JP2015525776A5 - - Google Patents
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- Publication number
- JP2015525776A5 JP2015525776A5 JP2015523570A JP2015523570A JP2015525776A5 JP 2015525776 A5 JP2015525776 A5 JP 2015525776A5 JP 2015523570 A JP2015523570 A JP 2015523570A JP 2015523570 A JP2015523570 A JP 2015523570A JP 2015525776 A5 JP2015525776 A5 JP 2015525776A5
- Authority
- JP
- Japan
- Prior art keywords
- carbons
- metathesis reaction
- general formula
- precursor
- catalyst
- 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.)
- Granted
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- LSMWOQFDLBIYPM-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-2h-imidazol-1-ium-2-ide Chemical compound CC1=CC(C)=CC(C)=C1N1[C-]=[N+](C=2C(=CC(C)=CC=2C)C)CC1 LSMWOQFDLBIYPM-UHFFFAOYSA-N 0.000 claims description 2
- XZDYFCGKKKSOEY-UHFFFAOYSA-N 1,3-bis[2,6-di(propan-2-yl)phenyl]-4,5-dihydro-2h-imidazol-1-ium-2-ide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1CCN(C=2C(=CC=CC=2C(C)C)C(C)C)[C]1 XZDYFCGKKKSOEY-UHFFFAOYSA-N 0.000 claims description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 18
- 238000005649 metathesis reaction Methods 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 7
- 239000002243 precursor Substances 0.000 claims 7
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- 239000007848 Bronsted acid Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000005865 alkene metathesis reaction Methods 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000005686 cross metathesis reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL400162A PL400162A1 (pl) | 2012-07-27 | 2012-07-27 | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
| PLP.400162 | 2012-07-27 | ||
| PCT/EP2013/065839 WO2014016422A1 (en) | 2012-07-27 | 2013-07-26 | Novel ruthenium complexes, their use in the metathesis reactions, and a process for carrying out the metathesis reaction |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015525776A JP2015525776A (ja) | 2015-09-07 |
| JP2015525776A5 true JP2015525776A5 (OSRAM) | 2016-11-04 |
| JP6121533B2 JP6121533B2 (ja) | 2017-04-26 |
Family
ID=48917515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523570A Active JP6121533B2 (ja) | 2012-07-27 | 2013-07-26 | 新規ルテニウム錯体、それらのメタセシス反応における使用方法、及びメタセシス反応を実施するための方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9328132B2 (OSRAM) |
| EP (1) | EP2877478B1 (OSRAM) |
| JP (1) | JP6121533B2 (OSRAM) |
| KR (1) | KR101749238B1 (OSRAM) |
| CN (1) | CN104428306B (OSRAM) |
| AU (1) | AU2013294909B2 (OSRAM) |
| CA (1) | CA2875956C (OSRAM) |
| IL (1) | IL236128A (OSRAM) |
| PL (2) | PL400162A1 (OSRAM) |
| RU (1) | RU2586213C1 (OSRAM) |
| SG (1) | SG11201408224SA (OSRAM) |
| WO (1) | WO2014016422A1 (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL400162A1 (pl) | 2012-07-27 | 2014-02-03 | Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
| PL238806B1 (pl) | 2015-09-30 | 2021-10-04 | Apeiron Synthesis Spolka Akcyjna | Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin |
| EP3386936B1 (en) * | 2015-12-10 | 2024-07-10 | Umicore AG & Co. KG | Olefin metathesis catalysts |
| EP3583088B1 (en) | 2017-02-17 | 2025-09-10 | Provivi, Inc. | Synthesis of pheromones and related materials via olefin metathesis |
| US11471867B2 (en) | 2017-06-23 | 2022-10-18 | Gwangju Institute Of Science And Technology | Ligand for forming ruthenium complex, ruthenium complex catalyst, production method therefor and use thereof |
| TWI758525B (zh) | 2017-08-10 | 2022-03-21 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| TWI777027B (zh) | 2018-01-26 | 2022-09-11 | 日商住友電木股份有限公司 | 聚環烯烴單體及由能夠產生光酸作為光學材料的化合物活化之催化劑 |
| US11939410B2 (en) | 2018-06-29 | 2024-03-26 | Apeiron Synthesis S.A. | Organoruthenium complexes as precatalysts for olefin metathesis |
| TWI794520B (zh) | 2018-06-29 | 2023-03-01 | 日商住友電木股份有限公司 | 作為 3d 列印材料之聚環烯烴單體及由能夠產生光酸之化合物活化之催化劑 |
| KR102513170B1 (ko) | 2018-12-21 | 2023-03-24 | 스미토모 베이클리트 컴퍼니 리미티드 | 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 |
| KR102670566B1 (ko) * | 2019-01-18 | 2024-05-31 | 광주과학기술원 | 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도 |
| US11692056B2 (en) | 2019-07-25 | 2023-07-04 | Promerus, Llc | Stable polycycloolefin polymer and inorganic nanoparticle compositions as optical materials |
| WO2021060061A1 (ja) * | 2019-09-27 | 2021-04-01 | 日本ゼオン株式会社 | 重合体含有物およびその製造方法、並びに、フィルム |
| US20240150384A1 (en) | 2021-02-02 | 2024-05-09 | Apeiron Synthesis S.A. | Long shelf life stable organoruthenium complexes as (pre)catalysts for olefin metathesis |
| TW202323266A (zh) | 2021-11-29 | 2023-06-16 | 美商普羅梅勒斯有限公司 | 作為光學材料之包含保存期限長期穩定的光活性本體聚合型多環烯烴組成物之雙重ｕｖ阻斷劑 |
| KR20250090340A (ko) | 2022-10-21 | 2025-06-19 | 메르크 파텐트 게엠베하 | 조성물 |
| WO2025012183A1 (en) | 2023-07-10 | 2025-01-16 | Merck Patent Gmbh | Composition |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2289568C2 (ru) * | 2001-03-26 | 2006-12-20 | Дау Глобал Текнолоджиз Инк. | Способ метатезиса сложных эфиров ненасыщенных жирных кислот или ненасыщенных жирных кислот с низшими олефинами и композиция гетерогенного катализатора, предназначенная для способа метатезиса |
| WO2002083742A2 (en) * | 2001-04-16 | 2002-10-24 | California Institute Of Technology | Group 8 transition metal carbene complexes as enantioselective olefin 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 |
| PL199428B1 (pl) | 2003-12-29 | 2008-09-30 | Polska Akademia Nauk Instytut | Nowe kompleksy rutenu, pochodne 2-alkoksy-4-nitrostyrenu jako (pre)katalizatory (54) reakcji metatezy, pochodne 2-alkoksy-4-nitrostyrenu jako związki pośrednie oraz sposób ich wytwarzania |
| RU2435778C2 (ru) * | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения |
| RU2311231C1 (ru) * | 2006-08-15 | 2007-11-27 | ООО "Объединенный центр исследований и разработок" | Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе |
| DE102006040569A1 (de) * | 2006-08-30 | 2008-03-06 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuken |
| DE102006043704A1 (de) | 2006-09-18 | 2008-03-27 | Umicore Ag & Co. Kg | Neue Metathesekatalysatoren |
| EP2255877B1 (en) | 2009-05-07 | 2014-09-24 | Umicore AG & Co. KG | Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands |
| RU2402572C1 (ru) * | 2009-07-09 | 2010-10-27 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" | Способ получения полидициклопентадиена и материалов на его основе |
| CN102476060B (zh) * | 2010-11-24 | 2013-07-10 | 中国石油化工股份有限公司 | 一种烯烃复分解催化剂及其制备方法 |
| PL400162A1 (pl) | 2012-07-27 | 2014-02-03 | Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
-
2012
- 2012-07-27 PL PL400162A patent/PL400162A1/pl unknown
-
2013
- 2013-07-26 US US14/406,741 patent/US9328132B2/en active Active
- 2013-07-26 WO PCT/EP2013/065839 patent/WO2014016422A1/en not_active Ceased
- 2013-07-26 AU AU2013294909A patent/AU2013294909B2/en active Active
- 2013-07-26 SG SG11201408224SA patent/SG11201408224SA/en unknown
- 2013-07-26 KR KR1020157000377A patent/KR101749238B1/ko not_active Expired - Fee Related
- 2013-07-26 PL PL13745377T patent/PL2877478T3/pl unknown
- 2013-07-26 RU RU2014152207/04A patent/RU2586213C1/ru active
- 2013-07-26 CN CN201380036034.XA patent/CN104428306B/zh active Active
- 2013-07-26 EP EP13745377.5A patent/EP2877478B1/en active Active
- 2013-07-26 JP JP2015523570A patent/JP6121533B2/ja active Active
- 2013-07-26 CA CA2875956A patent/CA2875956C/en active Active
-
2014
- 2014-12-08 IL IL236128A patent/IL236128A/en active IP Right Grant
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