WO1995021871A1 - Liquides ioniques - Google Patents

Liquides ioniques Download PDF

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Publication number
WO1995021871A1
WO1995021871A1 PCT/GB1995/000252 GB9500252W WO9521871A1 WO 1995021871 A1 WO1995021871 A1 WO 1995021871A1 GB 9500252 W GB9500252 W GB 9500252W WO 9521871 A1 WO9521871 A1 WO 9521871A1
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Prior art keywords
ionic liquid
imidazolium
halide
alkyl
process according
Prior art date
Application number
PCT/GB1995/000252
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English (en)
Inventor
Ala'a K Abdul-Sada
Philip William Ambler
Philip Kenneth Gordon Hodgson
Kenneth Richard Seddon
Nevin John Stewart
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
Priority claimed from GB9402572A external-priority patent/GB9402572D0/en
Priority claimed from GB9404104A external-priority patent/GB9404104D0/en
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to MX9504271A priority Critical patent/MX9504271A/es
Priority to BR9505775A priority patent/BR9505775A/pt
Priority to JP7521046A priority patent/JPH08509242A/ja
Priority to AU15848/95A priority patent/AU1584895A/en
Priority to EP95907752A priority patent/EP0693088A1/fr
Publication of WO1995021871A1 publication Critical patent/WO1995021871A1/fr
Priority to NO954015A priority patent/NO954015L/no
Priority to FI954807A priority patent/FI954807A0/fi

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56—Addition to acyclic hydrocarbons
    • C07C2/58—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron

Definitions

  • This invention relates to novel ionic liquids and to the use thereof as the reaction medium and catalyst for various chemical reaction such as eg producing olefin polymers, especially butene polymers from raffinates I and II from a refining process and which contain Inter alia a mixture of butene-1, butene-2 and iso-butene.
  • Ionic liquids are primarily mixtures of salts which melt below room temperature.
  • Such salt mixtures include aluminium halides in combination with one or more of imidazolium halides, pyridinium halides or phosphonium halides and the latter being preferably substituted. Examples of the latter include one or more of l-methyl-3-butyl imidazolium halides, 1-butyl pyridinium halide and tetrabutyl phosphonium halides.
  • FR-A-2611700 (Institut Francais du Petrole) describes a process for the oligomerization of olefins including inter alia butene-1 and butene-2 using a nickel catalyst in the liquid phase; the catalyst used is specifically a nickel complex dissolved in an ionic liquid, the latter being the liquid phase.
  • FR-A-2626572 describes a process for alkylation using as catalyst an ionic liquid comprising at least one halide of aluminium or boron and at least one quaternary ammonium halide.
  • the quaternary ammonium halide can be a dialkylimidazolium halide in which one of the alkyl substituents can be an amyl group, ie it has 5 carbon atoms.
  • the present invention is an ionic liquid comprising a dialkyl substituted imidazolium halide wherein at least one of the said alkyl substituents has 6 or more carbon atoms.
  • imidazolium compounds when used in ionic liquids contain at least two alkyl groups substituted in the 1- and the 3-positions of the imidazolium structure.
  • the substituents in these two positions are, by and large interchangeable.
  • at least one of the substituents in the 1- or the 3-position is an alkyl group having at least 6 carbon atoms.
  • the precise position of each is immaterial since such 1,3-disubstituted imidazolium halide is a symmetrical molecule.
  • This alkyl substituent having 6 or more carbon atoms can be a straight chain alkyl group or a branched chain alkyl group.
  • These alkyl groups suitably contain from 6-30 carbon atoms, preferably from 6-18 carbon atoms.
  • the halide group in the imidazolium compounds of the present invention may be a chloride, a bromide or an iodide group.
  • Specific examples of imidazolium compounds present in the ionic liquids include:
  • the imidazolium halides of the present invention can be prepared by the following method:
  • a l-methyl-3-(C6+) lkyl imidazolium halide (wherein "C6+” represents 6 or more carbon atoms) can be prepared by mixing dry 1-methylimidazole with 1-(C6+)alkyl haloalkane (and optionally with a solvent such as eg acetonitrile, if a homogeneous mixture is desired) and placing them eg in a Corius tube inside a dry box. The Corius tube is then closed using a super seal in the dry box and sealed under vacuum. The two components form two layers inside the Corius tube and the resulting mixture is then heated to about 90°C for about a week.
  • the resultant product is then cooled to room temperature to form a viscous product which is then transferred from the dry box to a Schlenk round bottomed flask and left under vacuum for a few hours.
  • the resultant viscous liquid is then purified by recrystallisation from acetonitrile and analysed for identification and characterisation of the l-methyl-3-(C6+)alkyl imidazolium halide.
  • a feature of the present invention is that where the chain length of at least one of the alkyl chains in the dialkyl imidazolium halide is greater than 5 carbon atoms, the catalytic activity of ionic liquids comprising such halides is increased for polymerization reactions with respect to alkyl chains having 4 carbon atoms or less.
  • the performance of such ionic liquids is particularly superior when the feedstock being polymerised is a raffinate I, raffinate II or isobutene.
  • the polymers produced using ionic liquids comprising the dialkyl imidazolium halides of the present invention can, if desired, have a higher molecular weight distribution than those obtained containing conventional imidazolium halides.
  • the ionic liquids of the present invention suitably contain in addition to the dialkyl imidazolium halides defined above an aluminium compound which is suitably an aluminium halide, such a aluminium trichloride or an alkyl aluminium halide such an alkyl aluminium dichloride or a dialkyl aluminium halide and is preferably ethyl aluminium dichloride.
  • an aluminium compound which is suitably an aluminium halide, such a aluminium trichloride or an alkyl aluminium halide such an alkyl aluminium dichloride or a dialkyl aluminium halide and is preferably ethyl aluminium dichloride.
  • a yet another feature of the present invention is that when preparing multi-component ionic liquids, the presence of the dialkyl imidazolium halides of the present invention enables such liquids to tolerate a higher proportion of the other componen (s) and still remain liquids, in some cases at room temperature, than is possible with conventional imidazolium halides.
  • Ionic liquids produced from imidazolium halides of the present invention can be used as catalysts for any of the reactions in which ionic liquids have conventionally been used. Such reactions include oligomerization, alkylation, polymerization and the like.
  • ionic liquids comprising the dialkyl imidazolium halides of the present invention are particularly suitable for the oligomerization and polymerization of olefins, especially feedstock comprising isobutenes.
  • the present invention is a process for the polymerization of an olefinic feedstock comprising one or more of C2-C4 olefins, said process comprising bringing the feedstock into contact with an ionic liquid comprising a) a compound of the formula R n MX3_ n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2, and b) a dialkyl substituted imidazolium halide in which at least one of the alkyl substituents has six (6) or more carbon atoms such that the melting point of the ionic liquid is below the reaction temperature.
  • an ionic liquid comprising a) a compound of the formula R n MX3_ n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2, and b) a dialkyl
  • the polymerization products referred to herein are meant to include: i. oligomers which are conventionally defined as "a very low molecular weight polymer in which the number of repeating units equals 2-10" (see Polymer Chemistry, An Introduction by R B Seymour and C E Carraher, 2nd Edition, 1988, p 14, and published by Marcel Dekker Inc), and ii. polymers which have at least 11 repeating units, ie an average molecular weight of 600 to 100,000.
  • the hydrocarbon feedstock for this process is suitably ethylene, propylene, butene-1, butene-2 and/or isobutene but is preferably a raffinate from the refining process and can be raffinate I or raffinate II.
  • Raffinate I is usually the butadiene raffinate which is a by ⁇ product formed during the thermal or catalytic cracking (whether or not fluid) operation in a refinery and principally comprises C4 hydrocarbons especially a mixture of butene-1, butene-2 and iso- butene along with some saturated hydrocarbons. More specifically, such raffinate I comprises at least 10% w/w of iso-butene, from 20- 40% w/w of butene-1 and butene-2, and from 10-20% w/w of butanes.
  • Raffinate II is the unpolymerised by-products recoverable when Raffinate I is subjected to polymerization using eg Lewis acid catalysts or the by-product gases resulting from the production of the lead-free anti-knock compound, methyl tertiary butyl ether (MTBE). In both processes the by-products have substantially the same composition and are rich in n-butenes.
  • MTBE methyl tertiary butyl ether
  • raffinate II typically contain from 30-55% w/w of butene-1, about 10% w/w of cis-butene-2, about 17% w/w of trans- butene-2, upto 6% w/w of iso-butene and upto 30% w/w of the saturated C4 hydrocarbons n-butane and iso-butane. Since raffinate II, an otherwise wasted material, is capable of being cationically polymerized to polybutenes, its value as raw material is readily apparent.
  • the ionic liquids that can be used comprise an aluminium or gallium compound which is suitably a halide, such as aluminium trichloride or gallium trichloride, or, an alkyl aluminium/gallium halide such as an alkyl aluminium/gallium dichloride or a dialkyl aluminium/gallium chloride and is preferably ethyl aluminium/gallium dichloride.
  • the component (b) in the ionic liquid is a dialkyl substituted imidazolium halide, especially the l-(Cl-C4)alkyl-3- (C6+)alkyl-imidazolium halides of the present invention described above.
  • l-methyl-3- octylimidazolium chloride is preferred.
  • the relative ratios of the two components (a) and (b) in the ionic liquid should be such that they are capable of remaining in the liquid state under the reaction conditions.
  • the relative mole ratio of aluminium/gallium compound to the component (b) in the ionic liquid is suitably in the range from 1 : 2 to 3 : 1, preferably from 1.5 : 1 to 2 : 1.
  • the amount of the component (a) can be less than 50 mole % of the total ionic liquid.
  • the amount of component (a) is preferably greater than 50 mole % of the total ionic liquid.
  • the polymerization reaction is suitably carried out at a temperature from -50°C to +100°C, preferably from -30°C to +70°C.
  • the reaction can be carried out either:
  • the polymer product forms a separate layer and floats on the surface of the ionic liquid.
  • This product layer is substantially free of any catalyst or ionic liquid contaminants.
  • the polymer product can thus be readily removed from the ionic liquid surface eg by tapping.
  • This feature has several advantages: A. Ease of separation of the product polymer from the catalytic component means that further reaction of the olefinic end-group in the polymer, such as eg isomerization, is minimised thereby retaining the structure of the polymer formed. This means that such further undesirable reactions are avoided without resort to the use of conventional reaction quenching agents such as aqueous alkali.
  • the polymer product formed need not be water-washed because of the relatively low levels of the catalytic ionic liquid in the product thereby avoiding a process step.
  • process (ii) it may be necessary to add a quenchant such as aqueous ammonia in order to terminate the reaction and/or to neutralise any catalytic components.
  • a quenchant such as aqueous ammonia
  • the products can then be water- washed and the product polymer separated. In this case, the unreacted material can be allowed to evaporate and the dried product isolated.
  • a further feature of the present invention is that this method enables a much higher percentage of n-butenes to be incorporated in the product polymer than would be possible in conventional cationic polymerization processes using eg aluminium trichloride or boron trifluoride.
  • polymer products produced by the process of the present invention can be used eg as lubricants or cutting fluids in the industry without further treatment.
  • these polymers can be maleinised and converted to corresponding succinic anhydride derivatives which in turn can be converted into the corresponding imide which is a detergent for lube oils and fuels.
  • the ionic liquids of the present invention can also be used eg for alkylation reactions.
  • this may be either the alkylation of isoparaffins such as isobutane with a C2-C4 olefin such as eg ethylene, to produce alkylates which enhance the octane rating of fuels, or, for the alkylation of aromatics with an olefins such as eg the conversion of benzene to ethyl benzene with a view to producing styrene therefrom.
  • the alkylation reaction is suitably carried out at a temperature of eg below 100°C, suitably from -30 to +50°C.
  • the ratio of the catalytic ionic liquid phase to the hydrocarbon phase used for alkylation would largely depend upon the reactivity of the olefin and the acidity of the particular ionic liquids chosen.
  • the mole ratio of catalyst to olefins is suitably in the range from 1000 : 1 to 1 : 1000.
  • the volume ratio of catalyst phase to hydrocarbon phase this would suitably be in the range from in the range from 100 : 1 to 1 : 100, and more preferably from 20 : 1 to 1 : 20.
  • the ratio of iso-paraffins to olefin is suitably in the range from 1000 : 1 to 1 : 1000.
  • the present invention is further illustrated with reference to the following Examples.
  • the 1-methylimidazole used was distilled over sodium hydroxide and was always handled under a cover of nitrogen.
  • the alkyl halides used were all dried over calcium hydride for a week and then distilled prior to use. It is not believed that any detailed analysis .of these compounds is necessary in order to ascertain their structure since the reactions are stoichiometric, no gases are evolved nor any solids deposited during the reaction. However, in order to prove that this is the case, 1 H NMR analyses has been carried out on the products from some of the Examples and on this basis a structure has been assigned for those products on which no NMR analyses have been carried out.
  • the intensity referred to is the peak height which corresponds to the number of protons in that position.
  • very strong, strong, medium and weak represent the following range of peak intensities (I/Io): very strong - 80-100 strong - 60-80 medium - 40-60 weak - 20-40 very weak - ⁇ 20 ⁇ (ppm) - chemical shift in parts per million
  • EXAMPLE 1 Preparation of l-hexyl-3-methyl Imidazolium Chloride: Dry 1-methylimidazole (9.03 g, 0.11 mol) was mixed with 1- chlorohexane (12.06 g, 0.1 mol) and placed in a Corius tube inside a dry box.
  • the Corius tube was then closed using a super seal in the dry box and sealed under vacuum.
  • the two components formed two layers, inside the Corius tube, and this mixture was heated at 100°C for a week.
  • the resulting product was allowed to cool to room temperature when it formed a viscous product.
  • the viscous product was transferred from the dry box to a Schlenk round bottomed flask where it was left under vacuum for 4 hours to form a viscous liquid.
  • the product was the ionic liquid l-hexyl-3-methyl imidazolium chloride at room temperature and the yield was 12.23 g (92.2%) with an m/ z value of 369.
  • EXAMPLE 2 Preparation of l-octyl-3-methyl Imidazolium Chloride: The process of Example 1 above was repeated except that 1- chlorooctane (14.9 g, 0.1 mol) was used instead of 1-chlorohexane. The product was the ionic liquid l-octyl-3-methyl imidazolium chloride at room temperature, the yield was 15.8 g (96.6%) and had an m/z value of 425.
  • EXAMPLE 3 Preparation of l-nonyl-3-methyl Imidazolium Chloride: The process of Example 1 was repeated except that 1- chlorononane (16.3 g, 0.1 mol) was used instead of 1-chlorohexane. The product was the ionic liquid l-nonyl-3-methyl imidazolium chloride at room temperature, the yield was 16.1 g (90.0%) and had an m/z value of 453.
  • EXAMPLE 4 Preparation of l-decyl-3-methyl Imidazolium Chloride: The process of Example 1 was repeated except that 1- chlorodecane (17.7 g, 0.1 mol) was used instead of 1-chlorohexane. The product was the ionic liquid l-decyl-3-methyl imidazolium chloride at room temperature, the yield was 18.3 g (94.2%) and had an m/z value of 481.
  • Example 1 The process of Example 1 was repeated except that 1- chlorododecane (20.48g 0.1 mol) was used instead of 1-chlorohexane.
  • the product upon heating at 100°C was waxy and was recrystallised from acetonitrile (50 ml) at -13°C for a week in a Schlenk round bottomed flask.
  • the crystals were isolated by Schlenk filtration and dried in vacuo for 48 hours.
  • the ⁇ H NMR analysis of the crystals is shown in Table 1 below. The crystals had a melting point of 52.5 °C, the yield was 19.4 g (86.1%) and had an m/z value of 537.
  • Example 5 The process of Example 5 was repeated except that 1- chlorotetradecane (23.3 g 0.1 mol) was used instead of 1- chlorododecane.
  • the crystals formed were not analysed by 1 H NMR but were assigned the structure l-tetradecyl-3-methyl imidazolium chloride by analogy with Example 5.
  • the crystals had a melting point of 56.89°C, the yield was 23.9 g (93.3%) and had an m/z value of 593.
  • Example 5 The process of Example 5 was repeated except that 1- chlorohexadecane (26.09 g 0.1 mol) was used instead of 1- chlorododecane.
  • the crystals were not analysed by ⁇ H NMR but were assigned the structure l-hexadecyl-3-methyl imidazolium chloride by analogy with Example 5.
  • the crystals had a melting point of 61.6°C, the yield was 25.7 g (89.6%) and had an m/ z value of 649.
  • EXAMPLE 8 Preparation of l-octadecyl-3-methyl Imidazolium Chloride:
  • Example 5 The process of Example 5 was repeated except that 1- chlorooctadecane (28.9 g 0.1 mol) was used instead of 1- chlorododecane.
  • the crystals were not analysed by 1 H NMR but the structure was assigned as l-octadecyl-3-methyl imidazolium chloride on the basis of analogy with Example 5.
  • the crystals had a melting point of 71.07°C, the yield was 31.77 g (93.3%) and had an m/z value of 705.
  • EXAMPLE 9 EXAMPLE 9:
  • An ionic liquid was prepared using l-methyl-3-octyl imidazolium chloride and aluminium trichloride in a mole ratio of 2:1 as described in Example 2 above. 5ml of the ionic liquid so formed was dispersed into 200g of raffinate II feedstock (having an olefinic content of 62% w/w and a composition shown in Table 2 below) in 750 ml of heptane with stirring at atmospheric pressure and at 10°C for a duration of 180 minutes. The reaction was exothermic but a temperature rise of no greater than 10°C was observed during the reaction period.
  • the yield of the polymer product was 76.8% wt/wt based on the weight of olefin present, ie 95.3 g of polymer product was obtained from 124.Og of olefin.
  • the number average molecular weight of the polymer, Mn, was 1042.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Lubricants (AREA)
  • Catalysts (AREA)

Abstract

L'invention porte sur un liquide ionique comprenant un halogénure d'imidazolium à substitution dialkyle dans lequel au moins un desdits substituants alkyle comporte au moins 6 atomes de carbone, sur un procédé de préparation desdits halogénures d'imidazolium et sur leur emploi dans les réactions de conversion d'hydrocarbures telles que l'oligomérisation ou la polymérisation d'oléfines ou pour l'alkylation par les oléfines de paraffines, d'isoparaffines et de composés aromatiques. La polymérisation des produits de raffinage à C4 recourant à ces liquides ioniques comme catalyseurs permet d'atteindre un pourcentage beaucoup plus élevé de n-butènes s'incorporant au polymère résultant que lors des procédés classiques de polymérisation cationique.
PCT/GB1995/000252 1994-02-10 1995-02-09 Liquides ioniques WO1995021871A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
MX9504271A MX9504271A (es) 1994-02-10 1995-02-09 Liquidos ionicos.
BR9505775A BR9505775A (pt) 1994-02-10 1995-02-09 Liquido iônico processo para produçao de liquido iônicos e processo para conversao de hidrocarbonetos olefinicos
JP7521046A JPH08509242A (ja) 1994-02-10 1995-02-09 イオン液体
AU15848/95A AU1584895A (en) 1994-02-10 1995-02-09 Ionic liquids
EP95907752A EP0693088A1 (fr) 1994-02-10 1995-02-09 Liquides ioniques
NO954015A NO954015L (no) 1994-02-10 1995-10-09 Ioniske væsker
FI954807A FI954807A0 (fi) 1994-02-10 1995-10-09 Ionisia nesteitä

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9402572A GB9402572D0 (en) 1994-02-10 1994-02-10 Ionic liquids
GB9404104.3 1994-03-03
GB9402572.3 1994-03-03
GB9404104A GB9404104D0 (en) 1994-03-03 1994-03-03 Ionic liquids

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JP (1) JPH08509242A (fr)
CN (1) CN1123031A (fr)
AU (1) AU1584895A (fr)
BR (1) BR9505775A (fr)
CA (1) CA2159479A1 (fr)
CZ (1) CZ257695A3 (fr)
FI (1) FI954807A0 (fr)
MX (1) MX9504271A (fr)
NO (1) NO954015L (fr)
WO (1) WO1995021871A1 (fr)

Cited By (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0791643A1 (fr) 1996-02-22 1997-08-27 BP Chemicals Limited Huiles lubrifiantes
US5731101A (en) * 1996-07-22 1998-03-24 Akzo Nobel Nv Low temperature ionic liquids
US5824832A (en) * 1996-07-22 1998-10-20 Akzo Nobel Nv Linear alxylbenzene formation using low temperature ionic liquid
WO1999014160A1 (fr) 1997-09-16 1999-03-25 British Nuclear Fuels Plc Traitement de dechets de retraitement par sels fondus
EP0989134A1 (fr) * 1998-09-11 2000-03-29 Akzo Nobel N.V. Procédé pour préparer un liquide ionique
WO2000034357A1 (fr) * 1998-12-10 2000-06-15 E.I. Du Pont De Nemours And Company Preparation de copolymeres olefiniques de dioxyde de soufre ou de monoxyde de carbone
WO2000037400A1 (fr) * 1998-12-18 2000-06-29 Ineos Chlor Limited Halogenation dans des liquides ioniques
WO2000072956A1 (fr) * 1999-05-26 2000-12-07 Personal Chemistry I Uppsala Ab Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes
WO2001038270A1 (fr) * 1999-11-26 2001-05-31 Sasol Technology (Pty) Ltd Traitement de conversion d'hydrocarbures
WO2001040146A1 (fr) * 1999-12-01 2001-06-07 The Queen's University Of Belfast Procede de preparation de liquides ioniques a la temperature ambiante
US6379634B1 (en) 1996-08-02 2002-04-30 British Nuclear Fuels Plc Ionic liquids as solvents
EP1201657A1 (fr) * 2000-10-27 2002-05-02 Centre National De La Recherche Scientifique (Cnrs) Sels d'imidazolium et l'utilisation de ces liquides ioniques en tant que solvant et catalyseur
FR2829132A1 (fr) * 2001-08-31 2003-03-07 Inst Francais Du Petrole Procede pour l'oligomerisation des olefines
FR2829133A1 (fr) * 2001-08-31 2003-03-07 Inst Francais Du Petrole Procede d'alkylation des olefines par les isoparaffines
WO2003089390A2 (fr) * 2002-04-22 2003-10-30 Chevron Phillips Chemical Company Lp Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques
KR100404587B1 (ko) * 2000-04-20 2003-11-05 한국과학기술연구원 키랄 에폭사이드의 제조방법
WO2004080974A1 (fr) * 2003-03-12 2004-09-23 Chemtech Research Incorporation Procede de purification de liquides ioniques permettant d'obtenir une grande purete
USRE38864E1 (en) 1998-10-30 2005-11-01 The University Of Southern Mississippi Research Foundation Process for making n-butyl esters from butadiene
US6984605B2 (en) 2002-04-22 2006-01-10 Chevron Phillips Chemical Company, Lp Method for manufacturing ionic liquid catalysts
US6991718B2 (en) 2001-11-21 2006-01-31 Sachem, Inc. Electrochemical process for producing ionic liquids
US6998152B2 (en) 1999-12-20 2006-02-14 Micron Technology, Inc. Chemical vapor deposition methods utilizing ionic liquids
US7053232B2 (en) 2002-08-16 2006-05-30 Sachem, Inc. Lewis acid ionic liquids
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EP1900763A1 (fr) * 2006-09-15 2008-03-19 Rütgers Chemicals GmbH procédé de préparation d'une résine hydrocarbonée
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US7615644B2 (en) 2004-09-17 2009-11-10 California Institute Of Technology Use of ionic liquids as coordination ligands for organometallic catalysts
WO2009108369A3 (fr) * 2008-02-29 2010-01-07 Exxonmobil Research And Engineering Company Fonctionnalisation de poly-α-oléfines par une diphénylamine
US7732651B2 (en) 2006-06-01 2010-06-08 Chevron Oronite Company, Llc Method of making an alkylated aromoatic using acidic ionic liquid catalyst
WO2010074843A2 (fr) * 2008-12-15 2010-07-01 Chevron U.S.A. Inc. Procédé de conversion d'hydrocarbure au moyen d'un catalyseur acide, procédé de fabrication du catalyseur acide et compositions le contenant
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EP2243539A2 (fr) 2002-04-05 2010-10-27 University Of South Alabama Liquides ioniques fonctionnalisés et leurs procédés d'utilisation
US7888412B2 (en) 2004-03-26 2011-02-15 Board Of Trustees Of The University Of Alabama Polymer dissolution and blend formation in ionic liquids
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US8143467B2 (en) 2007-12-18 2012-03-27 Exxonmobil Research And Engineering Company Process for synthetic lubricant production
US8232265B2 (en) 2005-10-07 2012-07-31 Board Of Trustees Of The University Of Alabama Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
US8668807B2 (en) 2008-02-19 2014-03-11 Board Of Trustees Of The University Of Alabama Ionic liquid systems for the processing of biomass, their components and/or derivatives, and mixtures thereof
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US9096743B2 (en) 2009-06-01 2015-08-04 The Board Of Trustees Of The University Of Alabama Process for forming films, fibers, and beads from chitinous biomass
US9278134B2 (en) 2008-12-29 2016-03-08 The Board Of Trustees Of The University Of Alabama Dual functioning ionic liquids and salts thereof
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US9394375B2 (en) 2011-03-25 2016-07-19 Board Of Trustees Of The University Of Alabama Compositions containing recyclable ionic liquids for use in biomass processing
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US10100131B2 (en) 2014-08-27 2018-10-16 The Board Of Trustees Of The University Of Alabama Chemical pulping of chitinous biomass for chitin
US10435491B2 (en) 2015-08-19 2019-10-08 Chevron Phillips Chemical Company Lp Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins
WO2020084557A1 (fr) * 2018-10-24 2020-04-30 Reliance Industries Limited Procédé de préparation de polyisobutylène fortement réactif
US10927191B2 (en) 2017-01-06 2021-02-23 The Board Of Trustees Of The University Of Alabama Coagulation of chitin from ionic liquid solutions using kosmotropic salts
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US6468495B1 (en) 1997-09-16 2002-10-22 British Nuclear Fuels Plc Treatment of molten salt reprocessing wastes
WO1999014160A1 (fr) 1997-09-16 1999-03-25 British Nuclear Fuels Plc Traitement de dechets de retraitement par sels fondus
EP0989134A1 (fr) * 1998-09-11 2000-03-29 Akzo Nobel N.V. Procédé pour préparer un liquide ionique
USRE38864E1 (en) 1998-10-30 2005-11-01 The University Of Southern Mississippi Research Foundation Process for making n-butyl esters from butadiene
WO2000034357A1 (fr) * 1998-12-10 2000-06-15 E.I. Du Pont De Nemours And Company Preparation de copolymeres olefiniques de dioxyde de soufre ou de monoxyde de carbone
WO2000037400A1 (fr) * 1998-12-18 2000-06-29 Ineos Chlor Limited Halogenation dans des liquides ioniques
WO2000072956A1 (fr) * 1999-05-26 2000-12-07 Personal Chemistry I Uppsala Ab Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes
US6596130B2 (en) 1999-05-26 2003-07-22 Personal Chemistry I Uppsala Ab Preparation and use of ionic liquids in microwave-assisted chemical transformations
WO2001038270A1 (fr) * 1999-11-26 2001-05-31 Sasol Technology (Pty) Ltd Traitement de conversion d'hydrocarbures
WO2001040146A1 (fr) * 1999-12-01 2001-06-07 The Queen's University Of Belfast Procede de preparation de liquides ioniques a la temperature ambiante
US6774240B2 (en) 1999-12-01 2004-08-10 The Queen's University Of Belfast Process for preparing ambient temperature ionic liquids
US6998152B2 (en) 1999-12-20 2006-02-14 Micron Technology, Inc. Chemical vapor deposition methods utilizing ionic liquids
KR100404587B1 (ko) * 2000-04-20 2003-11-05 한국과학기술연구원 키랄 에폭사이드의 제조방법
US7259284B2 (en) 2000-05-31 2007-08-21 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US7915426B2 (en) 2000-10-27 2011-03-29 Centre National De La Recherche Scientifique (C.N.R.S.) Imidazolium salts and their use of these ionic liquids as a solvent
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
EP1201657A1 (fr) * 2000-10-27 2002-05-02 Centre National De La Recherche Scientifique (Cnrs) Sels d'imidazolium et l'utilisation de ces liquides ioniques en tant que solvant et catalyseur
FR2829133A1 (fr) * 2001-08-31 2003-03-07 Inst Francais Du Petrole Procede d'alkylation des olefines par les isoparaffines
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US6991718B2 (en) 2001-11-21 2006-01-31 Sachem, Inc. Electrochemical process for producing ionic liquids
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US7053232B2 (en) 2002-08-16 2006-05-30 Sachem, Inc. Lewis acid ionic liquids
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US7888412B2 (en) 2004-03-26 2011-02-15 Board Of Trustees Of The University Of Alabama Polymer dissolution and blend formation in ionic liquids
US7615644B2 (en) 2004-09-17 2009-11-10 California Institute Of Technology Use of ionic liquids as coordination ligands for organometallic catalysts
US7550520B2 (en) 2005-05-31 2009-06-23 The University Of Alabama Method of preparing high orientation nanoparticle-containing sheets or films using ionic liquids, and the sheets or films produced thereby
US8883193B2 (en) 2005-06-29 2014-11-11 The University Of Alabama Cellulosic biocomposites as molecular scaffolds for nano-architectures
US8232265B2 (en) 2005-10-07 2012-07-31 Board Of Trustees Of The University Of Alabama Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
US8802596B2 (en) 2005-10-07 2014-08-12 Board Of Trustees Of The University Of Alabama Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
WO2007050491A3 (fr) * 2005-10-27 2007-06-14 Du Pont Isomerisation d'olefines
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US7732651B2 (en) 2006-06-01 2010-06-08 Chevron Oronite Company, Llc Method of making an alkylated aromoatic using acidic ionic liquid catalyst
EP1900763A1 (fr) * 2006-09-15 2008-03-19 Rütgers Chemicals GmbH procédé de préparation d'une résine hydrocarbonée
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US8668807B2 (en) 2008-02-19 2014-03-11 Board Of Trustees Of The University Of Alabama Ionic liquid systems for the processing of biomass, their components and/or derivatives, and mixtures thereof
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US8784691B2 (en) 2009-07-24 2014-07-22 Board Of Trustees Of The University Of Alabama Conductive composites prepared using ionic liquids
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US9328037B2 (en) 2014-07-09 2016-05-03 Uop Llc Benzene alkylation using acidic ionic liquids
US10100131B2 (en) 2014-08-27 2018-10-16 The Board Of Trustees Of The University Of Alabama Chemical pulping of chitinous biomass for chitin
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US10927191B2 (en) 2017-01-06 2021-02-23 The Board Of Trustees Of The University Of Alabama Coagulation of chitin from ionic liquid solutions using kosmotropic salts
US10941258B2 (en) 2017-03-24 2021-03-09 The Board Of Trustees Of The University Of Alabama Metal particle-chitin composite materials and methods of making thereof
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EP0693088A1 (fr) 1996-01-24
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FI954807A (fi) 1995-10-09
FI954807A0 (fi) 1995-10-09
BR9505775A (pt) 1996-02-27
CA2159479A1 (fr) 1995-08-17
JPH08509242A (ja) 1996-10-01
CZ257695A3 (en) 1996-01-17
MX9504271A (es) 1997-04-30

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