DE2045169A1 - Treatment of oxo reaction mixts - by addn of aqs alkali hydroxide - Google Patents
Treatment of oxo reaction mixts - by addn of aqs alkali hydroxideInfo
- Publication number
- DE2045169A1 DE2045169A1 DE19702045169 DE2045169A DE2045169A1 DE 2045169 A1 DE2045169 A1 DE 2045169A1 DE 19702045169 DE19702045169 DE 19702045169 DE 2045169 A DE2045169 A DE 2045169A DE 2045169 A1 DE2045169 A1 DE 2045169A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- oxo
- catalyst
- hydrogen
- carbon monoxide
- 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.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 23
- 150000008044 alkali metal hydroxides Chemical class 0.000 title claims abstract description 9
- 229910001854 alkali hydroxide Inorganic materials 0.000 title claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 150000001336 alkenes Chemical class 0.000 claims abstract description 13
- 150000003003 phosphines Chemical class 0.000 claims abstract description 12
- 150000001298 alcohols Chemical class 0.000 claims abstract description 8
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 8
- 150000002739 metals Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 6
- 239000011574 phosphorus Substances 0.000 abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 229910017052 cobalt Inorganic materials 0.000 description 10
- 239000010941 cobalt Substances 0.000 description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 2
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- -1 fatty acids Salts Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BMWOMXHGRVLKCW-UHFFFAOYSA-N methyl(dioctyl)phosphane Chemical compound CCCCCCCCP(C)CCCCCCCC BMWOMXHGRVLKCW-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045169 DE2045169A1 (en) | 1970-09-12 | 1970-09-12 | Treatment of oxo reaction mixts - by addn of aqs alkali hydroxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045169 DE2045169A1 (en) | 1970-09-12 | 1970-09-12 | Treatment of oxo reaction mixts - by addn of aqs alkali hydroxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2045169A1 true DE2045169A1 (en) | 1972-03-23 |
| DE2045169B2 DE2045169B2 (enrdf_load_stackoverflow) | 1973-11-22 |
Family
ID=5782262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702045169 Pending DE2045169A1 (en) | 1970-09-12 | 1970-09-12 | Treatment of oxo reaction mixts - by addn of aqs alkali hydroxide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2045169A1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160249A3 (en) * | 1984-04-28 | 1987-05-27 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
| US4714784A (en) * | 1985-08-06 | 1987-12-22 | Huls Aktiengesellschaft | Method for removing n-butyraldehyde from gas streams |
| WO1989001467A1 (en) * | 1987-08-10 | 1989-02-23 | Eastman Kodak Company | Low pressure rhodium catalyzed hydroformylation of olefins |
| WO1997020792A1 (en) * | 1995-12-06 | 1997-06-12 | Union Carbide Chemicals & Plastics Technology Corporation | Improved metal-ligand complex catalyzed processes |
| EP0824095A1 (de) * | 1996-08-13 | 1998-02-18 | Hoechst Aktiengesellschaft | Verfahren zur Abtrennung von Phosphinoxiden und Alklarylphosphinen aus Reaktionsgemischen einer homogenen Hydroformylierung |
-
1970
- 1970-09-12 DE DE19702045169 patent/DE2045169A1/de active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160249A3 (en) * | 1984-04-28 | 1987-05-27 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
| US4714784A (en) * | 1985-08-06 | 1987-12-22 | Huls Aktiengesellschaft | Method for removing n-butyraldehyde from gas streams |
| WO1989001467A1 (en) * | 1987-08-10 | 1989-02-23 | Eastman Kodak Company | Low pressure rhodium catalyzed hydroformylation of olefins |
| JPH03500770A (ja) * | 1987-08-10 | 1991-02-21 | イーストマン ケミカル カンパニー | オレフィンの低圧ロジウム接触ヒドロホルミル化 |
| JP2831011B2 (ja) | 1987-08-10 | 1998-12-02 | イーストマン ケミカル カンパニー | オレフィンの低圧ロジウム接触ヒドロホルミル化 |
| WO1997020792A1 (en) * | 1995-12-06 | 1997-06-12 | Union Carbide Chemicals & Plastics Technology Corporation | Improved metal-ligand complex catalyzed processes |
| EA001482B1 (ru) * | 1995-12-06 | 2001-04-23 | Юнион Карбайд Кемикалз Энд Пластикс Текнолоджи Корпорейшн | Способ гидроформилирования для получения альдегидов в присутствии металл-органофосфитного комплексного катализатора |
| CN1090169C (zh) * | 1995-12-06 | 2002-09-04 | 联合碳化化学品及塑料技术公司 | 改进的金属－配体络合物催化的方法 |
| EP0824095A1 (de) * | 1996-08-13 | 1998-02-18 | Hoechst Aktiengesellschaft | Verfahren zur Abtrennung von Phosphinoxiden und Alklarylphosphinen aus Reaktionsgemischen einer homogenen Hydroformylierung |
| US5932770A (en) * | 1996-08-13 | 1999-08-03 | Hoechst Aktiengesellschaft | Process for recovery of phosphine oxides and alklylsarylphosphines from reaction mixtures of a homogeneous hydroformylation |
| AU724918B2 (en) * | 1996-08-13 | 2000-10-05 | Celanese Chemicals Europe Gmbh | Process for separating off phosphine oxides and alkylarylphosphines from reaction mixtures of a homogeneous hydroformylation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2045169B2 (enrdf_load_stackoverflow) | 1973-11-22 |
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