CH314911A - Process for the preparation of carbonyl compounds from olefins - Google Patents
Process for the preparation of carbonyl compounds from olefinsInfo
- Publication number
- CH314911A CH314911A CH314911DA CH314911A CH 314911 A CH314911 A CH 314911A CH 314911D A CH314911D A CH 314911DA CH 314911 A CH314911 A CH 314911A
- Authority
- CH
- Switzerland
- Prior art keywords
- water vapor
- carbon oxide
- olefins
- catalysts
- carbonyl compounds
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 150000001728 carbonyl compounds Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- -1 carbonyl hydrogen Chemical compound 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- HDGGXRVYODTLEJ-UHFFFAOYSA-N cobalt thorium Chemical compound [Co].[Th] HDGGXRVYODTLEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000004767 nitrides Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Carbonylverbindungen aus Olefinen
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellwng von Carbonylver- bindungendurchUmsetzungvon Kohlenoxyd mit Wasserdampf und Olefinen bei höheren Temperaturen und gegebenenfalls hohen Drucken. Die Umsetzung von Olefinen mit Kohlenoxyd und Wasserdampf ist bereits von K. Ziegler Prä. parative organisehe Chemie , Band 36, Teil I, dietrichsche Verlagsbuchhandlung, 1948, Seiten 115 bis 154, beschrie- ben worden. Diese Umsetzungen wurden bis lier in Gegenwart von Metallcarbonylen und Metallearbonylwasserstoff als Katalysatoren durchgeführt.
Es wurde nun. gefunden, dass die genannte Umsetzung besonders vorteilhaft durchgeführt werden kann, wenn man Katalysatoren verwendet, die mindestens ein WIetall der S. grippe des periodisehen Systems entweder als solches oder in Form einer Verbindung mit metallischem Bindungszustand, beispielsweise als Carbid oder Nitrid, enthalten, und die Menue des angewandten'Wasserdampfes so begrenzt, dass das Volumenverhältnis von n Kohlenoxyd zu Wasserdampf mindestens 2 beträgt. Die Umsetzung kann bei gewöhn Uehem Druek oder bei erhöhtem Druek erfolgen.
Beispiel rober einen Kobalt-Thorium-Katalysator, der auf 100 Teile Kobalt, 15 Teile Thorium und 200 Teile Kieselgur enthält, wird bei einer Temperatur von 180 und einem Druck von 100 atü ein Reaktionsgemisch geleitet, das aus Äthylen, Kohlenoxyd und Wasserdampf im Verhältnis 2 : 2 : 1 besteht. Bei einer Gasraum- gesehwihdigkeit von 100 Liter Ausgangsgas- gemisch/h auf 1 Liter Kontakt werden je Nebm a. ngewandtes Äthylen + Kohlenoxyd 450 g flüssige Reaktionsprodukte erh. alten, die sich wie folgt zusammensetzen :
40% Propionaldehyd, 20 /a Diäthylketon,
40% höhersiedende Aldehyde und Ketone.
PATENTANSPRUCH
Verfahren zur Herstellung von Carbonyl- verbindungen durch Umsetzung von Kohlen- oxyd mit Wasserdampf und Olefinen in Gegenwart von katalysatoren bei höheren Temperaturen, dadurch gekennzeichnet, dass man Katalysatoren verwendet, die mindestens ein Metall der 8i. Gruppe des periodischen Systems entweder als solches oder in Form einer Verbindung mit metallischem Bindungszustand enthalten, und die Menge des angewandten Wasserdampfes so begrenzt, dass das Volu- menverhältnis von Kohlenoxyd zu Wasserdampf mindestens 2 beträgt.
UNTERANSPRUCH
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man bei erhöhtem Druck arbeitet.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of carbonyl compounds from olefins
The present invention relates to a process for the production of carbonyl compounds by reacting carbon oxide with water vapor and olefins at higher temperatures and optionally high pressures. The implementation of olefins with carbon monoxide and steam is already by K. Ziegler Prä. parative organisehe Chemie, Volume 36, Part I, Dietrichsche Verlagsbuchhandlung, 1948, pages 115 to 154, has been described. These reactions were carried out up to lier in the presence of metal carbonyls and metal carbonyl hydrogen as catalysts.
It was now. found that the reaction mentioned can be carried out particularly advantageously if one uses catalysts which contain at least one WIetall der S. flu of the periodic system either as such or in the form of a compound with a metallic bond state, for example as a carbide or nitride, and which contain The menu of the applied water vapor is limited so that the volume ratio of carbon oxide to water vapor is at least 2. The implementation can take place with normal pressure or with increased pressure.
Example of a cobalt-thorium catalyst containing 100 parts of cobalt, 15 parts of thorium and 200 parts of kieselguhr, a reaction mixture is passed at a temperature of 180 and a pressure of 100 atü, which consists of ethylene, carbon oxide and water vapor in a ratio of 2 : 2: 1 exists. With a gas space density of 100 liters of starting gas mixture / h per 1 liter of contact, a. Applied ethylene + carbon oxide obtain 450 g of liquid reaction products, which are composed as follows:
40% propionaldehyde, 20 / a diethyl ketone,
40% higher boiling aldehydes and ketones.
PATENT CLAIM
Process for the production of carbonyl compounds by reacting carbon oxide with steam and olefins in the presence of catalysts at higher temperatures, characterized in that catalysts are used which contain at least one metal of the 8i. Group of the periodic table either as such or in the form of a compound with a metallic bond state, and the amount of water vapor used is limited so that the volume ratio of carbon oxide to water vapor is at least 2.
UNDER CLAIM
Process according to claim, characterized in that one works at increased pressure.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314911X | 1951-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314911A true CH314911A (en) | 1956-07-15 |
Family
ID=6148489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314911D CH314911A (en) | 1951-08-01 | 1952-07-10 | Process for the preparation of carbonyl compounds from olefins |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314911A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3130399A1 (en) | 2015-08-12 | 2017-02-15 | Basf Se | Method for the hydroformylation of olefins and/or alkynes in the gas phase with a mixture of hydrogen and carbon monoxide in the presence of heterogeneous catalyst |
| WO2017025593A1 (en) * | 2015-08-12 | 2017-02-16 | Basf Se | Catalyst comprising a phosphide-containing active component and method for insertion of carbon monoxide in reactant components |
-
1952
- 1952-07-10 CH CH314911D patent/CH314911A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3130399A1 (en) | 2015-08-12 | 2017-02-15 | Basf Se | Method for the hydroformylation of olefins and/or alkynes in the gas phase with a mixture of hydrogen and carbon monoxide in the presence of heterogeneous catalyst |
| WO2017025593A1 (en) * | 2015-08-12 | 2017-02-16 | Basf Se | Catalyst comprising a phosphide-containing active component and method for insertion of carbon monoxide in reactant components |
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