WO2010093208A3 - 하이드로포밀화 반응용 촉매 조성물 및 이를 이용하는 알데히드의 제조방법 - Google Patents
하이드로포밀화 반응용 촉매 조성물 및 이를 이용하는 알데히드의 제조방법 Download PDFInfo
- Publication number
- WO2010093208A3 WO2010093208A3 PCT/KR2010/000921 KR2010000921W WO2010093208A3 WO 2010093208 A3 WO2010093208 A3 WO 2010093208A3 KR 2010000921 W KR2010000921 W KR 2010000921W WO 2010093208 A3 WO2010093208 A3 WO 2010093208A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydroformylation
- catalyst composition
- same
- aldehydes
- preparing aldehydes
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title abstract 6
- 150000001299 aldehydes Chemical class 0.000 title abstract 4
- 238000007037 hydroformylation reaction Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
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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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
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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
- B01J31/20—Carbonyls
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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
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
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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
- B01J31/24—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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657127—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) condensed with carbocyclic or heterocyclic rings or ring systems
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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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
- 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
- B01J2531/822—Rhodium
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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
- 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
- B01J2531/827—Iridium
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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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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- General Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
본 발명은 트리아릴포스핀 리간드; 특정의 화학식으로 표시되는 포스핀 옥사이드 또는 포스핀 설파이드 리간드; 및 전이금속 촉매를 포함하는 하이드로포밀화 반응용 촉매 조성물 및 이를 이용하는 알데히드의 제조방법에 관한 것으로, 상기 촉매 조성물을 올레핀으로부터 알데히드를 제조하는 하이드로포밀화 반응에 이용할 경우 촉매 활성 및 안정성이 우수하고, 노르말-알데히드에 대한 높은 선택성을 보인다.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10741425.2A EP2404671B2 (en) | 2009-02-12 | 2010-02-12 | Catalyst composition for hydroformylation and method for preparing aldehydes using the same |
CN201080004413.7A CN102271812B (zh) | 2009-02-12 | 2010-02-12 | 用于加氢甲酰化反应的催化剂组合物以及使用该催化剂组合物制备醛的方法 |
ES10741425.2T ES2515266T5 (es) | 2009-02-12 | 2010-02-12 | Composición de catalizador para hidroformilación y procedimiento para la preparación de aldehídos utilizando la misma |
US13/092,817 US8426651B2 (en) | 2009-02-12 | 2011-04-22 | Catalyst composition for hydroformylation and method for producing aldehyde using the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20090011408 | 2009-02-12 | ||
KR10-2009-0011408 | 2009-02-12 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/092,817 Continuation US8426651B2 (en) | 2009-02-12 | 2011-04-22 | Catalyst composition for hydroformylation and method for producing aldehyde using the same |
Publications (2)
Publication Number | Publication Date |
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WO2010093208A2 WO2010093208A2 (ko) | 2010-08-19 |
WO2010093208A3 true WO2010093208A3 (ko) | 2010-11-25 |
Family
ID=42562207
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2010/000921 WO2010093208A2 (ko) | 2009-02-12 | 2010-02-12 | 하이드로포밀화 반응용 촉매 조성물 및 이를 이용하는 알데히드의 제조방법 |
Country Status (6)
Country | Link |
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US (1) | US8426651B2 (ko) |
EP (1) | EP2404671B2 (ko) |
KR (1) | KR101150557B1 (ko) |
CN (1) | CN102271812B (ko) |
ES (1) | ES2515266T5 (ko) |
WO (1) | WO2010093208A2 (ko) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
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US8627965B2 (en) | 2001-05-17 | 2014-01-14 | Rtc Industries, Inc. | Multi-component display and merchandise systems |
US8047385B2 (en) | 2004-02-03 | 2011-11-01 | Rtc Industries, Inc. | Product securement and management system |
US9375100B2 (en) | 2004-02-03 | 2016-06-28 | Rtc Industries, Inc. | Product securement and management system |
US11375826B2 (en) | 2004-02-03 | 2022-07-05 | Rtc Industries, Inc. | Product securement and management system |
US9706857B2 (en) | 2004-02-03 | 2017-07-18 | Rtc Industries, Inc. | Product securement and management system |
KR101095775B1 (ko) * | 2010-09-02 | 2011-12-21 | 주식회사 엘지화학 | 올레핀계 화합물의 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 올레핀계 화합물의 히드로포밀화 방법 |
DE102012014396B4 (de) * | 2012-07-13 | 2018-01-11 | Oxea Gmbh | Verfahren zur Herstellung eines Vinylestergemisches aus einem Gemisch stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
WO2015046924A1 (ko) * | 2013-09-30 | 2015-04-02 | (주) 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 올레핀의 히드로포밀화 방법 |
KR101615028B1 (ko) | 2013-09-30 | 2016-04-22 | 주식회사 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 올레핀의 히드로포밀화 방법 |
KR101962092B1 (ko) | 2015-10-05 | 2019-03-26 | 주식회사 엘지화학 | 인계 리간드를 포함하는 촉매 조성물 및 이를 이용한 하이드로포밀화 방법 |
KR102092803B1 (ko) | 2016-01-13 | 2020-03-24 | 주식회사 엘지화학 | 인계 리간드를 포함하는 촉매 조성물을 이용한 하이드로포밀화 방법 |
WO2018008928A1 (ko) | 2016-07-08 | 2018-01-11 | (주) 엘지화학 | 하이드로포밀화 촉매, 이를 포함하는 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
KR102073732B1 (ko) | 2016-07-08 | 2020-02-05 | 주식회사 엘지화학 | 하이드로포밀화 촉매, 이를 포함하는 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
KR102131788B1 (ko) | 2017-05-29 | 2020-07-09 | 주식회사 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
EP3466540B1 (en) | 2017-05-29 | 2022-04-06 | LG Chem, Ltd. | Catalyst composition for hydroformylation reaction and method for preparing aldehyde using same |
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JP2021525166A (ja) * | 2018-05-30 | 2021-09-24 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | モノホスフィン、テトラホスフィン配位子の組み合わせを含む触媒組成物、およびそれを使用するヒドロホルミル化プロセス |
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CN114057558B (zh) * | 2021-12-01 | 2024-01-30 | 上海簇睿低碳能源技术有限公司 | 一种3,5,5-三甲基己醛的合成方法、催化体系及应用 |
KR20230115562A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 알데히드의 제조방법 |
KR20230115559A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 하이드로포밀화 방법 |
KR20230115563A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 알코올의 제조방법 |
KR20230115558A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 하이드로포밀화 방법 |
KR20230115501A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 알코올의 제조방법 |
KR20230115560A (ko) | 2022-01-27 | 2023-08-03 | 주식회사 엘지화학 | 하이드로포밀화용 용매의 제조방법 및 알데히드의 제조방법 |
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US4408078A (en) * | 1981-12-23 | 1983-10-04 | Shell Oil Company | Process for the hydroformylation of olefins |
US4528403A (en) * | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
US6040483A (en) * | 1997-05-27 | 2000-03-21 | Institut Francais Du Petrole | Process for hydroformylating olefins |
US20050119495A1 (en) * | 2001-11-09 | 2005-06-02 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
Family Cites Families (5)
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FR2428021A1 (fr) * | 1978-06-05 | 1980-01-04 | Kuraray Co | Hydroformylation de composes olefiniques |
JPS5829928B2 (ja) * | 1978-08-07 | 1983-06-25 | 株式会社クラレ | オレフイン性化合物のカルボニル化方法 |
KR100596365B1 (ko) | 2004-06-12 | 2006-07-03 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
KR100547587B1 (ko) * | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
KR100744477B1 (ko) † | 2004-09-15 | 2007-08-01 | 주식회사 엘지화학 | 인 화합물을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
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2010
- 2010-02-12 WO PCT/KR2010/000921 patent/WO2010093208A2/ko active Application Filing
- 2010-02-12 CN CN201080004413.7A patent/CN102271812B/zh active Active
- 2010-02-12 EP EP10741425.2A patent/EP2404671B2/en active Active
- 2010-02-12 ES ES10741425.2T patent/ES2515266T5/es active Active
- 2010-02-12 KR KR1020100013531A patent/KR101150557B1/ko active IP Right Grant
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- 2011-04-22 US US13/092,817 patent/US8426651B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4408078A (en) * | 1981-12-23 | 1983-10-04 | Shell Oil Company | Process for the hydroformylation of olefins |
US4528403A (en) * | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
US6040483A (en) * | 1997-05-27 | 2000-03-21 | Institut Francais Du Petrole | Process for hydroformylating olefins |
US20050119495A1 (en) * | 2001-11-09 | 2005-06-02 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
Also Published As
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EP2404671A2 (en) | 2012-01-11 |
US20110201844A1 (en) | 2011-08-18 |
EP2404671B1 (en) | 2014-09-10 |
KR101150557B1 (ko) | 2012-06-01 |
WO2010093208A2 (ko) | 2010-08-19 |
EP2404671B2 (en) | 2018-07-25 |
US8426651B2 (en) | 2013-04-23 |
ES2515266T5 (es) | 2018-12-03 |
ES2515266T3 (es) | 2014-10-29 |
CN102271812B (zh) | 2014-04-02 |
KR20100092399A (ko) | 2010-08-20 |
EP2404671A4 (en) | 2012-05-09 |
CN102271812A (zh) | 2011-12-07 |
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