DE2912230B1 - Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten Oxosynthese - Google Patents
Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten OxosyntheseInfo
- Publication number
- DE2912230B1 DE2912230B1 DE2912230A DE2912230A DE2912230B1 DE 2912230 B1 DE2912230 B1 DE 2912230B1 DE 2912230 A DE2912230 A DE 2912230A DE 2912230 A DE2912230 A DE 2912230A DE 2912230 B1 DE2912230 B1 DE 2912230B1
- Authority
- DE
- Germany
- Prior art keywords
- rhodium
- phosphine
- catalysts
- catalyst
- activity
- 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.)
- Withdrawn
Links
- 239000010948 rhodium Substances 0.000 title claims description 75
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims description 60
- 239000003054 catalyst Substances 0.000 title claims description 52
- 229910052703 rhodium Inorganic materials 0.000 title claims description 51
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims description 49
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 13
- 238000011084 recovery Methods 0.000 title claims description 9
- 239000007795 chemical reaction product Substances 0.000 title claims description 3
- 230000007420 reactivation Effects 0.000 title claims 3
- 230000000694 effects Effects 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 17
- 238000007037 hydroformylation reaction Methods 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 150000003283 rhodium Chemical class 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000003003 phosphines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 150000003284 rhodium compounds Chemical class 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 230000008929 regeneration Effects 0.000 claims 3
- 238000011069 regeneration method Methods 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000007423 decrease Effects 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- FERQZYSWBVOPNX-UHFFFAOYSA-N carbonyl dichloride;rhodium;triphenylphosphane Chemical compound [Rh].ClC(Cl)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FERQZYSWBVOPNX-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- 230000003292 diminished effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 38
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 32
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 28
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 239000011552 falling film Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HJSXRRURKUSSJW-UHFFFAOYSA-N C(=O)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Rh] Chemical compound C(=O)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Rh] HJSXRRURKUSSJW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical compound P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 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
- B01J31/24—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
- B01J31/20—Carbonyls
-
- 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
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2912230A DE2912230B1 (de) | 1979-03-28 | 1979-03-28 | Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten Oxosynthese |
| ZA00801452A ZA801452B (en) | 1979-03-28 | 1980-03-12 | Hydroformylation catalyst reactivation |
| NO800820A NO156742C (no) | 1979-03-28 | 1980-03-21 | Fremgangsmaate for fremstilling av et hydroformyleringsmedium, og fremgangsmaate for fremstilling av aldehyder. |
| YU810/80A YU43217B (en) | 1979-03-28 | 1980-03-24 | Process for preparing agent for hydroformilation from used up agent for hydroformilation |
| BR8001825A BR8001825A (pt) | 1979-03-28 | 1980-03-26 | Processo para preparacao de um meio de hidroformilacao, meio de hidroformilacao, aperfeicoamento em processo para hidroformilaco, processo para recuperacao e aumento de atividade de catalisadores e uso de um catalisador |
| AU56868/80A AU541966B2 (en) | 1979-03-28 | 1980-03-26 | Hydroformylation catalyst reactivation |
| JP3826980A JPS55159841A (en) | 1979-03-28 | 1980-03-27 | Reactivation of hydroformylation catalyst |
| SU802901402A SU1704628A3 (ru) | 1979-03-28 | 1980-03-27 | Способ получени среды гидроформилировани |
| EP80101665A EP0017183B1 (en) | 1979-03-28 | 1980-03-27 | Hydroformylation medium, process of production thereof and process for producing aldehydes using the hydroformylation medium |
| AT80101665T ATE7222T1 (de) | 1979-03-28 | 1980-03-27 | Hydroformylierungsmittel, verfahren zu dessen herstellung und verwendung dieses hydroformylierungsmittels bei der herstellung von aldehyden. |
| ES489995A ES8104175A1 (es) | 1979-03-28 | 1980-03-27 | Procedimiento para preparar un medio de hidroformilacion |
| HU80721A HU188563B (en) | 1979-03-28 | 1980-03-27 | Process for production of concentrates of rhodiumcomplex and hydroformilizing reacting medium |
| MX80181737A MX155342A (es) | 1979-03-28 | 1980-03-27 | Procedimiento para preparar un medio de reaccion de hidroformilacion reactivo a partir de un medio de hidroformilacion agotado |
| DK132780A DK132780A (da) | 1979-03-28 | 1980-03-27 | Hydroformyleringsmedium fremgangsmaade til dets fremstilling og anvndelse deraf ved fremstilling af aldehyder i naervaerelse af en kompleks rhodium katalysator |
| DE8080101665T DE3067607D1 (en) | 1979-03-28 | 1980-03-27 | Hydroformylation medium, process of production thereof and process for producing aldehydes using the hydroformylation medium |
| ES494730A ES8104781A1 (es) | 1979-03-28 | 1980-09-03 | Procedimiento de hidroformilacion para preparar aldehidos |
| SG869/86A SG86986G (en) | 1979-03-28 | 1986-10-31 | Hydroformylation medium,process of production thereof and process for producing aldehydes using the hydroformylation medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2912230A DE2912230B1 (de) | 1979-03-28 | 1979-03-28 | Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten Oxosynthese |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2912230B1 true DE2912230B1 (de) | 1980-10-09 |
Family
ID=6066676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2912230A Withdrawn DE2912230B1 (de) | 1979-03-28 | 1979-03-28 | Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten Oxosynthese |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS55159841A (enrdf_load_stackoverflow) |
| DE (1) | DE2912230B1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA801452B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3017651A1 (de) * | 1979-05-11 | 1980-11-27 | Mitsubishi Chem Ind | Verfahren zur hydroformylierung von olefinen |
| EP0097891A1 (en) * | 1982-06-18 | 1984-01-11 | Union Carbide Corporation | A method for refining crude aldehyde products |
| DE3338340A1 (de) * | 1982-10-21 | 1984-05-03 | Mitsubishi Chemical Industries Ltd., Tokyo | Hydroformylierungsverfahren |
| WO2006115644A3 (en) * | 2005-04-21 | 2007-03-15 | Celanese Int Corp | Processes for recovery of a triarylphosphine from a group viii metal catalyst complex mixture |
| BE1030099B1 (nl) * | 2021-12-24 | 2023-07-25 | Indaver Nv | Werkwijze voor het screenen van vloeibare farmacochemische en/of fijnchemische afvalstoffen omvattende organische solventen en edelmetalen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7639833B2 (ja) * | 2021-12-14 | 2025-03-05 | 三菱ケミカル株式会社 | アルデヒドの製造方法及びアルコールの製造方法、並びに触媒組成物 |
-
1979
- 1979-03-28 DE DE2912230A patent/DE2912230B1/de not_active Withdrawn
-
1980
- 1980-03-12 ZA ZA00801452A patent/ZA801452B/xx unknown
- 1980-03-27 JP JP3826980A patent/JPS55159841A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3017651A1 (de) * | 1979-05-11 | 1980-11-27 | Mitsubishi Chem Ind | Verfahren zur hydroformylierung von olefinen |
| EP0097891A1 (en) * | 1982-06-18 | 1984-01-11 | Union Carbide Corporation | A method for refining crude aldehyde products |
| DE3338340A1 (de) * | 1982-10-21 | 1984-05-03 | Mitsubishi Chemical Industries Ltd., Tokyo | Hydroformylierungsverfahren |
| WO2006115644A3 (en) * | 2005-04-21 | 2007-03-15 | Celanese Int Corp | Processes for recovery of a triarylphosphine from a group viii metal catalyst complex mixture |
| BE1030099B1 (nl) * | 2021-12-24 | 2023-07-25 | Indaver Nv | Werkwijze voor het screenen van vloeibare farmacochemische en/of fijnchemische afvalstoffen omvattende organische solventen en edelmetalen |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA801452B (en) | 1981-08-26 |
| JPH0116532B2 (enrdf_load_stackoverflow) | 1989-03-24 |
| JPS55159841A (en) | 1980-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8263 | Opposition against grant of a patent | ||
| 8230 | Patent withdrawn | ||
| 8227 | New person/name/address of the applicant |
Free format text: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |