DE2614799C2 - Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen - Google Patents
Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von HydroformylierungsgemischenInfo
- Publication number
- DE2614799C2 DE2614799C2 DE2614799A DE2614799A DE2614799C2 DE 2614799 C2 DE2614799 C2 DE 2614799C2 DE 2614799 A DE2614799 A DE 2614799A DE 2614799 A DE2614799 A DE 2614799A DE 2614799 C2 DE2614799 C2 DE 2614799C2
- Authority
- DE
- Germany
- Prior art keywords
- rhodium
- aqueous
- catalysts
- carbon monoxide
- regeneration
- 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
- 239000010948 rhodium Substances 0.000 title claims description 36
- 229910052703 rhodium Inorganic materials 0.000 title claims description 29
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims description 28
- 239000003054 catalyst Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 25
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 19
- 238000004821 distillation Methods 0.000 title claims description 14
- 230000008929 regeneration Effects 0.000 title claims description 8
- 238000011069 regeneration method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 150000002978 peroxides Chemical class 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- -1 rhodium cations Chemical class 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000001145 hydrido group Chemical group *[H] 0.000 description 6
- 150000003003 phosphines Chemical group 0.000 description 6
- 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 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 239000010970 precious metal Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000010626 work up procedure 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
- B01J31/40—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
- B01J31/20—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
-
- 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
-
- 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
-
- 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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2614799A DE2614799C2 (de) | 1976-04-06 | 1976-04-06 | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
| IT21148/77A IT1085517B (it) | 1976-04-06 | 1977-03-10 | Processo per la separazione e la rigenerazione di catalizzatori contenenti rodio dai residui di distillazione che si ottengono nelle idroformilazioni |
| US05/780,297 US4113754A (en) | 1976-04-06 | 1977-03-23 | Isolation and regeneration of rhodium-containing catalysts from distillation residues of hydroformylation reactions |
| CA274,599A CA1093057A (en) | 1976-04-06 | 1977-03-23 | Isolation and regeneration of rhodium-containing catalysts from distillation residues of hydroformylation reactions |
| FR7709902A FR2347099A1 (fr) | 1976-04-06 | 1977-04-01 | Procede pour separer et regenerer des catalyseurs contenant du rhodium a partir de residus de distillation obtenus dans les hydroformylations |
| SU772466670A SU898951A3 (ru) | 1976-04-06 | 1977-04-04 | Способ регенерации родийсодержащего катализатора гидроформилировани олефинов |
| AT236477A AT347909B (de) | 1976-04-06 | 1977-04-05 | Verfahren zur abtrennung und regenerierung von rhodiumkomplexkatalysatoren |
| GB14274/77A GB1576514A (en) | 1976-04-06 | 1977-04-05 | Production of rhodium-containing catalysts from distillation residues of hydroformylation reactions |
| BE176421A BE853246A (fr) | 1976-04-06 | 1977-04-05 | Procede pour separer et regenerer des catalyseurs contenant du rodhium a partir de residus de distillation obtenus dans les hydroformulations |
| ES457530A ES457530A1 (es) | 1976-04-06 | 1977-04-05 | Procedimiento para separar y regenerar catalizadores conte- niendo rodio de los residuos de destilacion que se obtienen en reacciones de hidroformilacion. |
| JP3817977A JPS52123397A (en) | 1976-04-06 | 1977-04-05 | Method of separating and regenerating rhodiummcontaining catalysts from distillation residues obtained at hydroformylation |
| NLAANVRAGE7703723,A NL180482C (nl) | 1976-04-06 | 1977-04-05 | Werkwijze voor het afscheiden en regenereren van rodium bevattende katalysatoren uit bij hydroformyleringen verkregen destillatieresiduen. |
| SE7703986A SE440609B (sv) | 1976-04-06 | 1977-04-05 | Forfarande for separering och regenerering av rodium-fosfin-katalysatorer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2614799A DE2614799C2 (de) | 1976-04-06 | 1976-04-06 | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2614799A1 DE2614799A1 (de) | 1977-10-27 |
| DE2614799C2 true DE2614799C2 (de) | 1986-02-27 |
Family
ID=5974560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2614799A Expired DE2614799C2 (de) | 1976-04-06 | 1976-04-06 | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4113754A (enExample) |
| JP (1) | JPS52123397A (enExample) |
| AT (1) | AT347909B (enExample) |
| BE (1) | BE853246A (enExample) |
| CA (1) | CA1093057A (enExample) |
| DE (1) | DE2614799C2 (enExample) |
| ES (1) | ES457530A1 (enExample) |
| FR (1) | FR2347099A1 (enExample) |
| GB (1) | GB1576514A (enExample) |
| IT (1) | IT1085517B (enExample) |
| NL (1) | NL180482C (enExample) |
| SE (1) | SE440609B (enExample) |
| SU (1) | SU898951A3 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007768A3 (en) * | 1978-07-27 | 1980-02-20 | DAVY McKEE (LONDON) LIMITED | Hydroformylation of alpha-olefinic compounds |
| US4297239A (en) * | 1979-07-16 | 1981-10-27 | 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 |
| 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 |
| US4388476A (en) * | 1981-05-01 | 1983-06-14 | Eastman Kodak Company | Hydroformylation process with rhodium catalyst and oxygen stabilization thereof |
| US4409149A (en) * | 1981-06-29 | 1983-10-11 | Union Carbide Corporation | Process for producing catalyst precursors |
| DE3126265A1 (de) * | 1981-07-03 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur hydroformylierung olefinisch ungesaettigter verbindungen |
| US4446074A (en) * | 1981-12-24 | 1984-05-01 | Union Carbide Corporation | Preparation of rhodium complex compounds |
| US4547595A (en) * | 1982-09-02 | 1985-10-15 | Ashland Oil, Inc. | Method of reactivating Group VIII anionic hydroformylation catalysts |
| US4894477A (en) * | 1986-10-14 | 1990-01-16 | Hoechst Celanese Corporation | Process for regenerating a carbonylation catalyst solution to remove corrosion metals and carbonylation of methanol to acetic acid |
| DE3744213A1 (de) * | 1987-12-24 | 1989-07-06 | Ruhrchemie Ag | Verfahren zur rueckgewinnung von rhodium aus rhodiumkomplexverbindungen enthaltenden waessrigen loesungen |
| DE4034501A1 (de) * | 1990-10-30 | 1992-05-07 | Hoechst Ag | Verfahren zur entfernung metallischer korrosionsprodukte aus wasserfrei betriebenen carbonylierungsreaktionen |
| DE4316180A1 (de) * | 1992-09-16 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| GB9305902D0 (en) * | 1993-03-22 | 1993-05-12 | Bp Chem Int Ltd | Process |
| BR9606526A (pt) * | 1995-07-18 | 1997-12-23 | Atochem North America Elf | Processo para purificar e seperar o catalisador de ródio ativo do catalisador de ródio anativo contido em uma corrente do processo de hidroformilação composição compreendendo uma resina de troca iônica ácida e processo de hidroformilação aperfeiçoado compreendendo uma reação de hidroformilação de uma olefina com h2 na presença de um complexo de catalisador organo-ródio |
| US5773665A (en) * | 1996-07-01 | 1998-06-30 | Elf Atochem North America, Inc. | Hydroformylation process with separation and recycle of active rhodium catalyst |
| GB0113080D0 (en) * | 2001-05-30 | 2001-07-18 | Kvaerner Process Tech Ltd | Process |
| GB0113079D0 (en) * | 2001-05-30 | 2001-07-18 | Kvaerner Process Tech Ltd | Process |
| RU2628609C2 (ru) * | 2015-12-30 | 2017-08-21 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Способ получения альдегидов гидроформилированием с модификацией лигандов ацетализацией |
| CN106187721B (zh) * | 2016-08-25 | 2019-04-02 | 浙江巴陵恒逸己内酰胺有限责任公司 | 利用蒸汽加热导热油进行环己醇脱氢反应的工艺系统 |
| 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 |
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| 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 |
| DE1954315C3 (de) * | 1969-10-29 | 1975-08-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Abtrennung von Metallcarbonylkatalysatoren aus Oxoreaktionsge mischen |
| 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 |
| AT312559B (de) * | 1972-01-07 | 1974-01-10 | Basf Ag | Verfahren zur Abscheidung von Rhodium aus Rhodiumcarbonylkomplexe enthaltenden Lösungen und Überführung des abgescheidenen Rhodiums in lösliche Rhodiumcarbonylkomplexe |
| IT1007026B (it) * | 1974-01-23 | 1976-10-30 | Montedison Spa | Procedimento per il ricupero di sistemi catalitici da grezzi di idroformilazione |
| 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 |
-
1976
- 1976-04-06 DE DE2614799A patent/DE2614799C2/de not_active Expired
-
1977
- 1977-03-10 IT IT21148/77A patent/IT1085517B/it active
- 1977-03-23 US US05/780,297 patent/US4113754A/en not_active Expired - Lifetime
- 1977-03-23 CA CA274,599A patent/CA1093057A/en not_active Expired
- 1977-04-01 FR FR7709902A patent/FR2347099A1/fr active Granted
- 1977-04-04 SU SU772466670A patent/SU898951A3/ru active
- 1977-04-05 SE SE7703986A patent/SE440609B/xx not_active IP Right Cessation
- 1977-04-05 ES ES457530A patent/ES457530A1/es not_active Expired
- 1977-04-05 JP JP3817977A patent/JPS52123397A/ja active Granted
- 1977-04-05 BE BE176421A patent/BE853246A/xx not_active IP Right Cessation
- 1977-04-05 NL NLAANVRAGE7703723,A patent/NL180482C/xx not_active IP Right Cessation
- 1977-04-05 GB GB14274/77A patent/GB1576514A/en not_active Expired
- 1977-04-05 AT AT236477A patent/AT347909B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS616703B2 (enExample) | 1986-02-28 |
| NL180482C (nl) | 1987-03-02 |
| IT1085517B (it) | 1985-05-28 |
| JPS52123397A (en) | 1977-10-17 |
| ES457530A1 (es) | 1978-03-16 |
| BE853246A (fr) | 1977-10-05 |
| FR2347099A1 (fr) | 1977-11-04 |
| DE2614799A1 (de) | 1977-10-27 |
| SE440609B (sv) | 1985-08-12 |
| ATA236477A (de) | 1978-06-15 |
| GB1576514A (en) | 1980-10-08 |
| AT347909B (de) | 1979-01-25 |
| SE7703986L (sv) | 1977-10-07 |
| SU898951A3 (ru) | 1982-01-15 |
| FR2347099B1 (enExample) | 1980-05-09 |
| NL7703723A (nl) | 1977-10-10 |
| CA1093057A (en) | 1981-01-06 |
| US4113754A (en) | 1978-09-12 |
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Ipc: C07C 45/50 |
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| 8105 | Search report available | ||
| 8181 | Inventor (new situation) |
Free format text: KUMMER, RUDOLF, DIPL.-CHEM. DR., 6710 FRANKENTHAL, DE SCHNEIDER, HEINZ-WALTER, DIPL.-CHEM. DR. SCHWIRTEN, KURT, DIPL.-CHEM. DR., 6700 LUDWIGSHAFEN, DE |
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