TWI586644B - 氫甲醯化方法 - Google Patents
氫甲醯化方法 Download PDFInfo
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- TWI586644B TWI586644B TW104139257A TW104139257A TWI586644B TW I586644 B TWI586644 B TW I586644B TW 104139257 A TW104139257 A TW 104139257A TW 104139257 A TW104139257 A TW 104139257A TW I586644 B TWI586644 B TW I586644B
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- WTWPQOWYFZRSFA-UHFFFAOYSA-N diamino hydrogen phosphate Chemical compound NOP(O)(=O)ON WTWPQOWYFZRSFA-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- XLGKKDZDZBIMRD-UHFFFAOYSA-N dimethyl phenyl phosphite Chemical compound COP(OC)OC1=CC=CC=C1 XLGKKDZDZBIMRD-UHFFFAOYSA-N 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000005461 organic phosphorous group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- FTIMWVSQXCWTAW-UHFFFAOYSA-N ruthenium Chemical compound [Ru].[Ru] FTIMWVSQXCWTAW-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 125000004079 stearyl 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])C([H])([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 description 1
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- 230000000153 supplemental effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- WUCQRXWCJPCWTQ-UHFFFAOYSA-N trans-3-pentenal Natural products CC=CCC=O WUCQRXWCJPCWTQ-UHFFFAOYSA-N 0.000 description 1
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- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
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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
-
- 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
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
-
- 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
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)
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| TW (1) | TWI586644B (enExample) |
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| PL3374340T3 (pl) | 2015-11-10 | 2022-04-11 | Dow Technology Investments Llc | Sposób wytwarzania aldehydów |
| RU2751511C9 (ru) | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
| CN107469860B (zh) * | 2017-08-22 | 2020-05-19 | 中国海洋石油集团有限公司 | 一种提高铑/双亚膦酸酯催化剂稳定性的方法 |
| TWI793216B (zh) | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| MY203235A (en) * | 2018-11-29 | 2024-06-19 | Dow Technology Investments Llc | Hydroformylation process |
| GB201907659D0 (en) | 2019-05-30 | 2019-07-17 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2021247177A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Alcohols production |
| EP4161696A4 (en) * | 2020-06-05 | 2025-05-28 | Scion Holdings LLC | BRANCHED ALCOHOLS |
| WO2021247516A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Branched alcohols |
| US12221404B2 (en) | 2020-06-05 | 2025-02-11 | SCION Holdings LLC | Composition comprising branched aldehydes |
| ES2974422T3 (es) * | 2020-07-30 | 2024-06-27 | Evonik Oxeno Gmbh & Co Kg | Procedimiento para la preparación de aldehídos y separación del sistema catalítico mediante separación por membrana |
| GB202012930D0 (en) * | 2020-08-19 | 2020-09-30 | Johnson Matthey Davy Technologies Ltd | Process for hydroformylation with removal of dissolved hydrogen |
| CN116261565A (zh) | 2020-10-13 | 2023-06-13 | 美国陶氏有机硅公司 | 具有醛官能团的有机硅化合物的制备 |
| CN112403401B (zh) * | 2020-11-06 | 2022-06-21 | 中国海洋石油集团有限公司 | 一种烯烃氢甲酰化制醛中醛和催化剂分离的装置和方法 |
| WO2022132372A1 (en) * | 2020-12-14 | 2022-06-23 | Dow Technology Investments Llc | Processes to improve catalytic metal accountability in hydroformylation processes |
| US12145904B2 (en) | 2020-12-17 | 2024-11-19 | SCION Holdings LLC | Branched products |
| 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 |
| KR20240074844A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 프로필이민-작용성 유기규소 화합물 및 1차 아미노프로필-작용성 유기규소 화합물의 제조 |
| JP2024536162A (ja) | 2021-10-06 | 2024-10-04 | ダウ グローバル テクノロジーズ エルエルシー | イミン官能性有機ケイ素化合物及び一級アミノ官能性有機ケイ素化合物の調製 |
| WO2023086718A1 (en) | 2021-11-11 | 2023-05-19 | Dow Technology Investments Llc | Processes for recovering rhodium from hydroformylation processes |
| EP4437031A2 (en) | 2021-11-22 | 2024-10-02 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carbinol functionality |
| CN118338965A (zh) | 2021-12-16 | 2024-07-12 | 陶氏技术投资有限责任公司 | 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 |
| EP4448170B1 (en) | 2021-12-16 | 2025-08-20 | Dow Technology Investments LLC | Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| EP4496833A1 (en) | 2022-03-21 | 2025-01-29 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carboxy functionality |
| EP4508106A1 (en) | 2022-04-13 | 2025-02-19 | Dow Global Technologies LLC | Silicone - vinylester functional compounds and methods for their preparation and use in personal care compositions |
| KR20250003565A (ko) | 2022-04-13 | 2025-01-07 | 다우 실리콘즈 코포레이션 | 조성물, 우레탄 프리폴리머, 및 관련 방법 및 용도 |
| US20250145647A1 (en) | 2022-04-13 | 2025-05-08 | Dow Silicones Corporation | Preparation of organosilicon compounds with vinylester functionality |
| CN118843652A (zh) | 2022-04-13 | 2024-10-25 | 陶氏环球技术有限责任公司 | 制备聚醚官能有机硅化合物 |
| CN114773172B (zh) * | 2022-06-20 | 2022-10-18 | 中海油天津化工研究设计院有限公司 | 一种烯烃氢甲酰化制醛工艺优化方法 |
| GB202213997D0 (en) | 2022-09-26 | 2022-11-09 | Johnson Matthey Davy Technologies Ltd | Parallel zone hydroformylation reaction |
| WO2024123510A1 (en) | 2022-12-06 | 2024-06-13 | Dow Technology Investments Llc | Process of controlling heavies in a recycle catalyst stream |
| GB202303617D0 (en) | 2023-03-13 | 2023-04-26 | Johnson Matthey Davy Technologies Ltd | Method and apparatus for producing aldehyde |
| WO2025029369A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
| WO2025038266A1 (en) | 2023-08-14 | 2025-02-20 | Dow Global Technologies Llc | Cobalt catalyzed hydroformylation of vinyl-functional polyorganosiloxanes |
| WO2025170897A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Optimized gas-stripping hydroformylation process for oxo aldehydes |
| WO2025170887A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Gas distribution in gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170886A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Purge for a gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170891A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Composition of matter for gas-stripping oxo aldehydes hydroformylation process |
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- 2015-11-18 WO PCT/US2015/061332 patent/WO2016089602A1/en not_active Ceased
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- 2015-11-18 BR BR112017011447-0A patent/BR112017011447B1/pt active IP Right Grant
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| EP3230248B1 (en) | 2019-12-25 |
| JP2017537918A (ja) | 2017-12-21 |
| TW201620863A (zh) | 2016-06-16 |
| RU2017121307A3 (enExample) | 2019-02-01 |
| CN107001218A (zh) | 2017-08-01 |
| JP2021008477A (ja) | 2021-01-28 |
| BR112017011447B1 (pt) | 2020-12-15 |
| MX2017006792A (es) | 2017-09-08 |
| PL3230248T3 (pl) | 2020-05-18 |
| WO2016089602A1 (en) | 2016-06-09 |
| RU2017121307A (ru) | 2018-12-19 |
| CA2969527A1 (en) | 2016-06-09 |
| MX381950B (es) | 2025-03-13 |
| US20170355656A1 (en) | 2017-12-14 |
| KR102507703B1 (ko) | 2023-03-09 |
| CA2969527C (en) | 2023-08-22 |
| RU2699368C2 (ru) | 2019-09-05 |
| MY184826A (en) | 2021-04-24 |
| US10023516B2 (en) | 2018-07-17 |
| BR112017011447A2 (pt) | 2018-02-27 |
| KR20170093152A (ko) | 2017-08-14 |
| EP3230248A1 (en) | 2017-10-18 |
| JP7128622B2 (ja) | 2022-08-31 |
| CN107001218B (zh) | 2021-02-26 |
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