WO2013061336A2 - Procédé de production d'hydrocarbures aromatiques alkylés - Google Patents

Procédé de production d'hydrocarbures aromatiques alkylés Download PDF

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WO2013061336A2
WO2013061336A2 PCT/IN2012/000561 IN2012000561W WO2013061336A2 WO 2013061336 A2 WO2013061336 A2 WO 2013061336A2 IN 2012000561 W IN2012000561 W IN 2012000561W WO 2013061336 A2 WO2013061336 A2 WO 2013061336A2
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group
hydrocarbon
aromatic hydrocarbon
catalyst
present disclosure
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PCT/IN2012/000561
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WO2013061336A3 (fr
Inventor
Pavankumar ADURI
Parasu Veera UPPARA
Mangesh SAKHALKAR
Uday RATNAPARKHI
Paresh Nanubhai TRIVEDI
Munish BHALLA
Narayanmadhav JAGADALE
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Reliance Industries Ltd
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Publication of WO2013061336A2 publication Critical patent/WO2013061336A2/fr
Publication of WO2013061336A3 publication Critical patent/WO2013061336A3/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
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/68—Catalytic processes with halides
    • 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
    • C07C2/70—Catalytic processes with acids
    • 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
    • C07C2527/08—Halides
    • 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
    • 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
    • C07C2531/025—Sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of the platinum group metals, iron group metals or copper
    • C07C2531/30—Halides

Definitions

  • the present disclosure relates to a process for preparing alkylated aromatic hydrocarbons.
  • Linear alkyl benzene sulfonic acids constitute the category of the most widely used precursors for the manufacturing of household detergents such as laundry liquids, dishwashing liquids and other house hold cleaners.
  • their use as a coupling agent, as an emulsifier for agricultural herbicides and as a catalyst in the emulsion polymerization is also well- known in prior-art.
  • Linear alkyl benzene sulfonic acid are often produced by the sulfonation of linear alkyl benzene with oleum in batch reactors.
  • the production of linear alkyl benzene is accomplished by contacting benzene/substituted benzene with an olefin or mixture of olefins, in the presence of a homogeneous or heterogeneous alkylation catalyst such as aluminum chloride, boron trifluoride, sulfuric acid, hydrofluoric acid, phosphoric acid and zeolite.
  • HF Hydrofluoric acid
  • United States Patent Documents 3104267 and 4219686 disclose the use of lewis acid catalysts such as the mixture containing titanium tetrachloride and alkylaluminum
  • solid catalysts have also been found to facilitate linear alkyl benzene production as disclosed in US3494971, US7737312, US 5334793, US3346657, US4358628, US4368342, U?4513156, US4973780, US5196574, US5196624, US5344997, US5574198, UK5777187, US5847254, US5894076, US6133492, US7655824, US201 101 18517 and US201 10144403.
  • the use of such solid catalysts calls for major structural modifications in the existing HF catalyst based alkylation processing plants.
  • ionic; liquid based compounds have also been employed in the alkylation reactions as described in WO1998003454, US5824832, WO 1999003163, WO2000041809, US 7285698, US7732651. Further, ionic liquid particularly chloroaluminate based ionic liquid has been indicated for the alkylation reaction by Zhu Hai-yan et. al. in Bulletin of Catalysis Society of India, 6, 2007, 83-89 and Ling H.E. et. al. in Chinese Chemical Letters, 2003, 17.3, 321-324. Apart from HF and ionic liquid based catalysts, other catalysts that have been explored for alkylation include sulfonic acid derivatives as disclosed in the Journal of Catalysts, 226, 2004, 301-307.
  • a process for preparing alkylated aromatic hydrocarbons comprising the following steps; alkylating an aromatic hydrocarbon with an alkylating agent that comprises a mixture of at least one C 2 to C 50 olefin and at least one C 2 to C 50 paraffin, in the presence of at least one acid catalyst selected from the group consisting of (i) compounds having the molecular formula of RS0 3 H, wherein R is independently selected from the group consisting of alkyl, aryl, halogen, or alkyl halide; (ii) ionic liquid composition comprising (a) at least one cationic precursor selected fror the group of compounds consisting of hydrogen donor compounds, tetra alkyl ammor ium halide, phosphonium halides, and imidazolium bromide; and (b) at least one ar. :nic precursor selected from the group consisting of metal halides and organic halides, at a temperature varying between 35°C and 90
  • the aromatic hydrocarbon is at least one selected from the group consisting of benzene and substituted benzene;said substituted benzene includes toluene, ethylbenzene, xylene and cumene.
  • the aromatic hydrocarbon is benzene.
  • the alkylating agent is a mixture of ct least one C 10 to C )4 olefin and at least one Cio to Ci 4 paraffin.
  • the molar ratio of olefin to paraffi in the alkylating agent varies between 10:90 to 20:80, preferably 15:85.
  • the proportion of aromatic hydrocarbon and alkylating agent expressed in term of molar ratio varies between 1 :1 to 15:1, preferably between 2: 1 to 8: 1.
  • the compound of molecular formuia RS0 3 H is selected from the group consisting of methane sulfonic acid, p-toluene sulfonic acid and combinations thereof
  • the cationic precursor is at least one selected from the group consisting of tetra butyl ammonium halide, 1-buty 1-3 -methyl imidazolium bromide, trihexyl tetradecyl phosphonium halide, methyl sulfonic acid, p-teluene sulfonic acid and combinations thereof
  • the metal halide is selected from the group consisting of aluminum chloride and ferric chloride.
  • the organic halide is choline chloride.
  • the proportion of acid catalyst to hydrocarbon varies between 0.1 and 1.5
  • the alkylation is carried out at temperature varying between 50-70 °C
  • the process in accordance with the first a: >ect of the present disclosure further comprising the following steps: i. separation of the hydrocarbon layer from the catalyst; (ii) purification of the hydrocarbon layer obtained in method step (i) either by washing with water or aqueous alkali solution or centrifugation or decantation; (iii) re-circulation of the catalyst obtained in method step (i) m the process of alkylating aromatic hydrocarbon; and (iv) subjecting the hydrocarbon layer obtained in method step (ii) to a distillation process to separate the alkylated aromatic hydrocarbon.
  • FIGURE 1 of the accompanying drawings illustrates a process flow diagram of the process of alkylation of aromatic hydrocarbon, it accordance with the present disclosure.
  • a process for preparing alkylated aromatic hydrocarbons comprising the following steps: alkylating an aromatic hydrocarbon with an alkylating agent that comprises a mixture of at least one C 2 to C 50 olefin and at least one C 2 to C 50 paraffin, in the presence of at least one acid catalyst selected from the group consisting of (i) compounds having the molecular formula of RS0 3 H, wherein R is independently selected from the group consisting of alkyl, aryl, halogen, or alkyl halide; (ii) ionic liquid composition comprising (a) at least one cationic precursor selected from the group of compounds consisting of hydrogen donor compounds, tetrs alkyl ammonium halide, phosphonium halides, and imidazolium bromide; and (b) at 3 ⁇ 4ast one anionic precursor selected from the group consisting of metal halides and organic halides, at a temperature
  • the aromatic hydrocarbon as used in the process of the present disclosure is benzene.
  • their substituted derivatives may also be used in the process of the present disclosure.
  • the substituted benzene is at least one selected from the group consisting of toluene, xylene, ethylbenze e and cumene.
  • the preferred aromatic hydrocarbon is benzene.
  • the alkylating agent as used in the process of the present disclosure is a mixture of olefin and paraffin.
  • the olefin is C 2 to C 50 olefin, preferably C )0 to C 15 olefin.
  • the olefin is mixed with paraffin having the same number of carbon atoms. Paraffin having 2 to 50 carbon atoms, preferable 10-15 carbon atoms is mixed with the olefin of the present disclosure to obtain an alkylating agent.
  • the olefin as used in the process of the present disclosure is a straight or branched chain olefin and alpha-olefin or non-alpha-olefin.
  • the varied combinations of ol lns and paraffins as the alkylating agent are suitably employed in the process of the pres : t disclosure.
  • the alkylating agent is a mixture of a single olefin and a single paraffin. In another embodiment, the alkylating agent is a mixture of a single olefin and two or more paraffins. In still another embodiment, the alkylating agent is a mixture of two or more olefins and a single paraffin. In yet another embodiment, the alkylating agent is a mixture of two or more olefins and two or more paraffins.
  • an aromatic hydrocarbon feed is mixed with an alkylating agent feed to obtain a pre-mix feed.
  • the pre-mixed feed is then charged in a reactor/vessel and further mixed with a catalyst feed to obtain a resultant feed.
  • the reactor is then heated at a temperature varying between 35 °C to 90°C under ambient pressure condition, to initiate the aikylation of .aromatic hydrocarbon, and to obtain an alkylated product
  • the weight proportion of hydrocarbori and alkylating agent expressed in terms of molar ratio varies between 1 :1 and 15: 1, preferably between 2: land 8: 1 , in accordance with the process of the present disclosure.
  • the alkylation of aromatic hydrocarbon in accordance with the present disclosure is accomplished by using a strong acid catalyst.
  • the inventors of the present disclosure particularly employ a strong acid catalyst for the alkylation of aromatic hydrocarbon which is non-hazardous and capable of being further used in the reaction.
  • the catalyst is a strong acid catalyst selected from the group consisting of compounds having the molecular formula of ROS 3 H, wherein R is independently selected from the group consisting of alkyl, aryl or halogen or alkyl halides.
  • the preferred examples of the compound of m ;. lecular formula RSO 3 H include at least one selected from the group consisting of met! me sulfonic acid and p-toluene sulfonic acid.
  • the catalyst is an ionic liquid composition
  • ionic liquid composition comprising (a) at least one cationic precursor selected from the group of compounds consisting of hydrogen donor compounds, tetra alkyl ammonium halide, alkyl or aryl imidazolium bromide, and alkyl or aryl phosphonium halides; and (b) at least one anionic precursor selected from the group consisting of metal halides and organic halides.
  • the ionic liquid composition as used in the process of the present disclosure is a eutectic mixture that comprises the combination of a' - organic salt and a metal halide or an organic halide as cationic and anionic precujcprs, respectively.
  • the anionic and the cationic precursors are mixed in a stoichiometric weight proportions to obtain eutectic ionic liquid compositions of the present disclosure.
  • the hydrogen donor compound in combination with at least one metal halide/organic halide is used as the ionic liquid catalyst.
  • the hydrogen donor compound is selected from the group consisting of methyl sulfonic acid, p-toluene sulfonic acid.
  • the combination of at least one cationic precursor selected from the group of compounds consisting of tetra alkyl ammonium halide, imidazolium bromide?:, and phosphonium halides, and at least one anionic precursor selected from the group consisting of metal halides and organic halide is used as the ionic liquid catalyst.
  • cationic precursors other than the hydrogen donor compounds include at least one selected from the group consisting of tetra butyl ammonium chloride, trihexyl tetradecyl phoshonium bromide, 1- Benzyl-3-methyl imidazolium bromide and 1- Butyl-3-methyl imidazolium bromide.
  • the metal halide in accordance with the process of the present disclosure includes at least one selected from the group consisting of aluminum chloride or ferric chloride.
  • the preferred organic halide is choline chloride.
  • the ratio of catalyst feed to hydrocarbon feed ir « accordance with the present disclosure typically varies between 0.1 and 1.5.
  • the ionic liquid compositions in accordance with the process of the present disclosure are either procured readymade or prepared by employing methods known in the prior-art.
  • the catalyst with 99.5 % purity is used.
  • the feed containing the pure catalyst is mixed with recycled/regenerated catalyst.
  • the alkylation of benzene or substituted benzete js in accordance with the process of the present disclosure produces alkylated benzene/alf lated substituted benzenes.
  • a hydrocarbon layer containing an alkylated aromatic hydrocarbon (hereinafter refer as an alkylated product) is obtained.
  • the hydrocarbon layer also comprises the residual hydrocarbon and the alkylating agent.
  • the feed containing the hydrocarbon layer along with the catalyst layer is processed further to separate the alkylated products.
  • the process of the present disclosure further comprises the following steps: (i) separating the catalyst layer from the hydrocarbon layer; (ii) purification of the hydrocarbon layer to remove traces of acid catalyst residues; (iii) subjecting the purified hydrocarbon layer obtained in method step (ii) to a fractional distillation to separate alkylated product and residual aromatic hydrocarbon; (iv) recycling of the residual hydrocarbon in the alkylation process, and (v) optionally, the purification of recovered and rec3 ⁇ 4ling.
  • the alkylation of aromatic hydrocarbon in accordance with the process of the present disclosure is carried out in a reactor or in a n ixer.
  • a mixer such as static mixer, jet mixer, pump mixer or stirrer is used.
  • a single reactor/mixer or a series of two or more mixers/reactors are used in the process of the present disclosure.
  • the feed as obtained from the mixer/reactor after completion of the reaction, is introduced in a settler wherein the catalyst feed separates from the hydrocarbon layer.
  • the hydrocarbon layer containing the alkylated product and the residual hydrocarbon is then subjected to de-acidification to remove traces of acid catalyst residues.
  • the acidification is carried out either by water- ash or neutralization with an alkali or centrifugation or chilling.
  • the de-acidified hydr ocarbon layer is then distilled to remove the alkylated product.
  • FIG. 1 illustrates the process flow diagram representing the sequence of unit operations involved during the alkylation of aromatic hydrocarbon in accordance with the present disclosure.
  • the aromatic hydrocarbon feed (2) is mixed wi&the" alkylating agent feed (4) to obtain a pre-mix feed.
  • the proportions of aromatic hydrocarbon and alkylating agent expressed in terms of molar ratio varies between 1 :1 and 15: 1, preferably between 2:1 to 8: 1.
  • the pre- mixed feed is then fed to a mixer Ml where it is mixed with a catalyst stream (6).
  • the volume ratio of catalyst to aromatic hydrocarbon feed varies between 0.1 and 1.5.
  • the first mixer Ml is maintained at a temperature typically varying between 30 to 80 °C, under pressure varying from 1 to 5 atmospheres to initiate the alkylation process.
  • the feed from the first mixer Ml is then transferred to a second mixer M2, through an outlet provided in Ml . Further alkylation of the feed.is accomplished in the second mixture M2.
  • the temperature and pressure conditions in the second mixer M2 are the same as in Ml. Alternatively, the temperature and pressure conditions are different from Ml .
  • the feed discharged from Ml is introduced in a settler provided between Ml and M2.
  • the feed received from Ml separates into two distinct layers: (i) an upper hydrocarbon layer containing the alkylated aromatic hydrocarbon and the residual aromatic hydrocarbon, and (ii) lower catalyst layer.
  • the upper hydrocarbon layer is then transferred to M2 and mixed with the catalyst feed (6), whereas the lower catalyst layer is recycled to mixer M1/M3 directly or through a c italyst recovery- unit (CRU).
  • CRU c italyst recovery- unit
  • the feed is transferred to settler SI.
  • SI the feed separats into two distinct layers, similar to the separation as observed in the above described settler.
  • the heavier catalyst layer via stream 8 is recycled to mixer Ml directly or through catalyst recovery unit CRU whereas the upper hydrocarbon layer is fed to mixer M3 via line 10 which is further mixed with a catalyst feed via line 6.
  • further alkylation of the feed is accomplished in Mixer M3 so as to achieve higher percent conversion of aromatic hydrocarbon to* alkylated aromatic hydrocarbon.
  • the feed from M3 is fed into settler S2 where separation of the hydrocarbon layer and tfie catalyst layer is accomplished, similar to the separation as carried out in settler SI.
  • the processing units Ml, M2, M3, and SI ami S2 as employed in the process of the present disclosure can be arranged in multiple ce, ⁇ figurations.
  • the alkylation of aromatic hydrocarbons is carried out in a single mixer.
  • the feed from mixer Ml is directly fed to settler S2.
  • the alkylation of hydrocarbons is carried out in a series of two mixers, for example in a series of Ml and M2.
  • the feed from second n ixer i.e. M2 is fed into settler S2.
  • the feed separates into an upper hydrocav on layer and a lower catalyst layer.
  • the lower catalyst layer via line 8 is recycled to mi;;er Ml through CRU whereas the upper hydrocarbon layer is fed to hydrocarbon layer purifier (PR) via line 14.
  • PR hydrocarbon layer purifier
  • the hydrocarbon layer is washed either with watc- or with alkali solution via line 16 to remove traces of acid catalyst.
  • the hydrocarbon layer is directly centrifuged
  • the hydrocarbon purifier is either a stirred vessel or a centrifuge separator or a crystallizer.
  • the traces of acid catalyst are crystallized by a sudden decrease in the temperature of the hydrocarbon layer i.e. below ⁇ 5 °C.
  • the volume ratio of water/alkali solu ion to hydrocarbon layer varies between 0.2: 1.
  • the concentration of alkali solution ranges' between 2 to 50%.
  • the alkylation of aromatic hydrocarbons is carried out in a series of three mixers i.e Ml , M2 and M3.
  • the upper hydrocarbon layer from settler SI is fed to a mixer M3 and further mixed with the catalyst stream (6) to somplete the alkylation of the residual t
  • hydrocarbon layer and the catalyst layer simile? to the separation as observed in settler SI .
  • the hydrocarbon layer from settler S2 1 ⁇ 2 then introduced into a hydrocarbon purification unit and processed further, similar to the process as described in above embodiment of the present disclosure.
  • the hydrocarbon layer from PR is directly fe ⁇ to settler S3 where separation of the alkylated product and the residual aromatic hydrocarbon occurs.
  • the bottcn layer in settler S3 is an aqueous layer.
  • the bottom aqueous layer is sent for effluent treatment via line 18.
  • the bottom layer in S3 is the catalyst layer with traces of acid catalyst, which is further fed to CRU via line 18.
  • the upper hydrocarbon layer from S3 is fed to fractionating column Dl where the
  • the mixture was stirred wall for 1 hr at 35-40 °C. After 1 hr the mixture was allowed to settle for 20-30 mins. The layers were then separated. The lower water layer was discarded while the upper hydrocarbon layer was collected and kept aside.
  • the hydrocarbon layer as obtained in accordance with the process of this example was analyzed quantitatively and about 3590 gm (4600 ml) of hydrocarbon layer was prepared.
  • the hydrocarbon layer was further subjected to distillation.
  • the distillation column contained a 5 lit glass flask as a reboiler which was connected at its upper end with a hollow cylindrical tube of 400 mm height and 40 mm diameter.
  • the cylindrical tube further contained a perforated plate at the bottom to withstand the packing; the tube was packed with 6-8mm glass raschig rings.
  • a reflux divider was provided to maintain the desired reflux ratio.
  • a condenser was provided at the top of the column.
  • a thermowell was inserted inside the reboiler. Another thermowell was kept in the reflux divider to measure the vapour temperature.
  • a manometer was assembled to the distilallation column to measure the vacuum inside the column. In the distillation column, benzene was distilled at atmospheric conditions whereas paraffin and linear alkyl benzene was di:.tilled under vacuum.
  • This example describes a process for the alkylation of benzene by using an ionic liquid catalyst composition.

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

Abstract

La présente invention a pour objet un procédé de préparation d'hydrocarbures aromatiques alkylés consistant à mettre en contact un hydrocarbure aromatique avec un agent d'alkylation qui comprend un mélange d'au moins une oléfine contenant C2 à C50 et d'au moins une paraffine contenant C2 à C50, en présence d'au moins un catalyseur acide sélectionné dans le groupe constitué (i) de composés ayant la formule moléculaire RSO3H, dans laquelle R est indépendamment sélectionné dans le groupe comprenant alkyle, aryle, halogène ou halogénure d'alkyle; (ii) d'une composition liquide ionique comprenant (a) au moins un précurseur cationique sélectionné dans le groupe de composés comprenant des composés donneurs d'hydrogène, un halogénure d'ammonium tétra alkyle, des halogénures de phosphonium ou un bromure d'imidazolium; et (b) au moins un précurseur anionique sélectionné dans le groupe comprenant des halogénures métalliques et des halogénures organiques, à une température variant entre 35 °C et 90 °C sous pression atmosphérique afin d'obtenir une couche d'hydrocarbures contenant un hydrocarbure aromatique alkylé.
PCT/IN2012/000561 2011-08-23 2012-08-23 Procédé de production d'hydrocarbures aromatiques alkylés WO2013061336A2 (fr)

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Cited By (7)

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WO2015118471A1 (fr) * 2014-02-07 2015-08-13 Saudi Basic Industries Corporation Élimination des impuretés aromatiques contenues dans un flux d'alcène à l'aide d'un catalyseur acide, tel qu'un liquide acide ionique
WO2015118470A1 (fr) * 2014-02-07 2015-08-13 Saudi Basic Industries Corporation Élimination d'impuretés aromatiques d'un écoulement d'alcène utilisant un catalyseur acide, tel qu'un acide de lewis
WO2017015255A1 (fr) * 2015-07-23 2017-01-26 Uop Llc Zone modifiée de réaction d'alkylation à hf pour l'alkylation de liquide ionique
WO2017080994A1 (fr) 2015-11-10 2017-05-18 Basf Se Procédé de retraitement d'acide alcanesulfonique
US10144685B2 (en) 2014-02-07 2018-12-04 Saudi Basic Industries Corporation Removal of aromatic impurities from an alkene stream using an acid catalyst
WO2022046543A1 (fr) * 2020-08-24 2022-03-03 University Of Kansas Acides alcane multi-sulfoniques, leurs compositions et procédés associés
CN114315505A (zh) * 2022-01-11 2022-04-12 中国石油大学(华东) 一种烷基苯的生产方法

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EP3684757B1 (fr) * 2017-09-22 2023-10-04 Indorama Ventures Oxides LLC Procédé de production d'alkylaromatiques

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WO1998003454A1 (fr) * 1996-07-22 1998-01-29 Akzo Nobel N.V. Formation d'alkylbenzene lineaire au moyen d'un liquide ionique basse temperature et d'un agent d'alkylation a chaine longue
WO1998050153A1 (fr) * 1997-05-01 1998-11-12 Akzo Nobel N.V. Formation in-situ de catalyseur liquide ionique pour une reaction chimique catalysee liquide ionique
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