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 molecule

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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
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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
Application number
DE1930664879D
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German (de)
Inventor
Paul Nashan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gutehoffnungshutte Oberhausen AG
Original Assignee
Gutehoffnungshutte Oberhausen AG
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Publication date
Application filed by Gutehoffnungshutte Oberhausen AG filed Critical Gutehoffnungshutte Oberhausen AG
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Publication of DE664879C publication Critical patent/DE664879C/en
Expired legal-status Critical Current

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    • 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

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  • 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)

PATENTANSPRtrciI 'Verfahren zur Herstellung von Formaldehyd und Acetaldehyd aus Olefinen mit ä bis q. Kohlenstoffatomen im Molekül und Sauerstoff oder diesen enthaltenden Gasen bei hohen Temperaturen, dadurch gekennzeichnet; däß man die Umsetzung in Gegenwart von Stickoxyden in Mengen von o, i bis 0,2% durchführt.PATENT APPLICATION 'Process for the production of formaldehyde and acetaldehyde from olefins with ä to q. Carbon atoms in the molecule and oxygen or these containing gases at high temperatures, characterized in that; that you can implement in the presence of nitrogen oxides in amounts of 0.1 to 0.2%.
DE1930664879D 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 Expired DE664879C (en)

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

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DE (1) DE664879C (en)

Cited By (11)

* Cited by examiner, † Cited by third party
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

Cited By (11)

* Cited by examiner, † Cited by third party
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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