DE1901145A1 - Verfahren zur Hydroformylierung von Olefinen - Google Patents
Verfahren zur Hydroformylierung von OlefinenInfo
- Publication number
- DE1901145A1 DE1901145A1 DE19691901145 DE1901145A DE1901145A1 DE 1901145 A1 DE1901145 A1 DE 1901145A1 DE 19691901145 DE19691901145 DE 19691901145 DE 1901145 A DE1901145 A DE 1901145A DE 1901145 A1 DE1901145 A1 DE 1901145A1
- Authority
- DE
- Germany
- Prior art keywords
- olefins
- catalyst
- process according
- carbon
- hydrogen
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 150000001336 alkenes Chemical class 0.000 title claims description 13
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 10
- 239000003446 ligand Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000010948 rhodium Substances 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003284 rhodium compounds Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- BALRIWPTGHDDFF-UHFFFAOYSA-N rhodium Chemical compound [Rh].[Rh] BALRIWPTGHDDFF-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- BHVGMUDWABJNRC-UHFFFAOYSA-N (±)-2-methylhexanal Chemical compound CCCCC(C)C=O BHVGMUDWABJNRC-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 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 2
- LCFKURIJYIJNRU-UHFFFAOYSA-N 2-methylhexan-1-ol Chemical compound CCCCC(C)CO LCFKURIJYIJNRU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- KTEDZFORYFITAF-UHFFFAOYSA-K rhodium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Rh+3] KTEDZFORYFITAF-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0396/68A GB1207561A (en) | 1968-01-10 | 1968-01-10 | Oxo process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1901145A1 true DE1901145A1 (de) | 1969-08-28 |
Family
ID=9721276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691901145 Pending DE1901145A1 (de) | 1968-01-10 | 1969-01-10 | Verfahren zur Hydroformylierung von Olefinen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE726744A (enrdf_load_stackoverflow) |
| DE (1) | DE1901145A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1600074A (enrdf_load_stackoverflow) |
| GB (1) | GB1207561A (enrdf_load_stackoverflow) |
| NL (1) | NL6818254A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946082A (en) * | 1972-03-24 | 1976-03-23 | Exxon Research & Engineering Co. | Preparation of zerovalent phosphine substituted rhodium compounds and their use in the selective carbonylation of olefins |
| DE2424526C2 (de) * | 1974-05-21 | 1983-12-29 | Exxon Research and Engineering Co., 07036 Linden, N.J. | Rhodium(O)verbindungen und ein Verfahren zu ihrer Herstellung |
| US4260828A (en) * | 1980-04-16 | 1981-04-07 | Union Carbide Corporation | Hydroformylation process |
| ATE16475T1 (de) * | 1982-06-11 | 1985-11-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| EP0096986B1 (en) * | 1982-06-11 | 1987-04-22 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
-
1968
- 1968-01-10 GB GB0396/68A patent/GB1207561A/en not_active Expired
- 1968-12-19 NL NL6818254A patent/NL6818254A/xx unknown
- 1968-12-30 FR FR1600074D patent/FR1600074A/fr not_active Expired
-
1969
- 1969-01-10 BE BE726744D patent/BE726744A/xx unknown
- 1969-01-10 DE DE19691901145 patent/DE1901145A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL6818254A (enrdf_load_stackoverflow) | 1969-07-14 |
| GB1207561A (en) | 1970-10-07 |
| BE726744A (enrdf_load_stackoverflow) | 1969-07-10 |
| FR1600074A (enrdf_load_stackoverflow) | 1970-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68905452T2 (de) | Hydroformylation von Olefinen unter schwachem Druck mit einem Rhodium-Katalysator. | |
| DE69005715T2 (de) | Hydroformylierungsverfahren. | |
| DE1793069A1 (de) | Verfahren zur Herstellung sauerstoffhaltiger Produkte | |
| DE3232557C2 (enrdf_load_stackoverflow) | ||
| EP0435084A1 (de) | Verfahren zur Herstellung von Aldehyden | |
| DE2064471A1 (de) | Katalytisches Verfahren | |
| DE2827300C2 (enrdf_load_stackoverflow) | ||
| EP0805138B1 (de) | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen | |
| DE1901145A1 (de) | Verfahren zur Hydroformylierung von Olefinen | |
| DE1812504C2 (de) | Verfahren zur Herstellung von Alkoholen und/oder Aldehyden nach der Oxosynthese | |
| DE2030575A1 (de) | Verfahren zur Hydroformylierung von Olefinen | |
| DE10206697A1 (de) | Hydroformylierungsverfahren | |
| EP1017492B1 (de) | Verfahren zur herstellung von aldehyden durch hydroformulierung | |
| EP0796836B1 (de) | Verfahren zur Herstellung von Aldehyden | |
| DE1282633C2 (de) | Verfahren zur herstellung von aldehyden und/oder alkoholen | |
| DE3126265C2 (enrdf_load_stackoverflow) | ||
| EP0795533B1 (de) | Verfahren zur Herstellung von Aldehyden mittels eines Rhodium und substituierte Diphenyldiphosphane enthaltenden Katalysatorsystems | |
| EP1178951B1 (de) | Eta 5-phospholylkomplexe und ihre verwendung in der hydroformylierung | |
| DE2106244A1 (enrdf_load_stackoverflow) | ||
| EP1017660B1 (de) | Verfahren zur herstellung von aldehyden durch hydroformylierung in gegenwart von kronenether | |
| DE1643678B2 (de) | Verfahren zur herstellung von alkoholen und aldehyden durch hydroformylierung von olefinen | |
| DE2463148C2 (de) | Verfahren zur Herstellung von Aldehyden | |
| EP0909218A1 (de) | Katalysator und ein verfahren zur herstellung von aldehyden in gegenwart dieses katalysators | |
| EP4155288A1 (de) | Verfahren zur verbesserten steuerung der isomerenverhältnisse in hydroformylierungen | |
| DE1946437A1 (de) | Verfahren zur Hydroformylierung von Olefinen sowie dafuer geeignete Katalysatoren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |