WO1994012452A1 - Procede de production d'olefines ramifiees - Google Patents

Procede de production d'olefines ramifiees Download PDF

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Publication number
WO1994012452A1
WO1994012452A1 PCT/GB1993/002407 GB9302407W WO9412452A1 WO 1994012452 A1 WO1994012452 A1 WO 1994012452A1 GB 9302407 W GB9302407 W GB 9302407W WO 9412452 A1 WO9412452 A1 WO 9412452A1
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WO
WIPO (PCT)
Prior art keywords
process according
olefin
zeo
feedstock
ethene
Prior art date
Application number
PCT/GB1993/002407
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English (en)
Inventor
Steven Ronald Wade
Original Assignee
The British Petroleum Company Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The British Petroleum Company Plc filed Critical The British Petroleum Company Plc
Priority to AU55684/94A priority Critical patent/AU5568494A/en
Publication of WO1994012452A1 publication Critical patent/WO1994012452A1/fr

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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
    • C07C2/02—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
    • C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65

Definitions

  • the present invention relates to a process for the production of a product rich in branched olefins by contacting an ethene feed with a minor proportion of higher olefins with a zeo- type catalyst.
  • Attempts to oligomerise ethene to provide low molecular weight hydrocarbon products have hitherto been relatively unsuccessful.
  • products rich in aromatic hydrocarbons are obtained or polyolefins such as polyethylene often result.
  • Processes for the conversion of a C2/C3 mixed feed are known.
  • JP 0341036 relates to the conversion of an ethene/propene feed to yield C5 olefins under relatively high pressure using an alkali metal based catalyst.
  • the product is mainly 1-pentene.
  • US 3 960 978 discloses the conversion of a C2 to C5 olefin feed over zeolite H-ZSM-5 to a range of liquid hydrocarbons.
  • US 4 227 992 also discloses the conversion of a C2 to Cg olefinic feed over pentasil zeolite catalysts to produce liquid products. Under chosen conditions, propene and butene conversions are 50-95%, but ethylene conversion is 10-20%.
  • the present invention provides a process for the production of a product containing at least one C4 and C5 branched
  • 1 olefin which comprises passing a feedstock containing ethene over a zeo-type catalyst in a reaction chamber characterised in that the feedstock also comprises at least one C3-C10 olefin, and being present in the feed at a concentration of up to 50% v/v relative to ethene and the zeo-type catalyst having a framework structure which includes a 10-member channel that is not intersected by another 10- or 12- member channel.
  • the process of the present invention provides a product containing low molecular weight branched olefins with low selectivity to undesirable aromatic hydrocarbons.
  • the process of the present invention comprises passing an ethene feed containing at least one C3 to C ⁇ Q olefin over a zeo- type catalyst under conditions capable of producing a product containing branched olefins.
  • the olefinic feedstock comprises ethene and the C3 to C ⁇ olefin wherein the C3 to C ⁇ Q olefin is present at a concentration of up to 50% v/v, for example, from 1 to 50% v/v.
  • the C3 to C ⁇ Q olefin is present from 1 to 40% v/v, especially from 10 to 35% v/v.
  • the C3 to C ⁇ Q olefin may suitably be a linear olefin or a branched olefin.
  • the olefinic feedstock comprises ethene and at least one C3 to C5 olefin.
  • the C3 to C5 olefin is present in a concentration of up to 50% v/v.
  • the C3 to C5 olefin accounts for the total C3 to C ⁇ Q olefin feed.
  • the preferred feed is a mixture of ethene and propene.
  • the olefin mixed feed of the process of the present invention may be derived from any suitable source.
  • the feedstock need not be a high purity feed.
  • olefins and streams containing alkanes, inert gas, hydrogen and carbon oxides may be used.
  • Suitable sources of the olefins include those generated by refinery processes, e.g. fuel gas streams rich in ethene as typically described in "Oil and Gas Journal", page 94, April 20 1992.
  • Mixed propene/propane and butene/butane streams produced as by-products of catalytic cracking are also particularly suitable for use as the C3 to C ⁇ Q olefinic cofeed.
  • Light olefins including ethene are also produced in large quantities by steam cracking of naphtha and higher hydrocarbons. Mixtures of olefins produced by the primary cracking process, impure streams generated as part of the separations process and mixtures of pure ethene and C3 to C ⁇ Q olefin products are all suitable feeds.
  • An ethene/C3 to C ⁇ Q mixture may also be obtained through the conversion of oxygenates for examples alcohols, esters, ketones and aldehydes and higher hydrocarbon feeds.
  • oxygenates for examples alcohols, esters, ketones and aldehydes and higher hydrocarbon feeds.
  • conversion of methanol to predominantly ethylene and propylene can be achieved with a zeolite SAPO catalyst as described in US
  • an ethene/C 3 to C 10 feed may also be derived via partial oxidation of suitable hydrocarbon feeds as disclosed in EP-A-033228 .
  • the zeo-type catalyst suitable for use in the process of the present invention is one whose framework structure includes channels defined by 10-membered rings which are not intersected by channels having 10- or 12-membered rings.
  • Zeo-type catalysts which may be used in the process include TON (Theta-1, Nu-10, ZSM- 22, KZ-2, ISI-1), MTT (ZSM-23, EU-13, ISI-4, KZ-1), EUO (EU-1 TP2- 3, ZSM-50), AEL (SAPO-11) and FER (Ferrierite, FU-9. Nu-23, ISI- 6, ZSM-35).
  • zeo-type catalysts with three dimensional channel structures such as MFI- and MEL- types which contain intersecting 10-ring channels and which tend to produce aromatics and saturated by-products.
  • the preferred zeo-type structures in the process of the present invention are TON and FER.
  • a synthetic zeolite immediately after synthesis contains cations which, depending upon the precise synthesis method used, may be hydrogen, aluminium, alkali metals, organic nitrogen cations or any combination thereof.
  • the zeo-type catalyst used in the process of the present invention is preferably in the hydrogen form.
  • the hydrogen form may be achieved by, in the case of organic containing zeo-type catalysts, calcination to remove the organics followed by either ammonium ion exchange or proton exchange with an acid solution or a combination of both.
  • the hydrogen form could be prepared by either direct ammonium ion-exchange followed by calcination or proton exchange with an acid solution or a combination of both. If so desired, the hydrogen form of the zeo- type catalyst may suitably be partially exchanged or impregnated with a metal such as gallium or magnesium and used in the process of the present invention.
  • the zeo-type catalyst may be modified to alter its acidity or shape selectivity in such a way to improve the catalytic performance.
  • the modifications may include a calcination regime, steam treatment, acid/stream treatment, chemical treatment, e.g. with a dealu inating agent such as SiCl , mineral acids, ammonium fluoride or bifluoride, EDTA etc or an aluminating agent such as sodium aluminate, aluminium chloride or inclusion of a phosphorus compound, a Lewis base, hydrogen fluoride etc.
  • the treatment step may be carried out during the preparation of the hydrogen-form or may be carried out after the preparation of the hydrogen form.
  • the zeo-type catalyst may be bound in a suitable binding material.
  • the binder may be one of the conventional binders such as alumina, silica, clay or may be an aluminophosphate binder or a combination of binders.
  • the process of the present invention may be suitably carried out at a temperature of from 200 to 700°C, preferably 300 to 600°C.
  • the process may be carried out under reduced or elevated pressure relative to atmospheric pressure.
  • a pressure of from 0. 1 to 100 bar absolute preferably 0. 5 to 50 bar absolute may be used .
  • the ethene and C3-C10 olefin streams may be passed into the reaction chamber separately and mixed therein. Alternately, the two streams may be pre-mixed prior to passage into the reactor.
  • the gaseous streams may be pre-heated prior to contact with the catalyst.
  • the pre-heat temperature is 50-
  • the feed may be fed into the reaction chamber at a rate of suitably from 10 to 10,000, preferably from 500 to 8000 gas hourly space velocity. It will of course be understood that the GHSV will vary for different feed compositions.
  • Time x volume of catalyst bed The process may be carried out in any suitable reactor, for example a fixed bed, a fluidised bed, a slurry reactor or a continuous catalyst regeneration reactor.
  • the process of the present invention provides a good conversion of ethene. Conversion can exceed 40% of ethene, preferably at least 50%.
  • the products of the process of the present invention suitably contain branched olefinic hydrocarbons, especially iso- butene and iso-pentenes.
  • branched olefinic hydrocarbons especially iso- butene and iso-pentenes.
  • selectivity to these branched olefins is greater than 30%, especially greater than 40%.
  • Additional products may include gaseous linear butenes and pentenes and a liquid product consisting essentially of Cg and Cy olefins with a lesser amount of Cg to C ⁇ Q olefins and traces of C ⁇ to C ⁇ 2 olefins.
  • a small amount of by-products such as C ⁇ to
  • unreacted feed olefins may be separated from the product stream and recycled back into the reaction chamber.
  • Liquid olefins such as Cg to C ⁇ Q olefins may also be separated from the product stream and recycled to the reaction chamber either in addition to or substantially as the sole source of the C3 to C ⁇ olefin feed.
  • the feed stream contains substantial amounts of light alkanes, e.g. C ⁇ to C3 alkanes or other diluents such as may be found in a catalytic cracker fuel gas stream, it is preferable not to recover unreacted ethylene.
  • light alkanes e.g. C ⁇ to C3 alkanes or other diluents such as may be found in a catalytic cracker fuel gas stream
  • a portion of the liquid products may be suitably removed by use of a continual bleed stream to avoid the build up of unreactive aromatic and paraffinic hydrocarbons.
  • the desired products namely the isobutenes and the isopentenes, may be isolated from the linear isomers through distillation or selective absorption.
  • Recovery of the branched isomers may also be effected through the further conversion to other desirable products, either as individual C4 and C5 streams or as a mixed C4 and C5 stream.
  • a typical process is the etherification of the branched C4 and C5 isomers within the normal/iso olefin mixture with an alcohol to yield valuable branched ethers.
  • Suitable alcohols include alkanols having 1 to 8 carbon atoms, for example, methanol, ethanol, 1-propanol, iso-propanol, 1-butanol and 2-butanol.
  • the branched olefin and the alcohol are reacted in equimolar quantities or either reactant may be in molar excess.
  • equimolar quantities of the alcohol and branched olefin are reacted.
  • the reaction with methanol to yield methyl tertiarybutyl ether (MTBE) and tertiaryamyl methyl ether (TAME) is particularly preferred.
  • a further conversion process suitable for the recovery of the branched olefins is the polymerisation to polyisobutene (PIB) , copolymerisation of isobutene and isopentene, and/or polyisopentene (PIP) .
  • This polymerisation reaction may suitable be carried out in the liquid phase at sub-ambient temperatures.
  • Suitable catalysts for the polymerisation reaction include alkylaluminium halides promoted by alkyl halides or boron trifluoride.
  • a still further conversion process is suitably the acid catalysed hydration to yield isobutanol and/or isopentanol.
  • the residual linear olefins may suitably be recycled to the reaction chamber either in addition to or as substantially the sole source of the C3 to C ⁇ Q olefinic co-feed.
  • the linear isomers may be structurally isomerised to yield a mixture of branched and linear isomers before being passed to the separation unit. Details of this process are disclosed in European Patent No. 0247802.
  • a portion of the linear C4 and C5 isomers may be removed by a continuous bleed stream to avoid build up of unreactive butanes and pentanes.
  • Theta-1 was synthesised using ammonia as the templating agent.
  • Sodium aluminate (30 g, ex BDH, 40 wt% AI2O3, 30 wt% a2 ⁇ and 30 wt% H2O) and sodium hydroxide (15.6 g ex BDH) were dissolved in distilled water (240 g) .
  • Ammonia solution (1400 g, SG 0.90° containing 25% NH3) was added with gentle mixing.
  • Silica gel sold, under the trademark Ludox AS40 (1200 g) which contained 40 wt% silica was added over fifteen minutes with stirring to maintain a homogeneous hydrogel.
  • the molar composition of the hydrogel was:
  • Theta-1 as synthesised which contained both Na + and H + ions was directly ion exchanged in order to remove the Na + ions.
  • the zeolite was mixed for one hour with an aqueous ammonium nitrate solution (IM, zeolite to solution weight ratio of 1:20).
  • IM aqueous ammonium nitrate solution
  • the zeolite was filtered, washed and the ion exchange treatment repeated twice.
  • the ammonium form of the zeolite was then dried at 100°C and calcined overnight in air at 550°C to convert it to the hydrogen form.
  • the X-ray diffraction pattern of the H-form is shown in Table 1.
  • Example 2 Catalyst Steaming and Acid Treatment of H-Theta-1
  • the H-form of the zeolite as prepared in Example 1 was pressed under 10 tonnes pressure into tablets which were broken into granules and these in turn were sieved to pass 600 micron, but not 250 micron sieves.
  • the granules were placed in a tubular reactor (60 mm ID) and heated to 550°C. There was a large pre ⁇ heating zone in which water was converted to steam before it came into contact with the catalyst granules. Distilled water and nitrogen were passed through the preheating zone over the catalyst at a range of 30 grams/hour and 60 ml/minute respectively.
  • Gallosilicate TON was prepared as detailed in example 1 of EP-A-0106478. It was converted to the hydrogen form (H-GaTON) as follows .
  • the as synthesised material was calcined at 550°C for 6 hours to remove the template. Residual sodium ions were exchanged for NH -_- by stirring with aqueous ammonium nitrate solution for a minimum of two hours (IM, gallosilicate to solution weight ratio 1:20).
  • IM gallosilicate to solution weight ratio 1:20
  • the gallosilicate was filtered, washed with distilled water, and the ion exchange treatment repeated twice.
  • the ammonium form of the gallosilicate was then dried at 100°C and calcined at 550°C in air for 6 hours to convert it to the hydrogen form.
  • Example 4 Preparation of H-ZSM-23
  • ZSM-23 was synthesised using diisopropanolamine as the templating agent according to GB patent application No. 2190910. This material was converted to the hydrogen form (H-ZSM-23) as follows. The as synthesised material was calcined at 550°C for 6 hours to remove the template. Residual sodium ions were exchanged
  • Ferrierite was synthesised using a 1-methylpiperidine template as follows. Sodium aluminate (40 wt% AI2O3 24.3 wt% Na20, 28.3% H20 and 7.4% NaOH) 3.83g was dissolved in water
  • Zeolite EU-1 was synthesised using a dual tetramethylammonium/hexamethonium bromide
  • Potassium and sodium ions were exchanged for NH4+ by stirring at room temperature with aqueous ammonium nitrate solution for a minimum of two hours (IM, zeolite to solution weight ratio 1:10).
  • IM zeolite to solution weight ratio 1:10
  • the zeolite was filtered, washed with distilled water, and the ion exchange treatment repeated twice.
  • the ammonium form of the zeolite was then dried at 100°C and calcined at 550°C in air for 6 hours to convert it to the hydrogen form.
  • SAPO-ll was prepared using a diisopropylamine templating agent. Aluminium isopropoxide (41 g) was added to 40 ml of water with overhead stirring. After 20 minutes, a solution of 85% phosphoric acid (22.25 g) in water (5 ml) was added to give a thick gel. To this was added diisopropylamine (20.3 g) , nickel nitrate nonahydrate (0.22 g) , LUDOX (40% Si0 2 , 4.5 g) and water (52.6 g) . The resultant thick gel was placed in a sonic bath for three minutes , and then triturated in a pestle and mortar to give a smooth gel.
  • Example 8 The H-form of Theta-1, prepared as described in Examples 1 and 2, was pressed into tablets at 10 tonnes pressure. The tablets were then broken and sieved into granules to pass 600 micron, but not 250 micron sieves. A charge of 10 ml of catalyst granules was loaded into a tubular reactor with a coaxial thermocouple well. The reactor was heated to 420°C and
  • Aromatics Benzene, C ⁇ to C benzenes
  • Example 8 The general process of Example 8 was repeated for a mixed feed of 2:1 (66.6/33.3%) ethene to propene using the various catalysts prepared according to Examples 3 to 7.
  • the mixed feed was fed into the reactor under a gas hourly space velocty of
  • Example 8 The procedure of Example 8 was repeated but passing a feedstock of ethene over H-Theta-1. The results are shown in
  • Example 8 The procedure of Example 8 was repeated but passing a feedstock of propene over H-Theta-1. The results are given in
  • Example 9 The process of Example 9 was repeated using H-ZSM-5 as the catalyst.
  • the ammonium form of ZSM-5 was purchased from PQ Corporation (VALFOR CBV 3002) and converted to the hydrogen form by calcination in air at 550°C for 16 hours prior to testing.
  • the results are given in Table 4. It can be seen that whilst high conversion of ethene is possible, low selectivities to iso-butenes and iso-pentenes are achieved.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé de production d'un produit contenant au moins une oléfine ramifiée C4 et C5, consistant à faire passer une charge d'alimentation contenant de l'éthène sur un catalyseur de type zéolite dans une chambre de réaction. La charge d'alimentaion comprend également au moins une oléfine C3-C10, qui est présente en une concentration ne dépassant pas 50 % v/v par rapport à l'éthène, et le catalyseur de type zéolite présente une structure qui comprend une voie à noyau de 10 éléments qui n'est pas entrecoupée par une autre voie à noyau de 10 ou 12 éléments.
PCT/GB1993/002407 1992-12-02 1993-11-23 Procede de production d'olefines ramifiees WO1994012452A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU55684/94A AU5568494A (en) 1992-12-02 1993-11-23 Process for the production of branched olefins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929225183A GB9225183D0 (en) 1992-12-02 1992-12-02 Process for the production of branched olefins
GB9225183.4 1992-12-02

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WO1994012452A1 true WO1994012452A1 (fr) 1994-06-09

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003035583A1 (fr) * 2001-10-24 2003-05-01 Exxonmobil Chemical Patents Inc. Oligomerisation d'olefine
WO2003035584A1 (fr) * 2001-10-24 2003-05-01 Exxonmobil Chemical Patents Inc. Procede d'oligomerisation d'olefines
FR2837199A1 (fr) * 2002-03-15 2003-09-19 Inst Francais Du Petrole Procede de conversion en plusieurs etapes d'une charge comprenant des olefines a quatre, cinq atomes de carbone ou plus, en vue de produire du propylene
EP2072484A1 (fr) 2004-06-01 2009-06-24 ExxonMobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
US7786337B2 (en) 2004-06-01 2010-08-31 Exxonmobil Chemical Patents Inc. Olefin oligomerization process
WO2012033562A1 (fr) 2010-09-07 2012-03-15 Exxonmobil Chemical Patents Inc. Extrudats comprenant des catalyseurs zéolites et leur utilisation dans des procédés d'oligomérisation
WO2013013884A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'élimination de nitriles présents dans des charges hydrocarbonées
WO2013013888A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
WO2013013887A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
WO2013013886A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfine
WO2013013885A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Système intégré d'adsorption et de désorption de substances toxiques de nitriles
WO2016150529A1 (fr) 2015-03-20 2016-09-29 Exxonmobil Chemical Patents Inc. Procédé pour convertir une charge hydrocarbonée oléfinique en un produit d'oligomérisation ou un produit d'oligomérisation hydrogéné
US10138175B2 (en) 2010-07-22 2018-11-27 Exxonmobil Chemical Patents Inc. Particles including zeolite catalysts and their use in oligomerization processes

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US5284989A (en) * 1992-11-04 1994-02-08 Mobil Oil Corporation Olefin oligomerization with surface modified zeolite catalyst

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EP0034444A2 (fr) * 1980-02-14 1981-08-26 Mobil Oil Corporation Augmentation de l'activité catalytique d'une zéolite
EP0269503A2 (fr) * 1986-11-21 1988-06-01 Institut Français du Pétrole Nouvelles ferriérites, leur procédé de préparation et leur utilisation
EP0311310A1 (fr) * 1987-10-07 1989-04-12 Mobil Oil Corporation Oligomérisation d'oléfines

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US4227992A (en) * 1979-05-24 1980-10-14 Mobil Oil Corporation Process for separating ethylene from light olefin mixtures while producing both gasoline and fuel oil
EP0034444A2 (fr) * 1980-02-14 1981-08-26 Mobil Oil Corporation Augmentation de l'activité catalytique d'une zéolite
EP0269503A2 (fr) * 1986-11-21 1988-06-01 Institut Français du Pétrole Nouvelles ferriérites, leur procédé de préparation et leur utilisation
EP0311310A1 (fr) * 1987-10-07 1989-04-12 Mobil Oil Corporation Oligomérisation d'oléfines

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003035583A1 (fr) * 2001-10-24 2003-05-01 Exxonmobil Chemical Patents Inc. Oligomerisation d'olefine
WO2003035584A1 (fr) * 2001-10-24 2003-05-01 Exxonmobil Chemical Patents Inc. Procede d'oligomerisation d'olefines
US7186874B2 (en) 2001-10-24 2007-03-06 Exxonmobil Chemical Patents Inc. Process for the oligomerization of olefins
CN1319913C (zh) * 2001-10-24 2007-06-06 埃克森美孚化学专利公司 烯烃低聚的方法
US7247763B2 (en) 2001-10-24 2007-07-24 Exxonmobil Chemical Patents Inc. Olefin oligomerization
US7420096B2 (en) 2001-10-24 2008-09-02 Exxonmobil Chemical Patents Inc. Olefin oligomerization
CN100425581C (zh) * 2001-10-24 2008-10-15 埃克森美孚化学专利公司 烯烃低聚
US7541507B2 (en) 2001-10-24 2009-06-02 Exxonmobil Chemical Patents Inc. Oligomerization and catalysts therefor
EP2311787A1 (fr) * 2001-10-24 2011-04-20 ExxonMobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
FR2837199A1 (fr) * 2002-03-15 2003-09-19 Inst Francais Du Petrole Procede de conversion en plusieurs etapes d'une charge comprenant des olefines a quatre, cinq atomes de carbone ou plus, en vue de produire du propylene
WO2003078364A1 (fr) * 2002-03-15 2003-09-25 Institut Francais Du Petrole Procede de conversion en plusieurs etapes d'une charge comprenant des olefines a quatre, cinq atomes de carbone ou plus, en vue de produire du propylene
US7262332B2 (en) 2002-03-15 2007-08-28 Institut Francais Du Petrole Process for multistage conversion of a charge comprising olefins with four, five or more carbon atoms, with the aim of producing propylene
US7786337B2 (en) 2004-06-01 2010-08-31 Exxonmobil Chemical Patents Inc. Olefin oligomerization process
US7834229B2 (en) 2004-06-01 2010-11-16 Exxonmobil Chemical Patents Inc. Olefin oligomerization process
EP2072484A1 (fr) 2004-06-01 2009-06-24 ExxonMobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
US8716542B2 (en) 2004-06-01 2014-05-06 Exxonmobil Chemical Patents Inc. Olefin oligomerization process
US10138175B2 (en) 2010-07-22 2018-11-27 Exxonmobil Chemical Patents Inc. Particles including zeolite catalysts and their use in oligomerization processes
WO2012033562A1 (fr) 2010-09-07 2012-03-15 Exxonmobil Chemical Patents Inc. Extrudats comprenant des catalyseurs zéolites et leur utilisation dans des procédés d'oligomérisation
WO2013013884A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'élimination de nitriles présents dans des charges hydrocarbonées
WO2013013888A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
WO2013013887A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfines
WO2013013886A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Procédé d'oligomérisation d'oléfine
WO2013013885A2 (fr) 2011-07-25 2013-01-31 Exxonmobil Chemical Patents Inc. Système intégré d'adsorption et de désorption de substances toxiques de nitriles
WO2016150529A1 (fr) 2015-03-20 2016-09-29 Exxonmobil Chemical Patents Inc. Procédé pour convertir une charge hydrocarbonée oléfinique en un produit d'oligomérisation ou un produit d'oligomérisation hydrogéné

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