JP2004507553A - アルキル架橋の配位子系及び遷移金属化合物の製造方法 - Google Patents
アルキル架橋の配位子系及び遷移金属化合物の製造方法 Download PDFInfo
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- JP2004507553A JP2004507553A JP2002523912A JP2002523912A JP2004507553A JP 2004507553 A JP2004507553 A JP 2004507553A JP 2002523912 A JP2002523912 A JP 2002523912A JP 2002523912 A JP2002523912 A JP 2002523912A JP 2004507553 A JP2004507553 A JP 2004507553A
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- Prior art keywords
- indenyl
- dichloride
- ethanediylbis
- cyclohexanediylbis
- propanediylbis
- Prior art date
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical class [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 35
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- 125000002950 monocyclic group Chemical group 0.000 claims description 15
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- 125000004434 sulfur atom Chemical group 0.000 claims description 3
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- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 291
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- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- CXYPKXYSWBMCRG-UHFFFAOYSA-N magnesium;pentane Chemical compound [Mg+2].CCCC[CH2-].CCCC[CH2-] CXYPKXYSWBMCRG-UHFFFAOYSA-N 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical class [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10042450 | 2000-08-29 | ||
| PCT/EP2001/009682 WO2002018397A1 (de) | 2000-08-29 | 2001-08-22 | VERFAHREN ZUR HERSTELLUNG VON AlKYLVERBRÜCKTEN LIGANDSYSTEMEN UND ÜBERGANGSMETALLVERBINDUNGEN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004507553A true JP2004507553A (ja) | 2004-03-11 |
| JP2004507553A5 JP2004507553A5 (https=) | 2008-10-16 |
Family
ID=7654212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002523912A Pending JP2004507553A (ja) | 2000-08-29 | 2001-08-22 | アルキル架橋の配位子系及び遷移金属化合物の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6784305B2 (https=) |
| EP (1) | EP1313747B1 (https=) |
| JP (1) | JP2004507553A (https=) |
| AT (1) | ATE293632T1 (https=) |
| AU (1) | AU2001289824A1 (https=) |
| DE (1) | DE50105968D1 (https=) |
| WO (1) | WO2002018397A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536905A (ja) * | 2007-08-27 | 2010-12-02 | ボレアリス テクノロジー オイ | 触媒 |
| JP2016504452A (ja) * | 2012-12-21 | 2016-02-12 | ボレアリス エージー | 触媒 |
| JP2017527525A (ja) * | 2014-06-09 | 2017-09-21 | エスシージー ケミカルズ カンパニー,リミテッド | インデンの合成のための方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6376410B1 (en) * | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376413B1 (en) * | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| DE10158656A1 (de) | 2001-11-30 | 2003-06-26 | Basell Polyolefine Gmbh | Organoübergangsmetallverbindung, Biscyclopentadienylligandsystem, Katalysatorsystem und Verfahren zur Herstellung von Polyolefinen |
| BR0312643A (pt) * | 2002-07-15 | 2005-04-19 | Basell Polyolefine Gmbh | Processo para preparar um catalisador para a polimerização de olefina, uso de um catalisador, catalisador, e, processo para a polimerização de olefinas |
| JP2006512410A (ja) * | 2002-12-06 | 2006-04-13 | バーゼル、ポリオレフィン、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | 有機金属遷移金属化合物、ビスシクロペンタジエニル配位子を有する化合物、触媒組成物、及びこれらを用いたポリオレフィンの製造法 |
| KR101278336B1 (ko) * | 2007-10-25 | 2013-06-25 | 루머스 노보렌 테크놀로지 게엠베하 | 안사-메탈로센 화합물의 라세모선택적 합성, 안사-메탈로센 화합물, 이를 포함하는 촉매, 그 촉매를 이용한 올레핀 폴리머 제조 공정, 그리고 올레핀 호모- 및 코폴리머 |
| US9834628B2 (en) | 2013-07-17 | 2017-12-05 | Exxonmobil Chemical Patents Inc. | Cyclopropyl substituted metallocene catalysts |
| ES2703344T3 (es) * | 2013-07-17 | 2019-03-08 | Exxonmobil Chemical Patents Inc | Metalocenos y composiciones catalíticas derivadas de ellos |
| EP3022238B1 (en) | 2013-07-17 | 2017-09-20 | ExxonMobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| US9988410B2 (en) | 2015-07-15 | 2018-06-05 | Exxonmobil Chemical Patents Inc. | Substituted bis indenyl metallocene catalyst compounds comprising-Si—Si-bridge |
| WO2019099250A1 (en) | 2017-11-14 | 2019-05-23 | Exxonmobil Chemical Patents Inc. | (di)silicon bridged metallocenes that produce polyethylene broad molecular weight distribution and molecular weight |
| US11214631B2 (en) | 2017-11-14 | 2022-01-04 | Exxonmobil Chemical Patents Inc. | (Di)silicon bridged metallocenes that produce polyethylene with broad molecular weight distribution and high molecular weight |
| US11130827B2 (en) | 2017-11-14 | 2021-09-28 | Exxonmobil Chemical Patents Inc. | Polyethylene compositions and articles made therefrom |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07267974A (ja) * | 1994-02-25 | 1995-10-17 | Witco Gmbh | 架橋した立体剛性のメタロセンの製造法およびメタロセン |
| JPH09202795A (ja) * | 1995-04-24 | 1997-08-05 | Mitsui Toatsu Chem Inc | キラルな新規メタロセン化合物とその合成方法及びそれを用いたオレフィンの重合方法 |
| JPH10204112A (ja) * | 1997-01-17 | 1998-08-04 | Mitsui Chem Inc | オレフィン重合用触媒、オレフィン重合体の製造方法およびオレフィン重合体 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| US4742597A (en) | 1987-08-07 | 1988-05-10 | Laflamme Daniel P | Paint roller apparatus |
| DE3742934A1 (de) | 1987-12-18 | 1989-06-29 | Hoechst Ag | Verfahren zur herstellung einer chiralen, stereorigiden metallocen-verbindung |
| US5017714A (en) * | 1988-03-21 | 1991-05-21 | Exxon Chemical Patents Inc. | Silicon-bridged transition metal compounds |
| NZ235032A (en) | 1989-08-31 | 1993-04-28 | Dow Chemical Co | Constrained geometry complexes of titanium, zirconium or hafnium comprising a substituted cyclopentadiene ligand; use as olefin polymerisation catalyst component |
| ATE286918T1 (de) | 1991-10-15 | 2005-01-15 | Basell Polyolefine Gmbh | Verfahren zur herstellung eines olefinpolymers unter verwendung von metallocenen mit speziell substituierten indenylliganden |
| TW309523B (https=) * | 1991-11-30 | 1997-07-01 | Hoechst Ag | |
| AU6401098A (en) | 1997-03-07 | 1998-09-29 | Targor Gmbh | Preparation of preparing substituted indanones |
| DE19713549A1 (de) | 1997-04-02 | 1998-10-08 | Targor Gmbh | Geträgertes Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
| DE19962905A1 (de) | 1999-12-23 | 2001-07-12 | Basell Polyolefine Gmbh | Übergangsmetallverbindung, Ligandensystem, Katalysatorsystem und seine Verwendung zur Polymerisation und Copolymerisation von Olefinen |
-
2001
- 2001-08-22 EP EP01969627A patent/EP1313747B1/de not_active Expired - Lifetime
- 2001-08-22 AT AT01969627T patent/ATE293632T1/de not_active IP Right Cessation
- 2001-08-22 DE DE50105968T patent/DE50105968D1/de not_active Expired - Lifetime
- 2001-08-22 JP JP2002523912A patent/JP2004507553A/ja active Pending
- 2001-08-22 US US10/362,581 patent/US6784305B2/en not_active Expired - Fee Related
- 2001-08-22 WO PCT/EP2001/009682 patent/WO2002018397A1/de not_active Ceased
- 2001-08-22 AU AU2001289824A patent/AU2001289824A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07267974A (ja) * | 1994-02-25 | 1995-10-17 | Witco Gmbh | 架橋した立体剛性のメタロセンの製造法およびメタロセン |
| JPH09202795A (ja) * | 1995-04-24 | 1997-08-05 | Mitsui Toatsu Chem Inc | キラルな新規メタロセン化合物とその合成方法及びそれを用いたオレフィンの重合方法 |
| JPH10204112A (ja) * | 1997-01-17 | 1998-08-04 | Mitsui Chem Inc | オレフィン重合用触媒、オレフィン重合体の製造方法およびオレフィン重合体 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536905A (ja) * | 2007-08-27 | 2010-12-02 | ボレアリス テクノロジー オイ | 触媒 |
| JP2016504452A (ja) * | 2012-12-21 | 2016-02-12 | ボレアリス エージー | 触媒 |
| US9988323B2 (en) | 2012-12-21 | 2018-06-05 | Borealis Ag | Catalyst |
| JP2017527525A (ja) * | 2014-06-09 | 2017-09-21 | エスシージー ケミカルズ カンパニー,リミテッド | インデンの合成のための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1313747A1 (de) | 2003-05-28 |
| US6784305B2 (en) | 2004-08-31 |
| US20030199703A1 (en) | 2003-10-23 |
| ATE293632T1 (de) | 2005-05-15 |
| WO2002018397A1 (de) | 2002-03-07 |
| EP1313747B1 (de) | 2005-04-20 |
| DE50105968D1 (de) | 2005-05-25 |
| AU2001289824A1 (en) | 2002-03-13 |
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