JPS6094923A - エチレンの二量化による１‐ブテンの改良合成方法 - Google Patents
エチレンの二量化による１‐ブテンの改良合成方法Info
- Publication number
- JPS6094923A JPS6094923A JP59198390A JP19839084A JPS6094923A JP S6094923 A JPS6094923 A JP S6094923A JP 59198390 A JP59198390 A JP 59198390A JP 19839084 A JP19839084 A JP 19839084A JP S6094923 A JPS6094923 A JP S6094923A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- ethylene
- temperature
- catalyst
- butene
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 39
- 239000005977 Ethylene Substances 0.000 title claims description 39
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims description 38
- 238000006471 dimerization reaction Methods 0.000 title description 4
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- -1 alkyl titanate Chemical compound 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 23
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 230000003993 interaction Effects 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 101100058670 Aeromonas hydrophila subsp. hydrophila (strain ATCC 7966 / DSM 30187 / BCRC 13018 / CCUG 14551 / JCM 1027 / KCTC 2358 / NCIMB 9240 / NCTC 8049) bsr gene Proteins 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 12
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- BBIDBFWZMCTRNP-UHFFFAOYSA-N ethylalumane Chemical compound CC[AlH2] BBIDBFWZMCTRNP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- ZWRLQFKXTNQSFW-UHFFFAOYSA-N 1,2-dimethoxyhexane Chemical compound CCCCC(OC)COC ZWRLQFKXTNQSFW-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- JXLWTLZBAJWNSG-UHFFFAOYSA-N CCCC[Ti] Chemical compound CCCC[Ti] JXLWTLZBAJWNSG-UHFFFAOYSA-N 0.000 description 1
- FWMGWNBHJYBRTH-UHFFFAOYSA-N CC[Ti](CC)(CC)CC Chemical compound CC[Ti](CC)(CC)CC FWMGWNBHJYBRTH-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229930010859 axane Natural products 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—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
- B01J31/143—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 of aluminium
-
- 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
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
-
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8315041 | 1983-09-20 | ||
| FR8315040A FR2552079B1 (fr) | 1983-09-20 | 1983-09-20 | Procede ameliore de synthese du butene-1 par dimerisation de l'ethylene |
| FR8315040 | 1983-09-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6094923A true JPS6094923A (ja) | 1985-05-28 |
| JPH0329767B2 JPH0329767B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-04-25 |
Family
ID=9292427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59198390A Granted JPS6094923A (ja) | 1983-09-20 | 1984-09-20 | エチレンの二量化による１‐ブテンの改良合成方法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6094923A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| FR (1) | FR2552079B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011240336A (ja) * | 2010-05-18 | 2011-12-01 | IFP Energies Nouvelles | チタンをベースとする錯体と、ヘテロ原子によって官能基化されたアルコキシリガンドとを含む組成物を用いる、エチレンのブタ−１−エンへの二量体化のための方法 |
| JP2013136576A (ja) * | 2011-12-20 | 2013-07-11 | IFP Energies Nouvelles | ブテンを形成するエチレンのダイマー化およびオクテンを形成するブテンのダイマー化によるオクテンの製造方法 |
| JP2014062094A (ja) * | 2012-09-21 | 2014-04-10 | Axens | エチレンを二量化し、得られたブテンを脱水素化することによって１，３−ブタジエンを製造する方法 |
| JP2016026868A (ja) * | 2014-07-04 | 2016-02-18 | イエフペ エネルジ ヌヴェルＩｆｐ Ｅｎｅｒｇｉｅｓ Ｎｏｕｖｅｌｌｅｓ | 触媒組成物およびエチレンの１−ブテンへの選択的ダイマー化方法 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1662996A1 (ru) * | 1987-07-13 | 1991-07-15 | Отделение Института химической физики АН СССР | Способ получени бутена-1 |
| EP0356518A4 (de) * | 1988-02-23 | 1990-06-26 | Inst Khim Fiz An Sssr | Verfahren zur herstellung von 1-butan und/oder hexenen. |
| WO1992010451A1 (en) * | 1990-12-07 | 1992-06-25 | Okhtinskoe Nauchno-Proizvodstvennoe Obiedinenie 'plastopolimer' | Method of obtaining butene-i |
| FR2879189B1 (fr) | 2004-12-13 | 2007-03-30 | Inst Francais Du Petrole | Methode pour transporter des hydrates en suspension dans des effluents de production utilisant un additif non-polluant |
| FR2880018B1 (fr) | 2004-12-27 | 2007-02-23 | Inst Francais Du Petrole | Production de propylene mettant en oeuvre la dimerisation de l'ethylene en butene-1, l'hydro-isomerisation en butene-2 et la metathese par l'ethylene |
| FR3008697B1 (fr) * | 2013-07-19 | 2015-07-31 | IFP Energies Nouvelles | Procede de dimerisation selective de l'ethylene en butene-1 utilisant une composition catalytique comprenant un complexe a base de titane additive en association avec un ligand alcoxy fonctionnalise par un hetero-atome |
| FR3023285B1 (fr) | 2014-07-04 | 2017-10-27 | Ifp Energies Now | Procede ameliore de dimerisation selective de l'ethylene en butene-1 |
| FR3068621B1 (fr) | 2017-07-10 | 2020-06-26 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en oeuvre un vortex |
| FR3068620B1 (fr) | 2017-07-10 | 2020-06-26 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en oeuvre un dispositf reactionnel comprenant un moyen de dispersion |
| FR3083235B1 (fr) | 2018-06-29 | 2021-12-03 | Ifp Energies Now | Procede d'oligomerisation en cascade de reacteurs gaz liquide agites avec injection etagee d'ethylene |
| FR3086288A1 (fr) | 2018-09-21 | 2020-03-27 | IFP Energies Nouvelles | Procede d'oligomerisation d'ethylene dans un reacteur gaz/liquide compartimente |
| FR3096587B1 (fr) | 2019-05-28 | 2021-06-11 | Ifp Energies Now | Reacteur d’oligomerisation compartimente |
| FR3099476B1 (fr) | 2019-07-31 | 2021-07-30 | Ifp Energies Now | Procede d’oligomerisation mettant en œuvre un recycle du ciel gazeux |
| FR3102685B1 (fr) | 2019-11-06 | 2021-10-29 | Ifp Energies Now | Procédé d’oligomérisation d’oléfines dans un réacteur d’oligomérisation |
| FR3105019B1 (fr) | 2019-12-18 | 2022-07-22 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation a zones successives de diametre variable |
| FR3105018B1 (fr) | 2019-12-18 | 2021-12-10 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation comprenant des internes transversaux |
| FR3108264B1 (fr) | 2020-03-19 | 2022-04-08 | Ifp Energies Now | Installation d’oligomérisation d’éthylène pour produire des alpha-oléfines |
| FR3112342A1 (fr) | 2020-07-09 | 2022-01-14 | IFP Energies Nouvelles | Procede d’oligomerisation mettant en œuvre un echangeur gaz/liquide |
| FR3112775B1 (fr) | 2020-07-24 | 2022-07-01 | Ifp Energies Now | Procédé d’oligomérisation mettant en oeuvre un recycle du ciel gazeux |
| FR3117891B1 (fr) | 2020-12-23 | 2024-12-20 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation comprenant une conduite centrale |
| FR3117890B1 (fr) | 2020-12-23 | 2024-01-12 | Ifp Energies Now | Reacteur gaz/liquide d’oligomerisation comprenant un double distributeur gaz/liquide |
| FR3121439B1 (fr) | 2021-03-30 | 2023-03-24 | Ifp Energies Now | Procede d'oligomerisation comprenant une etape de recyclage d'un solvant prealablement refroidi |
| FR3123354B1 (fr) | 2021-05-28 | 2023-05-26 | Ifp Energies Now | Procede d'oligomerisation dans un reacteur a zones de diametres variables comprenant une etape de recyclage d'un solvant prealablement refroidi |
| FR3156333A1 (fr) | 2023-12-06 | 2025-06-13 | IFP Energies Nouvelles | Procede d’oligomerisation d’une charge olefinique en reacteur tubulaire a boucle |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57169430A (en) * | 1981-04-14 | 1982-10-19 | Mitsui Toatsu Chem Inc | Dimerization of ethylene |
| JPS58146518A (ja) * | 1982-02-24 | 1983-09-01 | Mitsubishi Petrochem Co Ltd | １−ブテンの製造法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1235631A (en) * | 1969-05-19 | 1971-06-16 | Bp Chem Int Ltd | Oligomerisation of ethylene |
| SU681032A1 (ru) * | 1976-02-23 | 1979-08-25 | Грозненский филиал Охтинского научно-производственного объединения "Пластполимер" | Способ получени димеров и содимеров -олефинов |
-
1983
- 1983-09-20 FR FR8315040A patent/FR2552079B1/fr not_active Expired
-
1984
- 1984-09-20 JP JP59198390A patent/JPS6094923A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57169430A (en) * | 1981-04-14 | 1982-10-19 | Mitsui Toatsu Chem Inc | Dimerization of ethylene |
| JPS58146518A (ja) * | 1982-02-24 | 1983-09-01 | Mitsubishi Petrochem Co Ltd | １−ブテンの製造法 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011240336A (ja) * | 2010-05-18 | 2011-12-01 | IFP Energies Nouvelles | チタンをベースとする錯体と、ヘテロ原子によって官能基化されたアルコキシリガンドとを含む組成物を用いる、エチレンのブタ−１−エンへの二量体化のための方法 |
| JP2013136576A (ja) * | 2011-12-20 | 2013-07-11 | IFP Energies Nouvelles | ブテンを形成するエチレンのダイマー化およびオクテンを形成するブテンのダイマー化によるオクテンの製造方法 |
| JP2014062094A (ja) * | 2012-09-21 | 2014-04-10 | Axens | エチレンを二量化し、得られたブテンを脱水素化することによって１，３−ブタジエンを製造する方法 |
| JP2016026868A (ja) * | 2014-07-04 | 2016-02-18 | イエフペ エネルジ ヌヴェルＩｆｐ Ｅｎｅｒｇｉｅｓ Ｎｏｕｖｅｌｌｅｓ | 触媒組成物およびエチレンの１−ブテンへの選択的ダイマー化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329767B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-04-25 |
| FR2552079A1 (fr) | 1985-03-22 |
| FR2552079B1 (fr) | 1986-10-03 |
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