JP2004532237A - ビス（シクロペンタジエニル）及びビス（インデニル）ルテニウム錯体の合成 - Google Patents
ビス（シクロペンタジエニル）及びビス（インデニル）ルテニウム錯体の合成 Download PDFInfo
- Publication number
- JP2004532237A JP2004532237A JP2002585451A JP2002585451A JP2004532237A JP 2004532237 A JP2004532237 A JP 2004532237A JP 2002585451 A JP2002585451 A JP 2002585451A JP 2002585451 A JP2002585451 A JP 2002585451A JP 2004532237 A JP2004532237 A JP 2004532237A
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentadienyl
- indenyl
- bis
- reaction mixture
- ethanol
- 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.)
- Pending
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 title claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- ZFNIANIHSTYACF-UHFFFAOYSA-N C1=CC2=CC=CC=C2C1[Ru]C1C2=CC=CC=C2C=C1 Chemical class C1=CC2=CC=CC=C2C1[Ru]C1C2=CC=CC=C2C=C1 ZFNIANIHSTYACF-UHFFFAOYSA-N 0.000 title description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 indenyl compound Chemical class 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- IQSUNBLELDRPEY-UHFFFAOYSA-N 1-ethylcyclopenta-1,3-diene Chemical compound CCC1=CC=CC1 IQSUNBLELDRPEY-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 4
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012327 Ruthenium complex Substances 0.000 abstract description 2
- BFCJQIXVGNRPBX-UHFFFAOYSA-N C1=CC=C2C([Ru])C=CC2=C1 Chemical compound C1=CC=C2C([Ru])C=CC2=C1 BFCJQIXVGNRPBX-UHFFFAOYSA-N 0.000 abstract 1
- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MWQKURVBJZAOSC-UHFFFAOYSA-N 1-propan-2-ylcyclopenta-1,3-diene Chemical compound CC(C)C1=CC=CC1 MWQKURVBJZAOSC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- YHGGQZOFJGJAMR-UHFFFAOYSA-N cyclopenta-1,3-diene ruthenium Chemical compound C1=CC=CC1.C1=CC=CC1.[Ru] YHGGQZOFJGJAMR-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- KRBSYIOFFXEHQK-UHFFFAOYSA-K ruthenium(3+);trichloride;dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cl-].[Ru+3] KRBSYIOFFXEHQK-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84562701A | 2001-04-30 | 2001-04-30 | |
| US09/938,952 US20020161253A1 (en) | 2001-04-30 | 2001-08-24 | Synthesis of bis (cyclopentadienyl) and bis (indenyl) ruthenium complexes |
| PCT/US2002/011834 WO2002088153A1 (en) | 2001-04-30 | 2002-04-11 | Synthesis of bis (cyclopendadienyl) and bis (indenyl) ruthenium complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004532237A true JP2004532237A (ja) | 2004-10-21 |
| JP2004532237A5 JP2004532237A5 (https=) | 2006-03-23 |
Family
ID=27126588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002585451A Pending JP2004532237A (ja) | 2001-04-30 | 2002-04-11 | ビス（シクロペンタジエニル）及びビス（インデニル）ルテニウム錯体の合成 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6642402B2 (https=) |
| EP (1) | EP1390375B1 (https=) |
| JP (1) | JP2004532237A (https=) |
| CA (1) | CA2445856C (https=) |
| WO (1) | WO2002088153A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011219475A (ja) * | 2010-04-13 | 2011-11-04 | Wc Heraeus Gmbh | 鉄族金属のビス（ペンタジエニル）錯体の製造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2912449A (en) * | 1955-06-02 | 1959-11-10 | Texaco Inc | Method for making bis-alkylated cyclopentadienyl compounds |
| US3306917A (en) * | 1965-08-02 | 1967-02-28 | Ethyl Corp | Process for preparing group viii metal cyclopentadienyl compounds |
| DE3205550A1 (de) * | 1982-02-17 | 1983-08-25 | Studiengesellschaft Kohle mbH, 4330 Mülheim | Herstellung von uebergangsmetallkomplexen |
| US4992305A (en) * | 1988-06-22 | 1991-02-12 | Georgia Tech Research Corporation | Chemical vapor deposition of transistion metals |
| JP3371328B2 (ja) * | 1997-07-17 | 2003-01-27 | 株式会社高純度化学研究所 | ビス（アルキルシクロペンタジエニル）ルテニウム錯 体の製造方法およびそれを用いたルテニウム含有薄膜 の製造方法 |
| US6002036A (en) * | 1997-07-17 | 1999-12-14 | Kabushikikaisha Kojundokagaku Kenkyusho | Process for producing bis(alkyl-cyclopentadienyl)ruthenium complexes and process for producing ruthenium-containing films by using the same |
| JP4512248B2 (ja) * | 2000-09-26 | 2010-07-28 | 田中貴金属工業株式会社 | ビス（アルキルシクロペンタジエニル）ルテニウムの製造方法及びその方法により製造されるビス（アルキルシクロペンタジエニル）ルテニウム並びにルテニウム薄膜又はルテニウム化合物薄膜の化学気相蒸着方法 |
| JP4759126B2 (ja) * | 2000-10-11 | 2011-08-31 | 田中貴金属工業株式会社 | 化学気相蒸着用の有機金属化合物及び化学気相蒸着用の有機金属化合物の製造方法並びに貴金属薄膜及び貴金属化合物薄膜の化学気相蒸着方法 |
| JP3598055B2 (ja) * | 2000-11-08 | 2004-12-08 | 田中貴金属工業株式会社 | ビス（アルキルシクロペンタジエニル）ルテニウムの製造方法及びその製造方法により製造されるビス（アルキルシクロペンタジエニル）ルテニウム並びにルテニウム薄膜又はルテニウム化合物薄膜の製造方法 |
| JP3620645B2 (ja) * | 2001-01-29 | 2005-02-16 | 田中貴金属工業株式会社 | ビス（シクロペンタジエニル）ルテニウム誘導体の製造方法及びその製造方法により製造されるビス（シクロペンタジエニル）ルテニウム誘導体並びにルテニウム薄膜又はルテニウム化合物薄膜の製造方法 |
| US20020161253A1 (en) * | 2001-04-30 | 2002-10-31 | Boulder Scientific Company | Synthesis of bis (cyclopentadienyl) and bis (indenyl) ruthenium complexes |
| US6521772B1 (en) * | 2001-09-27 | 2003-02-18 | Praxair Technology, Inc. | Synthesis of substituted ruthenocene complexes |
-
2002
- 2002-04-11 JP JP2002585451A patent/JP2004532237A/ja active Pending
- 2002-04-11 WO PCT/US2002/011834 patent/WO2002088153A1/en not_active Ceased
- 2002-04-11 CA CA2445856A patent/CA2445856C/en not_active Expired - Lifetime
- 2002-04-11 EP EP02719511A patent/EP1390375B1/en not_active Expired - Lifetime
- 2002-06-21 US US10/178,014 patent/US6642402B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011219475A (ja) * | 2010-04-13 | 2011-11-04 | Wc Heraeus Gmbh | 鉄族金属のビス（ペンタジエニル）錯体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2445856A1 (en) | 2002-11-07 |
| EP1390375A1 (en) | 2004-02-25 |
| EP1390375A4 (en) | 2007-04-11 |
| US6642402B2 (en) | 2003-11-04 |
| EP1390375B1 (en) | 2008-11-19 |
| CA2445856C (en) | 2011-11-01 |
| WO2002088153A1 (en) | 2002-11-07 |
| US20030045737A1 (en) | 2003-03-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20020161253A1 (en) | Synthesis of bis (cyclopentadienyl) and bis (indenyl) ruthenium complexes | |
| CN1612880A (zh) | 制备苯基丝氨酸及其类似物的方法 | |
| RU2337104C2 (ru) | СПОСОБ ДИАСТЕРЕОСЕЛЕКТИВНОГО СИНТЕЗА РАЦЕМИЧЕСКИХ ДИОРГАНОСИЛИЛБИС(2-МЕТИЛБЕНЗО[е]ИНДЕНИЛ)ЦИРКОНИЕВЫХ СОЕДИНЕНИЙ И РАЦЕМИЧЕСКОЕ СОЕДИНЕНИЕ ПЕРЕХОДНОГО МЕТАЛЛА | |
| JP2004532237A (ja) | ビス（シクロペンタジエニル）及びビス（インデニル）ルテニウム錯体の合成 | |
| CN1429230A (zh) | 钌化合物的制备方法 | |
| JP2004532237A5 (https=) | ||
| JPH03130293A (ja) | アリル基の除去方法 | |
| JP3673174B2 (ja) | チタノセンの芳香族誘導体の製造方法 | |
| AU2002250588A1 (en) | Synthesis of bis (cyclopendadienyl) and bis (indenyl) ruthenium complexes | |
| NO179101B (no) | Fremgangsmåte for fremstilling av dibeskyttet 2,3-hydroksymetyl-cyklobutanol | |
| JP2002020397A (ja) | 重合用触媒 | |
| US20250114775A1 (en) | Process for the preparation of [ru(oac)2(ligand)] catalysts | |
| JP2006503910A (ja) | 部分的に水素化されたラセミ体のａｎｓａ−メタロセン錯体の製造方法 | |
| JP4414225B2 (ja) | シクロペンタジエニルシリルアミンからチタンビスアルコキシ部位又はチタンジクロリド部位を含む有機金属錯体への転化 | |
| US20020107425A1 (en) | Method for synthesis of hydrocarbyl bridged indenes | |
| JP2002523479A (ja) | 銅触媒によるエナンチオ選択性アリル位置換反応 | |
| JPH0925284A (ja) | シクロペンタジエニルチタントリアルコキシ誘導体の製造方法 | |
| JP2005514423A (ja) | ジアルキル−アンサ−メタロセンの製造 | |
| RU2184739C1 (ru) | Способ получения галогенидов металлоценов | |
| RU2214415C1 (ru) | Способ получения галогенидов металлоценов (варианты) | |
| JP3804346B2 (ja) | パラジウムホスフィン錯体の精製方法 | |
| JP2946678B2 (ja) | キラルなフェロセン誘導体 | |
| KR20040099990A (ko) | 올레핀 중합용 라세믹 메탈로센 촉매 및 그 중간체인 비스인데닐 리간드의 제조방법 | |
| JPS62201836A (ja) | ３―（３―ハロゲノ―４―アルコキシフェニル）―３―メチルブタナール類の製造方法 | |
| JP2001131745A (ja) | 銅薄膜形成用有機銅化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050411 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060106 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060201 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20060912 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20061219 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20070316 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20070327 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20070816 |