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.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Catalysts (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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• 1994
  • 1994-12-13 GB GBGB9425105.5A patent/GB9425105D0/en active Pending
• 1995
  • 1995-11-28 CA CA002182894A patent/CA2182894A1/en not_active Abandoned
  • 1995-11-28 WO PCT/GB1995/002781 patent/WO1996018459A1/en not_active Application Discontinuation
  • 1995-11-28 EP EP95938493A patent/EP0743878A1/en not_active Withdrawn
  • 1995-11-28 AU AU39864/95A patent/AU3986495A/en not_active Abandoned
  • 1995-11-28 JP JP8518427A patent/JPH09509888A/ja active Pending
  • 1995-11-28 CN CN95191587A patent/CN1140422A/zh active Pending
  • 1995-12-07 ZA ZA9510411A patent/ZA9510411B/xx unknown
• 1996
  • 1996-08-07 NO NO963294A patent/NO963294D0/no unknown
  • 1996-08-09 FI FI963134A patent/FI963134L/fi unknown

Non-Patent Citations (1)

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