JP2003510382A5 - - Google Patents
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- JP2003510382A5 JP2003510382A5 JP2001525247A JP2001525247A JP2003510382A5 JP 2003510382 A5 JP2003510382 A5 JP 2003510382A5 JP 2001525247 A JP2001525247 A JP 2001525247A JP 2001525247 A JP2001525247 A JP 2001525247A JP 2003510382 A5 JP2003510382 A5 JP 2003510382A5
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- hydrocarbyl
- boron
- borate
- compounds
- 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.)
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- 238000000034 method Methods 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- -1 (perfluorophenyl) borate compound Chemical class 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 239000012190 activator Substances 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 7
- 150000003624 transition metals Chemical class 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical group CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000000743 hydrocarbylene group Chemical group 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 2
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 2
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 2
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- BRTALTYTFFNPAC-UHFFFAOYSA-N boroxin Chemical class B1OBOBO1 BRTALTYTFFNPAC-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40186799A | 1999-09-23 | 1999-09-23 | |
| US09/401,867 | 1999-09-23 | ||
| PCT/US2000/023127 WO2001021675A1 (en) | 1999-09-23 | 2000-08-23 | Oligomer oils and their manufacture |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003510382A JP2003510382A (ja) | 2003-03-18 |
| JP2003510382A5 true JP2003510382A5 (https=) | 2011-09-22 |
| JP4958358B2 JP4958358B2 (ja) | 2012-06-20 |
Family
ID=23589557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001525247A Expired - Lifetime JP4958358B2 (ja) | 1999-09-23 | 2000-08-23 | オリゴマーオイル及びその製造方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6548723B2 (https=) |
| EP (1) | EP1141043B1 (https=) |
| JP (1) | JP4958358B2 (https=) |
| KR (1) | KR100676105B1 (https=) |
| CN (1) | CN1252097C (https=) |
| AT (1) | ATE283293T1 (https=) |
| AU (1) | AU6798900A (https=) |
| BR (1) | BR0007167B1 (https=) |
| CA (1) | CA2351329C (https=) |
| DE (1) | DE60016169T2 (https=) |
| ES (1) | ES2231239T3 (https=) |
| ID (1) | ID29402A (https=) |
| PT (1) | PT1141043E (https=) |
| RU (1) | RU2235756C2 (https=) |
| TW (1) | TW548280B (https=) |
| WO (1) | WO2001021675A1 (https=) |
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY139205A (en) * | 2001-08-31 | 2009-08-28 | Pennzoil Quaker State Co | Synthesis of poly-alpha olefin and use thereof |
| US6680417B2 (en) * | 2002-01-03 | 2004-01-20 | Bp Corporation North America Inc. | Oligomerization using a solid, unsupported metallocene catalyst system |
| US6706828B2 (en) | 2002-06-04 | 2004-03-16 | Crompton Corporation | Process for the oligomerization of α-olefins having low unsaturation |
| US7022784B2 (en) * | 2002-10-25 | 2006-04-04 | Exxonmobil Research And Engineering Company | Synthetic lubricant composition and process |
| US7510674B2 (en) * | 2004-12-01 | 2009-03-31 | Chevron U.S.A. Inc. | Dielectric fluids and processes for making same |
| JP4731181B2 (ja) * | 2005-02-21 | 2011-07-20 | 出光興産株式会社 | 不飽和炭化水素化合物の製造方法 |
| US7482312B2 (en) * | 2005-04-01 | 2009-01-27 | Shell Oil Company | Engine oils for racing applications and method of making same |
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| JP5390738B2 (ja) * | 2005-11-15 | 2014-01-15 | 出光興産株式会社 | 内燃機関用潤滑油組成物 |
| JP2007137951A (ja) * | 2005-11-15 | 2007-06-07 | Idemitsu Kosan Co Ltd | 潤滑油組成物、軸受油及びそれを用いた軸受 |
| EP2333034B1 (en) * | 2005-11-15 | 2016-01-27 | Idemitsu Kosan Co., Ltd. | Transmission fluid composition |
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2000
- 2000-08-23 BR BRPI0007167-6A patent/BR0007167B1/pt not_active IP Right Cessation
- 2000-08-23 WO PCT/US2000/023127 patent/WO2001021675A1/en not_active Ceased
- 2000-08-23 CN CNB008019819A patent/CN1252097C/zh not_active Expired - Lifetime
- 2000-08-23 DE DE60016169T patent/DE60016169T2/de not_active Expired - Lifetime
- 2000-08-23 CA CA002351329A patent/CA2351329C/en not_active Expired - Lifetime
- 2000-08-23 EP EP00955853A patent/EP1141043B1/en not_active Expired - Lifetime
- 2000-08-23 KR KR1020017006466A patent/KR100676105B1/ko not_active Expired - Lifetime
- 2000-08-23 AT AT00955853T patent/ATE283293T1/de not_active IP Right Cessation
- 2000-08-23 ID IDW00200101377A patent/ID29402A/id unknown
- 2000-08-23 PT PT00955853T patent/PT1141043E/pt unknown
- 2000-08-23 AU AU67989/00A patent/AU6798900A/en not_active Abandoned
- 2000-08-23 RU RU2001115694/04A patent/RU2235756C2/ru active
- 2000-08-23 ES ES00955853T patent/ES2231239T3/es not_active Expired - Lifetime
- 2000-08-23 JP JP2001525247A patent/JP4958358B2/ja not_active Expired - Lifetime
- 2000-09-22 TW TW089119652A patent/TW548280B/zh not_active IP Right Cessation
-
2001
- 2001-03-22 US US09/814,500 patent/US6548723B2/en not_active Expired - Lifetime
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