KR920021700A - 플루오레닐 화합물 제조 방법 - Google Patents
플루오레닐 화합물 제조 방법 Download PDFInfo
- Publication number
- KR920021700A KR920021700A KR1019920007931A KR920007931A KR920021700A KR 920021700 A KR920021700 A KR 920021700A KR 1019920007931 A KR1019920007931 A KR 1019920007931A KR 920007931 A KR920007931 A KR 920007931A KR 920021700 A KR920021700 A KR 920021700A
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- South Korea
- Prior art keywords
- fluorenyl
- unsubstituted
- cyclopentadienyl
- compound
- substituted
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 29
- -1 fluorenyl compound Chemical class 0.000 title claims abstract 15
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract 20
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 7
- 239000003085 diluting agent Substances 0.000 claims 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 6
- GLNMPSDOLMREPM-UHFFFAOYSA-N [9-(chloromethyl)fluoren-9-yl]-trimethylsilane Chemical compound C1=CC=C2C([Si](C)(C)C)(CCl)C3=CC=CC=C3C2=C1 GLNMPSDOLMREPM-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 229910052718 tin Inorganic materials 0.000 claims 2
- DXTQPHNKEMTOHB-UHFFFAOYSA-N 2,7-ditert-butyl-9-(cyclopenta-2,4-dien-1-ylmethyl)-9H-fluorene Chemical compound CC(C)(C)C1=CC2=C(C=C1)C3=C(C2CC4C=CC=C4)C=C(C=C3)C(C)(C)C DXTQPHNKEMTOHB-UHFFFAOYSA-N 0.000 claims 1
- XYFYUUANIGCWGZ-UHFFFAOYSA-N 9-(cyclopenta-2,4-dien-1-ylmethyl)-9h-fluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1CC1C=CC=C1 XYFYUUANIGCWGZ-UHFFFAOYSA-N 0.000 claims 1
- YFPRGLHBYSNHMW-UHFFFAOYSA-N 9h-fluoren-9-yl(trimethyl)silane Chemical compound C1=CC=C2C([Si](C)(C)C)C3=CC=CC=C3C2=C1 YFPRGLHBYSNHMW-UHFFFAOYSA-N 0.000 claims 1
- KEAVGNWNELDTSN-UHFFFAOYSA-N C[Si](C1C2=CC=CC=C2C=2C=CC=C(C1=2)[Li])(C)C Chemical class C[Si](C1C2=CC=CC=C2C=2C=CC=C(C1=2)[Li])(C)C KEAVGNWNELDTSN-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- VMRZYTKLQVKYKQ-UHFFFAOYSA-N lithium;1,9-dihydrofluoren-1-ide Chemical class [Li+].C1=C[C-]=C2CC3=CC=CC=C3C2=C1 VMRZYTKLQVKYKQ-UHFFFAOYSA-N 0.000 claims 1
- DBKDYYFPDRPMPE-UHFFFAOYSA-N lithium;cyclopenta-1,3-diene Chemical compound [Li+].C=1C=C[CH-]C=1 DBKDYYFPDRPMPE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract 1
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- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (35)
- 비-극성 유기 액체로 본질적으로 구성되는 희석액내에서 일반식 X-R-X의 디할로 화합물과 비치환 또는 치환 플루오레닐 리튬염의 반응으로 구성되는, 일반식 Z-X-Z (이때, R은 1내지 20탄소 원자를 지닌 알킬렌이거나 Ge, Si, B, Al, P 또는 Sn의 이가 라디칼이고; X는 Cl, Br 또는 I이며; Z는 비치환 또는 치환 플루오레닐임)의 플루오레닐 화합물 제조방법.
- 제1항에 있어서, 상기 희석액은 액체 알칸 또는 액체 방향족 화합물인 방법.
- 제2항에 있어서, 상기 희석액은 펜탄, 헥산, 톨루엔 또는 이들의 혼합물인 방법.
- 제1-3항중 어느 한 항에 있어서, 일반식 F1-R-X 의 상기 플루오레닐 화합물이 실질적으로 순수한 형태로 희석액으로부터 분리되는 방법.
- 제1-3항중 어느 한 항에 있어서, 플루오레닐 염대 디할로 화합물의 몰비는 약1/1 이하인 방법.
- 제1-3항 중 어느 한 항에 있어서, 상기 디할로 화합물 상기 플루오레닐 염이 주위 온도에서 반응되는 방법.
- 제1-3항 중 어느 한 항에 있어서, 플루오레닐염이 디할로 화합물 및 희석액의 용액에 점차로 첨가되는 방법.
- 제1-3항 중 어느 한 항에 있어서, R이 1내지 20탄소 원자를 지닌 알킬렌 라디칼인 방법.
- 제8항에 있어서, R이 1내지 5탄소원자를 함유하는 방법.
- 제9항에 있어서, R이 -CH2-인 방법.
- 제9항에 있어서, R이 주사슬내에 2내지 4탄소 원자를 함유하는 방법.
- 제1-3항중 어느 한 항에 있어서, R이 디메틸실릴인 방법.
- 제1-3항중 어느 한 항에 있어서, 상기 플루오레닐이 비치환 플루오레닐인 방법.
- 제1-3항중 어느 한 항에 있어서. 플루오레닐이 탄화수소 치환체가 9 위치이외의 위치에 있는 탄화수소-치환 플루오레닐인 방법.
- 제1-3항중 어느 한 항에 있어서, 9-(트리메틸실릴)플루오레닐 염이 디클로로메탄과 반응되어 9-(트리메틸실릴)-9-(클로로메틸) 플루오렌을 생성하고, 이때, 상기 9-(트리메틸실릴)플루오레닐 리튬염은 9-(트리메틸실릴)플루오렌을 알킬리튬과 반응시킴으로써 제조되는 방법.
- 제15항에 있어서, 결과 생성된 9-(트리메틸실릴)-9-(클로로메틸)플루오렌을 시클로펜타디엔의 알칼리금속 염과 반응시킴으로 구성되는 1-(시클로펜타디에닐)-1-(플루오레닐)메탄 제조 방법.
- 제16항에 있어서, 상기 9-(트리메틸실릴)-9-(클로로 메틸)플루오렌이 플로필렌 탄산염의 존재하에서 시클로펜타디에닐 나트륨과 반응되는 방법.
- 제16항에 있어서, 상기 9-(트리메틸실릴)-9-(클로로 메틸)플루오렌이 헥사메틸 인산 트리아미드의 존재하에서 시클로펜타디에닐 리튬과 반응되는 방법.
- 일반식 Z-R-X (이때, X가 Cl, Br또는 I임)의 플루오레닐 할로겐화물과 Z'의 알칼리 금속 염의 반응으로 구성되는, 일반식 Z-R-Z' (이때, Z는 비치환 또는 치환 플루오레닐이고, Z'은 Z와 상이한 것으로, 비치환 플루오레닐, 치환 플루오레닐, 비치환 시클로펜타디에닐, 치환 시클로펜타디에닐, 비치환 인데닐, 치환 인데닐 또는 테트라히드로인데닐이고, R은 알킬렌이거나 이가의 Ge, Si, B, Al, P 또는 Sn 라디칼임)의 플루오레닐화합물 제조방법.
- 제19항에 있어서, 플루오레닐 할로겐화물이 제1-18항 중 어느 한 항에 따른 방법에 의해 제조되는 방법.
- 제19항에 있어서, Z-R-X 는 Z'염을 위한 비-극성 액체 용매내에서 Z의 알칼리 금속 염과 반응되는 방법.
- 제19-21항중 어느 한 항에 있어서, 일반식 Z-R-Z'의 결과의 화합물은 실질적으로 순수한 형태로 희석액으로부터 분리되는 방법.
- 제19-21항 중 어느 한 항에 있어서, R은 -CH2-CH2-, -CH2-CH2-CH2-, 또는인 방법.
- 제19-21항 중 어느 한 항에 있어서, Z는 비치환 플루오레닐인 방법.
- 제24항에 있어서, Z'은 비치환 시클로펜타디에닐, 비치환인데닐, 또는 메틸 시클로펜타디에닐인 방법.
- 제19-21항 중 어느 한 항에 있어서, Z는 알킬-치환 플루오레닐인 방법.
- 일반식 Z-Si(CH3)3의 화합물을 알칼리 금속 알킬과 반응시켜 Z-Si(CH3)3의 알칼리 금속 알킬 염을 형성하고, 상기 알칼리 금속 알킬염을, 디할로 메탄(이때, 디할로 메탄의 할로겐이 각각 개별적으로 Cl, Br또는 I임)과 반응시켜 9-할로겐화메틸 -9- 트리메틸 실릴 Z를 생성하며, 상기 9-할로겐화메틸 -9- 트리메틸 실릴 Z를 Z'의 알칼리 금속염과 반응시킴으로 구성되는, 식 Z-CH2-Z'(이때, Z및 Z'은 상이한 것으로, Z는 비치환 플루오레닐 또는 치환 플루오레닐이고 Z'은 비치환 시클로펜타디에닐, 치환 시클로펜타디에닐, 비치환 인데닐, 치환 인데닐, 테드라히드로 인데닐, 비치환 플루오레닐, 또는 치환 플루오레닐임) 의 플루오레닐 화합물의 제조방법.
- 제27항에 있어서, Z는 2,7-디-삼차-부틸-플루 오레닐인 방법.
- 제27또는 28항에 있어서, Z'은 시클로펜타디에닐 인 방법.
- 제27항에 있어서, Z는 비치환 플루오레닐이고, Z'은 비치환 시클로펜타디에닐인 방법.
- 제27항에 있어서, Z는 비치환 플루오레닐이고, Z'은 비치환 인데닐인 방법.
- 1-(2,7-디-삼차-부틸-9-플루오레닐)-1-(시클로펜타디에닐)메탄.
- 1-(9-플루오레닐)-1-(시클로펜타디에닐)메탄.
- 9-(트리메틸실릴)-9-(클로로메틸)플루오렌.
- 제1-3항중 어느 한 항에 따른 방법에 의해 제조된 화합물로부터의 제32-34항중 어느 한 항에 따른 화합물로부터 제조되는 메탈로센 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US07/697,363 US5191132A (en) | 1991-05-09 | 1991-05-09 | Cyclopentadiene type compounds and method for making |
US07/697,363 | 1991-05-09 | ||
US7/697,363 | 1991-05-09 |
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US11845814B2 (en) | 2022-02-01 | 2023-12-19 | Chevron Phillips Chemical Company Lp | Ethylene polymerization processes and reactor systems for the production of multimodal polymers using combinations of a loop reactor and a fluidized bed reactor |
US20230331875A1 (en) | 2022-04-19 | 2023-10-19 | Chevron Phillips Chemical Company Lp | Loop slurry periodogram control to prevent reactor fouling and reactor shutdowns |
WO2023239560A1 (en) | 2022-06-09 | 2023-12-14 | Formosa Plastics Corporaton, U.S.A. | Clay composite support-activators and catalyst compositions |
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US3426069A (en) * | 1967-09-11 | 1969-02-04 | Union Carbide Corp | Bis(9-(substituted alkyl)fluoren-9-yl)alkanes |
US4547603A (en) * | 1982-04-23 | 1985-10-15 | Ethyl Corporation | Methylcyclopentadiene synthesis |
DE3443087A1 (de) * | 1984-11-27 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von polyolefinen |
DE3508887A1 (de) * | 1985-03-13 | 1986-09-25 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von optisch aktiven polyolefinen |
US4808561A (en) * | 1985-06-21 | 1989-02-28 | Exxon Chemical Patents Inc. | Supported polymerization catalyst |
US4794096A (en) * | 1987-04-03 | 1988-12-27 | Fina Technology, Inc. | Hafnium metallocene catalyst for the polymerization of olefins |
US4892851A (en) * | 1988-07-15 | 1990-01-09 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
DE3840772A1 (de) * | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
IT8919252A0 (it) * | 1989-01-31 | 1989-01-31 | Ilano | Catalizzatori per la polimerizzazione di olefine. |
DE3907964A1 (de) * | 1989-03-11 | 1990-09-13 | Hoechst Ag | Verfahren zur herstellung eines syndiotaktischen polyolefins |
DE3907965A1 (de) * | 1989-03-11 | 1990-09-13 | Hoechst Ag | Verfahren zur herstellung eines syndiotaktischen polyolefins |
DE3916553A1 (de) * | 1989-05-20 | 1990-11-22 | Hoechst Ag | Syndio- isoblockpolymer und verfahren zu seiner herstellung |
JPH0469394A (ja) * | 1990-07-09 | 1992-03-04 | Mitsui Toatsu Chem Inc | 新規遷移金属化合物及びこれを用いたシンジオタクチックポリ―α―オレフィンの製造方法 |
JP2956042B2 (ja) * | 1990-11-01 | 1999-10-04 | 三菱化学株式会社 | オレフィン重合体の製造法 |
EP0485823B1 (de) * | 1990-11-12 | 1995-03-08 | Hoechst Aktiengesellschaft | 2-Substituierte Bisindenylmetallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren bei der Olefinpolymerisation |
DE59107926D1 (de) * | 1990-11-12 | 1996-07-18 | Hoechst Ag | Metallocene mit Liganden aus 2-substituierten Indenylderivaten, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
US5347026A (en) * | 1993-06-11 | 1994-09-13 | Phillips Petroleum Company | Fluorene compounds and methods for making |
-
1991
- 1991-05-09 US US07/697,363 patent/US5191132A/en not_active Expired - Lifetime
-
1992
- 1992-02-20 CA CA002061559A patent/CA2061559C/en not_active Expired - Fee Related
- 1992-03-14 CN CN92101762A patent/CN1030068C/zh not_active Expired - Fee Related
- 1992-05-07 NO NO92921805A patent/NO921805L/no unknown
- 1992-05-08 EP EP92107781A patent/EP0512554B1/en not_active Expired - Lifetime
- 1992-05-08 JP JP4116375A patent/JPH05148166A/ja active Pending
- 1992-05-08 ES ES92107781T patent/ES2106795T3/es not_active Expired - Lifetime
- 1992-05-08 MX MX9202154A patent/MX9202154A/es unknown
- 1992-05-08 KR KR1019920007931A patent/KR0178279B1/ko not_active IP Right Cessation
- 1992-05-08 AT AT92107781T patent/ATE158269T1/de not_active IP Right Cessation
- 1992-05-08 DE DE69222221T patent/DE69222221T2/de not_active Expired - Fee Related
-
1993
- 1993-01-11 US US08/003,221 patent/US5406013A/en not_active Expired - Lifetime
-
1994
- 1994-08-15 US US08/290,315 patent/US5541351A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1030068C (zh) | 1995-10-18 |
NO921805L (no) | 1992-11-10 |
DE69222221T2 (de) | 1998-01-15 |
ES2106795T3 (es) | 1997-11-16 |
EP0512554B1 (en) | 1997-09-17 |
CA2061559C (en) | 1998-01-06 |
CA2061559A1 (en) | 1992-11-10 |
US5406013A (en) | 1995-04-11 |
DE69222221D1 (de) | 1997-10-23 |
ATE158269T1 (de) | 1997-10-15 |
EP0512554A2 (en) | 1992-11-11 |
JPH05148166A (ja) | 1993-06-15 |
KR0178279B1 (ko) | 1999-05-15 |
MX9202154A (es) | 1992-11-01 |
EP0512554A3 (en) | 1994-06-01 |
US5191132A (en) | 1993-03-02 |
NO921805D0 (no) | 1992-05-07 |
US5541351A (en) | 1996-07-30 |
CN1066440A (zh) | 1992-11-25 |
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