WO1998050153A1 - Formation in-situ de catalyseur liquide ionique pour une reaction chimique catalysee liquide ionique - Google Patents

Formation in-situ de catalyseur liquide ionique pour une reaction chimique catalysee liquide ionique Download PDF

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Publication number
WO1998050153A1
WO1998050153A1 PCT/EP1998/002456 EP9802456W WO9850153A1 WO 1998050153 A1 WO1998050153 A1 WO 1998050153A1 EP 9802456 W EP9802456 W EP 9802456W WO 9850153 A1 WO9850153 A1 WO 9850153A1
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ionic liquid
alkyl
reaction
reagent
metal halide
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PCT/EP1998/002456
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English (en)
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Dale Stanley Steichen
Lieh-Jiun Shyu
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Akzo Nobel N.V.
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Publication of WO1998050153A1 publication Critical patent/WO1998050153A1/fr

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    • 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
    • C07C2/60—Catalytic processes with halides
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • 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
    • B01J31/0279—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 cationic portion being acyclic or nitrogen being a substituent on a ring
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
    • B01J35/27—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a liquid or molten state
    • 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
    • C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
    • 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
    • B01J2231/20—Olefin oligomerisation or telomerisation
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126—Aluminium chloride
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention relates to the in-situ formation of an ionic liquid catalyst for use in an ionic liquid-catalyzed chemical reaction.
  • the present invention relies upon the separate addition of the reagents needed to form an ionic liquid into the reactor intended to be used to form the ionic liquid-catalyzed chemical reaction so that the ionic liquid catalyst is formed in-situ in that reactor.
  • the instant process relies upon the presence of at least one reagent needed to form the ionic liquid catalyst (for example, a metal halide, which may not itself be a catalyst itself for the desired reaction) in the reactor in which the ionic liquid- catalyzed chemical reaction is to take place along with at least one of the reagents for the desired chemical reaction. Thereafter, either before the initiation of the reaction or during that reaction, the other reagent or reagents needed to form the ionic liquid are added.
  • the other reagent can be a base which, when combined with the metal halide will form the desired ionic liquid catalyst.
  • This invention relates, in the most preferred alkylation reaction, to the catalytic alkylation of an aromatic molecule with a suitable alkylating reagent (e.g., a C 2 to C 20 , such as a C 4 to C 14 olefin or a halogenated alkane of similar chain length) using, as the catalyst, a composition which is liquid at low temperatures and which is formed in situ as previously described.
  • a suitable alkylating reagent e.g., a C 2 to C 20 , such as a C 4 to C 14 olefin or a halogenated alkane of similar chain length
  • linear alkylbenzene formation is intended to cover the process by which higher alkyl moieties are placed on benzene compounds, with the term “alkyl” being intended to cover the conventional paraffinic alkane substituents, "higher” being intended to mean C 4 or longer, preferably C 8 or longer, and the "benzene” including both unsubstituted as well as substituted (e.g., lower alkyl- substituted) benzene compounds.
  • this process is practiced by the catalytic reaction of an unsubstituted or lower alkyl-substituted benzene compound with a higher alkene or a halo-substituted higher alkane, such as a chloro-substituted higher alkane.
  • the alkylating agent is one or more a long chain alkene or halogenated alkane, such as dodecylchloride or dodecene.
  • Recent patents which illustrate an alkylation reaction of this type include U.S. Patent Nos. 5,196,574 to J.A. Kocal and 5,386,072 to P. Cozzi et al.
  • the Cozzi patent which describes the use of aluminum trichloride as a preferred alkylation catalyst, is a particular example of a prior art alkylation process to which the present invention in an improvement.
  • a recent publication discussing the LAB reaction, in general terms, is contained in INFORM, Vol. 8, No. 1 (Jan. 1997), pp. 19-24.
  • a class of ionic liquids which is of special interest to the present in situ process, as the desired product thereof, is the class of fused salt compositions which are molten at low temperature.
  • Such compositions are mixtures of components which are liquid at temperatures below the individual melting points of the components. The mixtures can form molten compositions simultaneously upon contacting the components together, or after heating and subsequent cooling.
  • Examples of conventional low temperature ionic liquids or molten fused salts which are capable of being made by the present invention, are the chloroaluminate salts discussed by J. S. Wilkes, et al., J. Inorg. Chem., Vol. 21 , 1263-1264, 1982.
  • Alkyl imidazolium or pyridinium salts for example, can also be formed from aluminum trichloride (AICI 3 ) forming the fused chloroaluminate salts.
  • AICI 3 aluminum trichloride
  • chlorogallate salts made from gallium trichloride and methylethyl- imidazolium chloride are discussed in Wicelinski et al., "Low Temperature Chlorogallate Molten Salt Systems," J.
  • U.S. Patent No. 4,764,440 to S.D. Jones describes ionic liquids which comprise a mixture of a metal halide, such as aluminum trichloride, and what is termed a "hydrocarbyl-saturated onium salt", such as trimethylphenylammonium chloride.
  • a metal halide such as aluminum trichloride
  • a hydrocarbyl-saturated onium salt such as trimethylphenylammonium chloride.
  • the onium salt component if based on the presence of a nitrogen atom, is fully saturated with four substituent groups. These can also be selected as the ultimate in situ products herein.
  • U.S. Patent No. 5,104,840 to Y. Chauvin et al. describes ionic liquids which comprise at least one alkylaluminum dihalide and at least one quaternary ammonium halide and/or at least one quaternary ammonium phosphonium halide; and their uses as solvents in catalytic reactions.
  • the in situ process of this invention can be used to make these species.
  • PCT International Patent Publication No. WO 95/21872 describes ternary ionic liquids which can comprise a metal halide, such as aluminum trichloride, an imidazolium or pyridinium halide, and a hydrocarbyl substituted quaternary ammonium halide or a hydrocarbyl substituted phosphonium halide. See page 4, lines 18-24 for the description of the hydrocarbyl substituted quaternary ammonium halide. These might also be selected as products to be made by this invention.
  • the related applications describe preferred ionic liquids which are intended to be made herein and these applications are incorporated herein by reference for such description.
  • the present invention relates to the in-situ formation of an ionic liquid catalyst for use in an ionic liquid-catalyzed reaction (e.g., an aromatic alkylation reaction) by means of the separate addition of the reagents needed to form that ionic liquid into the desired reactor.
  • an ionic liquid-catalyzed reaction e.g., an aromatic alkylation reaction
  • the present invention can be practiced by the addition to at least one reagent for the formation of the ionic liquid catalyst (e.g., a metal halide) and at least one reagent for the desired reaction, in the desired reaction vessel, of the other reagent or reagents used to form the ionic liquid (e.g., at least one base) which other reagent(s) is or are capable, upon combination with the initially added reagent for the ionic liquid, of forming an ionic liquid catalyst, either before the initiation or during the desired ionic liquid catalyzed reaction (e.g., an alkylation reaction).
  • the ionic liquid catalyst e.g., a metal halide
  • the other reagent or reagents used to form the ionic liquid e.g., at least one base
  • the low temperature molten compositions, or ionic liquids, which are used as catalysts in this invention can be referred to as fused salt compositions, or ionic aprotic solvents.
  • low temperature molten is meant that the compositions are in liquid form below about 100°C at standard pressure.
  • the molten composition is in liquid form below about 60° C, and more preferably below about 30°C at standard pressure.
  • the metal halides useful in this invention are those compounds which can form anions containing polyatomic chloride bridges in the presence of the alkyl- containing amine hydrohalide salt.
  • Preferred metal halides are covalently bonded metal halides.
  • Suitable metals which can be selected for use herein include those from Groups VIII and IB, IIB and MIA of the Periodic Table of the Elements. Especially preferred metals are selected from the group comprising aluminum, gallium, iron, copper, zinc, and indium, with aluminum being most preferred.
  • the corresponding most preferred halide is chloride and therefore, the most preferred metal halide is aluminum trichloride.
  • Other possible choices for metal halides to select include those of copper (e.g., copper monochloride), iron (e.g., ferric trichloride), and zinc (e.g., zinc dichloride).
  • Aluminum trichloride is most preferred because it is readily available and can form the polynuclear ion having the formula AI 2 CI 7 M Furthermore, the molten compositions comprising this polynuclear ion are useful as described hereinbefore. Mixtures of more than one of these metal halides can be used.
  • Granular (+4 -14 mesh) aluminum trichloride can be an especially preferred metal halide to employ. It is easy to handle in air without fuming problems and has good flow properties. Its reaction with trimethylamine hydrochloride, for example, is slower and more uniform than with aluminum trichloride powder, with a temperature exotherm to about 150°C. While the resulting ionic liquid is slightly hazy due to the presence of insoluble impurities from the aluminum trichloride, the insoluble, which settle out upon storage of the liquid, do not have an adverse effect on the catalytic performance of the ionic liquid in regard to the process of the present invention.
  • alkyl-containing amine hydrohalide salt is intended to cover monoamines, as well as diamines, triamines, other oligoamines and cyclic amines which comprises one or more "alkyl” groups and a hydrohalide anion.
  • alkyl is intended to cover not only conventional straight and branched alkyl groups of the formula -(CH 2 ) n CH 3 where n is from 0 to about 29, preferably 0 to about 17, in particular 0 to 3, but other structures containing heteroatoms (such as oxygen, sulfur, silicon, phosphorus, or nitrogen). Such groups can carry substituents. Representative structures include ethylenediamine, ethylenetriamine, morpholino, and poloxyalkylamine substituents. "Alkyl” includes "cycloalkyl” as well.
  • the preferred alkyl-containing amine hydrohalide salts useful in the present invention have at least one alkyl substituent and can contain as many as three alkyl substituents. They are distinguishable from quaternary ammonium salts which have all four of their substituent positions occupied by hydrocarbyl groups.
  • the preferred compounds that are contemplated herein have the generic formula R 3 N.HX, where at least one of the "R" groups is alkyl, preferably alkyl of from one to eight carbon atoms (preferably, lower alkyl of from one to four carbon atoms) and X is halogen, preferably chloride.
  • each of the three R groups is designated R.,, R 2 and R 3 , respectively, the following possibilities exist in certain embodiments: each of R R 3 can be lower alkyl optionally interrupted with nitrogen or oxygen or substituted with aryl; R-, and R 2 can form a ring with R 3 being as previously described for R ⁇ R 2 and R 3 can either be hydrogen with R-, being as previously described; or R 1 t R 2 and R 3 can form a bicyclic ring. Most preferably, these groups are methyl or ethyi groups. If desired the di- and trialkyl species can be used. One or two of the R groups can be aryl, but this is not preferred.
  • the alkyl groups, and aryl, if present, can be substituted with other groups, such as a halogen. Phenyl and benzyl are representative examples of possible aryl groups to select. However, such further substitution may undesirably increase the size of the group, and correspondingly increase the viscosity of the melt. Therefore, it is highly desirable that the alkyl groups, and aryl, if present, be comprised of carbon and hydrogen groups, exclusively. Such short chains are preferred because they form the least viscous or the most conductive melts. Mixtures of these alkyl-containing amine hydrohalide salts can be used.
  • the mole ratio of alkyl-containing amine hydrohalide salt which is to be combined with the metal halide by in situ addition can, in general, range from about 1 :1 to about 1 :2.5.
  • the low temperature molten composition useful as a catalyst in this invention consists essentially of the metal halide and the alkyl-containing amine hydrohalide salt.
  • the most preferred low temperature molten composition formed by the instant in situ process is a mixture consisting essentially of a mole ratio of trimethylamine hydrochloride to aluminum trichloride of from about 1 :1.5 to about 1 :2, preferably about 1 :2.
  • the metal halide and the alkyl-containing amine hydrohalide salt are solids at low temperature, i.e., below about 100° C. at standard pressure.
  • the mixture can be heated until the mixture becomes a liquid.
  • the heat generated by the addition of the two solids will result in forming a liquid without the need for additional external heating.
  • the mixture remains a liquid at low temperature, i.e., below about 100°C, preferably below about 60°C, and more preferably below about 30°C.
  • Another type of base which can be used in the instant in situ process is a guanidinium salt as will be described in further detail.
  • guanidinium salts comprise the reaction product of a guanidine or substituted guanidine compound that has been reacted with an acid to form the corresponding guanidinium salt of the acid.
  • pKa 13.65
  • Alkyl guanidines are also strongly basic and form very stable salts. In salt formation, the proton is added to the dicoordinated nitrogen, forming a trigonally symmetrical cation, in which all three nitrogen atoms are seen to be equivalent.
  • the cation with HCI for example, can be represented as [C-(NH 2 ) 3 ] + CIM
  • the cation can be represented as an immonium ion with a double bond to any of the three nitrogens or as a carbonium ion.
  • a metal halide salt such as aluminum chloride with a melting point of 190°C, for example, in a molar ratio of 1 :2, respectively, an exothermic reaction takes place, resulting in the formation of a product that is a liquid about 70°C.
  • the chloride ion present in the guanidine HCI will react with aluminum trichloride, for example, to form the AICI 4 " anion. The result is an ionic liquid.
  • Line 11 shows the introduction of the paraffin reagent for the chemical reaction into dehydration vessel 12 with a paraffin/olefin feedstock for the reaction passing through line 13 into reactor 14.
  • the other reagent for the reaction (benzene) is introduced into the reactor 14 by line 22.
  • the LAB product is eventually withdrawn through line 15 into separator 16 where the ionic liquid 18 is separated and recycled through line 19 into reactor 14 and benzene reagent is also separated and recycled through line 17 into reactor 14.
  • the LAB product is collected via line 25.
  • the in-situ preparation of the ionic liquid is practiced by the separate introduction of the reagents needed to form it into the reactor.
  • appropriate amounts of each reagent to form either the original ionic liquid (or needed make up ionic liquid) can be added by lines 20-24 so that they combine in reactor 14.
  • in-situ addition has a number of advantages. It uses existing equipment needed for the actual reaction and avoids the need for a separate ionic liquid makeup reactor.
  • the individual reagents are separately added through any of the respective inlet lines 13 or 22 for the reagents and/or the recycle lines 17 or 19. Since the process of forming the ionic liquid may be highly exothermic, the in-situ preparation affords a desired dilution effect on that reaction. Also, corrosion problems that could take place if a separate reactor and/or feed lines is or are for the ionic liquid formation and transport might be alleviated by having the ionic liquid, when formed, largely present with other substances which dilute it (except possibly for recycle line 19 in the Drawing.
  • This Example demonstrates the in-situ preparation of an ionic liquid catalyst by adding trimethylamine hydrochloride and aluminum trichloride separately during the alkylation of benzene with an olefin reagent.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour former in situ un catalyseur liquide ionique, dans une cuve de réacteur prévue pour la mise en oeuvre d'une réaction chimique catalysée liquide et ionique. Ce procédé consiste à ajouter séparément dans le réacteur les réactifs requis pour former le liquide ionique destiné à permettre la réaction chimique. On peut introduire dans la cuve de réacteur au moins un réactif pour ce type de catalyseur liquide ionique et au moins un réactif pour la réaction chimique requise, avant d'ajouter l'autre réactif ou les autres réactifs requis pour former le catalyseur liquide ionique in situ. La formation in situ du catalyseur liquide ionique peut ainsi s'effectuer avant l'initiation de la réaction chimique requise ou au cours de cette dernière (qui peut être une réaction d'alkylation d'un réactif aromatique ou d'une paraffine ou l'oligomérisation d'une oléfine). Une réaction chimique particulièrement préférée consiste à former un alkylbenzène linéaire avec comme réactif initial pour former le liquide ionique un trichlorure d'aluminium et comme autre réactif requis pour former le catalyseur liquide ionique in situ une base (un sel d'hydrohalogénure d'amine contenant de l'alkyle ou un sel de guanidium).
PCT/EP1998/002456 1997-05-01 1998-04-22 Formation in-situ de catalyseur liquide ionique pour une reaction chimique catalysee liquide ionique WO1998050153A1 (fr)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000037400A1 (fr) * 1998-12-18 2000-06-29 Ineos Chlor Limited Halogenation dans des liquides ioniques
WO2001032308A1 (fr) * 1999-11-05 2001-05-10 Imperial Chemical Industries Plc Liquides ioniques immobilises
WO2004106288A3 (fr) * 2003-06-02 2005-03-17 Merck Patent Gmbh Liquides ioniques contenant des cations de guanidine
US6984605B2 (en) 2002-04-22 2006-01-10 Chevron Phillips Chemical Company, Lp Method for manufacturing ionic liquid catalysts
WO2007075404A2 (fr) 2005-12-21 2007-07-05 Chevron Oronite Company Llc Procede de fabrication d’un sulfonate de petrole synthetique
US7309805B2 (en) 2003-10-31 2007-12-18 Chevron Phillips Chemical Company Lp Method and system to contact an ionic liquid catalyst with oxygen to improve a chemical reaction
WO2007143513A3 (fr) * 2006-06-01 2008-02-21 Chevron Oronite Co Méthode de fabrication d'un aromatique alkylé impliquant un mélange incluant un catalyseur acide ionique liquide
US7351780B2 (en) 2002-04-22 2008-04-01 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US20080306319A1 (en) * 2005-12-12 2008-12-11 The Queen's University Of Belfast Oligomerisation
US7951889B2 (en) 2003-10-31 2011-05-31 Chevron Phillips Chemical Company Lp Method and system to add high shear to improve an ionic liquid catalyzed chemical reaction
WO2012139823A1 (fr) * 2011-04-15 2012-10-18 Evonik Degussa Gmbh Nouveau procédé d'amorçage de la polymérisation par activation de liquides ioniques
WO2013061336A2 (fr) * 2011-08-23 2013-05-02 Reliance Industries Ltd Procédé de production d'hydrocarbures aromatiques alkylés
US8524965B2 (en) 2005-12-21 2013-09-03 Chevron Oronite Company Llc Method of making an alkylated aromatic using acidic ionic liquid catalyst
US8653318B2 (en) 2009-08-06 2014-02-18 Shell Oil Company Process for preparing an alkylate
CN107827742A (zh) * 2017-11-22 2018-03-23 陕西煤业化工技术研究院有限责任公司 一种co2直接羧化法制备芳香酸的方法
CN108129296A (zh) * 2018-02-05 2018-06-08 陕西煤业化工技术研究院有限责任公司 一种二氧化碳直接羧化制备芳香酸的装置及方法
US10144685B2 (en) 2014-02-07 2018-12-04 Saudi Basic Industries Corporation Removal of aromatic impurities from an alkene stream using an acid catalyst
US10519080B2 (en) 2014-02-07 2019-12-31 Saudi Basic Industries Corporation Removal of aromatic impurities from an alkene stream using an acid catalyst, such as an acidic ionic liquid
CN114671733A (zh) * 2022-05-05 2022-06-28 合肥工业大学 一种乙苯的合成方法
CN115124400A (zh) * 2022-05-27 2022-09-30 合肥工业大学 一种乙苯的合成方法

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US7309805B2 (en) 2003-10-31 2007-12-18 Chevron Phillips Chemical Company Lp Method and system to contact an ionic liquid catalyst with oxygen to improve a chemical reaction
US8163856B2 (en) 2003-10-31 2012-04-24 Chevron Phillips Chemical Company Lp Method and system to add high shear to improve an ionic liquid catalyzed chemical reaction
US20080306319A1 (en) * 2005-12-12 2008-12-11 The Queen's University Of Belfast Oligomerisation
US8664460B2 (en) * 2005-12-12 2014-03-04 The Queen's University Of Belfast Oligomerisation with indium (III) chloride
EP1954672A2 (fr) * 2005-12-21 2008-08-13 Chevron Oronite Company LLC Procede de fabrication d un sulfonate de petrole synthetique
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WO2007143513A3 (fr) * 2006-06-01 2008-02-21 Chevron Oronite Co Méthode de fabrication d'un aromatique alkylé impliquant un mélange incluant un catalyseur acide ionique liquide
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US8653318B2 (en) 2009-08-06 2014-02-18 Shell Oil Company Process for preparing an alkylate
WO2012139823A1 (fr) * 2011-04-15 2012-10-18 Evonik Degussa Gmbh Nouveau procédé d'amorçage de la polymérisation par activation de liquides ioniques
WO2013061336A2 (fr) * 2011-08-23 2013-05-02 Reliance Industries Ltd Procédé de production d'hydrocarbures aromatiques alkylés
WO2013061336A3 (fr) * 2011-08-23 2013-06-20 Reliance Industries Ltd Procédé de production d'hydrocarbures aromatiques alkylés
US10144685B2 (en) 2014-02-07 2018-12-04 Saudi Basic Industries Corporation Removal of aromatic impurities from an alkene stream using an acid catalyst
US10519080B2 (en) 2014-02-07 2019-12-31 Saudi Basic Industries Corporation Removal of aromatic impurities from an alkene stream using an acid catalyst, such as an acidic ionic liquid
CN107827742A (zh) * 2017-11-22 2018-03-23 陕西煤业化工技术研究院有限责任公司 一种co2直接羧化法制备芳香酸的方法
CN107827742B (zh) * 2017-11-22 2021-04-27 陕西煤业化工技术研究院有限责任公司 一种co2直接羧化法制备芳香酸的方法
CN108129296A (zh) * 2018-02-05 2018-06-08 陕西煤业化工技术研究院有限责任公司 一种二氧化碳直接羧化制备芳香酸的装置及方法
CN108129296B (zh) * 2018-02-05 2023-08-25 陕西煤业化工技术研究院有限责任公司 一种二氧化碳直接羧化制备芳香酸的装置及方法
CN114671733A (zh) * 2022-05-05 2022-06-28 合肥工业大学 一种乙苯的合成方法
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