DE639291C - Process for the production of condensation products of acetaldehyde - Google Patents
Process for the production of condensation products of acetaldehydeInfo
- Publication number
- DE639291C DE639291C DEI48636D DEI0048636D DE639291C DE 639291 C DE639291 C DE 639291C DE I48636 D DEI48636 D DE I48636D DE I0048636 D DEI0048636 D DE I0048636D DE 639291 C DE639291 C DE 639291C
- Authority
- DE
- Germany
- Prior art keywords
- acetaldehyde
- condensation products
- production
- diethylamine
- products
- 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
- C07C45/61—Preparation 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
- C07C45/67—Preparation 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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- 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
- C07C45/61—Preparation 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
- C07C45/67—Preparation 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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation 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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Einwirkung von organischen Aminen auf Aldehyde ist bekannt. Acetaldehyd .setzt sich damit so langsam um, daß er beispielsweise beim Hinzufügen von Y2 0/0 Diäthylamin sich nicht erwärmt und daß beim Stehenlassen bei Zimmertemperatur die Dichte sich erst nach vielen Tagen über 1 erhöht.The action of organic amines on aldehydes is known. Acetaldehyde reacts so slowly that it does not heat up when Y 2 0/0 diethylamine is added, for example, and that when left to stand at room temperature the density does not increase above 1 until after many days.
Es wurde nun gefunden, daß die durch Einwirkung eines Amins auf Acetaldehyd hervorgerufene Umsetzung durch Zugabe von Formaldehyd sehr beschleunigt wird. Je nach den Versuchsbedingungen und dem Mischungsverhältnis entstehen hauptsächlich Aldol oder höher kondensierte Verbindungen des Acetaldchyds oder gemischte Kondensationsprodukte aus Formaldehyd und Acetaldehyd.It has now been found that the by the action of an amine on acetaldehyde the reaction caused by the addition of formaldehyde is very accelerated. Depending on the test conditions and the mixing ratio mainly result in aldol or higher condensed compounds of acetaldehyde or mixed condensation products from formaldehyde and acetaldehyde.
ι. ι kg Acetaldehyd wird in einem Gefäß, das mit Rührer und Rückflußkühler versehen ist, durch den Kältelauge fließt, mit 100 g 35°/oiger wäßriger Formaldehydlösung vermischt. Nach Zugabe von 5 g Diäthylamin kommt die Mischung in mittelstarkes Sieden, die Temperatur steigt dabei im Reaktionsgefäß innerhalb von 3 Stunden auf 540, um dann während weiterer 3 Stunden auf 250 zurückzugehen. Das Reaktionsgemisch besitzt eine Dichte von 1,095 bei 250 und ist mit Wasser in jedem Verhältnis klar mischbar. Neben etwas unverändertem Acetaldehyd besteht es aus Aldol, dem außerdem höher kondensierte Produkte beigemengt sind.ι. ι kg of acetaldehyde is in a vessel equipped with a stirrer and reflux condenser, through which the cold liquor flows, mixed with 100 g of 35% aqueous formaldehyde solution. After addition of 5 g of diethylamine, the mixture comes in medium strong boiling, the temperature increases in the reaction vessel within 3 hours at 54 0, and then go back for another 3 hours at 25 0th The reaction mixture has a density of 1.095 at 25 and 0 is clearly miscible with water in any ratio. In addition to somewhat unchanged acetaldehyde, it consists of aldol to which more highly condensed products are added.
2. Eine Mischung von 10 kg Acetaldehyd und 750 g 350/oiger wäßriger Formaldehydlösung wird unter Rühren und unter Stickstoff mit 50 g Diäthylamin versetzt. Die Temperatur hält man 1 Tag bei 8 bis 120 und 3 bis 6 Tage bei 18 bis 21°. Die Dichte beträgt dann 1,085 bei 190. Die Reaktionsmasse besteht aus Aldol, dem nur spurenweise höher kondensierte Substanzen beigemengt sind, und etwas nicht umgesetztem Acetaldehyd.2. A mixture of 10 kg of acetaldehyde and 750 g of 350% aqueous formaldehyde solution is mixed with 50 g of diethylamine while stirring and under nitrogen. The temperature is maintained to 1 day at 8 to 12 0 and 3 to 6 days at 18 to 21 °. The density is then 1.085 at 19 0 . The reaction mass consists of aldol, to which only traces of highly condensed substances are added, and some unreacted acetaldehyde.
3. Wie im Beispiel 1 läßt man 1 kg' Acetaldehyd, 100 g 350ZoIgC wäßrige Formaldehydlösung und 5 g Diäthylamin reagieren. Sobald die Temperatur nicht höher steigt, werden noch 5 g Diäthylamin hinzugegeben und mehrere Stunden auf dem Dampfbad unter Rückfluß gekocht. Es bildet sich ein in Wasser unlösliches Öl.3. As in Example 1 is allowed to 1 Kg 'acetaldehyde, 100 g 35 0 ZoIgC aqueous formaldehyde solution and 5 g of diethylamine react. As soon as the temperature does not rise higher, 5 g of diethylamine are added and refluxed for several hours on the steam bath. An oil which is insoluble in water is formed.
4. Zu einer Mischung von 220 g Acetaldehyd und 500 g 350/oiger Formaldehydlösung werden xmter Rühren in kleinen Anteilen 5 g Diäthylamin gegeben. Die Temperatur steigt allmählich bis 74". Anschließend wird auf dem Dampfbad einige Stunden unter Rückfluß gekocht. Das Reaktionsprodukt stellt nach dem Versetzen mit der dem Diäthylamin äquivalenten Menge einer starken Säure, ζ. B. Salzsäure, und nach dem Abdestillieren des Wassers, am zweckmäßig-4. To a mixture of 220 g of acetaldehyde and 500 g of 350% formaldehyde solution 5 g of diethylamine are added in small portions xmter stirring. The temperature Gradually increases to 74 ". Subsequently, taking a few hours on the steam bath Refluxed. After the addition of the amount equivalent to the diethylamine, the reaction product is a strong one Acid, ζ. B. hydrochloric acid, and after distilling off the water, the most appropriate-
*) Von dem Patentsucher ist als der Erfinder angegeben worden:*) The patent seeker stated as the inventor:
Dr. Kurt Billig in Frankfurt a. M.-Höchst.Dr. Kurt Cheap in Frankfurt a. M.-Höchst.
sten unter vermindertem Druck, einen dicken Sirup dar. der sich auch unter vermindertem Druck rieht unzersetzt destillieren läßt und der mit Wasser in jedem Verhältnis klar mischbar ist.most under reduced pressure, a thick syrup Pressure can be distilled undecomposed and that with water is clear in every ratio is miscible.
Ganz ähnliche Produkte erhält man bei Anwendung größerer Mengen Formaldehyd, z. B. der 2- bis 3 fachen Menge.Very similar products are obtained when using larger amounts of formaldehyde, z. B. 2 to 3 times the amount.
Die nach dem beanspruchten Verfahren erhältlichen Produkte sollen ganz allgemein als Zwischenprodukte für die Herstellung von Textilhilfsmitteln. ferner von Lösungs- und Weichmachungsmitteln Verwendung finden. Wir-erwähnen, daß mit Hilfe der verfahrensgemäß erhaltenen Kondensationsprodukte beispielsweise Verbindungen, wie 1,3-Butylenglykol, Crotonaldehyd, und die daraus abgeleiteten Verbindungen, wie Butyraldehyd usw., leicht zugänglich sind.The products obtainable by the claimed process are intended to be very general as intermediate products for the manufacture of textile auxiliaries. also of solution and Find plasticizers use. We-mention that using the procedural obtained condensation products, for example compounds such as 1,3-butylene glycol, Crotonaldehyde, and the compounds derived therefrom, such as butyraldehyde, etc., are easily accessible.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48636D DE639291C (en) | 1933-12-23 | 1933-12-23 | Process for the production of condensation products of acetaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48636D DE639291C (en) | 1933-12-23 | 1933-12-23 | Process for the production of condensation products of acetaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE639291C true DE639291C (en) | 1936-12-02 |
Family
ID=7192339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48636D Expired DE639291C (en) | 1933-12-23 | 1933-12-23 | Process for the production of condensation products of acetaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE639291C (en) |
-
1933
- 1933-12-23 DE DEI48636D patent/DE639291C/en not_active Expired
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