JP6360067B2 - エチレンのヒドロホルミル化用二座配位子 - Google Patents

エチレンのヒドロホルミル化用二座配位子 Download PDF

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JP6360067B2
JP6360067B2 JP2015545090A JP2015545090A JP6360067B2 JP 6360067 B2 JP6360067 B2 JP 6360067B2 JP 2015545090 A JP2015545090 A JP 2015545090A JP 2015545090 A JP2015545090 A JP 2015545090A JP 6360067 B2 JP6360067 B2 JP 6360067B2
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reaction
ligand
hydroformylation
rhodium
catalyst
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JP2016500123A5 (enExample
JP2016500123A (ja
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オリヴァー・ディアボロ
ヒューゴ・トリカス
ペトリュス・ダブリュ・エヌ・エム・ヴァン・ルーエン
ヘザー・アン・スピネイ
ロバート・デイビッド・ジョン・フローゼ
マイケル・エイ・ブラマー
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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
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
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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
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • B01J31/186—Mono- or diamide derivatives thereof
    • 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
    • B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
    • B01J31/187—Amide derivatives thereof
    • 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
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

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  • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
JP2015545090A 2012-12-04 2013-11-19 エチレンのヒドロホルミル化用二座配位子 Active JP6360067B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12382481.5A EP2740535A1 (en) 2012-12-04 2012-12-04 Bidentate ligands for hydroformylation of ethylene
EP12382481.5 2012-12-04
PCT/US2013/070753 WO2014088800A1 (en) 2012-12-04 2013-11-19 Bidentate ligands for hydroformylation of ethylene

Publications (3)

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JP2016500123A JP2016500123A (ja) 2016-01-07
JP2016500123A5 JP2016500123A5 (enExample) 2017-08-24
JP6360067B2 true JP6360067B2 (ja) 2018-07-18

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US (1) US9795952B2 (enExample)
EP (1) EP2740535A1 (enExample)
JP (1) JP6360067B2 (enExample)
KR (1) KR102157915B1 (enExample)
CN (2) CN104822456A (enExample)
WO (1) WO2014088800A1 (enExample)
ZA (1) ZA201503184B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102291247B1 (ko) 2013-10-28 2021-08-20 롬 앤드 하아스 컴패니 메타크롤레인을 분리하는 방법
RU2751511C9 (ru) * 2016-02-11 2021-08-18 Дау Текнолоджи Инвестментс Ллк Способы превращения олефинов в спирты, простые эфиры или их комбинации
RU2619951C1 (ru) * 2016-06-21 2017-05-22 ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) Двухстадийный способ получения пропионового альдегида
TW201840362A (zh) * 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
TW201840363A (zh) * 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 處理氫甲醯化催化劑溶液之方法
TWI758353B (zh) * 2016-11-08 2022-03-21 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
US10183899B2 (en) 2016-11-10 2019-01-22 Chevron Phillips Chemical Company Lp Normal alpha olefin synthesis using metathesis and dehydroformylation
CN109311002B (zh) * 2017-05-29 2021-12-10 Lg化学株式会社 用于加氢甲酰化反应的催化剂组合物和使用其制备醛的方法
KR102131788B1 (ko) 2017-05-29 2020-07-09 주식회사 엘지화학 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드 제조방법
WO2019165350A1 (en) 2018-02-26 2019-08-29 Bischof Steven M Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
US11123723B2 (en) 2018-02-26 2021-09-21 The Regents Of The University Of California Oxidative dehydroxymethylation of alcohols to produce olefins
CN110327975B (zh) * 2019-06-06 2020-05-19 浙江新和成股份有限公司 氢甲酰化催化剂及其制备方法和应用
CN113713862B (zh) * 2020-05-26 2023-04-11 中国科学院大连化学物理研究所 烯烃氢甲酰化反应的Co基多相催化剂及制备和应用
CN116685401B (zh) 2020-09-25 2025-10-03 利安德化学技术有限公司 在加氢甲酰化中将乙烯与烯丙醇共进料以制备1,4-丁二醇和正丙醇
CN113385236B (zh) * 2021-06-16 2023-02-03 上海华谊（集团）公司 烯烃氢甲酰化催化剂组合物和氢甲酰化方法
CN115536695B (zh) * 2021-06-30 2025-10-14 中国石油化工股份有限公司 一种含有聚乙二醇氨基的非对称膦配体及其应用
CN115536697A (zh) * 2021-06-30 2022-12-30 中国石油化工股份有限公司 膦配体化合物、用于催化氢甲酰化制备醛的催化剂组合物及方法
CN115536698A (zh) * 2021-06-30 2022-12-30 中国石油化工股份有限公司 膦配体化合物、用于均相氢甲酰化反应的催化剂组合物及方法
CN113583046B (zh) * 2021-09-02 2023-08-25 成都欣华源科技有限责任公司 双齿膦配体及其制备方法、应用
US12151993B2 (en) 2021-09-10 2024-11-26 Chevron Phillips Chemical Company Lp Selective 1-hexene/1-octene production with 1-decene
KR20240074844A (ko) 2021-10-06 2024-05-28 다우 글로벌 테크놀로지스 엘엘씨 프로필이민-작용성 유기규소 화합물 및 1차 아미노프로필-작용성 유기규소 화합물의 제조
CN118019747A (zh) 2021-10-06 2024-05-10 陶氏环球技术有限责任公司 丙基亚胺官能化有机硅化合物和伯氨基丙基官能化有机硅化合物的制备
CN114163476B (zh) * 2021-12-02 2023-09-19 万华化学集团股份有限公司 一种单齿膦型配体、氢甲酰化催化剂，一种烯烃氢甲酰化制备线性醛的方法
CN114736239B (zh) * 2022-05-26 2024-01-16 重庆理工大学 一种双齿膦配体及其制备方法、应用

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527809A (en) 1967-08-03 1970-09-08 Union Carbide Corp Hydroformylation process
US4148830A (en) 1975-03-07 1979-04-10 Union Carbide Corporation Hydroformylation of olefins
US4247486A (en) 1977-03-11 1981-01-27 Union Carbide Corporation Cyclic hydroformylation process
JPS5376262A (en) 1976-12-20 1978-07-06 Tokico Ltd Shoe clearance automatic regulator
US5110990A (en) 1984-03-30 1992-05-05 Union Carbide Chemicals & Plastics Technology Corporation Process for recovery of phosphorus ligand from vaporized aldehyde
US4668651A (en) 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
US4774361A (en) 1986-05-20 1988-09-27 Union Carbide Corporation Transition metal complex catalyzed reactions
EP0314759A4 (en) 1987-05-14 1990-01-29 Univ Colorado State Res Found Asymmetric hydroformylations of prochiral olefins to chiral aldehydes in high enantiomeric excess.
US5102505A (en) 1990-11-09 1992-04-07 Union Carbide Chemicals & Plastics Technology Corporation Mixed aldehyde product separation by distillation
CN1029774C (zh) * 1992-06-19 1995-09-20 联合碳化化学品及塑料有限公司 铑络合物加氢甲酰化催化剂以及该催化剂的前体组合物
US5312996A (en) 1992-06-29 1994-05-17 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process for producing 1,6-hexanedials
US5288918A (en) 1992-09-29 1994-02-22 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process
US5430194A (en) 1994-06-24 1995-07-04 Union Carbide Chemicals & Plastics Technology Corporation Process for improving enantiomeric purity of aldehydes
US5756855A (en) 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process
KR970703805A (ko) 1995-05-01 1997-08-09 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 막 분리방법(Membrane Separation)
DE19619527A1 (de) * 1996-05-15 1997-11-20 Hoechst Ag Katalysatorsysteme auf der Basis von Rhodium-Komplexverbindungen mit Diphosphin-Liganden und ihre Verwendung bei der Herstellung von Aldehyden
US5744650A (en) 1995-12-06 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Metal-Ligand complex catalyzed processes
US5710344A (en) * 1996-11-08 1998-01-20 E. I. Du Pont De Nemours And Company Process to prepare a linear aldehyde
DE69918093T2 (de) * 1998-04-16 2005-07-28 Invista Technologies S.A.R.L., Wilmington Hydrocyanierung von olefinen und isomerisierung von nichtkonjugierten 2-alkyl-3-monoalken- nitrilen
US6090987A (en) * 1998-07-06 2000-07-18 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
JP2002047294A (ja) * 2000-07-28 2002-02-12 Mitsubishi Chemicals Corp 二座リン化合物及びそれを用いるヒドロホルミル化方法
ES2253552T3 (es) 2001-03-29 2006-06-01 Basf Aktiengesellschaft Ligandos para complejos de quelato de pnicogeno con un metal del grupo viii secundario y empleo de los complejos como catalizadores para la hidroformilacion, la carbonilacion, la hidrocianacion o la hidrogenacion.
WO2003018192A2 (de) * 2001-08-24 2003-03-06 Basf Aktiengesellschaft Verfahren zur herstellung von 2-propylheptanol sowie dafür geeignete hydroformylierungskatalysatoren und deren weitere verwendung zur carbonylierung, hydrocyanierung und hydrierung
CN1202064C (zh) * 2002-01-25 2005-05-18 四川大学 一种乙烯制丙醛的方法
DE10333519A1 (de) * 2003-07-23 2005-02-17 Basf Ag Zweistufiges Hydroformylierungsverfahren
CN100412046C (zh) * 2003-10-21 2008-08-20 巴斯福股份公司 连续制备醛的方法
DE10349343A1 (de) * 2003-10-23 2005-06-02 Basf Ag Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden
KR100596365B1 (ko) * 2004-06-12 2006-07-03 주식회사 엘지화학 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법
CN100430139C (zh) 2006-06-09 2008-11-05 中国科学院上海有机化学研究所 联萘酚骨架的取代双齿亚磷酰胺配体在烯烃氢甲酰化反应中的应用
CN102143933B (zh) * 2008-07-03 2014-09-17 陶氏技术投资有限公司 控制再循环催化剂料流中重物质的方法
US20100069679A1 (en) * 2008-09-12 2010-03-18 Eastman Chemical Company Acetylene tolerant hydroformylation catalysts
CN101462932B (zh) * 2009-01-21 2012-04-18 成都欣华源科技有限责任公司 一种低碳烯烃氢甲酰化制备醛的方法
EP2942343B1 (en) * 2009-12-22 2019-09-04 Dow Technology Investments LLC Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process
KR101310552B1 (ko) * 2010-04-20 2013-09-23 주식회사 엘지화학 올레핀의 하이드로포르밀화에 의한 알데히드 제조 방법
CN102260147B (zh) * 2011-06-01 2013-11-06 中国科学院过程工程研究所 一种在离子液体溶剂中烯烃氢甲酰化反应的方法
CN102746338B (zh) 2012-07-13 2015-07-08 中国科学院上海有机化学研究所 螺缩酮骨架的双齿亚磷酰胺配体及其制备方法和应用

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CN109364997A (zh) 2019-02-22
KR20150092144A (ko) 2015-08-12
ZA201503184B (en) 2017-07-26
CN104822456A (zh) 2015-08-05
WO2014088800A1 (en) 2014-06-12
US9795952B2 (en) 2017-10-24
US20150328628A1 (en) 2015-11-19
JP2016500123A (ja) 2016-01-07
KR102157915B1 (ko) 2020-09-21
EP2740535A1 (en) 2014-06-11

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