AU623711B2 - Minimising catalyst loss in the production of alcohols - Google Patents
Minimising catalyst loss in the production of alcohols Download PDFInfo
- Publication number
- AU623711B2 AU623711B2 AU46050/89A AU4605089A AU623711B2 AU 623711 B2 AU623711 B2 AU 623711B2 AU 46050/89 A AU46050/89 A AU 46050/89A AU 4605089 A AU4605089 A AU 4605089A AU 623711 B2 AU623711 B2 AU 623711B2
- Authority
- AU
- Australia
- Prior art keywords
- cobalt
- water
- process according
- oxonation
- carbon dioxide
- 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
- 239000003054 catalyst Substances 0.000 title claims description 20
- 150000001298 alcohols Chemical class 0.000 title description 12
- 238000004519 manufacturing process Methods 0.000 title description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 229910017052 cobalt Inorganic materials 0.000 claims description 44
- 239000010941 cobalt Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 44
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 43
- 239000001569 carbon dioxide Substances 0.000 claims description 30
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 27
- 150000001868 cobalt Chemical class 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 21
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 claims description 18
- 229910021446 cobalt carbonate Inorganic materials 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 16
- 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 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 238000007037 hydroformylation reaction Methods 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000010802 sludge Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 210000002837 heart atrium Anatomy 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003518 caustics Substances 0.000 description 9
- 239000002351 wastewater Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 3
- SAXCKUIOAKKRAS-UHFFFAOYSA-N cobalt;hydrate Chemical compound O.[Co] SAXCKUIOAKKRAS-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910000428 cobalt oxide Inorganic materials 0.000 description 2
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- -1 ether alcohols Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 229910000001 cobalt(II) carbonate Inorganic materials 0.000 description 1
- PKSIZOUDEUREFF-UHFFFAOYSA-N cobalt;dihydrate Chemical compound O.O.[Co] PKSIZOUDEUREFF-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- B01J31/20—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
- B01J31/40—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
-
- 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
- B01J31/4061—Regeneration or reactivation of catalysts containing metals involving membrane separation
-
- 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
- B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- 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)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8828695 | 1988-12-08 | ||
| GB888828695A GB8828695D0 (en) | 1988-12-08 | 1988-12-08 | Minimising catalyst loss in production of alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4605089A AU4605089A (en) | 1990-06-14 |
| AU623711B2 true AU623711B2 (en) | 1992-05-21 |
Family
ID=10648190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU46050/89A Ceased AU623711B2 (en) | 1988-12-08 | 1989-12-08 | Minimising catalyst loss in the production of alcohols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5130107A (enExample) |
| EP (1) | EP0372925B1 (enExample) |
| JP (1) | JPH02265654A (enExample) |
| CN (1) | CN1028971C (enExample) |
| AR (1) | AR245389A1 (enExample) |
| AT (1) | ATE112701T1 (enExample) |
| AU (1) | AU623711B2 (enExample) |
| BR (1) | BR8906368A (enExample) |
| CA (1) | CA2004894A1 (enExample) |
| DE (1) | DE68918815T2 (enExample) |
| GB (1) | GB8828695D0 (enExample) |
| IN (1) | IN178459B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750772A (en) * | 1997-01-30 | 1998-05-12 | E. I. Du Pont De Nemours And Company | Decolorization of hydroxy-containing methacrylate homopolymers and copolymers |
| WO2003082789A2 (en) * | 2002-03-29 | 2003-10-09 | Exxonmobil Chemical Patents Inc. | Oxon process |
| US7214290B2 (en) * | 2002-09-04 | 2007-05-08 | Shaw Liquid Solutions Llc. | Treatment of spent caustic refinery effluents |
| GB0706887D0 (en) * | 2007-04-10 | 2007-05-16 | Exxonmobil Chem Patents Inc | Cobalt recovery from cobalt catalysed hydroformylation reactions |
| WO2008145672A1 (en) * | 2007-05-30 | 2008-12-04 | Shell Internationale Research Maatschappij B.V. | Process for the removal of catalyst degradation products |
| BR112012007968A2 (pt) * | 2009-10-07 | 2015-09-08 | Mitsubishi Chem Corp | método para produzir ácido alifático dicarboxílico |
| CN111302404A (zh) * | 2020-03-11 | 2020-06-19 | 吕文广 | 一种降低碳酸镍或碳酸钴中杂质的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4041057A (en) * | 1975-07-02 | 1977-08-09 | Ethyl Corporation | Hydroesterification process |
| US4041082A (en) * | 1974-07-25 | 1977-08-09 | Mitsubishi Chemical Industries Limited | Process for producing aldehydes |
| FR2480276A1 (fr) * | 1980-04-14 | 1981-10-16 | Delnik Vladlen | Procede d'elimination du cobalt de produits d'hydroformylation des composes insatures |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3816337A (en) * | 1970-09-01 | 1974-06-11 | Toa Nenryo Kogyo Kk | Process for preparing a catalytic cobalt carbonyl reaction product |
| US3810967A (en) * | 1970-09-14 | 1974-05-14 | Daicel Ltd | Process for recovering cobalt from oxo reaction products |
| DE2103454C3 (de) * | 1971-01-26 | 1974-11-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen Herstellung von Metallcarbonylen |
| DE2949878A1 (de) * | 1979-12-12 | 1981-06-19 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur hydrierenden aufarbeitung der bei der hydrocarboxylierung eingesetzten kobalthaltigen katalysatoren |
| US4404119A (en) * | 1981-12-23 | 1983-09-13 | Exxon Research & Engineering Co. | Process for recovery of cobalt oxo catalysts |
| US4435517A (en) * | 1982-09-02 | 1984-03-06 | Texaco Inc. | Cobalt hydroformylation catalysts |
-
1988
- 1988-12-08 GB GB888828695A patent/GB8828695D0/en active Pending
-
1989
- 1989-12-06 DE DE68918815T patent/DE68918815T2/de not_active Expired - Fee Related
- 1989-12-06 EP EP89312708A patent/EP0372925B1/en not_active Expired - Lifetime
- 1989-12-06 IN IN1157DE1989 patent/IN178459B/en unknown
- 1989-12-06 AT AT89312708T patent/ATE112701T1/de not_active IP Right Cessation
- 1989-12-07 CA CA002004894A patent/CA2004894A1/en not_active Abandoned
- 1989-12-07 AR AR89315629A patent/AR245389A1/es active
- 1989-12-08 BR BR898906368A patent/BR8906368A/pt not_active IP Right Cessation
- 1989-12-08 JP JP1320355A patent/JPH02265654A/ja active Pending
- 1989-12-08 AU AU46050/89A patent/AU623711B2/en not_active Ceased
- 1989-12-08 CN CN89109117A patent/CN1028971C/zh not_active Expired - Fee Related
-
1990
- 1990-12-21 US US07/632,037 patent/US5130107A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4041082A (en) * | 1974-07-25 | 1977-08-09 | Mitsubishi Chemical Industries Limited | Process for producing aldehydes |
| US4041057A (en) * | 1975-07-02 | 1977-08-09 | Ethyl Corporation | Hydroesterification process |
| FR2480276A1 (fr) * | 1980-04-14 | 1981-10-16 | Delnik Vladlen | Procede d'elimination du cobalt de produits d'hydroformylation des composes insatures |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1028971C (zh) | 1995-06-21 |
| AR245389A1 (es) | 1994-01-31 |
| GB8828695D0 (en) | 1989-01-11 |
| AU4605089A (en) | 1990-06-14 |
| JPH02265654A (ja) | 1990-10-30 |
| CA2004894A1 (en) | 1990-06-08 |
| DE68918815T2 (de) | 1995-02-09 |
| BR8906368A (pt) | 1990-08-21 |
| DE68918815D1 (de) | 1994-11-17 |
| EP0372925B1 (en) | 1994-10-12 |
| ATE112701T1 (de) | 1994-10-15 |
| CN1043310A (zh) | 1990-06-27 |
| US5130107A (en) | 1992-07-14 |
| IN178459B (enExample) | 1997-05-03 |
| EP0372925A1 (en) | 1990-06-13 |
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