CA2445856C - Synthesis of bis(cyclopendadienyl) and bis(indenyl) ruthenium complexes - Google Patents
Synthesis of bis(cyclopendadienyl) and bis(indenyl) ruthenium complexes Download PDFInfo
- Publication number
- CA2445856C CA2445856C CA2445856A CA2445856A CA2445856C CA 2445856 C CA2445856 C CA 2445856C CA 2445856 A CA2445856 A CA 2445856A CA 2445856 A CA2445856 A CA 2445856A CA 2445856 C CA2445856 C CA 2445856C
- Authority
- CA
- Canada
- Prior art keywords
- ruthenecene
- bis
- indenyl
- treating
- reaction mixture
- 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.)
- Expired - Lifetime
Links
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 230000015572 biosynthetic process Effects 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 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 23
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 indenyl compound Chemical class 0.000 claims abstract description 11
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- IQSUNBLELDRPEY-UHFFFAOYSA-N 1-ethylcyclopenta-1,3-diene Chemical compound CCC1=CC=CC1 IQSUNBLELDRPEY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 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
- 239000012327 Ruthenium complex Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 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 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 150000001875 compounds Chemical class 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
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000003303 ruthenium Chemical class 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 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
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical class [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 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
- 238000005187 foaming Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000000203 mixture Substances 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84562701A | 2001-04-30 | 2001-04-30 | |
| US09/845,627 | 2001-04-30 | ||
| US09/938,952 | 2001-08-24 | ||
| 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 |
|---|---|
| CA2445856A1 CA2445856A1 (en) | 2002-11-07 |
| CA2445856C true CA2445856C (en) | 2011-11-01 |
Family
ID=27126588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2445856A Expired - Lifetime CA2445856C (en) | 2001-04-30 | 2002-04-11 | Synthesis of bis(cyclopendadienyl) and bis(indenyl) ruthenium complexes |
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=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7893290B1 (en) * | 2010-04-13 | 2011-02-22 | W.C. Heraeus Gmbh | Process for the preparation of bis(pentadienyl)-complexes of iron group metals |
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
Also Published As
| Publication number | Publication date |
|---|---|
| CA2445856A1 (en) | 2002-11-07 |
| EP1390375A1 (en) | 2004-02-25 |
| EP1390375A4 (en) | 2007-04-11 |
| JP2004532237A (ja) | 2004-10-21 |
| US6642402B2 (en) | 2003-11-04 |
| EP1390375B1 (en) | 2008-11-19 |
| WO2002088153A1 (en) | 2002-11-07 |
| US20030045737A1 (en) | 2003-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220411 |