JP2015502333A5 - - Google Patents
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- JP2015502333A5 JP2015502333A5 JP2014535775A JP2014535775A JP2015502333A5 JP 2015502333 A5 JP2015502333 A5 JP 2015502333A5 JP 2014535775 A JP2014535775 A JP 2014535775A JP 2014535775 A JP2014535775 A JP 2014535775A JP 2015502333 A5 JP2015502333 A5 JP 2015502333A5
- Authority
- JP
- Japan
- Prior art keywords
- ruthenium
- substituted
- group
- rucl
- unsubstituted
- 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.)
- Ceased
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- 229910052707 ruthenium Inorganic materials 0.000 claims description 116
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 100
- 239000003446 ligand Substances 0.000 claims description 77
- -1 ammonium cations Chemical class 0.000 claims description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 43
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 42
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 33
- 239000012433 hydrogen halide Substances 0.000 claims description 33
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 229910052698 phosphorus Inorganic materials 0.000 claims description 30
- 239000011574 phosphorus Substances 0.000 claims description 30
- 239000002243 precursor Substances 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 29
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 10
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 8
- RZUNIXAGSKNOIB-HSFFGMMNSA-N (1z,3e)-cyclododeca-1,3-diene Chemical compound C1CCCC\C=C/C=C/CCC1 RZUNIXAGSKNOIB-HSFFGMMNSA-N 0.000 claims description 7
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 7
- MZJCFRKLOXHQIL-CCAGOZQPSA-N (1Z,3Z)-cyclodeca-1,3-diene Chemical compound C1CCC\C=C/C=C\CC1 MZJCFRKLOXHQIL-CCAGOZQPSA-N 0.000 claims description 5
- HVSYSQGJZITGQV-CCAGOZQPSA-N (1Z,3Z)-cyclonona-1,3-diene Chemical compound C1CC\C=C/C=C\CC1 HVSYSQGJZITGQV-CCAGOZQPSA-N 0.000 claims description 5
- KGGDRNQJDOBVII-CCAGOZQPSA-N (1Z,3Z)-cycloundeca-1,3-diene Chemical compound C1CCC\C=C/C=C\CCC1 KGGDRNQJDOBVII-CCAGOZQPSA-N 0.000 claims description 5
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229940087305 limonene Drugs 0.000 claims description 5
- 235000001510 limonene Nutrition 0.000 claims description 5
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003003 phosphines Chemical class 0.000 claims description 5
- 229930006978 terpinene Natural products 0.000 claims description 5
- 150000003507 terpinene derivatives Chemical class 0.000 claims description 5
- 150000003303 ruthenium Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 44
- 239000000543 intermediate Substances 0.000 description 32
- 239000003638 chemical reducing agent Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 239000012327 Ruthenium complex Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 6
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 6
- 230000001419 dependent effect Effects 0.000 description 6
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- RADGOBKLTHEUQO-UHFFFAOYSA-N ruthenium(4+) Chemical compound [Ru+4] RADGOBKLTHEUQO-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 4
- 150000005671 trienes Chemical class 0.000 description 4
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910021474 group 7 element Inorganic materials 0.000 description 3
- 229910021472 group 8 element Inorganic materials 0.000 description 3
- 238000010335 hydrothermal treatment Methods 0.000 description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical group Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical compound CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 238000007101 Grubbs Olefin metathesis reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/272,788 | 2011-10-13 | ||
| US13/272,788 US8779152B2 (en) | 2011-10-13 | 2011-10-13 | Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes |
| US13/606,640 | 2012-09-07 | ||
| US13/606,640 US8975414B2 (en) | 2011-10-13 | 2012-09-07 | Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes |
| PCT/US2012/059280 WO2013055644A2 (en) | 2011-10-13 | 2012-10-09 | Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015502333A JP2015502333A (ja) | 2015-01-22 |
| JP2015502333A5 true JP2015502333A5 (cg-RX-API-DMAC7.html) | 2015-11-19 |
Family
ID=47116392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014535775A Ceased JP2015502333A (ja) | 2011-10-13 | 2012-10-09 | ルテニウムカルベン錯体の先駆物質を調製するための方法およびルテニウムカルベン錯体 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8975414B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2766378B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2015502333A (cg-RX-API-DMAC7.html) |
| CN (1) | CN104302652B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2012323398B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112014008924A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2851899A1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2014DN03420A (cg-RX-API-DMAC7.html) |
| MX (1) | MX349199B (cg-RX-API-DMAC7.html) |
| MY (1) | MY185097A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2619112C2 (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201401419UA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013055644A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201402630B (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8779152B2 (en) * | 2011-10-13 | 2014-07-15 | Elevance Renewable Sciences, Inc. | Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes |
| US9512157B2 (en) | 2012-11-30 | 2016-12-06 | Elevance Renewable Sciences, Inc. | Methods for preparing ruthenium carbene complexes and precursors thereto |
| EP3063592B1 (en) | 2013-10-30 | 2021-04-07 | California Institute of Technology | Direct photopatterning of robust and diverse materials |
| CN112705268B (zh) * | 2019-10-25 | 2024-02-13 | 香港中文大学 | 用于催化有氧氧化反应的两性离子-钌络合物 |
| KR102666413B1 (ko) * | 2020-12-14 | 2024-05-17 | 한화솔루션 주식회사 | 사이클로도데카트리엔의 선택수첨 반응을 위한 촉매 제조 방법 및 이의 제조방법으로 제조된 촉매 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130805A1 (de) * | 1981-08-04 | 1983-02-24 | Basf Ag, 6700 Ludwigshafen | Neue ruthenium/kohle-hydrierkatalysatoren, deren herstellung und verwendung zur selektiven hydrierung von ungesaettigten carbonylverbindungen |
| FR2651152B1 (fr) | 1989-08-23 | 1991-11-29 | Elf Aquitaine | Perfectionnement a la preparation de catalyseurs chiraux a base de complexes du ruthenium et du phosphore. |
| US5831108A (en) | 1995-08-03 | 1998-11-03 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
| US7329758B1 (en) | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| PL199412B1 (pl) * | 2002-10-15 | 2008-09-30 | Boehringer Ingelheim Int | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| KR100601984B1 (ko) * | 2005-01-20 | 2006-07-18 | 삼성에스디아이 주식회사 | 담지 촉매 및 그 제조방법 |
| JP4347857B2 (ja) * | 2006-02-28 | 2009-10-21 | 日鉱金属株式会社 | ：ヘキサクロロルテニウム酸アンモニウムを製造する方法 |
| JP2007302498A (ja) * | 2006-05-10 | 2007-11-22 | Sumitomo Metal Mining Co Ltd | 酸化ルテニウム粉とその製造方法 |
| US8779152B2 (en) * | 2011-10-13 | 2014-07-15 | Elevance Renewable Sciences, Inc. | Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes |
-
2012
- 2012-09-07 US US13/606,640 patent/US8975414B2/en active Active
- 2012-10-09 BR BR112014008924A patent/BR112014008924A2/pt not_active IP Right Cessation
- 2012-10-09 MY MYPI2014001042A patent/MY185097A/en unknown
- 2012-10-09 EP EP12780590.1A patent/EP2766378B1/en not_active Not-in-force
- 2012-10-09 MX MX2014004462A patent/MX349199B/es active IP Right Grant
- 2012-10-09 IN IN3420DEN2014 patent/IN2014DN03420A/en unknown
- 2012-10-09 AU AU2012323398A patent/AU2012323398B2/en not_active Ceased
- 2012-10-09 WO PCT/US2012/059280 patent/WO2013055644A2/en not_active Ceased
- 2012-10-09 CN CN201280050575.3A patent/CN104302652B/zh not_active Expired - Fee Related
- 2012-10-09 CA CA2851899A patent/CA2851899A1/en not_active Abandoned
- 2012-10-09 SG SG11201401419UA patent/SG11201401419UA/en unknown
- 2012-10-09 JP JP2014535775A patent/JP2015502333A/ja not_active Ceased
- 2012-10-09 RU RU2014117297A patent/RU2619112C2/ru active
-
2014
- 2014-04-10 ZA ZA2014/02630A patent/ZA201402630B/en unknown
-
2015
- 2015-01-30 US US14/610,519 patent/US9637510B2/en not_active Expired - Fee Related
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