DE2045745C3 - Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der Oxosynthese - Google Patents
Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der OxosyntheseInfo
- Publication number
- DE2045745C3 DE2045745C3 DE2045745A DE2045745A DE2045745C3 DE 2045745 C3 DE2045745 C3 DE 2045745C3 DE 2045745 A DE2045745 A DE 2045745A DE 2045745 A DE2045745 A DE 2045745A DE 2045745 C3 DE2045745 C3 DE 2045745C3
- Authority
- DE
- Germany
- Prior art keywords
- cobalt
- phosphines
- organic
- aqueous
- oxo
- 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.)
- Expired
Links
- 239000010941 cobalt Substances 0.000 title claims description 18
- 229910017052 cobalt Inorganic materials 0.000 title claims description 18
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 17
- 150000003003 phosphines Chemical class 0.000 title claims description 17
- 238000004821 distillation Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 238000003786 synthesis reaction Methods 0.000 title claims description 5
- 238000011084 recovery Methods 0.000 title claims 4
- 239000012074 organic phase Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 7
- 239000011707 mineral Substances 0.000 claims 7
- 150000007513 acids Chemical class 0.000 claims 6
- 230000001590 oxidative effect Effects 0.000 claims 6
- -1 Decyl ester Chemical class 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 229910001882 dioxygen Inorganic materials 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000010908 decantation Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 229910001385 heavy metal Inorganic materials 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- MOSFSEPBWRXKJZ-UHFFFAOYSA-N tridecylphosphane Chemical compound CCCCCCCCCCCCCP MOSFSEPBWRXKJZ-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 2
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 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
- B01J31/40—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
-
- 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
- B01J31/40—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
- B01J31/403—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing iron group metals or copper
-
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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
-
- 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)
- Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2045745A DE2045745C3 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der Oxosynthese |
| CA122,591A CA952915A (en) | 1970-09-16 | 1971-09-10 | Recovery of cobalt and organic phosphines which do not form water-soluble salts from distillation residues resulting from the oxo reaction |
| IT52874/71A IT942171B (it) | 1970-09-16 | 1971-09-14 | Procedimento per il recupero di cobalto e fosfine organiche che non formano sali idrosolubili dai residui di distillazione della ossosintesi |
| BE772574A BE772574A (fr) | 1970-09-16 | 1971-09-14 | Procede de recuperation de cobalt et de phosphines organiques ne formant pas de sels hydrosolubles |
| FR7133285A FR2107719A5 (OSRAM) | 1970-09-16 | 1971-09-15 | |
| GB4292071A GB1354793A (en) | 1970-09-16 | 1971-09-15 | Recovery of cobalt and organic phosphines which do not form water-soluble salts from distillation residues resulting from the oxo reaction |
| NL7112687A NL7112687A (OSRAM) | 1970-09-16 | 1971-09-15 | |
| AT800771A AT309392B (de) | 1970-09-16 | 1971-09-15 | Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der Oxo-Synthese |
| ES395134A ES395134A1 (es) | 1970-09-16 | 1971-09-16 | Procedimiento para la recuperacion de cobalto y fosfinas organicas que forman sales insolubles en agua, de residuos de destilacion de la sintesis oxo. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2045745A DE2045745C3 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der Oxosynthese |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2045745A1 DE2045745A1 (de) | 1972-03-23 |
| DE2045745B2 DE2045745B2 (de) | 1973-09-20 |
| DE2045745C3 true DE2045745C3 (de) | 1974-04-25 |
Family
ID=5782580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2045745A Expired DE2045745C3 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur Wiedergewinnung von Kobalt und organischen Phosphinen, die keine wasserlöslichen Salze bilden, aus Destillationsrückständen der Oxosynthese |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT309392B (OSRAM) |
| BE (1) | BE772574A (OSRAM) |
| CA (1) | CA952915A (OSRAM) |
| DE (1) | DE2045745C3 (OSRAM) |
| ES (1) | ES395134A1 (OSRAM) |
| FR (1) | FR2107719A5 (OSRAM) |
| GB (1) | GB1354793A (OSRAM) |
| IT (1) | IT942171B (OSRAM) |
| NL (1) | NL7112687A (OSRAM) |
-
1970
- 1970-09-16 DE DE2045745A patent/DE2045745C3/de not_active Expired
-
1971
- 1971-09-10 CA CA122,591A patent/CA952915A/en not_active Expired
- 1971-09-14 IT IT52874/71A patent/IT942171B/it active
- 1971-09-14 BE BE772574A patent/BE772574A/xx unknown
- 1971-09-15 FR FR7133285A patent/FR2107719A5/fr not_active Expired
- 1971-09-15 AT AT800771A patent/AT309392B/de not_active IP Right Cessation
- 1971-09-15 NL NL7112687A patent/NL7112687A/xx unknown
- 1971-09-15 GB GB4292071A patent/GB1354793A/en not_active Expired
- 1971-09-16 ES ES395134A patent/ES395134A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA952915A (en) | 1974-08-13 |
| IT942171B (it) | 1973-03-20 |
| AT309392B (de) | 1973-08-10 |
| GB1354793A (en) | 1974-06-05 |
| FR2107719A5 (OSRAM) | 1972-05-05 |
| BE772574A (fr) | 1972-03-14 |
| DE2045745B2 (de) | 1973-09-20 |
| ES395134A1 (es) | 1974-11-16 |
| DE2045745A1 (de) | 1972-03-23 |
| NL7112687A (OSRAM) | 1972-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete disclaimer |