MX2022005287A - Procesos para la recuperación de rodio procedente de un proceso de hidroformilación. - Google Patents
Procesos para la recuperación de rodio procedente de un proceso de hidroformilación.Info
- Publication number
- MX2022005287A MX2022005287A MX2022005287A MX2022005287A MX2022005287A MX 2022005287 A MX2022005287 A MX 2022005287A MX 2022005287 A MX2022005287 A MX 2022005287A MX 2022005287 A MX2022005287 A MX 2022005287A MX 2022005287 A MX2022005287 A MX 2022005287A
- Authority
- MX
- Mexico
- Prior art keywords
- hydroformylation process
- catalyst
- aqueous phase
- organic phase
- organophosphorous ligand
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 8
- 238000007037 hydroformylation reaction Methods 0.000 title abstract 5
- 238000011084 recovery Methods 0.000 title abstract 2
- 229910052703 rhodium Inorganic materials 0.000 title abstract 2
- 239000010948 rhodium Substances 0.000 title abstract 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000003446 ligand Substances 0.000 abstract 3
- 239000012074 organic phase Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 238000010926 purge Methods 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 239000010970 precious metal Substances 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 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
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
-
- 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
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- 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
-
- 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
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Abstract
La presente invención generalmente se refiere a procesos para la recuperación de rodio de una corriente de purga de catalizador de un proceso de hidroformilación de olefinas C6 o superior. En una modalidad, el proceso comprende (a) tratar una corriente de purga líquida que contiene el catalizador del proceso de hidroformilación, en donde el catalizador comprende un metal precioso y un ligando organofosforado, con un oxidante en presencia de una fase acuosa líquida separada que comprende un ácido libre de haluros a una temperatura suficiente para efectuar la oxidación de la mayoría del ligando organofosforado contenido, en donde el ácido libre de haluros es un ácido orgánico C1-C6 o un ácido fosforoso; (b) recuperar la fase acuosa; (c) poner en contacto la fase acuosa con una fase orgánica separada mediante la mezcla de las dos fases bajo una atmósfera de gas de síntesis, en donde la fase orgánica separada comprende un ligando organofosforado hidrolizable e insoluble en agua y la olefina reciclada de un proceso de hidroformilación; y (d) separar la fase orgánica a reciclar de regreso a un proceso de hidroformilación.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962930833P | 2019-11-05 | 2019-11-05 | |
| PCT/US2020/056414 WO2021091687A1 (en) | 2019-11-05 | 2020-10-20 | Processes for recovery of rhodium from a hydroformylation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2022005287A true MX2022005287A (es) | 2022-08-02 |
Family
ID=73402148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2022005287A MX2022005287A (es) | 2019-11-05 | 2020-10-20 | Procesos para la recuperación de rodio procedente de un proceso de hidroformilación. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US12246310B2 (es) |
| EP (1) | EP4054762B1 (es) |
| JP (1) | JP7787809B2 (es) |
| KR (1) | KR20220130096A (es) |
| CN (1) | CN114728278B (es) |
| BR (1) | BR112022008189A2 (es) |
| MX (1) | MX2022005287A (es) |
| MY (1) | MY209835A (es) |
| PL (1) | PL4054762T3 (es) |
| TW (1) | TWI874467B (es) |
| WO (1) | WO2021091687A1 (es) |
| ZA (1) | ZA202204869B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4685126A1 (de) | 2024-07-23 | 2026-01-28 | Evonik Oxeno GmbH & Co. KG | Verfahren zur herstellung von c9-aldehyden bzw. c9-alkoholen aus buten-haltigen kohlenwasserstoffströmen |
Family Cites Families (60)
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|---|---|---|---|---|
| US3415906A (en) | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| DE2448005C2 (de) | 1974-10-09 | 1983-10-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Regenerierung von Rhodium oder Iridium enthaltenden Katalysatoren aus Destillationsrückständen von Hydroformylierungsgemischen |
| 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 |
| EP0007768A3 (en) | 1978-07-27 | 1980-02-20 | DAVY McKEE (LONDON) LIMITED | Hydroformylation of alpha-olefinic compounds |
| US4196096A (en) | 1979-02-12 | 1980-04-01 | Eastman Kodak Company | Process for regeneration of rhodium hydroformylation catalysts |
| US4374278A (en) | 1980-02-28 | 1983-02-15 | Union Carbide Corporation | Hydroformylation catalyst reactivation |
| US4710587A (en) | 1980-04-16 | 1987-12-01 | Union Carbide Corp. | Process for removing triorganophosphine from an organic liquid |
| US4605780A (en) | 1980-09-24 | 1986-08-12 | Union Carbide Corporation | Reactivation of rhodium complex hydroformylation catalysts |
| US4400547A (en) | 1981-04-10 | 1983-08-23 | Eastman Kodak Company | Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof |
| US4518809A (en) | 1981-06-11 | 1985-05-21 | Monsanto Company | Preparation of pentyl nonanols |
| US4528403A (en) | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
| GB8334359D0 (en) | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US5110990A (en) | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
| US4567302A (en) | 1984-07-20 | 1986-01-28 | Angus Chemical | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof |
| US4737588A (en) | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| 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 |
| US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| WO1988008835A1 (en) | 1987-05-14 | 1988-11-17 | Colorado State University Research Foundation | 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 |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5237106A (en) * | 1992-01-24 | 1993-08-17 | Union Carbide Chemicals & Plastics Technology Corporation | Reactivation of hydroformylation catalysts |
| 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 |
| US5395979A (en) | 1993-02-25 | 1995-03-07 | Exxon Chemical Patents Inc. | Method for separating catalyst from a hydroformylation reaction product using alkylated ligands |
| US5290743A (en) | 1993-03-22 | 1994-03-01 | Arco Chemical Technology L.P. | Process for regenerating a deactivated rhodium hydroformylation catalyst system |
| 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) |
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| GB0021715D0 (en) | 2000-09-05 | 2000-10-18 | Ici Plc | Recovery of metals |
| DE10164720B4 (de) | 2001-07-07 | 2013-12-19 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
| DE102011002640B4 (de) | 2011-01-13 | 2021-10-07 | Evonik Operations Gmbh | Verfahren zur Aufreinigung von Biphephos |
| SA112330271B1 (ar) * | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
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| DE102014201756A1 (de) | 2014-01-31 | 2015-08-06 | Evonik Degussa Gmbh | Reinigung chlorverschmutzter Organophosphorverbindungen |
| KR102362007B1 (ko) * | 2014-03-31 | 2022-02-11 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포르밀화 공정 |
| DE102015202722A1 (de) | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Monophosphit-Gemischen |
| WO2015176928A1 (de) | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Verfahren zur herstellung von monophosphiten |
| EP3031817B1 (de) | 2014-12-04 | 2019-05-01 | Evonik Degussa GmbH | Terphenyl-2-oxy-phosphite als liganden in hydroformylierungskatalysatoren |
| RU2585285C1 (ru) | 2015-04-20 | 2016-05-27 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ непрерывного гидроформилирования олефинов c2-c8 |
| EP3176174A1 (de) | 2015-12-03 | 2017-06-07 | Evonik Degussa GmbH | Verfahren zur reduzierung des chlorgehalts von organotetraphosphiten |
| 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 |
| 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 |
| KR102307815B1 (ko) | 2017-07-06 | 2021-10-01 | 주식회사 엘지화학 | 하이드로포밀화 반응에 의한 알데히드 제조방법 |
| RU2020117417A (ru) * | 2017-11-13 | 2021-11-29 | Дау Текнолоджи Инвестментс Ллк | Способы извлечения родия из процесса гидроформилирования |
| TWI793216B (zh) | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| KR20190127277A (ko) | 2018-05-04 | 2019-11-13 | 주식회사 삼양바이오팜 | mRNA 전달용 고분자 나노입자 조성물 및 그 제조방법 |
-
2020
- 2020-10-06 TW TW109134555A patent/TWI874467B/zh active
- 2020-10-20 US US17/754,163 patent/US12246310B2/en active Active
- 2020-10-20 MX MX2022005287A patent/MX2022005287A/es unknown
- 2020-10-20 KR KR1020227018482A patent/KR20220130096A/ko active Pending
- 2020-10-20 CN CN202080078656.9A patent/CN114728278B/zh active Active
- 2020-10-20 BR BR112022008189A patent/BR112022008189A2/pt unknown
- 2020-10-20 WO PCT/US2020/056414 patent/WO2021091687A1/en not_active Ceased
- 2020-10-20 JP JP2022523812A patent/JP7787809B2/ja active Active
- 2020-10-20 MY MYPI2022002297A patent/MY209835A/en unknown
- 2020-10-20 PL PL20807190.2T patent/PL4054762T3/pl unknown
- 2020-10-20 EP EP20807190.2A patent/EP4054762B1/en active Active
-
2022
- 2022-05-03 ZA ZA2022/04869A patent/ZA202204869B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN114728278B (zh) | 2025-06-06 |
| EP4054762B1 (en) | 2024-12-18 |
| US12246310B2 (en) | 2025-03-11 |
| TW202126385A (zh) | 2021-07-16 |
| BR112022008189A2 (pt) | 2022-07-12 |
| JP7787809B2 (ja) | 2025-12-17 |
| MY209835A (en) | 2025-08-07 |
| EP4054762A1 (en) | 2022-09-14 |
| JP2023501124A (ja) | 2023-01-18 |
| PL4054762T3 (pl) | 2025-03-10 |
| CN114728278A (zh) | 2022-07-08 |
| TWI874467B (zh) | 2025-03-01 |
| US20220288574A1 (en) | 2022-09-15 |
| KR20220130096A (ko) | 2022-09-26 |
| ZA202204869B (en) | 2023-11-29 |
| WO2021091687A1 (en) | 2021-05-14 |
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