KR930009968A - 치환된 인덴의 제조방법 및 메탈로센 촉매용 리간드 시스템으로서의 이의 용도 - Google Patents
치환된 인덴의 제조방법 및 메탈로센 촉매용 리간드 시스템으로서의 이의 용도 Download PDFInfo
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- KR930009968A KR930009968A KR1019920022688A KR920022688A KR930009968A KR 930009968 A KR930009968 A KR 930009968A KR 1019920022688 A KR1019920022688 A KR 1019920022688A KR 920022688 A KR920022688 A KR 920022688A KR 930009968 A KR930009968 A KR 930009968A
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- 238000000034 method Methods 0.000 title claims 4
- 150000002469 indenes Chemical class 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 239000012968 metallocene catalyst Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 150000001336 alkenes Chemical class 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 239000013067 intermediate product Substances 0.000 claims abstract 2
- 238000006116 polymerization reaction Methods 0.000 claims abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052710 silicon Inorganic materials 0.000 claims 4
- 239000010703 silicon Substances 0.000 claims 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 229910052726 zirconium Inorganic materials 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 229910052735 hafnium Inorganic materials 0.000 claims 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 239000010955 niobium Substances 0.000 claims 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 229910052715 tantalum Inorganic materials 0.000 claims 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
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Abstract
본 발명은 일반식(I)의 화합물을 일반식(Ⅱ)의 화합물과 반응시켜 상응하는 인다논을 수득하고, 당해 화합물을 환원 및 탈수시킴으로써 일반식(Ⅳ)또는 (Ⅳa)의 화합물로 전환시킴을 특징으로 하여, 일반식(Ⅳ)또는 일반식(Ⅳa)의 화합물을 제조하는 방법에 관한 것이다.
상기식에서, R1내지 R5는 바람직하게는 수소 또는 알킬이고, X1및 X2는 바람직하게는 할로겐이다. 일반식 (Ⅳ) 및 (Ⅳa)의 화합물은 올레핀 중합용으로 적합한 촉매 성분인 키랄 메탈로센 착물을 제조하기 위한 중요한 중간 생성물이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (22)
- 일반식 (I)의 화합물을 프리델-크라프츠 촉매의 존재하에 일반식(Ⅱ)의 화합물 또는 이의 무수물과 반응시켜 일반식(Ⅲ)또는 일반식(Ⅲa)의 화합물을 수득하고, 당해 화합물을 공지된 방법으로 환원 및 탈수시킴으로써 일반식(Ⅳ) 또는 (Ⅳa)의 화합물로 전환시킴을 특징으로 하여, 일반식(Ⅳ)의 화합물 또는 이의 이성체인 일반식(Ⅳa)의 화합물을 제조하는 방법.
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- 상기식에서, R1, R2, R3, R4및 R5는 동일하거나 상이하고, 수소, (C1-C20)알킬, (C6-C14)아릴, (C1-C10)알콕시, (C2-C10)알케닐, (C7-C20)아릴알킬, (C7-C20)알킬아릴, (C6-C10)아릴옥시, (C1-C10)플루오로알킬, (C6-C10)할로게노아릴, (C2-C10)알키닐, 라디칼-SiR6 3(여기서, R6은 (C1-C10)알킬이다), 할로겐 원자 또는 1개 이상의 헤테로 원자를 함유할 수 있는 5 또는 6원환의 헤테로 방향족 라디칼이거나, 인접한 라디칼 R1내지 R4는 이들을 결합하는 원자와 함께 1개 이상의 환을 형성하고, X1및 X2는 동일하거나 상이하고, 친핵성 이탈그룹이다.
- 제1항에 있어서, 일반식(Ⅳ) 및 (Ⅳa)에서, R1, R2, R3및 R4가 동일하거나 상이하고, 수소, (C1-C10)알킬, (C6-C14)아릴, (C1-C4)알콕시, (C2-C6)알케닐, (C1-C6)플루오로알킬, 할로겐 원자 또는 1개 이상의 헤테로 원자를 함유할 수 있는 5 또는 6원환의 헤테로 방향족 라디칼이거나, 인접한 라디칼 R1내지 R4가 이들을 결합하는 원자와 함께 1개의 환을 형성하고, R5가 (C1-C10)알킬인 방법.
- 제1항 또는 제2항에 있어서, 일반식(Ⅳ) 및 (Ⅳa)에서, R1, R2, R3및 R4가 동일하거나 상이하고, 수소, (C1-C10)알킬이거나, 라디칼 R1및 R2또는 R3및 R4가 이들을 결합하는 원자와 함께 1개의 환을 형성하고, R5가 메틸인 방법.
- 제1항 내지 제3항 중의 어느 한 항에 있어서, 일반식(Ⅱ)에서 X1및 X2가 할로겐 원자인 방법.
- 제1항 내지 제4항 중의 어느 한 항에 있어서, AlCl3가 프리델-크라프츠 촉매로서 사용되는 방법.
- 제1항 내지 제3항 중의 어느 한 항에 따른 일반식(Ⅳ) 또는 (Ⅳa)의 화합물의 메탈로센 착물 제조시의 중간 생성물로서의 용도.
- 일반식(Ⅵ)의 화합물.
-
- 상기식에서, M1은 티탄, 지르코늄, 하프늄, 바나듐, 니오브 또는 탄탈이고, R1, R2, R3, R4및 R5는 동일하거나 상이하고, 수소, (C1-C20)알킬, (C6-C14) 아릴, (C1-C10)알콕시, (C2-C10)알케닐, (C7-C20)아릴알킬, (C7-C20)알킬아릴, (C6-C10)아릴옥시, (C1-C10)플루오로알킬, (C6-C10)할로게노아릴, (C2-C10)알키닐, 라디칼-SiR6 3(여기서, R6은 (C1-C10)알킬이다), 할로겐 원자 또는 1개 이상의 헤테로 원자를 함유할 수 있는 5 또는 6원환의 헤테로 방향족 라디칼이거나, 인접한 라디칼 R1내지 R4는 이들을 결합하는 원자와 함께 1개 이상의 환을 형성하며, R7은 라디칼
-
- (여기서, M2는 탄소, 규소, 게르마늄 또는 주석이고, R8및 R9는 동일하거나 상이하며, 수소, (C1-C20)알킬, (C6-C14)아릴, (C1-C10)알콕시, (C2-C10)알케닐, (C7-C20)아릴알킬, (C7-C20)알킬아릴, (C6-C10)아릴옥시, (C1-C10)플루오로알킬, (C6-C10)할로게노아릴, (C2-C10)알키닐 또는 할로겐이거나, R8및 R9는 이들을 결합하는 원자와 함께 환을 형성하고, p는 0, 1, 2 또는 3이다)이고, R10및 R11은 동일하거나 상이하며, (C1-C10)알킬, (C1-C10)알콕시, (C6-C10)아릴, (C6-C10)아릴옥시, (C2-C10)알케닐, , (C7-C40)아릴알킬, (C7-C40)알킬아릴, (C8-C40)아릴알케닐, 하이드록실 또는 할로겐 원자이다.
- 제7항에 있어서, M1이 지르코늄 또는 하프늄, 특히 지르코늄이고, R1, R2, R3및 R4는 동일하거나 상이하며 수소, (C1-C10)알킬, (C6-C14)아릴, (C1-C4)알콕시, (C2-C6)알케닐, (C1-C6)플로오로알킬, 할로겐 원자 또는 1개이상의 헤테로 원자를 함유할수 있는 5 또는 6원 환의 헤테로 방향족 라디칼이거나, 인접한 라디칼 R1내지 R4가 이들을 결합하는 원자와 함께 환을 형성하고, R5는 (C1-C10)알킬이며, M2가 탄소 또는 규소, 특히 규소이고, R8및 R9가 동일하거나 상이하며 수소, (C1-C6)알킬, (C6-C10)아릴, (C1-C6)알콕시, (C2-C4)알케닐, (C7-C10)아릴알킬 또는 (C7-C10)알킬아릴이거나, R8및 R9는 이들을 결합하는 원자와 함께 환을 형성하고, p가 1 또는 2, 바람직하게는 1이며, R10및 R11이 동일하거나 상이하고 수소, (C1-C3)알킬, 특히 메틸, (C1-C3)알콕시, (C6-C8)아릴, (C6-C8)아릴옥시, (C2-C4)알케닐, (C7-C10)아릴알킬, (C7-C10)알킬아릴, (C8-C12)아릴알케닐 또는 할로겐 원자, 바람직하게는 염소인 일반식(Ⅵ)의 화합물.
- 제7항 또는 제8항에 있어서, M2가 규소이고, R8및 R9가 동일하거나 상이하며 (C1-C6)알킬 또는 (C6-C10)아릴인 일반식(Ⅵ)의 화합물.
- 제7항 내지 제9항 중의 어느 한 항에 있어서, 일반식(Ⅵ)의 인데닐 라디칼이 2,6-위치, 2,4,6-위치, 2,4,5-위치, 2,4,5,6-위치 또는 2,4,5,6,7-위치에서 치환된 일반식(Ⅵ)의 화합물.
- 제7항 내지 제10항 중의 어느 한 항에 있어서, 일반식(Ⅵ)의 인데닐 라디칼이 2,4,6-위치와 2,4,5-위치에서 치환된 일반식 (Ⅵ)의 화합물.
- 제10항 또는 제11항에 있어서, 일반식(Ⅵ)의 인데닐 라디칼이 (C1-C4)알킬에 의해 치환된 일반식(Ⅵ)의 화합물.
- 제10항 또는 제11항에 있어서, 일반식(Ⅵ)의 인데닐 라디칼이 벤조-융합된 일반식 (Ⅵ)의 화합물.
- 올레핀의 중합에 있어서, 제7항 내지 제13항 중의 어느 한 항에 따른 일반식(Ⅵ)의 화합물의 촉매 성분으로서의 용도.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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-
1992
- 1992-09-30 TW TW081107748A patent/TW309523B/zh active
- 1992-11-27 EP EP92120289A patent/EP0545304B1/de not_active Expired - Lifetime
- 1992-11-27 AU AU29727/92A patent/AU655088B2/en not_active Ceased
- 1992-11-27 CA CA002084016A patent/CA2084016C/en not_active Expired - Lifetime
- 1992-11-27 ES ES92120289T patent/ES2177523T3/es not_active Expired - Lifetime
- 1992-11-27 DE DE59209962T patent/DE59209962D1/de not_active Expired - Lifetime
- 1992-11-27 ZA ZA929215A patent/ZA929215B/xx unknown
- 1992-11-27 JP JP31910192A patent/JP3290218B2/ja not_active Expired - Fee Related
- 1992-11-27 AT AT92120289T patent/ATE219494T1/de not_active IP Right Cessation
- 1992-11-28 KR KR1019920022688A patent/KR100322976B1/ko not_active IP Right Cessation
- 1992-11-30 RU RU92004483/04A patent/RU2103250C1/ru not_active IP Right Cessation
-
1995
- 1995-06-05 US US08/462,588 patent/US5852142A/en not_active Expired - Lifetime
- 1995-06-05 US US08/464,459 patent/US6051522A/en not_active Expired - Lifetime
- 1995-06-05 US US08/462,587 patent/US5840948A/en not_active Expired - Lifetime
-
1997
- 1997-07-10 US US08/890,942 patent/US5929264A/en not_active Expired - Lifetime
-
2001
- 2001-12-12 JP JP2001379159A patent/JP3434288B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AU2972792A (en) | 1993-06-03 |
ZA929215B (en) | 1993-05-27 |
JP2002226405A (ja) | 2002-08-14 |
JP3434288B2 (ja) | 2003-08-04 |
EP0545304A1 (de) | 1993-06-09 |
US5929264A (en) | 1999-07-27 |
JP3290218B2 (ja) | 2002-06-10 |
ATE219494T1 (de) | 2002-07-15 |
TW309523B (ko) | 1997-07-01 |
US5840948A (en) | 1998-11-24 |
RU2103250C1 (ru) | 1998-01-27 |
DE59209962D1 (de) | 2002-07-25 |
EP0545304B1 (de) | 2002-06-19 |
US6051522A (en) | 2000-04-18 |
CA2084016C (en) | 2004-06-22 |
ES2177523T3 (es) | 2002-12-16 |
US5852142A (en) | 1998-12-22 |
AU655088B2 (en) | 1994-12-01 |
KR100322976B1 (ko) | 2002-05-01 |
CA2084016A1 (en) | 1993-05-31 |
JPH06206890A (ja) | 1994-07-26 |
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