WO2000034211A1 - Procede d'oligomerisation - Google Patents

Procede d'oligomerisation Download PDF

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Publication number
WO2000034211A1
WO2000034211A1 PCT/GB1999/004010 GB9904010W WO0034211A1 WO 2000034211 A1 WO2000034211 A1 WO 2000034211A1 GB 9904010 W GB9904010 W GB 9904010W WO 0034211 A1 WO0034211 A1 WO 0034211A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
chromium
process according
polyolefin product
alpha
Prior art date
Application number
PCT/GB1999/004010
Other languages
English (en)
Inventor
Michael David Jones
Seifgried Grimm
Wilhelm Keim
Peter Wasserscheid
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
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to AU13992/00A priority Critical patent/AU1399200A/en
Publication of WO2000034211A1 publication Critical patent/WO2000034211A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
    • 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
    • C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
    • 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
    • C07C2527/132—Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • 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
    • C07C2531/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of chromium, molybdenum or tungsten

Definitions

  • This invention relates to a process for oligomerising olefins and, in particular, to a process for the trimerisation of olefins using catalyst compositions comprising a source of chromium.
  • EP-A-0780353 describes a process for oligomerising olefins using a catalyst system comprising a chromium source, a pyrrole-containing compound and a metal alkyl.
  • the catalyst system is supported on an inorganic oxide.
  • Suitable trimerisation olefins are disclosed as C2-C30 olefins e.g ethylene, propylene, the butenes, 1-pentene, 4-methyl-l- pentene, 1-hexene, 1-heptene, the four normal octenes, the four normal nonenes, vinylcyclohexane and mixtures thereof. More specifically, this reference discloses the trimerisation of ethylene to 1-hexene, 1,3 -butadiene to 1,5-cyclooctadiene, or the co- trimerisation of ethylene and hexene to form 1-decene or 1-tetradecene.
  • US 5137994 describes a method of producing a copolymer of ethylene and 1- hexene in which ethylene is simultaneously trimerised to 1-hexene which is copolymerised with further aliquots of ethylene in the presence of a bis-triarylsilyl chromate compound.
  • US 5087789 describes the oligomerisation of propylene and/or ethylene in the presence of a chromium catalyst on an aluminophosphate support and a selectivity modifier.
  • the present invention provides a process for the oligomerisation of C8-C36 alpha-olefins to give a polyolefin product comprising trimer which process comprises contacting the C8-C36 alpha-olefin with a catalyst in a solvent at a temperature below 20°C wherein the catalyst comprises a complex of a chromium compound and a 1,3,5-triazacyclohexane and the polyolefin product comprises at least 70 mole% of trimer.
  • trimer is meant a polyolefin product formed by the reaction of three alpha- olefin molecules.
  • 1-octene, 1-decene, 1-dodecene can trimerise to give olefin products containing 24, 30 and 36 carbon atoms respectively.
  • the alpha-olefin that may be trimerised according to the process of the present invention preferably has 10 or more carbon atoms and more preferably has from 10-30 carbon atoms.
  • the alpha-olefin may be a straight or branched chain olefin.
  • suitable alpha-olefins include octene-1, decene-1, dodecene-1, hexadecene- 1, octadecene-1 and eicosene.
  • the process of the present invention selectively converts an alpha-olefin to trimers.
  • the selective conversion of alpha-olefin to trimer is preferably at least 80 mol% e.g 80-99 mol%, preferably at least 90 mol%, more preferably at least 95 mol%, especially at least 98 mol%.
  • the yields of dimers, tetramers or other oligomers are reduced compared with known oligomerisation processes.
  • the trimerisation catalyst used in the process of the present invention is a complex of a chromium compound and a 1,3,5-triazacyclohexane (hereinafter referred to as a chromium/triazacyclohexane catalyst). Preparation of such a complex is illustrated in the reaction scheme yiven below:- R
  • the 1,3,5-triazacyclohexane may be prepared by known processes in the art e.g by reacting a primary amine with formaldehyde.
  • the R group of the primary amine is suitably a hydrocarbyl group, such as an alkyl, cycloalkyl, aryl, alkaryl or aralkyl group
  • the hydrocarbyl group may have from 6 to 12 carbon atoms
  • the hydrocarbyl group is selected from a dimethyl hexyl, n-octyl, methyl benzyl, dimethyl undecanyl and n-dodecanyl group
  • the R group in the 1,3,5- triazacyclohexane compound will correspond to the R group in the reactant amine
  • n-octyl amine is used as the amine reactant i e where R is n-octyl
  • the 1,3,5-t ⁇ azacyclohexane compound produced will be tri-n-n
  • chromium complex of R 3 TAC R 3 TAC is reacted with a chromium compound in the presence of a solvent
  • Suitable chromium compounds include those chromium compounds having labile ligands e g chromium halides such as chromium chlorides having labile ligands Suitable labile ligands are those capable of being replaced by R3TAC e g tetrahydrofuran (THF)
  • a suitable chromium compound is e g a complex of tetrahydrofuran with chromium trichloride ((THF) 3 CrCl 3 )
  • the solvent used for carrying out the reaction of R 3 TAC with the chromium compound is suitably a saturated hydrocarbon e.g.
  • reaction may be carried out by refluxing a solution containing the chromium compound and the R 3 TAC.
  • the resultant (R 3 TAC)chromium complex can be recovered by removing the solvent under vacuum and purifying the product by column chromatography.
  • reaction scheme THF
  • 3 CrCl 3 is refluxed with R.TAC in e.g. equimolar amounts.
  • the final chromium complex obtained and usable as a catalyst in the trimerisation process of the present invention is (R 3 TAC)CrCl 3 .
  • the alpha-olefin is contacted with a (R 3 TAC)chromium complex in the presence of a solvent.
  • the catalyst may be activated by a modifier such as an alkyl alumoxane.
  • the alumoxane is methyl alumoxane (MAO).
  • the solvent is suitably a saturated hydrocarbon or an aromatic solvent which does not actively participate in the reaction. Examples of solvents that may be used include n-hexane, n-heptane, cyclohexane, benzene, toluene and the xylenes.
  • the contacting of the alpha-olefin and the chromium/triazacyclohexane catalyst is suitably carried out in an atmosphere inert under the process conditions such as eg nitrogen, argon and the like.
  • the oligomerisation process is carried out at relatively low temperatures of less than 20°C, suitably in the range from about -30°C to +20°C, preferably in the range from about -25 to +5°C, eg 0°C. At temperatures of the order of about 0°C, the trimerisation reaction goes through to completion with minimum deactivation of the chromium/triazacyclohexane catalyst.
  • the process of the present invention may be carried out by initially mixing a solution of the alpha-olefin and the chromium/triazacyclohexane catalyst, cooling this solution down and then gradually adding a solution of the catalyst modifier to this mixture whilst allowing the reaction mixture to warm up. During the warming up of the reaction mixture, it may change colour.
  • the reaction mixture so formed is then neutralised by the addition of a strong acid, eg hydrochloric acid thereto. This results in a biphasic mixture comprising an aqueous and an organic phase.
  • the biphasic mixture is separated eg using a centrifuge to recover the organic phase.
  • the organic phase is dried and the ol % of trimers in the polyolefin product is determined e.g. by gas chromatography.
  • the polyolefin product may then be catalytically hydrogenated to form lubricating oils.
  • the hydrogenation may be carried out in solution.
  • the catalyst may be any suitable hydrogenation catalyst, but is preferably, a palladium catalyst supported on activated carbon or a Raney nickel catalyst.
  • the hydrogenation is suitably carried out at elevated pressure, eg from about 2000-10000 KPa, preferably from about 4500-8000 KPa.
  • the hydrogenation reaction is suitably carried out at a temperature in the range from 15- 200°C, preferably from about 30-70°C.
  • the duration of the hydrogenation reaction may be a few minutes to several days.
  • the reaction mixture is cooled down, depressurised and the solvent used removed by vacuum distillation.
  • the purity of the hydrogenated product can be determined by gas chromatography and the viscosity of the resulting lubricant measured by rotary viscosimetry.
  • hydrocarbyl group, R in a catalyst complex such as (R 3 TAC)CrCl 3 does not seem to affect or influence the selectivity to the desired trimers but it does have some effect on the distribution of isomers in the trimeric product. This enables the viscosity of the lubricating oil to be controlled.
  • Chromium compounds L 3 CrCl 3 (where L 3 represents a tridentate ligand) are prepared by refluxing a solution of 0.1 mmol of a ligand L 3 and 0.1 mmol (THF) 3 CrCl3 (where THF represents a tetrahydrofuranyl group) in toluene (10 ml) for 1 hour. The solvent is thereafter removed under vacuum and the resultant chromium complex of THF is purified using column chromatography.
  • the resulting biphasic mixture comprising an aqueous and an organic phase was separated using a centrifuge.
  • the organic phase was recovered, dried and the conversion was determined using Gas Chromatography.
  • Trimers of 1-decene and 1-dodecene prepared by the process of the present invention using different chromium triazacyclohexane catalysts were hydrogenated to lubricating oils. Any solvents and internal standards used were removed from the trimer product by vacuum distillation. The residual organic phase was diluted with the same amount of cyclohexane and a hydrogenation catalyst (Pd on activated carbon, 5 % Pd, ex Fluka, 0.01 g for 1 g of the trimerised product) was suspended in the solution of the organic phase in an autoclave. The autoclave was pressurised with hydrogen (7000 KPa (70 bar)) and heated up to 50°C for 18 hours.
  • a hydrogenation catalyst Pd on activated carbon, 5 % Pd, ex Fluka, 0.01 g for 1 g of the trimerised product
  • the reaction mixture was then cooled down to room temperature, the autoclave was depressurised, and the solvent was removed by vacuum distillation.
  • the purity of the products was determined by Gas Chromatography and the viscosity thereof by rotary viscosimetry (ISO 3104: 1994).
  • the viscosity, viscosity index (VI) and pour points of the lubricating oils are given in Table 2 below.
  • Table 2 shows the viscosity, viscosity index (VI) and pour point measurements of polyalpha- olefin (PAO) lubricating oils.
  • PAO's are prepared by hydrogenation of the olefinic product resulting from the conventional oligomerisation of alpha-olefins using a BF3- alcohol catalyst.
  • PAO(Feluy) is a commercially available polyalpholefin from Feluy under the tradename Durasyn 164. From Table 2 it can be seen that the lubricating oils of the present invention have higher i.e. superior viscosity index (VI) than the polyalpha-olefins lubricating oils prepared by conventional processes.
  • VI superior viscosity index

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé d'oligomérisation de C8-C6 alpha-oléfines pour obtenir un produit polyoléfine comprenant un trimère dont le traitement consiste à mettre en contact le C8-C6 alpha-oléfine avec un catalyseur dans un solvant à une température inférieure à 20 °C, le catalyseur comprenant un complexe d'un composé de chrome et un 1,3,5-triazacyclohexane, et le produit polyoléfine au moins 70 en môles de trimère. Le produit polyoléfine peut être hydrogéné par catalyse en huiles lubrifiantes.
PCT/GB1999/004010 1998-12-04 1999-12-01 Procede d'oligomerisation WO2000034211A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU13992/00A AU1399200A (en) 1998-12-04 1999-12-01 Oligomerisation process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9826755.2A GB9826755D0 (en) 1998-12-04 1998-12-04 Oligomerisation process
GB9826755.2 1998-12-04

Publications (1)

Publication Number Publication Date
WO2000034211A1 true WO2000034211A1 (fr) 2000-06-15

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AU (1) AU1399200A (fr)
GB (1) GB9826755D0 (fr)
WO (1) WO2000034211A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000058319A1 (fr) * 1999-03-29 2000-10-05 Basf Aktiengesellschaft Catalyseur d'oligomerisation
WO2001098377A2 (fr) * 2000-06-20 2001-12-27 Basf Aktiengesellschaft Cires de polyolefine oxydees
WO2001098379A1 (fr) * 2000-06-20 2001-12-27 Basf Aktiengesellschaft Pates contenant un solvant et en plus de la cire de polyolefine
WO2003076367A2 (fr) * 2002-03-14 2003-09-18 Basell Polyolefine Gmbh Procede d'oligomerisation d'olefines utilisant un triazacyclohexane substitue par cycloalkylalkyle
EP1487764A1 (fr) * 2002-03-14 2004-12-22 Basf Aktiengesellschaft Olegomerisation d'olefines comportant au moins trois atomes de carbone
US6858071B2 (en) 2000-06-20 2005-02-22 Basf Aktiengesellschaft Solvent-containing pastes containing in addition polyolefin wax
EP1564198A1 (fr) * 2004-02-11 2005-08-17 Total Petrochemicals Research Feluy Catalyseurs au chrome hétérogènes
WO2005082815A1 (fr) * 2004-02-11 2005-09-09 Total Petrochemicals Research Feluy Catalyseurs de chrome heterogenes
WO2010051405A1 (fr) * 2008-10-31 2010-05-06 Chevron Phillips Chemical Company Lp Compositions et systèmes catalyseurs de précurseurs métalliques et de diluants oléfiniques
CN102869445A (zh) * 2010-04-30 2013-01-09 切弗朗菲利浦化学公司 低聚催化剂系统以及低聚烯烃的方法
WO2014069668A1 (fr) * 2012-11-02 2014-05-08 住友化学株式会社 Procédé de production d'un composé
US8889931B2 (en) 2011-11-17 2014-11-18 Exxonmobil Research And Engineering Company Processes for preparing low viscosity lubricating oil base stocks
US8936719B2 (en) 2006-03-22 2015-01-20 Ultraclean Fuel Pty Ltd. Process for removing sulphur from liquid hydrocarbons
US9441169B2 (en) 2013-03-15 2016-09-13 Ultraclean Fuel Pty Ltd Process for removing sulphur compounds from hydrocarbons
CN106565618A (zh) * 2016-10-10 2017-04-19 常州大学 一种由α‑烯烃直接合成润滑油基础油的催化剂配体及其配合物以及制备方法和应用
WO2019014393A1 (fr) 2017-07-12 2019-01-17 Stora Enso Oyj Nouveaux procédés de préparation d'acide 2,5-furandicarboxylique
US10214697B2 (en) 2013-03-15 2019-02-26 Ultraclean Fuel Pty Limited Process for removing sulphur compounds from hydrocarbons
FR3073846A1 (fr) * 2017-11-22 2019-05-24 Total Marketing Services Catalyseur pour la preparation de trimeres d'alpha-olefine(s)
FR3073845A1 (fr) * 2017-11-22 2019-05-24 Total Marketing Services Procede de preparation de trimeres de 1-decene
CN111285903A (zh) * 2018-12-06 2020-06-16 中国石油天然气股份有限公司 一种铬系催化剂、催化剂的制备方法及其应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0583072A1 (fr) * 1992-07-28 1994-02-16 BP Chemicals Limited Production d'huiles lubrifiantes
US5744677A (en) * 1991-10-16 1998-04-28 Amoco Corporation Ethylene oligomerization

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5744677A (en) * 1991-10-16 1998-04-28 Amoco Corporation Ethylene oligomerization
EP0583072A1 (fr) * 1992-07-28 1994-02-16 BP Chemicals Limited Production d'huiles lubrifiantes

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000058319A1 (fr) * 1999-03-29 2000-10-05 Basf Aktiengesellschaft Catalyseur d'oligomerisation
WO2001098377A2 (fr) * 2000-06-20 2001-12-27 Basf Aktiengesellschaft Cires de polyolefine oxydees
WO2001098379A1 (fr) * 2000-06-20 2001-12-27 Basf Aktiengesellschaft Pates contenant un solvant et en plus de la cire de polyolefine
WO2001098377A3 (fr) * 2000-06-20 2002-11-07 Basf Ag Cires de polyolefine oxydees
US6825283B2 (en) 2000-06-20 2004-11-30 Basf Aktiengesellschaft Oxidized polyolefin waxes
US6858071B2 (en) 2000-06-20 2005-02-22 Basf Aktiengesellschaft Solvent-containing pastes containing in addition polyolefin wax
US7081557B2 (en) 2002-03-14 2006-07-25 Basell Polyolefine Gmbh Method for the oligomerization of olefins using a cycloalkylalkyl-substituted triazacyclohexane
WO2003076367A2 (fr) * 2002-03-14 2003-09-18 Basell Polyolefine Gmbh Procede d'oligomerisation d'olefines utilisant un triazacyclohexane substitue par cycloalkylalkyle
WO2003076367A3 (fr) * 2002-03-14 2003-12-18 Basell Polyolefine Gmbh Procede d'oligomerisation d'olefines utilisant un triazacyclohexane substitue par cycloalkylalkyle
EP1487764A1 (fr) * 2002-03-14 2004-12-22 Basf Aktiengesellschaft Olegomerisation d'olefines comportant au moins trois atomes de carbone
WO2005082815A1 (fr) * 2004-02-11 2005-09-09 Total Petrochemicals Research Feluy Catalyseurs de chrome heterogenes
EP1564198A1 (fr) * 2004-02-11 2005-08-17 Total Petrochemicals Research Feluy Catalyseurs au chrome hétérogènes
US8936719B2 (en) 2006-03-22 2015-01-20 Ultraclean Fuel Pty Ltd. Process for removing sulphur from liquid hydrocarbons
CN105195219A (zh) * 2008-10-31 2015-12-30 切弗朗菲利浦化学公司 金属前躯体和烯属稀释剂的组合物和催化剂系统
WO2010051405A1 (fr) * 2008-10-31 2010-05-06 Chevron Phillips Chemical Company Lp Compositions et systèmes catalyseurs de précurseurs métalliques et de diluants oléfiniques
CN102196862A (zh) * 2008-10-31 2011-09-21 切弗朗菲利浦化学公司 金属前躯体和烯属稀释剂的组合物和催化剂系统
US9375708B2 (en) 2008-10-31 2016-06-28 Chevron Phillips Chemical Company Lp Compositions and catalyst systems of metal precursors and olefinic diluents
AU2009308790B2 (en) * 2008-10-31 2015-05-07 Chevron Phillips Chemical Company Lp Compositions and catalyst systems of metal precursors and olefinic diluents
CN102869445A (zh) * 2010-04-30 2013-01-09 切弗朗菲利浦化学公司 低聚催化剂系统以及低聚烯烃的方法
CN102869445B (zh) * 2010-04-30 2015-11-25 切弗朗菲利浦化学公司 低聚催化剂系统以及低聚烯烃的方法
US8889931B2 (en) 2011-11-17 2014-11-18 Exxonmobil Research And Engineering Company Processes for preparing low viscosity lubricating oil base stocks
WO2014069668A1 (fr) * 2012-11-02 2014-05-08 住友化学株式会社 Procédé de production d'un composé
JPWO2014069668A1 (ja) * 2012-11-02 2016-09-08 住友化学株式会社 化合物の製造方法
US9441169B2 (en) 2013-03-15 2016-09-13 Ultraclean Fuel Pty Ltd Process for removing sulphur compounds from hydrocarbons
US10214697B2 (en) 2013-03-15 2019-02-26 Ultraclean Fuel Pty Limited Process for removing sulphur compounds from hydrocarbons
CN106565618A (zh) * 2016-10-10 2017-04-19 常州大学 一种由α‑烯烃直接合成润滑油基础油的催化剂配体及其配合物以及制备方法和应用
WO2019014393A1 (fr) 2017-07-12 2019-01-17 Stora Enso Oyj Nouveaux procédés de préparation d'acide 2,5-furandicarboxylique
FR3073846A1 (fr) * 2017-11-22 2019-05-24 Total Marketing Services Catalyseur pour la preparation de trimeres d'alpha-olefine(s)
FR3073845A1 (fr) * 2017-11-22 2019-05-24 Total Marketing Services Procede de preparation de trimeres de 1-decene
WO2019102153A1 (fr) * 2017-11-22 2019-05-31 Total Marketing Services Catalyseur pour la preparation de trimeres d'alpha-olefine(s)
WO2019102152A1 (fr) * 2017-11-22 2019-05-31 Total Marketing Services Procede de preparation de trimeres de 1-decene
CN111285903A (zh) * 2018-12-06 2020-06-16 中国石油天然气股份有限公司 一种铬系催化剂、催化剂的制备方法及其应用

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Publication number Publication date
GB9826755D0 (en) 1999-01-27
AU1399200A (en) 2000-06-26

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