DE69119011T2 - Verfahren zur Herstellung von Olefinoligomeren - Google Patents
Verfahren zur Herstellung von OlefinoligomerenInfo
- Publication number
- DE69119011T2 DE69119011T2 DE69119011T DE69119011T DE69119011T2 DE 69119011 T2 DE69119011 T2 DE 69119011T2 DE 69119011 T DE69119011 T DE 69119011T DE 69119011 T DE69119011 T DE 69119011T DE 69119011 T2 DE69119011 T2 DE 69119011T2
- Authority
- DE
- Germany
- Prior art keywords
- anhydride
- olefin
- catalyst
- alcohol
- water
- 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.)
- Expired - Fee Related
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 85
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 63
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 79
- 239000003426 co-catalyst Substances 0.000 claims description 47
- 229910015900 BF3 Inorganic materials 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- -1 aliphatic carboxylic anhydride Chemical class 0.000 claims description 6
- 150000003138 primary alcohols Chemical class 0.000 claims description 5
- 150000003333 secondary alcohols Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000004711 α-olefin Substances 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 57
- 230000000052 comparative effect Effects 0.000 description 34
- 235000019441 ethanol Nutrition 0.000 description 29
- 239000000047 product Substances 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 10
- 239000000314 lubricant Substances 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- UOGBWVLAMKCFBK-UHFFFAOYSA-N acetyl acetate;hydrate Chemical compound O.CC(=O)OC(C)=O UOGBWVLAMKCFBK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FXVQIAPSJGBLJJ-UHFFFAOYSA-N butan-1-ol;trifluoroborane Chemical compound FB(F)F.CCCCO FXVQIAPSJGBLJJ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ANLISICGYWBHKU-UHFFFAOYSA-N methyl acetate;hydrate Chemical compound O.COC(C)=O ANLISICGYWBHKU-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
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
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- 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
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- 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
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2251446A JPH0764757B2 (ja) | 1990-09-20 | 1990-09-20 | オレフィンオリゴマーの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69119011D1 DE69119011D1 (de) | 1996-05-30 |
| DE69119011T2 true DE69119011T2 (de) | 1996-09-12 |
Family
ID=17222951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69119011T Expired - Fee Related DE69119011T2 (de) | 1990-09-20 | 1991-09-12 | Verfahren zur Herstellung von Olefinoligomeren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5191140A (enExample) |
| EP (1) | EP0477673B1 (enExample) |
| JP (1) | JPH0764757B2 (enExample) |
| KR (1) | KR0146376B1 (enExample) |
| BR (1) | BR9104025A (enExample) |
| DE (1) | DE69119011T2 (enExample) |
| TW (1) | TW228005B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5252922A (en) * | 1991-04-30 | 1993-10-12 | Hewlett-Packard Company | Radiofrequency focusing of magnetic resonance images |
| US5286823A (en) * | 1991-06-22 | 1994-02-15 | Basf Aktiengesellschaft | Preparation of highly reactive polyisobutenes |
| US5396013A (en) * | 1993-07-12 | 1995-03-07 | Albemarle Corporation | Olefin oligomerization process |
| US5420373A (en) * | 1994-03-24 | 1995-05-30 | Chevron Chemical Company | Controlled formation of olefin oligomers |
| US5650548A (en) * | 1995-06-16 | 1997-07-22 | Amoco Corporation | Olefin oligomerization process |
| DE69511548T2 (de) * | 1995-09-13 | 2000-05-04 | Amoco Corp., Chicago | Verfahren zur Herstellung von Oligomeren von Mono-Olefinen |
| US5633420A (en) * | 1995-09-22 | 1997-05-27 | Amoco Corporation | Olefin oligomerization process |
| US5744676A (en) * | 1996-02-26 | 1998-04-28 | Theriot; Kevin J. | Olefin oligomerization process |
| US5714661A (en) * | 1996-05-31 | 1998-02-03 | Tuli; Deepak Kumar | Process for the preparation of synthetic lubricant base stocks |
| US5994605A (en) * | 1996-12-03 | 1999-11-30 | Chevron Chemical Company | High viscosity polyalphaolefins |
| US6133386A (en) | 1997-01-08 | 2000-10-17 | Hercules Incorporated | Metal oxide solid acids as catalysts for the preparation of hydrocarbon resins |
| US5922636A (en) * | 1997-11-19 | 1999-07-13 | Sarin; Rakesh | Catalyst for oligomerization of alpha-olefins |
| EP0933416A1 (en) * | 1998-01-30 | 1999-08-04 | Chevron Chemical S.A. | Use of polyalfaolefins (PAO) derived from 1-dodecene or 1-tetradecene to improve thermal stability in engine oil in internal combustion engine |
| GB9819456D0 (en) * | 1998-09-07 | 1998-10-28 | Univ York | Synthesis of a new supported bf-complex solid acid catalyst |
| JP2001122816A (ja) * | 1999-10-21 | 2001-05-08 | Idemitsu Kosan Co Ltd | ビニルエーテル系オリゴマーの製造方法 |
| US6410812B1 (en) * | 2000-03-01 | 2002-06-25 | Chevron Phillips Chemical Company Lp | Process for recovering boron trifluoride from a catalyst complex |
| US6734329B1 (en) * | 2000-10-02 | 2004-05-11 | Chevron U.S.A. Inc. | Oligomerization of alpha olefins in the presence of carboxylic acids |
| US6824671B2 (en) * | 2001-05-17 | 2004-11-30 | Exxonmobil Chemical Patents Inc. | Low noack volatility poly α-olefins |
| CN110627603A (zh) * | 2018-06-21 | 2019-12-31 | 中国石化工程建设有限公司 | 连续法生产聚α-烯烃的装置及方法 |
| SG11202010806QA (en) | 2018-09-20 | 2020-11-27 | Novvi Llc | Process for preparing hydrocarbon mixture exhibiting unique branching structure |
| CN111321002A (zh) | 2018-12-14 | 2020-06-23 | 中国石油天然气股份有限公司 | 一种低粘度聚α-烯烃润滑油及其合成方法 |
| CN115212922B (zh) | 2021-04-15 | 2024-11-26 | 中国石油天然气股份有限公司 | 一种α-烯烃聚合的催化剂组合物及其制备与应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382291A (en) * | 1965-04-23 | 1968-05-07 | Mobil Oil Corp | Polymerization of olefins with bf3 |
| US3763244A (en) * | 1971-11-03 | 1973-10-02 | Ethyl Corp | Process for producing a c6-c16 normal alpha-olefin oligomer having a pour point below about- f. |
| US3769363A (en) * | 1972-03-13 | 1973-10-30 | Mobil Oil Corp | Oligomerization of olefins with boron trifluoride |
| US3997621A (en) * | 1974-02-04 | 1976-12-14 | Mobil Oil Corporation | Controlled oligomerization of olefins |
| GB1497524A (en) * | 1975-11-20 | 1978-01-12 | Gulf Research Development Co | Method of oligomerizing 1-olefins |
| US4239930A (en) * | 1979-05-17 | 1980-12-16 | Pearsall Chemical Company | Continuous oligomerization process |
| US4436947A (en) * | 1981-09-11 | 1984-03-13 | Gulf Research & Development Company | Olefin oligomerization using boron trifluoride and a three-component cocatalyst |
| US4409415A (en) * | 1981-09-18 | 1983-10-11 | Gulf Research & Development Company | Olefin oligomerization using boron trifluoride and an alcohol-polyol cocatalyst |
| DE3376262D1 (en) * | 1983-09-21 | 1988-05-19 | Texaco Development Corp | Oligomerization of olefins and synthetic lubricant comprising olefin oligomers |
| DE3642456A1 (de) * | 1986-12-12 | 1988-06-23 | Basf Ag | Verfahren zur herstellung von decenoligomeren und deren verwendung als schmieroele |
| US4849572A (en) * | 1987-12-22 | 1989-07-18 | Exxon Chemical Patents Inc. | Process for preparing polybutenes having enhanced reactivity using boron trifluoride catalysts (PT-647) |
| CA1321606C (en) * | 1988-06-27 | 1993-08-24 | Matthew J. Lynch | Olefin oligomer synlube process |
| US4902846A (en) * | 1988-07-29 | 1990-02-20 | Ethyl Corporation | Synlube process |
| US4956513A (en) * | 1988-10-17 | 1990-09-11 | Ethyl Corporation | Recovery of BF3 from olefin oligomer process |
-
1990
- 1990-09-20 JP JP2251446A patent/JPH0764757B2/ja not_active Expired - Fee Related
-
1991
- 1991-09-09 US US07/756,508 patent/US5191140A/en not_active Expired - Fee Related
- 1991-09-12 EP EP91115417A patent/EP0477673B1/en not_active Expired - Lifetime
- 1991-09-12 DE DE69119011T patent/DE69119011T2/de not_active Expired - Fee Related
- 1991-09-19 TW TW080107439A patent/TW228005B/zh active
- 1991-09-20 BR BR919104025A patent/BR9104025A/pt not_active Application Discontinuation
- 1991-09-20 KR KR1019910016485A patent/KR0146376B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9104025A (pt) | 1992-06-02 |
| KR920006261A (ko) | 1992-04-27 |
| DE69119011D1 (de) | 1996-05-30 |
| EP0477673B1 (en) | 1996-04-24 |
| US5191140A (en) | 1993-03-02 |
| EP0477673A1 (en) | 1992-04-01 |
| TW228005B (enExample) | 1994-08-11 |
| JPH04128242A (ja) | 1992-04-28 |
| KR0146376B1 (ko) | 1998-08-17 |
| JPH0764757B2 (ja) | 1995-07-12 |
Similar Documents
| Publication | Publication Date | Title |
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