RU2002128740A - Одностадийный способ получения 1,3-диола - Google Patents
Одностадийный способ получения 1,3-диолаInfo
- Publication number
- RU2002128740A RU2002128740A RU2002128740/04A RU2002128740A RU2002128740A RU 2002128740 A RU2002128740 A RU 2002128740A RU 2002128740/04 A RU2002128740/04 A RU 2002128740/04A RU 2002128740 A RU2002128740 A RU 2002128740A RU 2002128740 A RU2002128740 A RU 2002128740A
- Authority
- RU
- Russia
- Prior art keywords
- complex
- hydroformylation
- bis
- ruthenium
- ethane
- Prior art date
Links
- 150000000185 1,3-diols Chemical class 0.000 title claims abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract 16
- 239000003054 catalyst Substances 0.000 claims abstract 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 12
- 238000000034 method Methods 0.000 claims abstract 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000003446 ligand Substances 0.000 claims abstract 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims abstract 5
- -1 ruthenium(0) compound Chemical class 0.000 claims abstract 5
- 238000006479 redox reaction Methods 0.000 claims abstract 4
- 239000012442 inert solvent Substances 0.000 claims abstract 3
- 238000005191 phase separation Methods 0.000 claims abstract 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910017052 cobalt Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- LNARZTIDDZTCPZ-UHFFFAOYSA-N phosphane ruthenium(1+) Chemical compound P.[Ru+] LNARZTIDDZTCPZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052707 ruthenium Inorganic materials 0.000 claims 2
- 150000003304 ruthenium compounds Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- NFRYVRNCDXULEX-UHFFFAOYSA-N (2-diphenylphosphanylphenyl)-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NFRYVRNCDXULEX-UHFFFAOYSA-N 0.000 claims 1
- ZKWQSBFSGZJNFP-UHFFFAOYSA-N 1,2-bis(dimethylphosphino)ethane Chemical compound CP(C)CCP(C)C ZKWQSBFSGZJNFP-UHFFFAOYSA-N 0.000 claims 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- RVINFUFGTOIYEP-UHFFFAOYSA-N 2,4,4-trimethylpentyl-[2-(2,4,4-trimethylpentylphosphanyl)ethyl]phosphane Chemical compound CC(C)(C)CC(C)CPCCPCC(C)CC(C)(C)C RVINFUFGTOIYEP-UHFFFAOYSA-N 0.000 claims 1
- BMMPGIDGJGNWFZ-UHFFFAOYSA-N 2-[bis(2-methylpropyl)phosphanyl]ethyl-bis(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CCP(CC(C)C)CC(C)C BMMPGIDGJGNWFZ-UHFFFAOYSA-N 0.000 claims 1
- MIOCUERTSIJEDP-UHFFFAOYSA-N 2-diethylphosphanylethyl(diethyl)phosphane Chemical compound CCP(CC)CCP(CC)CC MIOCUERTSIJEDP-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- UMYVESYOFCWRIW-UHFFFAOYSA-N cobalt;methanone Chemical compound O=C=[Co] UMYVESYOFCWRIW-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- JGZAWKIDUQNXCA-UHFFFAOYSA-N dibutyl(3-diethylphosphanylpropyl)phosphane Chemical compound CCCCP(CCCC)CCCP(CC)CC JGZAWKIDUQNXCA-UHFFFAOYSA-N 0.000 claims 1
- BOUYBUIVMHNXQB-UHFFFAOYSA-N dicyclohexyl(2-dicyclohexylphosphanylethyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCP(C1CCCCC1)C1CCCCC1 BOUYBUIVMHNXQB-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic 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
-
- 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
-
- 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
-
- 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
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- 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
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening 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
- 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
-
- 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
-
- 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
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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
- Y02P20/584—Recycling of catalysts
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)
- Saccharide Compounds (AREA)
Claims (10)
1. Способ получения катализатора гидроформилирования, который включает a) получение комплекса (А) контактированием соединения рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильным соединением кобальта (0).
2. Способ по п.1, где дитретичный фосфиновый лиганд имеет общую формулу
где каждая группа R и R’ независимо или вместе представляет углеводородный фрагмент, содержащий вплоть до 30 атомов углерода;
Q представляет органическую мостиковую группу длиной от 2 до 4 атомов.
3. Способ по п.2, где группы R и R’ каждая независимо представляет алкильную, циклоалкильную, бициклоалкильную или арильную группу.
4. Способ по п.2 или 3, где группа Q включает атомы углерода.
5. Способ по п.4, где Q представляет алкиленовую группу длиной в 2, 3 или 4 атома углерода.
6. Способ по любому из пп.1-5, где дитретичный фосфиновый лиганд выбирают из одного или более из 1,2-бис-(дициклогексилфосфино)этана,
1,2-бис(дифенилфосфино)этана, 1,2-бис(диэтилфосфино)этана,
1-(диэтилфосфино)-3-(дибутилфосфино)пропана,
1,2-бис(дифенилфосфино)бензола,
1,2-бис-(диметилфосфино)этана,
1,2-бис(2,4,4-триметилпентилфосфино)этана,
1,2-бис(диизобутилфосфино)этана,
1,2-Р,Р’-бис(9-фосфабицикло[3.3.1] и/или [4.2.1]нонил)этана,
их 1,2-Р,Р’-пропанового или их 1,3-Р,Р’-пропанового аналогов.
7. Катализатор гидроформилирования, полученный способом, который включает a) получение комплекса (А) в результате контактирования рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильным соединением кобальта (0).
8. Одностадийный способ гидроформилирования для получения 1,3-диола, включающий реакцию взаимодействия оксирана с синтетическим газом в условиях гидроформилирования в инертном растворителе в присутствии катализатора гидроформилирования, полученного способом, который включает a) получение комплекса (А) в результате контактирования рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильньм соединением кобальта (0).
9. Одностадийный способ гидроформилирования для получения 1,3-диола, включающий реакцию оксирана с синтетическим газом в условиях гидроформилирования инертном растворителе в присутствии катализатора гидроформилирования, который представляет собой бидентатный комплекс рутений (+1)-фосфин: кобальт (-1), где лигированным металлом является рутений, в условиях, которые предпочтительно после завершения реакции оксиран/синтетический газ вызывают фазовое разделение реакционной смеси на верхнюю фазу растворителя с высоким содержанием катализатора и нижнюю фазу растворителя с высоким содержанием 1,3-диола, рециклизацию верхней фазы с высоким содержанием катализатора непосредственно в реакцию гидроформилирования для дальнейшей реакции с непрореагировавшими ранее исходными материалами, и выделение 1,3-диола из нижней фазы с высоким содержанием 1,3-диола.
10. Катализатор гидроформилирования, который представляет собой бидентатный комплекс рутений(+1)-фосфин : кобальт(-1), где лигированным металлом является рутений.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19219100P | 2000-03-27 | 2000-03-27 | |
| US60/192,191 | 2000-03-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002128740A true RU2002128740A (ru) | 2004-02-27 |
| RU2257262C2 RU2257262C2 (ru) | 2005-07-27 |
Family
ID=22708620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002128740/04A RU2257262C2 (ru) | 2000-03-27 | 2001-03-27 | Одностадийный способ получения 1,3-диола |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US6469222B2 (ru) |
| EP (1) | EP1268060B1 (ru) |
| JP (1) | JP2003528717A (ru) |
| KR (1) | KR100768594B1 (ru) |
| CN (1) | CN1318362C (ru) |
| AT (1) | ATE266470T1 (ru) |
| AU (1) | AU2001260164A1 (ru) |
| BR (1) | BR0109659A (ru) |
| CA (1) | CA2404758A1 (ru) |
| DE (1) | DE60103263T2 (ru) |
| MX (1) | MXPA02009392A (ru) |
| RU (1) | RU2257262C2 (ru) |
| WO (1) | WO2001072675A2 (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW592819B (en) * | 2001-05-18 | 2004-06-21 | Kevin Dale Allen | One-step production of 1,3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst |
| US6576802B2 (en) | 2001-06-04 | 2003-06-10 | Shell Oil Company | One-step production of 1, 3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand |
| US6660892B2 (en) * | 2002-02-13 | 2003-12-09 | Shell Oil Company | Synthesis of aliphatic 1,3-diols utilizing reduced ligand concentration and water extraction |
| US7056439B2 (en) * | 2003-05-06 | 2006-06-06 | Tate & Lyle Ingredidents Americas, Inc. | Process for producing 1, 3-propanediol |
| US7615671B2 (en) | 2007-11-30 | 2009-11-10 | Eastman Chemical Company | Hydrogenation process for the preparation of 1,2-diols |
| US8886112B2 (en) | 2008-09-24 | 2014-11-11 | Apple Inc. | Media device with enhanced data retrieval feature |
| KR101127730B1 (ko) | 2009-12-10 | 2012-03-22 | 호남석유화학 주식회사 | 계면활성제를 이용한 1,3-프로판디올 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4253987A (en) | 1980-04-10 | 1981-03-03 | Union Carbide Corporation | Homologation process for the production of ethanol from methanol |
| US4451680A (en) * | 1982-10-21 | 1984-05-29 | Texaco Inc. | Alcohols prepared from olefins and synthesis gas |
| US4895987A (en) | 1986-06-06 | 1990-01-23 | Sun Refining And Marketing Company | Phosphonite-and phosphonite-promoted ruthenium - cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers |
| US4873378A (en) | 1986-08-20 | 1989-10-10 | Hoechst Celanese Corporation | Process for making 1,3-diols from epoxides |
| RU2038844C1 (ru) * | 1990-05-04 | 1995-07-09 | Юнион Карбайд Кемикалз Энд Пластикс Текнолоджи Корпорейшн | Каталитическая композиция для гидроформилирования этиленоксида, способ ее получения и способ получения 1,3-пропандиола и 3-гидроксипропионового альдегида |
| US5053562A (en) | 1990-07-31 | 1991-10-01 | Hoechst Celanese Corporation | Process for making 1,3-diols from epoxides |
| US5200539A (en) * | 1990-08-27 | 1993-04-06 | Louisiana State University Board Of Supervisors, A Governing Body Of Louisiana State University Agricultural And Mechanical College | Homogeneous bimetallic hydroformylation catalysts, and processes utilizing these catalysts for conducting hydroformylation reactions |
| US5304691A (en) * | 1993-07-13 | 1994-04-19 | Shell Oil Company | Process for making 1,3-propanediol and 3-hydroxypropanal |
-
2001
- 2001-03-15 US US09/808,974 patent/US6469222B2/en not_active Expired - Fee Related
- 2001-03-27 RU RU2002128740/04A patent/RU2257262C2/ru active
- 2001-03-27 CA CA002404758A patent/CA2404758A1/en not_active Abandoned
- 2001-03-27 AU AU2001260164A patent/AU2001260164A1/en not_active Abandoned
- 2001-03-27 MX MXPA02009392A patent/MXPA02009392A/es active IP Right Grant
- 2001-03-27 KR KR1020027012733A patent/KR100768594B1/ko not_active Expired - Fee Related
- 2001-03-27 EP EP01933767A patent/EP1268060B1/en not_active Expired - Lifetime
- 2001-03-27 BR BR0109659-1A patent/BR0109659A/pt not_active Application Discontinuation
- 2001-03-27 JP JP2001570591A patent/JP2003528717A/ja active Pending
- 2001-03-27 DE DE60103263T patent/DE60103263T2/de not_active Expired - Fee Related
- 2001-03-27 WO PCT/EP2001/003497 patent/WO2001072675A2/en not_active Ceased
- 2001-03-27 CN CNB018084427A patent/CN1318362C/zh not_active Expired - Fee Related
- 2001-03-27 AT AT01933767T patent/ATE266470T1/de not_active IP Right Cessation
- 2001-09-20 US US09/957,561 patent/US6468940B1/en not_active Expired - Fee Related
- 2001-09-20 US US09/957,279 patent/US6518466B2/en not_active Expired - Fee Related
-
2002
- 2002-04-23 US US10/127,957 patent/US6706656B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1635987A (zh) | 2005-07-06 |
| RU2257262C2 (ru) | 2005-07-27 |
| WO2001072675A2 (en) | 2001-10-04 |
| EP1268060A2 (en) | 2003-01-02 |
| DE60103263D1 (de) | 2004-06-17 |
| US6468940B1 (en) | 2002-10-22 |
| KR20020084259A (ko) | 2002-11-04 |
| US6706656B2 (en) | 2004-03-16 |
| AU2001260164A1 (en) | 2001-10-08 |
| JP2003528717A (ja) | 2003-09-30 |
| KR100768594B1 (ko) | 2007-10-18 |
| MXPA02009392A (es) | 2003-02-12 |
| US20020161251A1 (en) | 2002-10-31 |
| CA2404758A1 (en) | 2001-10-04 |
| US6518466B2 (en) | 2003-02-11 |
| BR0109659A (pt) | 2004-06-22 |
| EP1268060B1 (en) | 2004-05-12 |
| US20020111516A1 (en) | 2002-08-15 |
| US6469222B2 (en) | 2002-10-22 |
| DE60103263T2 (de) | 2005-05-25 |
| WO2001072675A3 (en) | 2002-01-03 |
| ATE266470T1 (de) | 2004-05-15 |
| CN1318362C (zh) | 2007-05-30 |
| US20020004617A1 (en) | 2002-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Klein et al. | Highly selective catalyst systems for the hydroformylation of internal olefins to linear aldehydes | |
| Weber | Phosphorus heterocycles: From laboratory curiosities to ligands in highly efficient catalysts | |
| KR100218841B1 (ko) | 히드로포르밀화법 및 여기에 사용되는 비스 포스파이트 화합물 | |
| Tricas et al. | Bulky monophosphite ligands for ethene hydroformylation | |
| RU2011143929A (ru) | Способ гидроформилирования с помощью двойного открыто-концевого бисфосфитного лиганда | |
| Sémeril et al. | Highly regioselective hydroformylation with hemispherical chelators | |
| CN101768060B (zh) | 一类双膦配体在烯烃氢甲酰化反应中的应用 | |
| EP2404671A2 (en) | Catalyst composition for hydroformylation and method for preparing aldehydes using the same | |
| Bellini et al. | Coordination studies on supramolecular chiral ligands and application in asymmetric hydroformylation | |
| KR100355697B1 (ko) | 5-포르밀발러레이트의제조방법 | |
| US20040199023A1 (en) | Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols | |
| KR100916954B1 (ko) | 알데하이드의 제조 방법 | |
| JPS611633A (ja) | アルデヒドの製造方法 | |
| RU2002128740A (ru) | Одностадийный способ получения 1,3-диола | |
| KR970073720A (ko) | 디포스핀 리간드를 함유하는 로듐 착물을 기본으로 하는 촉매계 및 알데히드 제조시의 이의 용도 | |
| CA2540473A1 (en) | Process for preparing cationic rhodium complexes | |
| Zhang et al. | The preparation and catalytic performance of novel amine-modified silica supported ruthenium complexes for supercritical carbon dioxide hydrogenation to formic acid | |
| JP2004506032A (ja) | 含酸素製品の製造 | |
| Meyer et al. | Pincer Ligand Enhanced Rhodium‐Catalyzed Carbonylation of Formaldehyde: Direct Ethylene Glycol Production | |
| Marson et al. | Chiral Calix [4] arene‐Based Diphosphites as Ligands in the Asymmetric Hydrogenation of Prochiral Olefins | |
| Zhu et al. | New Staudinger Strategy Enabled N-Acyl Phosphinamidites Synthesis | |
| RU2003137822A (ru) | Одностадийный способ получения 1,3-пропандиола из этиленоксида и синтез-газа с катализатором с фосфоланоалкановым лигандом | |
| CN111825537A (zh) | 一种无合成气的高效合成α,β-不饱和醛的方法 | |
| Zhou et al. | A new air‐stable and reusable tetraphosphine ligand for rhodium‐catalyzed hydroformylation of terminal olefins at low temperature | |
| RU2318790C2 (ru) | Способ теломеризации диена с сопряженными двойными связями, катализатор и бидентатный лиганд, используемые в указанном способе |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| QB4A | Licence on use of patent |
Effective date: 20081209 |