KR101749238B1 - 신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 - Google Patents

신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 Download PDF

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KR101749238B1
KR101749238B1 KR1020157000377A KR20157000377A KR101749238B1 KR 101749238 B1 KR101749238 B1 KR 101749238B1 KR 1020157000377 A KR1020157000377 A KR 1020157000377A KR 20157000377 A KR20157000377 A KR 20157000377A KR 101749238 B1 KR101749238 B1 KR 101749238B1
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catalyst
metathesis
metathesis reaction
general formula
complex
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KR20150023672A (ko
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크리츠토프 스코워스키
미칼 비에니크
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아페이론 신세시스 에스.아.
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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
    • 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
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F132/02—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
    • C08F132/06—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/46—Ruthenium, rhodium, osmium or iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • 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]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
KR1020157000377A 2012-07-27 2013-07-26 신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 Expired - Fee Related KR101749238B1 (ko)

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

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KR20150023672A KR20150023672A (ko) 2015-03-05
KR101749238B1 true KR101749238B1 (ko) 2017-06-20

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US (1) US9328132B2 (https=)
EP (1) EP2877478B1 (https=)
JP (1) JP6121533B2 (https=)
KR (1) KR101749238B1 (https=)
CN (1) CN104428306B (https=)
AU (1) AU2013294909B2 (https=)
CA (1) CA2875956C (https=)
IL (1) IL236128A (https=)
PL (2) PL400162A1 (https=)
RU (1) RU2586213C1 (https=)
SG (1) SG11201408224SA (https=)
WO (1) WO2014016422A1 (https=)

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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
KR20180116238A (ko) * 2015-12-10 2018-10-24 우미코레 아게 운트 코 카게 올레핀 복분해 촉매
HUE073559T2 (hu) 2017-02-17 2026-01-28 Provivi Inc Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül
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
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
US11939410B2 (en) 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
JP7223854B2 (ja) 2018-12-21 2023-02-16 プロメラス， エルエルシー ポリシクロオレフィンモノマー及び架橋剤に由来する高衝撃強度の３ｄ印刷材料
KR102670566B1 (ko) * 2019-01-18 2024-05-31 광주과학기술원 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도
CN114144450A (zh) * 2019-07-25 2022-03-04 普罗米鲁斯有限责任公司 作为光学材料的稳定的聚环烯烃聚合物及无机纳米组合物
CN114174373B (zh) * 2019-09-27 2024-07-30 日本瑞翁株式会社 含有聚合物的物质及其制造方法、以及膜
KR20230144001A (ko) 2021-02-02 2023-10-13 아페이론 신세시스 에스.아. 올레핀 복분해를 위한 (전)촉매로서의 긴 저장 수명 안정성을 갖는 유기 루테늄 복합체
TWI895585B (zh) 2021-02-02 2025-09-01 日商住友電木股份有限公司 作為光學材料之保存期限長期穩定的光活性本體聚合型多環烯烴組成物
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
EP4605438A1 (en) 2022-10-21 2025-08-27 Merck Patent GmbH Composition
KR20260035273A (ko) 2023-07-10 2026-03-12 메르크 파텐트 게엠베하 조성물

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CN104428306B (zh) 2017-05-24
RU2586213C1 (ru) 2016-06-10
AU2013294909B2 (en) 2015-11-19
EP2877478A1 (en) 2015-06-03
KR20150023672A (ko) 2015-03-05
US9328132B2 (en) 2016-05-03
AU2013294909A1 (en) 2015-01-22
CN104428306A (zh) 2015-03-18
IL236128A0 (en) 2015-02-01
EP2877478B1 (en) 2016-11-16
CA2875956C (en) 2016-01-19
WO2014016422A1 (en) 2014-01-30
IL236128A (en) 2017-07-31
SG11201408224SA (en) 2015-01-29
JP2015525776A (ja) 2015-09-07
PL2877478T3 (pl) 2017-05-31
JP6121533B2 (ja) 2017-04-26
US20150158896A1 (en) 2015-06-11
PL400162A1 (pl) 2014-02-03
CA2875956A1 (en) 2014-01-30

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