DE2502233A1 - Verfahren zur rueckgewinnung von rhodium und triphenylphosphin - Google Patents
Verfahren zur rueckgewinnung von rhodium und triphenylphosphinInfo
- Publication number
- DE2502233A1 DE2502233A1 DE19752502233 DE2502233A DE2502233A1 DE 2502233 A1 DE2502233 A1 DE 2502233A1 DE 19752502233 DE19752502233 DE 19752502233 DE 2502233 A DE2502233 A DE 2502233A DE 2502233 A1 DE2502233 A1 DE 2502233A1
- Authority
- DE
- Germany
- Prior art keywords
- triphenylphosphine
- rhodium
- acid
- aldehyde
- recovery
- 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.)
- Ceased
Links
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 title claims description 49
- 239000010948 rhodium Substances 0.000 title claims description 24
- 229910052703 rhodium Inorganic materials 0.000 title claims description 23
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 16
- 238000011084 recovery Methods 0.000 title claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000007037 hydroformylation reaction Methods 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- -1 aliphatic aldehyde Chemical class 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000004678 hydrides Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- SKAFPBSZWJKMPR-UHFFFAOYSA-N phosphanylidenemethanone Chemical compound O=C=P SKAFPBSZWJKMPR-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical group 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- B01J31/20—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
-
- 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
- B01J31/4053—Regeneration or reactivation of catalysts containing metals with recovery of phosphorous catalyst system constituents
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19691/74A IT1007026B (it) | 1974-01-23 | 1974-01-23 | Procedimento per il ricupero di sistemi catalitici da grezzi di idroformilazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2502233A1 true DE2502233A1 (de) | 1975-07-24 |
Family
ID=11160412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752502233 Ceased DE2502233A1 (de) | 1974-01-23 | 1975-01-21 | Verfahren zur rueckgewinnung von rhodium und triphenylphosphin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3968134A (en, 2012) |
| JP (1) | JPS50104790A (en, 2012) |
| BE (1) | BE824700A (en, 2012) |
| CA (1) | CA1051854A (en, 2012) |
| DE (1) | DE2502233A1 (en, 2012) |
| ES (1) | ES434027A1 (en, 2012) |
| FR (1) | FR2258357B1 (en, 2012) |
| GB (1) | GB1495025A (en, 2012) |
| IT (1) | IT1007026B (en, 2012) |
| NL (1) | NL7500556A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3017651A1 (de) * | 1979-05-11 | 1980-11-27 | Mitsubishi Chem Ind | Verfahren zur hydroformylierung von olefinen |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2614799C2 (de) * | 1976-04-06 | 1986-02-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
| US4196096A (en) * | 1979-02-12 | 1980-04-01 | Eastman Kodak Company | Process for regeneration of rhodium hydroformylation catalysts |
| US4297239A (en) * | 1979-07-16 | 1981-10-27 | Union Carbide Corporation | Hydroformylation catalyst reactivation |
| US4283304A (en) * | 1979-05-21 | 1981-08-11 | Union Carbide Corporation | Process for removing triorganophosphine from a liquid composition |
| US4710587A (en) * | 1980-04-16 | 1987-12-01 | Union Carbide Corp. | Process for removing triorganophosphine from an organic liquid |
| JPS5850234B2 (ja) * | 1980-10-23 | 1983-11-09 | 三菱化学株式会社 | 第８族貴金属固体錯体の取得方法 |
| US4363764A (en) * | 1980-12-30 | 1982-12-14 | Union Carbide Corporation | Preparation of rhodium complex compounds |
| GB2097795B (en) * | 1981-05-01 | 1984-08-01 | Johnson Matthey Plc | Recovering triaryl phosphine from poisoned thodium catalyst systems |
| US4459365A (en) * | 1981-05-29 | 1984-07-10 | Mitsubishi Gas Chemical Company, Inc. | Method of recovering a catalytic metal |
| DE3235029A1 (de) * | 1982-09-22 | 1984-03-22 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur rueckgewinnung von wasserloeslichen, rhodium enthaltenden hydroformylierungskatalysatoren |
| US4935550A (en) * | 1988-08-12 | 1990-06-19 | Union Carbide Chemicals And Plastics Company Inc. | Catalytic metal recovery from non-polar organic solutions |
| US5675041A (en) * | 1995-01-18 | 1997-10-07 | Exxon Research & Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene |
| US5520722A (en) * | 1995-01-18 | 1996-05-28 | Exxon Research And Engineering Company | Multiunsaturates removal process |
| US5516965A (en) * | 1995-01-18 | 1996-05-14 | Exxon Research And Engineering Company | Unsaturates recovery and recycle process |
| CZ283697A3 (cs) * | 1996-09-11 | 1998-04-15 | Mitsubishi Chemical Corporation | Způsob přípravy roztoku komplexu rhodia a jeho použití |
| KR100969474B1 (ko) * | 2006-10-24 | 2010-07-14 | 주식회사 엘지화학 | 하이드로포밀화 반응생성물로부터의 로듐촉매 회수방법 |
| CN102617308B (zh) * | 2012-03-13 | 2013-11-27 | 青岛科技大学 | 一种烯烃两相氢甲酰化方法 |
| JP7269238B2 (ja) | 2017-11-13 | 2023-05-08 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセスからロジウムを回収するためのプロセス |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515757A (en) * | 1966-04-01 | 1970-06-02 | Ethyl Corp | Organic compounds and processes |
| US3547964A (en) * | 1968-07-24 | 1970-12-15 | Union Oil Co | Group viii noble metal catalyst recovery |
| US3560539A (en) * | 1968-08-21 | 1971-02-02 | Union Oil Co | Selective catalyst recovery |
| DE2045416C3 (de) * | 1970-09-15 | 1979-10-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Elution von Rhodium, das als Rhodiumcarbonylat auf einem basischen Ionenaustauscher gebunden ist |
| IT950259B (it) * | 1972-03-16 | 1973-06-20 | Montedison Spa | Procedimento per il ricupero di si stemi catalitici costituiti da com plessi di metalli di transizione con leganti organici |
-
1974
- 1974-01-23 IT IT19691/74A patent/IT1007026B/it active
-
1975
- 1975-01-17 NL NL7500556A patent/NL7500556A/xx not_active Application Discontinuation
- 1975-01-20 FR FR7501591A patent/FR2258357B1/fr not_active Expired
- 1975-01-21 DE DE19752502233 patent/DE2502233A1/de not_active Ceased
- 1975-01-22 US US05/543,151 patent/US3968134A/en not_active Expired - Lifetime
- 1975-01-22 JP JP50008800A patent/JPS50104790A/ja active Pending
- 1975-01-22 ES ES434027A patent/ES434027A1/es not_active Expired
- 1975-01-22 CA CA218,454A patent/CA1051854A/en not_active Expired
- 1975-01-23 BE BE152643A patent/BE824700A/xx unknown
- 1975-01-23 GB GB3046/75A patent/GB1495025A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3017651A1 (de) * | 1979-05-11 | 1980-11-27 | Mitsubishi Chem Ind | Verfahren zur hydroformylierung von olefinen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2258357A1 (en, 2012) | 1975-08-18 |
| ES434027A1 (es) | 1976-12-01 |
| CA1051854A (en) | 1979-04-03 |
| GB1495025A (en) | 1977-12-14 |
| FR2258357B1 (en, 2012) | 1979-09-28 |
| US3968134A (en) | 1976-07-06 |
| NL7500556A (nl) | 1975-07-25 |
| JPS50104790A (en, 2012) | 1975-08-19 |
| IT1007026B (it) | 1976-10-30 |
| BE824700A (fr) | 1975-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C 27/22 |
|
| 8131 | Rejection |