PL414234A1 - Sposób wytwarzania kompleksów rutenu i związków pośrednich oraz ich zastosowanie w metatezie olefin - Google Patents
Sposób wytwarzania kompleksów rutenu i związków pośrednich oraz ich zastosowanie w metatezie olefinInfo
- Publication number
- PL414234A1 PL414234A1 PL414234A PL41423415A PL414234A1 PL 414234 A1 PL414234 A1 PL 414234A1 PL 414234 A PL414234 A PL 414234A PL 41423415 A PL41423415 A PL 41423415A PL 414234 A1 PL414234 A1 PL 414234A1
- Authority
- PL
- Poland
- Prior art keywords
- application
- ruthenium
- metathesis
- olefins
- intermediate compounds
- Prior art date
Links
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical class [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title 1
- 150000001336 alkenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000005649 metathesis reaction Methods 0.000 title 1
- 229910052707 ruthenium Inorganic materials 0.000 title 1
- 150000003303 ruthenium Chemical class 0.000 abstract 2
- 238000005865 alkene metathesis reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012041 precatalyst Substances 0.000 abstract 1
Classifications
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/40—Non-coordinating groups comprising nitrogen
- B01J2540/44—Non-coordinating groups comprising nitrogen being derivatives of carboxylic or carbonic acids, e.g. amide (RC(=O)-NR2, RC(=O)-NR-C(=O)R), nitrile, urea (R2N-C(=O)-NR2), guanidino (R2N-C(=NR)-NR2) groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Przedmiotem zgłoszenia jest nowy sposób wytwarzania kompleksów rutenu o wzorze (1) i związków pośrednich. Zgłoszenie dotyczy także zastosowania kompleksów rutenu o wzorze 1, jako prekatalizatorów i/lub katalizatorów w reakcjach metatezy olefin.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL414234A PL238806B1 (pl) | 2015-09-30 | 2015-09-30 | Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin |
| CA2999412A CA2999412C (en) | 2015-09-30 | 2016-07-27 | PROCESS FOR THE PRODUCTION OF RUTHENIUM COMPLEXES AND ASSOCIATED INTERMEDIARIES AND THEIR USE IN OLEFIN METATHESIS |
| CN201680056336.7A CN108137631B (zh) | 2015-09-30 | 2016-07-27 | 制备钌配位化合物及其中间体的方法和它们在烯烃复分解中的用途 |
| JP2018516190A JP6905978B2 (ja) | 2015-09-30 | 2016-07-27 | ルテニウム錯体およびその中間体の製造方法並びにオレフィンメタセシスにおけるその使用方法 |
| EP16774982.9A EP3356379B2 (en) | 2015-09-30 | 2016-07-27 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| AU2016330158A AU2016330158B2 (en) | 2015-09-30 | 2016-07-27 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| PCT/IB2016/054486 WO2017055945A1 (en) | 2015-09-30 | 2016-07-27 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| RU2018113805A RU2735724C1 (ru) | 2015-09-30 | 2016-07-27 | Способ получения комплексов рутения и их промежуточных соединений и их применение в метатезисе олефинов |
| KR1020187010104A KR102637889B1 (ko) | 2015-09-30 | 2016-07-27 | 루테늄 복합체 및 그의 중간체를 제조하는 방법 및 올레핀 복분해에서 그의 사용방법 |
| US15/764,123 US11192911B2 (en) | 2015-09-30 | 2016-07-27 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| EP21161627.1A EP3868769A1 (en) | 2015-09-30 | 2016-07-27 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| IL258354A IL258354B (en) | 2015-09-30 | 2018-03-26 | A process for creating complexes of ruthenium and their intermediates and their use in the metathesis of olefins |
| US17/513,752 US11976085B2 (en) | 2015-09-30 | 2021-10-28 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| US18/234,753 US12173015B2 (en) | 2015-09-30 | 2023-08-16 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
| US18/943,268 US12448404B2 (en) | 2015-09-30 | 2024-11-11 | Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL414234A PL238806B1 (pl) | 2015-09-30 | 2015-09-30 | Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL414234A1 true PL414234A1 (pl) | 2017-04-10 |
| PL238806B1 PL238806B1 (pl) | 2021-10-04 |
Family
ID=57045229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL414234A PL238806B1 (pl) | 2015-09-30 | 2015-09-30 | Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US11192911B2 (pl) |
| EP (2) | EP3868769A1 (pl) |
| JP (1) | JP6905978B2 (pl) |
| KR (1) | KR102637889B1 (pl) |
| CN (1) | CN108137631B (pl) |
| AU (1) | AU2016330158B2 (pl) |
| CA (1) | CA2999412C (pl) |
| IL (1) | IL258354B (pl) |
| PL (1) | PL238806B1 (pl) |
| RU (1) | RU2735724C1 (pl) |
| WO (1) | WO2017055945A1 (pl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL441535A1 (pl) * | 2022-06-23 | 2023-12-27 | Uniwersytet Warszawski | Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3129347T3 (pl) | 2014-04-10 | 2022-02-07 | California Institute Of Technology | Reakcje w obecności kompleksów rutenu |
| 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 |
| HUE069420T2 (hu) | 2016-11-09 | 2025-03-28 | Verbio Ver Bioenergie Ag | Metatézisreakciók katalizálására hasznosító ruténiumkomplexek |
| PL241085B1 (pl) * | 2016-11-10 | 2022-08-01 | Apeiron Synthesis Spolka Akcyjna | Zastosowanie kompleksów rutenu w reakcji metatezy olefin |
| PL243369B1 (pl) * | 2018-04-16 | 2023-08-14 | Apeiron Synthesis Spolka Akcyjna | Nowe kompleksy rutenu oraz ich zastosowanie w reakcjach metatezy olefin |
| CN112088044B (zh) | 2018-04-27 | 2023-10-24 | 阿朗新科德国有限责任公司 | 钌和锇催化剂用于丁腈橡胶复分解的用途 |
| PL426318A1 (pl) * | 2018-07-12 | 2020-01-13 | Apeiron Synthesis Spółka Akcyjna | Zastosowanie N-chelatujących kompleksów rutenu w reakcji metatezy |
| EP3650436A1 (en) * | 2018-11-06 | 2020-05-13 | Skotan S.A. | Method of preparing a mixture of 9-decenoic acid ethyl and 1-decene in an ethenolysis reaction from a raw material of technical purity |
| WO2020109217A2 (en) * | 2018-11-29 | 2020-06-04 | Umicore Ag & Co. Kg | Metal organic compounds |
| PL242934B1 (pl) * | 2019-12-23 | 2023-05-22 | Apeiron Synthesis Spolka Akcyjna | Kompleks rutenu i zastosowanie kompleksu rutenu jako katalizatora |
| US20230095887A1 (en) * | 2020-03-05 | 2023-03-30 | Firmenich Sa | Process for preparing perfuming intermediate |
| PL246181B1 (pl) | 2020-08-17 | 2024-12-16 | Apeiron Synthesis Spolka Akcyjna | Nowe kompleksy rutenu i ich zastosowanie w reakcji krzyżowej metatezy olefin |
| PL439977A1 (pl) * | 2021-12-23 | 2023-06-26 | Apeiron Synthesis Spółka Akcyjna | Nowe sterycznie aktywowane chelatujące kompleksy rutenu, sposób ich otrzymywania oraz ich zastosowanie w reakcjach metatezy olefin |
| CN114634436B (zh) * | 2022-04-08 | 2022-12-02 | 安徽泽升科技有限公司 | 一种含钌催化剂及其制备方法与用途 |
| PL442226A1 (pl) * | 2022-09-08 | 2024-03-11 | Uniwersytet Warszawski | Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin |
| WO2024262906A1 (ko) * | 2023-06-20 | 2024-12-26 | 포항공과대학교 산학협력단 | 루테늄 착화합물, 이를 포함하는 촉매, 및 상기 루테늄 착화합물의 합성방법 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6613910B2 (en) | 2001-04-02 | 2003-09-02 | California Institute Of Technology | One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts |
| US6818586B2 (en) | 2001-08-01 | 2004-11-16 | Cymetech, Llp | Hexacoordinated ruthenium or osmium 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 |
| EP1905777B2 (en) | 2005-07-04 | 2018-06-27 | Zannan Scitech Co., Ltd. | Ruthenium complex ligand, ruthenium complex, carried ruthenium complex catalyst and the preparing methods and the use thereof |
| US8067610B2 (en) | 2006-07-13 | 2011-11-29 | Yann Schrodi | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
| WO2008046106A2 (en) * | 2006-10-13 | 2008-04-17 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| FR2934178B1 (fr) * | 2008-07-25 | 2010-09-10 | Rhodia Operations | Compositions catalytiques pour la metathese de corps gras insatures avec des olefines et procedes de metathese les mettant en oeuvre |
| FR2947189B1 (fr) | 2009-06-29 | 2011-07-29 | Rhodia Operations | Procede de peparation d'une composition catalytique pour la metathese de corps gras insatures |
| EP2498909B1 (en) * | 2009-11-09 | 2014-08-27 | ExxonMobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
| CN102985409A (zh) | 2010-01-08 | 2013-03-20 | 蓝星有机硅法国两合公司 | 在溶液中制备卡宾的方法、尤其通过该方法获得的卡宾的新的稳定形式及其在催化中的应用 |
| 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 |
| FR2999184B1 (fr) | 2012-12-12 | 2015-01-09 | Ecole Nationale Superieure De Chimie De Rennes | Complexes de ruthenium comprenant un diaminocarbene n-heterocyclique insature dissymetrique |
| US9249170B2 (en) | 2013-04-11 | 2016-02-02 | California Institute Of Technology | Cyclic alkyl amino carbene (CAAC) ruthenium complexes as improved catalysts for ethenolysis reactions |
| PL3129347T3 (pl) | 2014-04-10 | 2022-02-07 | California Institute Of Technology | Reakcje w obecności kompleksów rutenu |
| 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 |
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2015
- 2015-09-30 PL PL414234A patent/PL238806B1/pl unknown
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2016
- 2016-07-27 US US15/764,123 patent/US11192911B2/en active Active
- 2016-07-27 CA CA2999412A patent/CA2999412C/en active Active
- 2016-07-27 JP JP2018516190A patent/JP6905978B2/ja active Active
- 2016-07-27 AU AU2016330158A patent/AU2016330158B2/en active Active
- 2016-07-27 RU RU2018113805A patent/RU2735724C1/ru active
- 2016-07-27 EP EP21161627.1A patent/EP3868769A1/en active Pending
- 2016-07-27 KR KR1020187010104A patent/KR102637889B1/ko active Active
- 2016-07-27 WO PCT/IB2016/054486 patent/WO2017055945A1/en not_active Ceased
- 2016-07-27 CN CN201680056336.7A patent/CN108137631B/zh active Active
- 2016-07-27 EP EP16774982.9A patent/EP3356379B2/en active Active
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2018
- 2018-03-26 IL IL258354A patent/IL258354B/en unknown
-
2021
- 2021-10-28 US US17/513,752 patent/US11976085B2/en active Active
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2023
- 2023-08-16 US US18/234,753 patent/US12173015B2/en active Active
-
2024
- 2024-11-11 US US18/943,268 patent/US12448404B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL441535A1 (pl) * | 2022-06-23 | 2023-12-27 | Uniwersytet Warszawski | Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3356379B2 (en) | 2025-09-03 |
| KR102637889B1 (ko) | 2024-02-19 |
| EP3868769A1 (en) | 2021-08-25 |
| PL238806B1 (pl) | 2021-10-04 |
| US12448404B2 (en) | 2025-10-21 |
| RU2735724C1 (ru) | 2020-11-06 |
| AU2016330158B2 (en) | 2021-05-13 |
| IL258354A (en) | 2018-05-31 |
| IL258354B (en) | 2022-03-01 |
| US20240076308A1 (en) | 2024-03-07 |
| US20250066402A1 (en) | 2025-02-27 |
| US11192911B2 (en) | 2021-12-07 |
| KR20180059822A (ko) | 2018-06-05 |
| JP2018535194A (ja) | 2018-11-29 |
| US11976085B2 (en) | 2024-05-07 |
| CA2999412C (en) | 2024-09-10 |
| JP6905978B2 (ja) | 2021-07-21 |
| US12173015B2 (en) | 2024-12-24 |
| CA2999412A1 (en) | 2017-04-06 |
| US20180298046A1 (en) | 2018-10-18 |
| CN108137631B (zh) | 2021-04-16 |
| AU2016330158A1 (en) | 2018-04-12 |
| EP3356379B1 (en) | 2021-03-10 |
| WO2017055945A1 (en) | 2017-04-06 |
| EP3356379A1 (en) | 2018-08-08 |
| US20220073549A1 (en) | 2022-03-10 |
| CN108137631A (zh) | 2018-06-08 |
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