PL125154B1 - Method of treatment of cobalt-containing catalyst used in hydrocarboxylation process - Google Patents
Method of treatment of cobalt-containing catalyst used in hydrocarboxylation process Download PDFInfo
- Publication number
- PL125154B1 PL125154B1 PL1980228360A PL22836080A PL125154B1 PL 125154 B1 PL125154 B1 PL 125154B1 PL 1980228360 A PL1980228360 A PL 1980228360A PL 22836080 A PL22836080 A PL 22836080A PL 125154 B1 PL125154 B1 PL 125154B1
- Authority
- PL
- Poland
- Prior art keywords
- cobalt
- hydrocarboxylation
- treatment
- catalyst
- reaction
- Prior art date
Links
- 239000010941 cobalt Substances 0.000 title claims description 65
- 229910017052 cobalt Inorganic materials 0.000 title claims description 65
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 49
- 239000003054 catalyst Substances 0.000 title claims description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 150000001336 alkenes Chemical class 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000001868 cobalt Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000011084 recovery Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000012188 paraffin wax Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940011182 cobalt acetate Drugs 0.000 description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
- -1 cyano, carboxymethyl Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001869 cobalt compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- NHBOQQFAITVOGY-UHFFFAOYSA-N dodecane;tetradecanoic acid Chemical class CCCCCCCCCCCC.CCCCCCCCCCCCCC(O)=O NHBOQQFAITVOGY-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 208000012639 Balance disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/94—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the iron group metals or copper
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792949878 DE2949878A1 (de) | 1979-12-12 | 1979-12-12 | Verfahren zur hydrierenden aufarbeitung der bei der hydrocarboxylierung eingesetzten kobalthaltigen katalysatoren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL228360A1 PL228360A1 (en, 2012) | 1981-07-24 |
| PL125154B1 true PL125154B1 (en) | 1983-04-30 |
Family
ID=6088201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980228360A PL125154B1 (en) | 1979-12-12 | 1980-12-10 | Method of treatment of cobalt-containing catalyst used in hydrocarboxylation process |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0032525B1 (en, 2012) |
| JP (1) | JPS56133034A (en, 2012) |
| AT (1) | AT382532B (en, 2012) |
| CA (1) | CA1178611A (en, 2012) |
| DE (1) | DE2949878A1 (en, 2012) |
| ES (1) | ES8200236A1 (en, 2012) |
| PL (1) | PL125154B1 (en, 2012) |
| RO (1) | RO81104B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8828695D0 (en) * | 1988-12-08 | 1989-01-11 | Exxon Chemical Patents Inc | Minimising catalyst loss in production of alcohols |
| DE3903909A1 (de) * | 1989-02-10 | 1990-08-16 | Hoechst Ag | Verfahren zur entfernung metallischer korrosionsprodukte aus einer bei der carbonylierung von methanol und/oder methylacetat und/oder dimethylether anfallenden, verunreinigten katalysatorloesung |
| DE102008056227A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von Dialkylphosphinsäuren, -estern und -salzen mittels Vinylverbindungen und ihre Verwendung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529236A (en) * | 1947-05-02 | 1950-11-07 | Shell Dev | Reactivation of cobalt oxo catalyst |
| US2542558A (en) * | 1949-01-29 | 1951-02-20 | Texas Co | Regeneration of a cobalt oxo synthesis catalyst |
| DE929250C (de) * | 1950-09-05 | 1955-06-23 | Ici Ltd | Verfahren zum Regenerieren von Kobaltkatalysatoren der Oxosynthese |
| GB1094726A (en) * | 1964-04-03 | 1967-12-13 | Teijin Ltd | Purification and recovery of cobalt-containing catalysts |
| US3507891A (en) * | 1966-09-06 | 1970-04-21 | Shell Oil Co | Carbonylation |
| JPS5533380B2 (en, 2012) * | 1973-10-06 | 1980-08-30 | ||
| DE2912489B2 (de) * | 1979-03-29 | 1981-04-02 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Alkylestern gesättigter aliphatischer Carbonsäuren |
-
1979
- 1979-12-12 DE DE19792949878 patent/DE2949878A1/de not_active Withdrawn
-
1980
- 1980-10-15 EP EP80106242A patent/EP0032525B1/de not_active Expired
- 1980-12-08 RO RO102796A patent/RO81104B/ro unknown
- 1980-12-10 PL PL1980228360A patent/PL125154B1/pl unknown
- 1980-12-11 AT AT0602380A patent/AT382532B/de not_active IP Right Cessation
- 1980-12-11 ES ES497618A patent/ES8200236A1/es not_active Expired
- 1980-12-11 JP JP17392980A patent/JPS56133034A/ja active Granted
- 1980-12-11 CA CA000366538A patent/CA1178611A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0032525B1 (de) | 1983-07-13 |
| RO81104A (ro) | 1983-04-29 |
| EP0032525A3 (en) | 1981-10-07 |
| RO81104B (ro) | 1983-04-30 |
| EP0032525A2 (de) | 1981-07-29 |
| AT382532B (de) | 1987-03-10 |
| JPS6315021B2 (en, 2012) | 1988-04-02 |
| CA1178611A (en) | 1984-11-27 |
| ATA602380A (de) | 1986-08-15 |
| ES497618A0 (es) | 1981-11-01 |
| JPS56133034A (en) | 1981-10-17 |
| ES8200236A1 (es) | 1981-11-01 |
| DE2949878A1 (de) | 1981-06-19 |
| PL228360A1 (en, 2012) | 1981-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4528403A (en) | Hydroformylation process for preparation of aldehydes and alcohols | |
| US3933919A (en) | Hydroformylation of mono-α-olefins and mono-α-acetylenes | |
| US9649625B1 (en) | Catalysts and processes for producing aldehydes | |
| DE2364446C2 (de) | Verfahren zur Herstellung von Carbonsäureanhydriden | |
| Forster et al. | Mechanistic pathways in the catalysis of olefin hydrocarboxylation by rhodium, iridium, and cobalt complexes | |
| US3984478A (en) | Hydroformylation process | |
| DE1543010A1 (de) | Verfahren zur Umwandlung eines Alkohols in den entsprechenden Kohlenwasserstoff | |
| PL125154B1 (en) | Method of treatment of cobalt-containing catalyst used in hydrocarboxylation process | |
| JP3763847B2 (ja) | オレフィンのカルボニル化によるカルボン酸の製造方法 | |
| JPH09510219A (ja) | アルコール及び／又はアルデヒドの製造方法 | |
| EP4011894B1 (de) | Platin-komplexe mit binaphthyl-diphosphin-liganden für die katalyse der hydroxycarbonylierung ethylenisch ungesättigter verbindungen | |
| DE1793217A1 (de) | Verfahren zum Epoxydieren von olefinischen Verbindungen | |
| DE2439951C2 (de) | Verfahren zur Herstellung von Propionsäure | |
| DE2510089A1 (de) | Verfahren zur herstellung eines carbonsaeureesters | |
| US20060293539A1 (en) | Oxidation of alkanes | |
| DE69122859T2 (de) | Verfahren zur gleichzeitigen herstellung einer aromatischen hydroxyverbindung und einer carbonylverbindung | |
| US4521526A (en) | Methods for reprocessing cobalt catalysts used in hydrocarboxylation | |
| DE2949847A1 (de) | Verfahren zur herstellung von carbonylverbindungen durch oxidation von olefinen | |
| US4400300A (en) | Method for recovering and reactivating cobalt catalysts used in the reaction of olefins with carbon monoxide and alkanols | |
| DE2913677A1 (de) | Verfahren zur herstellung von acetaldehyddimethylacetal | |
| CA1178298A (en) | Method for extractive processing of cobalt-containing catalysts used in hydrocarboxylating | |
| DE2159139B2 (de) | Verfahren zur herstellung von methylestern gesaettigter aliphatischer carbonsaeuren | |
| DE2042815C3 (de) | 27.07.70 USA 59338 Verfahren zur Herstellung von Aldehyden oder Ketonen durch Oxydation von Olefinen in der Gasphase in Gegenwart von palladiumhaltigen Katalysatoren Union Carbide Corp., New York | |
| DE60104384T2 (de) | Verfahren zur Herstellung von Sauerstoff-enthaltenden aromatischen Verbindungen | |
| EP0795533A1 (de) | Verfahren zur Herstellung von Aldehyden mittels eines Rhodium und substituierte Diphenyldiphosphane enthaltenden Katalysatorsystems |