998-09-24 2000-03-30 Bp Chemicals Limited Ionic liquids
WO2000020115A1 (en) * 1998-10-06 2000-04-13 Bp Chemicals Limited Ionic salts
US6998152B2 (en) 1999-12-20 2006-02-14 Micron Technology, Inc. Chemical vapor deposition methods utilizing ionic liquids
US6939974B2 (en) 2000-04-07 2005-09-06 The Queens University Of Belfast Imidazole carbenes
WO2001077081A1 (en) * 2000-04-07 2001-10-18 The Queen's University Of Belfast Imidazole carbenes
US6881698B2 (en) 2000-04-26 2005-04-19 Atofina Ion liquids derived from Lewis acid based on titanium, niobium, tantalum, tin or antimony, and uses thereof
GB2371805B (en) * 2000-06-20 2003-01-15 Chevron Usa Inc Separation of olefins from paraffins
GB2371805A (en) * 2000-06-20 2002-08-07 Chevron Usa Inc Separation of olefins from paraffins
US7053261B2 (en) 2002-03-22 2006-05-30 Haldor Topsoe A/S Process for paraffin hydrocarbon isomerization and composite catalyst therefore
DE10336001B4 (en) * 2002-08-05 2017-02-09 IFP Energies Nouvelles Process for the isomerization of olefins
US7501522B2 (en) 2003-07-21 2009-03-10 Basf Aktiengesellschaft Method for the production of purified 1,3-substituted imidazolium salts
WO2005030392A1 (en) 2003-09-29 2005-04-07 Total Petrochemicals Research Feluy Ionic liquids as supports
WO2005085305A1 (en) 2004-03-02 2005-09-15 Total Petrochemicals Research Feluy Ionic liquids for heterogenising metallocene catalysts
US7605271B2 (en) 2005-03-29 2009-10-20 Dai-Ichi Kogyo Seiyaku Co., Ltd Superhigh purity ionic liquid
EP1707265A1 (en) * 2005-03-29 2006-10-04 Dai-Ichi Kogyo Seiyaku Co., Ltd. Superhigh purity ionic liquid
KR100770925B1 (en) * 2005-03-29 2007-10-26 다이이치 고교 세이야쿠 가부시키가이샤 Superhigh purity ionic liquid
WO2007006388A1 (en) * 2005-07-14 2007-01-18 Merck Patent Gmbh Method for the production of onium alkyl sulfites
US7999111B2 (en) 2005-07-14 2011-08-16 Merck Patent Gesellschaft Mit Beschrankter Haftung Process for the preparation of onium alkylsulfonates
US7732651B2 (en) 2006-06-01 2010-06-08 Chevron Oronite Company, Llc Method of making an alkylated aromoatic using acidic ionic liquid catalyst
CN100443157C (en) * 2006-11-16 2008-12-17 中国科学院长春应用化学研究所 Application of continuous microwave reactor
DE102008059702A1 (en) 2008-12-01 2010-06-02 Byk-Chemie Gmbh Process for the preparation of rheologically active urea urethanes in organic salts
US8956452B2 (en) 2008-12-01 2015-02-17 Byk-Chemie Gmbh Method for producing rheologically effective urea urethanes in organic salts
WO2010094640A1 (en) * 2009-02-23 2010-08-26 Basf Se Distillation of ionic liquids using an auxiliary distillation agent
US8500961B2 (en) 2009-02-23 2013-08-06 Basf Se Distillation of ionic liquids using an auxiliary distillation agent
WO2013079617A1 (en) 2011-11-29 2013-06-06 Total Research & Technology Feluy Planar chromatography with an inverse gradient elution
WO2013079613A1 (en) 2011-11-29 2013-06-06 Total Research & Technology Feluy Improved planar chromatography
CN103934023A (en) * 2014-04-25 2014-07-23 中国石油大学(华东) Ionic liquid catalyst for C5/C6 alkane isomerization and preparation and using method of catalyst
CN103934023B (en) * 2014-04-25 2016-02-03 中国石油大学(华东) For ionic-liquid catalyst and the preparation and application thereof of C5/C6 alkane isomerization
KR20230129782A (en) 2022-03-02 2023-09-11 엠파오 랩 더블유.엘.엘 Method for preparing olefin-based polymer using metal-containing ionic liquid catalyst

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CN1140422A (en) 1997-01-15
NO963294D0 (en) 1996-08-07
CA2182894A1 (en) 1996-06-20
AU3986495A (en) 1996-07-03
ZA9510411B (en) 1997-06-09
NO963294L (en) 1996-08-07
GB9425105D0 (en) 1995-02-08
FI963134A (en) 1996-08-09

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