KR102157915B1 - 에틸렌의 하이드로포밀화를 위한 두자리 리간드 - Google Patents
에틸렌의 하이드로포밀화를 위한 두자리 리간드 Download PDFInfo
- Publication number
- KR102157915B1 KR102157915B1 KR1020157014700A KR20157014700A KR102157915B1 KR 102157915 B1 KR102157915 B1 KR 102157915B1 KR 1020157014700 A KR1020157014700 A KR 1020157014700A KR 20157014700 A KR20157014700 A KR 20157014700A KR 102157915 B1 KR102157915 B1 KR 102157915B1
- Authority
- KR
- South Korea
- Prior art keywords
- ligand
- hydroformylation
- reaction
- rhodium
- catalyst
- 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.)
- Active
Links
- 0 *C(C1)(*=C)c2c(*)c(*)c(*)c(P(*)*)c2OC1(CC1(*)S)Oc(c(P(*)*)c2*)c1c(*)c2O* Chemical compound *C(C1)(*=C)c2c(*)c(*)c(*)c(P(*)*)c2OC1(CC1(*)S)Oc(c(P(*)*)c2*)c1c(*)c2O* 0.000 description 6
- PMKYNXBUZIFIHB-UHFFFAOYSA-N C(CCc1c2-c(c(CCCC3)c3cc3)c3OP([n]3cccc3)[n]3cccc3)Cc1ccc2OP([n]1cccc1)[n]1cccc1 Chemical compound C(CCc1c2-c(c(CCCC3)c3cc3)c3OP([n]3cccc3)[n]3cccc3)Cc1ccc2OP([n]1cccc1)[n]1cccc1 PMKYNXBUZIFIHB-UHFFFAOYSA-N 0.000 description 1
- VADPFECQVIUDCF-UHFFFAOYSA-N ClP([n]1cccc1)[n]1cccc1 Chemical compound ClP([n]1cccc1)[n]1cccc1 VADPFECQVIUDCF-UHFFFAOYSA-N 0.000 description 1
- UTXIFKBYNJRJPH-UHFFFAOYSA-N Oc1ccc(CCCC2)c2c1-c1c(CCCC2)c2ccc1O Chemical compound Oc1ccc(CCCC2)c2c1-c1c(CCCC2)c2ccc1O UTXIFKBYNJRJPH-UHFFFAOYSA-N 0.000 description 1
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
- B01J31/18—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| KR20150092144A KR20150092144A (ko) | 2015-08-12 |
| KR102157915B1 true KR102157915B1 (ko) | 2020-09-21 |
Family
ID=47355985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157014700A Active KR102157915B1 (ko) | 2012-12-04 | 2013-11-19 | 에틸렌의 하이드로포밀화를 위한 두자리 리간드 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9795952B2 (https=) |
| EP (1) | EP2740535A1 (https=) |
| JP (1) | JP6360067B2 (https=) |
| KR (1) | KR102157915B1 (https=) |
| CN (2) | CN109364997A (https=) |
| WO (1) | WO2014088800A1 (https=) |
| ZA (1) | ZA201503184B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9765007B2 (en) | 2013-10-28 | 2017-09-19 | Rohm And Haas Company | Dehydration process |
| MX2018009690A (es) * | 2016-02-11 | 2018-09-11 | Dow Technology Investments Llc | Procesos para convertir olefinas en alcoholes, eteres o combinaciones de los mismos. |
| 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 |
| 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 |
| 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 |
| US10183899B2 (en) | 2016-11-10 | 2019-01-22 | Chevron Phillips Chemical Company Lp | Normal alpha olefin synthesis using metathesis and dehydroformylation |
| EP3466540B1 (en) * | 2017-05-29 | 2022-04-06 | LG Chem, Ltd. | Catalyst composition for hydroformylation reaction and method for preparing aldehyde using same |
| KR102131788B1 (ko) | 2017-05-29 | 2020-07-09 | 주식회사 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
| US11123723B2 (en) | 2018-02-26 | 2021-09-21 | The Regents Of The University Of California | Oxidative dehydroxymethylation of alcohols to produce olefins |
| EP3759063A1 (en) | 2018-02-26 | 2021-01-06 | Bischof, Steven M. | Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation |
| 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 |
| WO2022081444A1 (en) | 2020-10-13 | 2022-04-21 | Dow Silicones Corporation | Preparation of organosilicon compounds with aldehyde functionality |
| 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 |
| CN115536698B (zh) * | 2021-06-30 | 2026-02-06 | 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 |
| 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 |
| 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 |
| 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 |
| WO2023060155A1 (en) | 2021-10-06 | 2023-04-13 | Dow Global Technologies Llc | Preparation of propylimine-functional organosilicon compounds and primary aminopropyl-functional organosilicon compounds |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| KR100851101B1 (ko) | 2001-03-29 | 2008-08-08 | 바스프 에스이 | Viii 아족 금속과의 니코겐 킬레이트 착물용 리간드및 히드로포르밀화, 카르보닐화, 히드로시안화 또는수소화 반응을 위한 촉매로서의 착물의 용도 |
| CN102746338A (zh) | 2012-07-13 | 2012-10-24 | 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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| 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 |
| JPH02501068A (ja) | 1987-05-14 | 1990-04-12 | コロラド ステイト ユニバーシティ リサーチ ファウンデイション | プロキラルオレフィン類の高エナンチオマー過剰でのキラルアルデヒド類への不斉ハイドロホルミル化 |
| 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 |
| US5763677A (en) | 1995-12-06 | 1998-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation processes |
| US5710344A (en) * | 1996-11-08 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Process to prepare a linear aldehyde |
| CA2328866A1 (en) * | 1998-04-16 | 1999-10-21 | E.I. Du Pont De Nemours And Company | Hydrocyanation of olefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
| US6090987A (en) * | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| AU2002324067A1 (en) * | 2001-08-24 | 2003-03-10 | Basf Aktiengesellschaft | Method for the production of 2-propylheptanol and hydroformylating catalysts and the further use thereof for carbonylation, hydrocyanation and hydrogenation |
| 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 |
| MX2010014570A (es) * | 2008-07-03 | 2011-08-15 | Dow Technology Investments Llc | Proceso para controlar pesados en una corriente de catalizador de reciclado. |
| 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 |
| CN102741210B (zh) * | 2009-12-22 | 2016-02-24 | 陶氏技术投资有限责任公司 | 控制混合配体加氢甲酰化工艺中的正构∶异构醛比率 |
| 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 |
-
2012
- 2012-12-04 EP EP12382481.5A patent/EP2740535A1/en not_active Withdrawn
-
2013
- 2013-11-19 JP JP2015545090A patent/JP6360067B2/ja active Active
- 2013-11-19 WO PCT/US2013/070753 patent/WO2014088800A1/en not_active Ceased
- 2013-11-19 CN CN201811183222.6A patent/CN109364997A/zh active Pending
- 2013-11-19 CN CN201380062320.3A patent/CN104822456A/zh active Pending
- 2013-11-19 KR KR1020157014700A patent/KR102157915B1/ko active Active
- 2013-11-19 US US14/648,803 patent/US9795952B2/en active Active
-
2015
- 2015-05-08 ZA ZA2015/03184A patent/ZA201503184B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| KR100851101B1 (ko) | 2001-03-29 | 2008-08-08 | 바스프 에스이 | Viii 아족 금속과의 니코겐 킬레이트 착물용 리간드및 히드로포르밀화, 카르보닐화, 히드로시안화 또는수소화 반응을 위한 촉매로서의 착물의 용도 |
| CN102746338A (zh) | 2012-07-13 | 2012-10-24 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150092144A (ko) | 2015-08-12 |
| JP6360067B2 (ja) | 2018-07-18 |
| WO2014088800A1 (en) | 2014-06-12 |
| CN109364997A (zh) | 2019-02-22 |
| EP2740535A1 (en) | 2014-06-11 |
| US20150328628A1 (en) | 2015-11-19 |
| CN104822456A (zh) | 2015-08-05 |
| US9795952B2 (en) | 2017-10-24 |
| JP2016500123A (ja) | 2016-01-07 |
| ZA201503184B (en) | 2017-07-26 |
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