DE2715685C2 - Kontinuierliches Verfahren zur Herstellung von Aldehyden mit 3 bis 6 Kohlenstoffatomen durch Hydroformylierung von α-Olefinen - Google Patents
Kontinuierliches Verfahren zur Herstellung von Aldehyden mit 3 bis 6 Kohlenstoffatomen durch Hydroformylierung von α-OlefinenInfo
- Publication number
- DE2715685C2 DE2715685C2 DE2715685A DE2715685A DE2715685C2 DE 2715685 C2 DE2715685 C2 DE 2715685C2 DE 2715685 A DE2715685 A DE 2715685A DE 2715685 A DE2715685 A DE 2715685A DE 2715685 C2 DE2715685 C2 DE 2715685C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- rhodium
- reaction
- carbon monoxide
- aldehyde
- 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 - Lifetime
Links
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 21
- 239000004711 α-olefin Substances 0.000 title claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 7
- 238000010924 continuous production Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001299 aldehydes Chemical class 0.000 title description 54
- 239000003054 catalyst Substances 0.000 claims description 84
- 239000010948 rhodium Substances 0.000 claims description 67
- 239000007789 gas Substances 0.000 claims description 53
- 229910052703 rhodium Inorganic materials 0.000 claims description 53
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 52
- 239000007788 liquid Substances 0.000 claims description 45
- 239000011541 reaction mixture Substances 0.000 claims description 42
- 239000007859 condensation product Substances 0.000 claims description 36
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 26
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 13
- 150000001336 alkenes Chemical class 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000008246 gaseous mixture Substances 0.000 claims 2
- 238000000034 method Methods 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000000047 product Substances 0.000 description 30
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 25
- 238000009835 boiling Methods 0.000 description 25
- 239000006227 byproduct Substances 0.000 description 23
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 22
- 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 21
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 19
- 239000003446 ligand Substances 0.000 description 17
- 239000013638 trimer Substances 0.000 description 17
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 15
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000007423 decrease Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 238000011027 product recovery Methods 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 241000069444 Tetrameres Species 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GPMUMMNTAZMBEC-UHFFFAOYSA-N bis(oxomethylidene)rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-] GPMUMMNTAZMBEC-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- -1 ethylene, propylene, 1-butene Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WQVMDOAYQORMRB-UHFFFAOYSA-N 1,1'-biphenyl;phosphane Chemical compound P.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 WQVMDOAYQORMRB-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- GOEGBJDTWXTPHP-UHFFFAOYSA-N 4-diphenylphosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GOEGBJDTWXTPHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000006423 Tishchenko reaction Methods 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- FQSDTIQFGVAWNS-UHFFFAOYSA-N rhodium;(triphenyl-$l^{5}-phosphanylidene)methanone Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C=O)C1=CC=CC=C1 FQSDTIQFGVAWNS-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- QAPGHLJQIVDTPT-UHFFFAOYSA-N tris(3-chlorophenyl)phosphane Chemical compound ClC1=CC=CC(P(C=2C=C(Cl)C=CC=2)C=2C=C(Cl)C=CC=2)=C1 QAPGHLJQIVDTPT-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67482376A | 1976-04-08 | 1976-04-08 | |
| US05/776,934 US4247486A (en) | 1977-03-11 | 1977-03-11 | Cyclic hydroformylation process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2715685A1 DE2715685A1 (de) | 1977-10-13 |
| DE2715685C2 true DE2715685C2 (de) | 1990-09-13 |
Family
ID=27101223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2715685A Expired - Lifetime DE2715685C2 (de) | 1976-04-08 | 1977-04-07 | Kontinuierliches Verfahren zur Herstellung von Aldehyden mit 3 bis 6 Kohlenstoffatomen durch Hydroformylierung von α-Olefinen |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5828857B2 (cg-RX-API-DMAC7.html) |
| AR (1) | AR218447A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU515005B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR7702192A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1090823A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2715685C2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES457609A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2360544A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1582010A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1076754B (cg-RX-API-DMAC7.html) |
| MX (1) | MX144327A (cg-RX-API-DMAC7.html) |
| NL (1) | NL186809C (cg-RX-API-DMAC7.html) |
| PL (1) | PL111026B1 (cg-RX-API-DMAC7.html) |
| SE (1) | SE441672B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2062703A1 (de) * | 1969-12-22 | 1971-07-01 | Union Carbide Corp , New York, N Y (V St A) | Hydroformylierungsverfahren |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215077A (en) * | 1978-02-09 | 1980-07-29 | Kuraray Co., Ltd. | Hydroformylation of olefins |
| EP0016286B1 (en) * | 1979-03-21 | 1983-04-06 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
| DE2965157D1 (en) * | 1979-03-21 | 1983-05-11 | Davy Mckee London | Process for the production of aldehydes by hydroformylation of alkenes |
| JPS5626830A (en) * | 1979-08-10 | 1981-03-16 | Kuraray Co Ltd | Hydroformylation of lower olefin |
| DE2932527A1 (de) * | 1979-08-10 | 1981-02-26 | Basf Ag | Tert.-butoxy-butanale und -butanole sowie bis-tert.-butoxypentanale und -pentanole |
| US4288380A (en) * | 1979-11-01 | 1981-09-08 | Union Carbide Corporation | Heteronuclear-bridged rhodium clusters |
| DE3114147A1 (de) * | 1981-04-08 | 1982-10-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von aldehyden |
| DE3126265A1 (de) * | 1981-07-03 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur hydroformylierung olefinisch ungesaettigter verbindungen |
| ATE16475T1 (de) * | 1982-06-11 | 1985-11-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| ATE26696T1 (de) * | 1982-06-11 | 1987-05-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| DE3301591A1 (de) * | 1983-01-19 | 1984-07-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen hydroformylierung olefinisch ungesaettigter verbindungen |
| JPS606630A (ja) * | 1983-06-24 | 1985-01-14 | Kuraray Co Ltd | アリルアルコ−ルの連続ヒドロホルミル化方法 |
| JPS60110838U (ja) * | 1983-12-28 | 1985-07-27 | 京セラミタ株式会社 | ズ−ム複写機の自動変倍装置 |
| JPH075579A (ja) * | 1994-05-16 | 1995-01-10 | Ricoh Co Ltd | ズーム変倍機能を有する複写装置 |
| JPH08169858A (ja) * | 1994-10-19 | 1996-07-02 | Mitsubishi Chem Corp | 分岐鎖アルデヒドの製造方法 |
| DE19925384A1 (de) * | 1999-06-02 | 2000-12-07 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Hydroformylierungen |
| DE19957528A1 (de) * | 1999-11-30 | 2001-05-31 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydroformylierung von Olefinen |
| GB0113080D0 (en) | 2001-05-30 | 2001-07-18 | Kvaerner Process Tech Ltd | Process |
| RU2337090C2 (ru) | 2002-08-31 | 2008-10-27 | Оксено Олефинхеми Гмбх | Способ гидроформилирования олефиновых соединений в присутствии циклических эфиров угольной кислоты |
| JP4736392B2 (ja) * | 2004-10-14 | 2011-07-27 | 三菱化学株式会社 | アルデヒドの製造方法 |
| JP5652052B2 (ja) * | 2010-08-24 | 2015-01-14 | 三菱化学株式会社 | アルデヒドの製造方法 |
| MX2014007651A (es) | 2011-12-20 | 2014-09-26 | Dow Technology Investments Llc | Un proceso de hidroformilacion. |
| CN104248860A (zh) * | 2013-06-27 | 2014-12-31 | 陶氏技术投资有限责任公司 | 热管理方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748167A (en) * | 1952-11-05 | 1956-05-29 | Eastman Kodak Co | Process of producing oxygenated organic compounds |
| US3487112A (en) * | 1967-04-27 | 1969-12-30 | Monsanto Co | Vapor phase hydroformylation process |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| CA918673A (en) * | 1969-12-22 | 1973-01-09 | L. Pruett Roy | Hydroformylation process |
| GB1312076A (en) * | 1970-05-15 | 1973-04-04 | Bp Chem Int Ltd | Hydroformylation process |
| GB1387657A (en) * | 1972-08-25 | 1975-03-19 | Davy Powergas Ltd | Hydroformylation process |
| JPS50123611A (cg-RX-API-DMAC7.html) * | 1974-03-12 | 1975-09-29 | ||
| JPS511687A (en) * | 1974-06-27 | 1976-01-08 | Sadao Ukita | Tenpura hanbaagunadono nenseizairyono katakeiseinisaishiteno atsumichoseisochi |
| JPS516124A (en) * | 1974-07-05 | 1976-01-19 | Hitachi Chemical Co Ltd | Kikinzoku oyobi ryusandono kaishuhoho |
-
1977
- 1977-03-25 CA CA274,742A patent/CA1090823A/en not_active Expired
- 1977-04-05 AU AU23987/77A patent/AU515005B2/en not_active Expired
- 1977-04-05 MX MX168657A patent/MX144327A/es unknown
- 1977-04-06 ES ES457609A patent/ES457609A1/es not_active Expired
- 1977-04-06 AR AR267127A patent/AR218447A1/es active
- 1977-04-06 BR BR7702192A patent/BR7702192A/pt unknown
- 1977-04-07 IT IT22260/77A patent/IT1076754B/it active
- 1977-04-07 GB GB14742/77A patent/GB1582010A/en not_active Expired
- 1977-04-07 SE SE7704141A patent/SE441672B/xx not_active IP Right Cessation
- 1977-04-07 JP JP52039093A patent/JPS5828857B2/ja not_active Expired
- 1977-04-07 PL PL1977197264A patent/PL111026B1/pl unknown
- 1977-04-07 NL NLAANVRAGE7703875,A patent/NL186809C/xx not_active IP Right Cessation
- 1977-04-07 FR FR7710577A patent/FR2360544A1/fr active Granted
- 1977-04-07 DE DE2715685A patent/DE2715685C2/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2062703A1 (de) * | 1969-12-22 | 1971-07-01 | Union Carbide Corp , New York, N Y (V St A) | Hydroformylierungsverfahren |
Also Published As
| Publication number | Publication date |
|---|---|
| AU515005B2 (en) | 1981-03-12 |
| AR218447A1 (es) | 1980-06-13 |
| PL197264A1 (pl) | 1978-01-02 |
| ES457609A1 (es) | 1978-07-01 |
| JPS52125103A (en) | 1977-10-20 |
| AU2398777A (en) | 1978-10-12 |
| BR7702192A (pt) | 1978-10-31 |
| IT1076754B (it) | 1985-04-27 |
| CA1090823A (en) | 1980-12-02 |
| NL186809C (nl) | 1991-03-01 |
| SE441672B (sv) | 1985-10-28 |
| NL7703875A (nl) | 1977-10-11 |
| PL111026B1 (en) | 1980-08-30 |
| FR2360544A1 (fr) | 1978-03-03 |
| SE7704141L (sv) | 1977-10-09 |
| JPS5828857B2 (ja) | 1983-06-18 |
| GB1582010A (en) | 1980-12-31 |
| NL186809B (nl) | 1990-10-01 |
| DE2715685A1 (de) | 1977-10-13 |
| FR2360544B1 (cg-RX-API-DMAC7.html) | 1983-11-04 |
| MX144327A (es) | 1981-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8125 | Change of the main classification |
Ipc: C07C 45/50 |
|
| 8126 | Change of the secondary classification |
Ipc: C07C 47/02 |
|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8366 | Restricted maintained after opposition proceedings | ||
| 8305 | Restricted maintenance of patent after opposition | ||
| D4 | Patent maintained restricted | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80803 MUENCHEN |