CA3096337A1 - Use of n-chelating ruthenium complexes in the metathesis reaction - Google Patents

Use of n-chelating ruthenium complexes in the metathesis reaction Download PDF

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Publication number
CA3096337A1
CA3096337A1 CA3096337A CA3096337A CA3096337A1 CA 3096337 A1 CA3096337 A1 CA 3096337A1 CA 3096337 A CA3096337 A CA 3096337A CA 3096337 A CA3096337 A CA 3096337A CA 3096337 A1 CA3096337 A1 CA 3096337A1
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CA
Canada
Prior art keywords
alkyl
optionally
aryl
alkoxy
heteroaryl
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
Application number
CA3096337A
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English (en)
French (fr)
Inventor
Rafal Gawin
Patryk KRAJCZY
Anna GAWIN
Krzysztof Skowerski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Apeiron Synthesis Sp zoo
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Apeiron Synthesis Sp zoo
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Publication date
Application filed by Apeiron Synthesis Sp zoo filed Critical Apeiron Synthesis Sp zoo
Publication of CA3096337A1 publication Critical patent/CA3096337A1/en
Pending legal-status Critical Current

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Classifications

    • 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)
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3096337A 2018-07-12 2019-07-10 Use of n-chelating ruthenium complexes in the metathesis reaction Pending CA3096337A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
PLPL426318 2018-07-12
PL426318A PL426318A1 (pl) 2018-07-12 2018-07-12 Zastosowanie N-chelatujących kompleksów rutenu w reakcji metatezy
PCT/IB2019/055864 WO2020012370A1 (en) 2018-07-12 2019-07-10 Use of n-chelating ruthenium complexes in the metathesis reaction

Publications (1)

Publication Number Publication Date
CA3096337A1 true CA3096337A1 (en) 2020-01-16

Family

ID=69141631

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3096337A Pending CA3096337A1 (en) 2018-07-12 2019-07-10 Use of n-chelating ruthenium complexes in the metathesis reaction

Country Status (7)

Country Link
US (1) US12251688B2 (enExample)
EP (1) EP3820609B1 (enExample)
JP (1) JP2021530432A (enExample)
KR (1) KR20210030938A (enExample)
CA (1) CA3096337A1 (enExample)
PL (2) PL426318A1 (enExample)
WO (1) WO2020012370A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102536751B1 (ko) * 2020-04-07 2023-05-24 주식회사 엘지화학 촉매 조성물, 이를 포함하는 세척액 조성물 및 이를 이용한 중합장치의 세척방법
PL246181B1 (pl) * 2020-08-17 2024-12-16 Apeiron Synthesis Spolka Akcyjna Nowe kompleksy rutenu i ich zastosowanie w reakcji krzyżowej metatezy olefin

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5314753B2 (ja) * 2008-05-22 2013-10-16 リミテッド・ライアビリティ・カンパニー・”ユナイテッド・リサーチ・アンド・デベロップメント・センター” ジシクロペンタジエンのメタセシス重合触媒、その製造方法および重合方法
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
CN102596407B (zh) 2009-11-09 2014-09-03 埃克森美孚化学专利公司 复分解催化剂和其应用方法
WO2011079439A1 (en) * 2009-12-30 2011-07-07 Zannan Scitech Co., Ltd. Highly active metathesis catalysts selective for romp and rcm reactions
RU2451692C2 (ru) * 2010-08-13 2012-05-27 Закрытое Акционерное Общество "Сибур Холдинг" Способ очистки полимеризационного оборудования от труднорастворимых отложений высокомолекулярного полимера (варианты)
RU2462308C1 (ru) * 2011-10-04 2012-09-27 Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" Катализатор полимеризации дициклопентадиена и способ его получения
PL225024B1 (pl) * 2012-08-16 2017-02-28 Univ Warszawski Nowe kompleksy rutenu oraz ich zastosowanie
RU2523321C1 (ru) * 2013-05-15 2014-07-20 Открытое акционерное общество "Нефтяная компания "Роснефть" Материал для проппанта и способ его получения
RU2552750C1 (ru) * 2014-02-18 2015-06-10 Открытое акционерное общество "Нефтяная компания "Роснефть" Способ получения микросфер полимерного проппанта из полимерной матрицы на основе метатезис-радикально сшитой смеси олигоциклопентадиенов
RU2577252C1 (ru) * 2015-02-26 2016-03-10 Открытое акционерное общество "Нефтяная компания "Роснефть" Способ получения катализатора метатезисной полимеризации дициклопентадиена
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
CN107233920A (zh) * 2016-03-29 2017-10-10 上海东杰高分子材料有限公司 一种钌络合物催化剂
WO2017185324A1 (en) * 2016-04-29 2017-11-02 Xia, Ling Group 8 transition metal catalysts and method for making same and process for use of same in olefin disproportionation reactions
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
US11291983B2 (en) * 2019-09-18 2022-04-05 Apeiron Synthesis S.A. Organoruthenium carbide complexes as precatalysts for olefin metathesis
PL246181B1 (pl) * 2020-08-17 2024-12-16 Apeiron Synthesis Spolka Akcyjna Nowe kompleksy rutenu i ich zastosowanie w reakcji krzyżowej metatezy olefin

Also Published As

Publication number Publication date
JP2021530432A (ja) 2021-11-11
PL426318A1 (pl) 2020-01-13
PL3820609T3 (pl) 2023-10-16
US12251688B2 (en) 2025-03-18
EP3820609B1 (en) 2023-06-28
US20210237045A1 (en) 2021-08-05
EP3820609A1 (en) 2021-05-19
WO2020012370A1 (en) 2020-01-16
KR20210030938A (ko) 2021-03-18

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