CN109364997A - 用于氢甲酰化乙烯的双齿配位体 - Google Patents
用于氢甲酰化乙烯的双齿配位体 Download PDFInfo
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- CN109364997A CN109364997A CN201811183222.6A CN201811183222A CN109364997A CN 109364997 A CN109364997 A CN 109364997A CN 201811183222 A CN201811183222 A CN 201811183222A CN 109364997 A CN109364997 A CN 109364997A
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- rhodium
- bidentate ligands
- catalyst
- hydroformylation
- ligand
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- 239000003446 ligand Substances 0.000 title claims abstract description 116
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 68
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000005977 Ethylene Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 81
- 239000003054 catalyst Substances 0.000 claims abstract description 69
- 239000010948 rhodium Substances 0.000 claims abstract description 59
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 56
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 40
- 239000012530 fluid Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 6
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical group [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims description 5
- 239000012018 catalyst precursor Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 30
- 239000001257 hydrogen Substances 0.000 abstract description 30
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- 125000003118 aryl group Chemical group 0.000 abstract description 17
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004577 thatch Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000005406 washing Methods 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
-
- 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)
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| EP12382481.5A EP2740535A1 (en) | 2012-12-04 | 2012-12-04 | Bidentate ligands for hydroformylation of ethylene |
| CN201380062320.3A CN104822456A (zh) | 2012-12-04 | 2013-11-19 | 用于氢甲酰化乙烯的双齿配位体 |
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| US (1) | US9795952B2 (enExample) |
| EP (1) | EP2740535A1 (enExample) |
| JP (1) | JP6360067B2 (enExample) |
| KR (1) | KR102157915B1 (enExample) |
| CN (2) | CN109364997A (enExample) |
| WO (1) | WO2014088800A1 (enExample) |
| ZA (1) | ZA201503184B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110327975A (zh) * | 2019-06-06 | 2019-10-15 | 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 |
| CN113385236A (zh) * | 2021-06-16 | 2021-09-14 | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015065610A1 (en) | 2013-10-28 | 2015-05-07 | Rohm And Haas Company | Process for separating methacrolein |
| BR112018016320B1 (pt) * | 2016-02-11 | 2022-07-12 | Dow Technology Investments Llc | Processo para converter olefinas em álcoois, éteres ou combinações dos mesmos |
| 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 |
| WO2018221830A1 (ko) * | 2017-05-29 | 2018-12-06 | (주) 엘지화학 | 히드로포밀화 반응용 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 |
| US10723672B2 (en) | 2018-02-26 | 2020-07-28 | Chervon Phillips Chemical Company Lp | 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| EP4413011A1 (en) | 2021-10-06 | 2024-08-14 | 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 |
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| WO2014088800A1 (en) | 2014-06-12 |
| ZA201503184B (en) | 2017-07-26 |
| JP6360067B2 (ja) | 2018-07-18 |
| US9795952B2 (en) | 2017-10-24 |
| EP2740535A1 (en) | 2014-06-11 |
| US20150328628A1 (en) | 2015-11-19 |
| JP2016500123A (ja) | 2016-01-07 |
| CN104822456A (zh) | 2015-08-05 |
| KR102157915B1 (ko) | 2020-09-21 |
| KR20150092144A (ko) | 2015-08-12 |
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