DE855106C - Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde - Google Patents

Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde

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Publication number
DE855106C
DE855106C DEP9867D DEP0009867D DE855106C DE 855106 C DE855106 C DE 855106C DE P9867 D DEP9867 D DE P9867D DE P0009867 D DEP0009867 D DE P0009867D DE 855106 C DE855106 C DE 855106C
Authority
DE
Germany
Prior art keywords
butyraldehyde
crotonaldehyde
butyl alcohol
simultaneous production
temperature
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
DEP9867D
Other languages
German (de)
Inventor
Hans Dr Anselm
Kurt Kamler
Michael Wimmer
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.)
HELLMUTH HOLZ DR
Original Assignee
HELLMUTH HOLZ DR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by HELLMUTH HOLZ DR filed Critical HELLMUTH HOLZ DR
Priority to DEP9867D priority Critical patent/DE855106C/en
Application granted granted Critical
Publication of DE855106C publication Critical patent/DE855106C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur gleichzeitigen Herstellung von Butyraldehyd und Butylalkohol aus Crotonaldehyd Es ist bekannt, darnpfförmigen Crotonaldehyd bei Temperaturen unterhalb 2.3o°, vornehmlich bei i8o°, mit zur Bildung von Butylalkohol unzureichenden llerigcn Wasserstoff in Gegenwart eines Katalysators gleichzeitig zu Butylalkohol und Butvraldehvd zu hydrieren. Versucht man die Leistun- der Hvdrierungsapparatur zu erhöhen durch yerrn",#lirte Beschickung mit Crotonaldehyd, so müssen Kühlvorrichtungen vorgesehen sein, die eine unzulässige Temperaturerhöhung verhindern. Es wurde gefunden, daß die gleichzeitige Herstellung von gefunden, und Butyraldehyd durch Hydrieren von dampfförmigem Crotonaldehyd in Gegenwart von Beschleunigern mit einer einfachen Apparatur, die auch ohne besondere Kühlvorrichtungen eine erhöhte Leistung aufweist, gelingt, %verni mit einem wesentlichen Wasserstoffüberschuß bei einer Temperatur über 25o° gearbeitet wird. Diese Möglichkeit ist überraschend, da bei dieser Temperatur Butyraldehyd sonst nur in geringem Umfange entsteht. Die Temperatur kann ohne Wärmezufuhr aufrechterhalten werden durch entsprechend reichliche Beschickung des Reaktionsgefäßes mit Crotonaldehyddampf. Andererseits verhindert der große Wasserstoffüberschuß örtliche Überhitzung der Umsetzungsteilnehmer .und des Kontakts, so daß daraus sich ergebende ungünstige Einflüsse auf die Umsetzung vermieden werden. Als Kontakte kommen .Metalle bzw. Legierungen in Betracht, deren Verwendung für Hydrierungen in der Gasphase an sich bekannt ist, z. B. Kupfer, Nickel.Process for the simultaneous production of butyraldehyde and butyl alcohol From crotonaldehyde It is known to produce gut-shaped crotonaldehyde at temperatures below 2.3o °, mainly at 180 °, with insufficient for the formation of butyl alcohol Generating hydrogen in the presence of a catalyst simultaneously yields butyl alcohol and to hydrogenate Butvraldehvd. If you try the power supply equipment to increase by yerrn ", # lirte loading with crotonaldehyde, so must cooling devices be provided that prevent an unacceptable increase in temperature. It was found, that found the simultaneous production of, and butyraldehyde by hydrogenation of vaporous crotonaldehyde in the presence of accelerators with a simple Apparatus that has an increased performance even without special cooling devices, succeeds in% verni with a substantial excess of hydrogen at one temperature working over 25o °. This possibility is surprising because at this temperature Otherwise butyraldehyde is only produced to a small extent. The temperature can be adjusted without the addition of heat are maintained by adequately loading the reaction vessel with crotonaldehyde vapor. On the other hand, the large excess of hydrogen prevents local Overheating of the participants in the reaction and of the contact, so that the resultant unfavorable influences on the implementation can be avoided. as contacts .Metals or alloys come into consideration, their use for hydrogenation is known per se in the gas phase, e.g. B. copper, nickel.

Die Regelung der Temperatur gestattet in vorteilhafter Weise, das Verhältnis des anfallenden Butyraldehyds und Butanols zu verändern. Bei niedriger Temperatur, z. B. 2,5o bi,s 300°, entsteht vorwiegend Butanol, über 300°, vornehmlich bei 350 bis 380°, überwiegend Butyraldehyd. Nach Trennung der Umsetzungsprodukte können der Wasserstoff und/oder nicht umgesetzter Crotonaldehyd, der gegebenenfalls auch noch Butyraldehyd und/oder Butylalkohol enthält, wieder zur Umsetzung verwendet werden. Es ist auch möglich, das Verfahren bei Über- oder Unterdruck auszuüben, wodurch ebenfalls eine Regelung des Verhältn)is.ses des anfallenden Butyraldehyds und Butylalkohols herbeigeführt werden kann.The regulation of the temperature allows in an advantageous manner that To change the ratio of the butyraldehyde and butanol produced. At lower Temperature, e.g. B. 2.5o bi, s 300 °, is mainly butanol, above 300 °, mainly at 350 to 380 °, predominantly butyraldehyde. After separation of the reaction products can be the hydrogen and / or unreacted crotonaldehyde, which optionally also contains butyraldehyde and / or butyl alcohol, used again for the reaction will. It is also possible to carry out the procedure with positive or negative pressure, which also regulates the ratio of the butyraldehyde produced and butyl alcohol can be brought about.

Beispiel i In einem im Kreislauf geführten Strom von i 5oo bis --ooo cbm Wasserstoff wenden stündlich 16o kg Crotonaldehyd, der einige Prozent Wasser ent, halten kann, verdampft. Das Gemisch wird auf i5o bis 16o° vorgewärmt und dann über 4,5 cbm auf Trägern niedergeschlagenen Kupferkontakt geleitet. Durch die Hydrierungswärme steigt die Temperatur im Kontakt auf 280 bis 300°. Beim Abkühlen des Gasgemischs erhält man ein Hydrierungserzeugnis, bestehend aus 3o bis 35 % Butyraldehyd, 5o bis 6o °/o Butylalkohol, 2 bis 5 0/0 ,Crotonaldehyd und gegebenenfalls einigen Prozent Wasser, das durch Fraktionierung abgetrennt wird.Example i In a circulating stream of 1500 to --ooo cbm of hydrogen, 160 kg of crotonaldehyde, which can contain a few percent water, evaporates every hour. The mixture is preheated to 150 to 160 degrees and then passed over 4.5 cubic meters of copper contact deposited on supports. The heat of hydrogenation increases the temperature in contact to 280 to 300 °. When the gas mixture is cooled, a hydrogenation product is obtained consisting of 3o to 35% butyraldehyde, 50 to 60% butyl alcohol, 2 to 5% crotonaldehyde and optionally a few percent water, which is separated off by fractionation.

Beispiel 2 Man verdampft, wie in Beispiel i angegeben, stündlichi2-5o kg Crotonaldehyd, dem ioo bis i5o kg crotonaldehydhalbiger Butylalkohol aus der Destillation des Hydrierungsprodukts beigemischt sein können. Die Konfakttemperatur steigt auf 350 bis 3,8o° an. Das Hydrierungserzeugnis besteht aus 40 bis -5o °/o Butyraldehyd, 30 bis 35 % Butylalkohol und io bis 2o °/o Crotonaldehyd.EXAMPLE 2 I2-5o kg of crotonaldehyde are evaporated every hour, as indicated in Example i, to which 100 to 150 kg of crotonaldehyde-half butyl alcohol from the distillation of the hydrogenation product can be admixed. The Konfakttemperatur rises to 350 ° 3,8o. The hydrogenation product consists of 40 to -5 ° / o butyraldehyde, 30 to 35% butyl alcohol and 10 to 20% crotonaldehyde.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur gleichzeitigen Herstellung von Butyraldehyd und Butylalkohol durch Hydrieren von dampfförmigem Crotonaldehyd in Gegenwart von beschleunigend wirkenden Metallen bei erhöhter Temperatur, dadurch gekennzeichnet, daß die Hydrierung unter @Anwendung von überschüssigem Wasserstoff bei Temperaturen über 25o° ausgeführt wird. PATENT CLAIMS: i. Process for the simultaneous production of butyraldehyde and butyl alcohol by hydrogenating vaporous crotonaldehyde in the presence of accelerating metals at elevated temperature, characterized that the hydrogenation with @use of excess hydrogen at temperatures is carried out over 25o °. 2. Verfahren nach !Anspruch i, dadurch gekennzeichnet, daß zur Regelung des Verhältnisses der anfallenden Mengen von Butyraldehyd und Butylalkohol die Reaktionstemperatur erhöht bzw. erniedrigt wird.2. The method according to! Claim i, characterized in that that to regulate the ratio of the amounts of butyraldehyde and butyl alcohol the reaction temperature is increased or decreased.
DEP9867D 1942-12-12 1942-12-12 Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde Expired DE855106C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP9867D DE855106C (en) 1942-12-12 1942-12-12 Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP9867D DE855106C (en) 1942-12-12 1942-12-12 Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde

Publications (1)

Publication Number Publication Date
DE855106C true DE855106C (en) 1952-11-10

Family

ID=7362527

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP9867D Expired DE855106C (en) 1942-12-12 1942-12-12 Process for the simultaneous production of butyraldehyde and butyl alcohol from crotonaldehyde

Country Status (1)

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DE (1) DE855106C (en)

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