DE664879C - Process for the production of formaldehyde and acetaldehyde from olefins with 2 to 4 carbon atoms in the molecule - Google Patents
Process for the production of formaldehyde and acetaldehyde from olefins with 2 to 4 carbon atoms in the moleculeInfo
- Publication number
- DE664879C DE664879C DE1930664879D DE664879DD DE664879C DE 664879 C DE664879 C DE 664879C DE 1930664879 D DE1930664879 D DE 1930664879D DE 664879D D DE664879D D DE 664879DD DE 664879 C DE664879 C DE 664879C
- Authority
- DE
- Germany
- Prior art keywords
- acetaldehyde
- formaldehyde
- molecule
- olefins
- carbon atoms
- 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
Links
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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Exhaust Gas Treatment By Means Of Catalyst (AREA)
Description
Verfahren zur Herstellung von Formaldehyd und Acetaldehyd aus Olefinen mit 2 bis 4 Kohlenstoffatomen im Molekül Bestrebungen, ungesättigte Kohlenwasserstofle, z. B. solche von z bis 4. C-Atomen im Molekül, wie sie in merklichen Mengen etwa im Kokereigas vorkommen, in ihre Oxydationsprodukte überzuführen, sind bekannt. Es sei erinnert an die Arbeiten von Will -s t ä t t e r und B o m m e r -und die vorausgehenden Untersuchungen von Bone und W h e e 1 e r. Auch anderweitig wurden schon Versuche gemacht, die eine solche Umsetzung mit Sauerstoff oder Ozon bezwecken; jedoch ließen diese Verfahren eine wirtschaftliche Verwertung nicht zu. Es ist auch belmnnt, daß die Behandlung des Äthylens mit Stickstoffdioxyd allein ohne Zugabe von Sauerstoff oder diesen .enthaltenden Gasen bei der Umsctzung zu Cyanwasserstotf führt.Process for the production of formaldehyde and acetaldehyde from olefins with 2 to 4 carbon atoms in the molecule aspirations, unsaturated hydrocarbons, z. B. those from z to 4. C atoms in the molecule, as they are in noticeable amounts for example Occurring in coke oven gas, converting it into their oxidation products, are known. Let us remind you of the work of Will -s tä t e r and B o m m e r -und die preliminary investigations by Bone and W h e e 1 e r. Also in other ways attempts have already been made to achieve such a reaction with oxygen or ozone; however, these processes did not allow an economic exploitation. It is also Belmnnt that the treatment of ethylene with nitrogen dioxide alone without addition of oxygen or gases containing it during the conversion to hydrogen cyanide leads.
Gemäß der Erfindung lassen sich die ungesättigten Kohlenwasserstofe mit ? bis q. CAtomen im Molekül, z. B. Äthylen, Butyllen u. d,-I., in ihre Oxydationsprodukte, wie Formaldehyd und Acetaldehyd, überführen, wenn man sie zusammen mit sauerstoffhaltigen Gasen, z. B. Luft, bei Temperaturen, die unter dem Entzündungspunkt des Gasgemisches licgen, unter Zusatz von Stickoxyden in Mengen von o,i bis o,2% an erhitzten Körpern 'vorbeileitet. Dabei entstehen je nach der Reaktionstemperatur und der Raumbeschwindigkeit des Ausgangsstoffes Formaldehyd und Acetaldehyd in wechselnden Mengen. Die Ausbeuten sind beträchtlich und als Grundlage für eine wirtschaftliche technische Verwertung des Verfahrens geeignet.According to the invention, the unsaturated hydrocarbons with ? to q. C atoms in the molecule, e.g. B. ethylene, butylene u. D, -I., In their oxidation products, such as formaldehyde and acetaldehyde, when taken together with oxygenated Gases, e.g. B. air, at temperatures below the ignition point of the gas mixture licgen, with the addition of nitrogen oxides in amounts of 0.1 to 0.2% on heated bodies 'passed. This results depending on the reaction temperature and the space velocity of the starting material formaldehyde and acetaldehyde in varying amounts. The yields are considerable and form the basis for economic technical recovery of the procedure.
Einmal behandeltes. Gasgemisch kann dem Verfahren für eine Steigerung der Ausbeute wiederholt unterworfen werden.Once treated. Gas mixture can increase the process subjected to the yield repeatedly.
Beispiele i. Äthylen und Luft, im Verhältnis 1: 7, wurden bei ,einer Raumgeschwindigkeit von Zoo cm/Sek. durch ein System enger Quarzröhren geführt, welches auf etwa 59o° erhitzt war. Es entstanden So g Formaldehyd und etwa Sog Acetaldehyd je Kubikmeter Äthylen.Examples i. Ethylene and air, in a ratio of 1: 7, were at one Space velocity of zoo cm / sec. guided through a system of narrow quartz tubes, which was heated to about 59o °. So g of formaldehyde and about suction acetaldehyde were produced per cubic meter of ethylene.
2. Propylen und Luft, im Verhältnis 1: 5, wurden bei einer Raumgeschwindigkeit von 185 cm/Sek. über eine duaikelrot glühende Spirale aus Chromnickeldraht geleitet. Es entstanden Sag Formaldehyd neben 25g Acetaldehyd.2. Propylene and air, in a ratio of 1: 5, were at space velocity of 185 cm / sec. conducted over a double-red glowing spiral made of chrome-nickel wire. Sag formaldehyde and 25g acetaldehyde were produced.
3. Das Restgas aus Beispiel i wurde nochmals derselben Behandlung unterworfen. Es wurden 75g, Formaldehyd und 32g Acetaldehyd gefunden. q.. Äthylen und Luft,, im Verhältnis i : 7,. wurden bei einer, Raumgeschwindigkeit vonaoo cm/Sek. und einer Temperatur von 4.8o° durch .ein mit Quarzglasscherben gefülltes Porzellanrohr geführt. Es entstanden zog Formaldehyd und q.6g Acetaldehyd.3. The residual gas from example i was subjected again to the same treatment. 75 g formaldehyde and 32 g acetaldehyde were found. q .. ethylene and air, in the ratio i: 7 ,. were at a, space velocity of aoo cm / sec. and a temperature of 4.8o ° through a porcelain tube filled with broken quartz glass. Formaldehyde and q.6g acetaldehyde were produced.
5. Butylen und Luft, im Verhältnis i : 9,' wurden mit einer Raumgeschwindigkeit von etwa igo cm/Sek. durch eine Porzellanröhre geleitet, die mit Silicagel gefüllt und auf 57o' erhitzt war. Es entstanden: 759 Formaldehyd neben Sog Acetaldehyd je Kubikmeter Butylen. Bei allen vorstehenden Beispielen wurden dem Ausgangsgasgemisch etwa o,i bis o,2 °!o Stickoxyde zugemischt.5. Butylene and air, in the ratio i: 9, 'were at a space velocity of about igo cm / sec. passed through a porcelain tube filled with silica gel and heated to 57o '. The result: 759 formaldehyde in addition to suction acetaldehyde per cubic meter of butylene. In all of the above examples, about 0.1 to 0.2% nitrogen oxides were added to the starting gas mixture.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE664879T | 1930-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE664879C true DE664879C (en) | 1938-09-16 |
Family
ID=6589477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1930664879D Expired DE664879C (en) | 1930-04-01 | 1930-04-01 | Process for the production of formaldehyde and acetaldehyde from olefins with 2 to 4 carbon atoms in the molecule |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE664879C (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE756487C (en) * | 1939-02-22 | 1953-03-16 | Gutehoffnungshuette Oberhausen | Process for the oxidation of lower hydrocarbons of the paraffin series |
DE1049845B (en) * | 1957-01-04 | 1959-02-05 | Consortium Elektrochem Ind | Process for the preparation of carbonyl compounds |
DE1059453B (en) * | 1957-09-06 | 1959-06-18 | Consortium Elektrochem Ind | Process for the preparation of carbonyl compounds from oxygen-containing organic compounds containing one or more carbon-carbon double bonds |
DE1061767B (en) * | 1957-06-07 | 1959-07-23 | Consortium Elektrochem Ind | Process for the production of aldehydes and ketones |
DE1077662B (en) * | 1957-12-02 | 1960-03-17 | Consortium Elektrochem Ind | Process for the oxidation of organic compounds containing one or more carbon-carbon triple bonds |
DE1118183B (en) * | 1957-07-10 | 1961-11-30 | Consortium Elektrochem Ind | Process for the preparation of aldehydes, ketones or acids corresponding to the aldehydes |
US3057915A (en) * | 1957-09-14 | 1962-10-09 | Hoechst Ag | Process for oxidizing olefins to aldehydes, ketones and acids |
US3076032A (en) * | 1957-10-31 | 1963-01-29 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
US3104263A (en) * | 1957-10-09 | 1963-09-17 | Hoechst Ag | Process for the manufacture of acetaldehyde |
US3106579A (en) * | 1957-10-31 | 1963-10-08 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
US3118001A (en) * | 1958-01-28 | 1964-01-14 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
-
1930
- 1930-04-01 DE DE1930664879D patent/DE664879C/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE756487C (en) * | 1939-02-22 | 1953-03-16 | Gutehoffnungshuette Oberhausen | Process for the oxidation of lower hydrocarbons of the paraffin series |
DE1049845B (en) * | 1957-01-04 | 1959-02-05 | Consortium Elektrochem Ind | Process for the preparation of carbonyl compounds |
DE1061767B (en) * | 1957-06-07 | 1959-07-23 | Consortium Elektrochem Ind | Process for the production of aldehydes and ketones |
DE1118183B (en) * | 1957-07-10 | 1961-11-30 | Consortium Elektrochem Ind | Process for the preparation of aldehydes, ketones or acids corresponding to the aldehydes |
DE1059453B (en) * | 1957-09-06 | 1959-06-18 | Consortium Elektrochem Ind | Process for the preparation of carbonyl compounds from oxygen-containing organic compounds containing one or more carbon-carbon double bonds |
US3057915A (en) * | 1957-09-14 | 1962-10-09 | Hoechst Ag | Process for oxidizing olefins to aldehydes, ketones and acids |
US3104263A (en) * | 1957-10-09 | 1963-09-17 | Hoechst Ag | Process for the manufacture of acetaldehyde |
US3076032A (en) * | 1957-10-31 | 1963-01-29 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
US3106579A (en) * | 1957-10-31 | 1963-10-08 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
DE1077662B (en) * | 1957-12-02 | 1960-03-17 | Consortium Elektrochem Ind | Process for the oxidation of organic compounds containing one or more carbon-carbon triple bonds |
US3118001A (en) * | 1958-01-28 | 1964-01-14 | Hoechst Ag | Process for oxidizing olefins to aldehydes and ketones |
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