PL111026B1 - Continuous process for aldehydes manufacture - Google Patents
Continuous process for aldehydes manufacture Download PDFInfo
- Publication number
- PL111026B1 PL111026B1 PL1977197264A PL19726477A PL111026B1 PL 111026 B1 PL111026 B1 PL 111026B1 PL 1977197264 A PL1977197264 A PL 1977197264A PL 19726477 A PL19726477 A PL 19726477A PL 111026 B1 PL111026 B1 PL 111026B1
- Authority
- PL
- Poland
- Prior art keywords
- catalyst
- rhodium
- reaction
- products
- liquid
- Prior art date
Links
- 150000001299 aldehydes Chemical class 0.000 title claims description 64
- 238000010924 continuous production Methods 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 70
- 230000008569 process Effects 0.000 claims description 53
- 239000004711 α-olefin Substances 0.000 claims description 26
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 17
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 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 claims description 2
- 239000003054 catalyst Substances 0.000 description 79
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000010948 rhodium Substances 0.000 description 56
- 239000007788 liquid Substances 0.000 description 49
- 229910052703 rhodium Inorganic materials 0.000 description 48
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 47
- 239000007789 gas Substances 0.000 description 45
- 239000007859 condensation product Substances 0.000 description 35
- 239000000047 product Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 28
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 25
- 238000009835 boiling Methods 0.000 description 24
- 239000006227 byproduct Substances 0.000 description 22
- 238000007037 hydroformylation reaction Methods 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 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 17
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000013638 trimer Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 13
- 150000001336 alkenes Chemical class 0.000 description 13
- 238000004821 distillation Methods 0.000 description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- -1 (triphenylphosphine) hydrides Chemical class 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000011027 product recovery Methods 0.000 description 5
- 150000003284 rhodium compounds Chemical class 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 150000003283 rhodium Chemical class 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006423 Tishchenko reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- XLSCTISUVQDDED-UHFFFAOYSA-N butanal;2-methylpropanal Chemical compound CCCC=O.CC(C)C=O XLSCTISUVQDDED-UHFFFAOYSA-N 0.000 description 1
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 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
- 230000008859 change Effects 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004678 hydrides Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000009418 renovation Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000009751 slip forming Methods 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
- 230000002459 sustained effect Effects 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 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
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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 |
|---|---|
| PL197264A1 PL197264A1 (pl) | 1978-01-02 |
| PL111026B1 true PL111026B1 (en) | 1980-08-30 |
Family
ID=27101223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977197264A PL111026B1 (en) | 1976-04-08 | 1977-04-07 | Continuous process for aldehydes manufacture |
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) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA918673A (en) * | 1969-12-22 | 1973-01-09 | L. Pruett Roy | Hydroformylation process |
| 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
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 |
| DE2715685C2 (de) | 1990-09-13 |
| 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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