DE575949C - Process for the preparation of oxyketones - Google Patents
Process for the preparation of oxyketonesInfo
- Publication number
- DE575949C DE575949C DEI41548D DEI0041548D DE575949C DE 575949 C DE575949 C DE 575949C DE I41548 D DEI41548 D DE I41548D DE I0041548 D DEI0041548 D DE I0041548D DE 575949 C DE575949 C DE 575949C
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- oxyketones
- preparation
- condensation
- ketones
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/497—Saturated compounds containing a keto group being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
Landscapes
- 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 Darstellung von Oxyketonen Es ist bekannt, daß man bei der Kondensation von Ketonen mit Formaldehyd oder formaldehydabgebenden Mitteln in Gegenwart von Alkalien oder alkalisch reagierenden Mitteln Oxyketone erhält.Process for the preparation of oxyketones It is known that in the condensation of ketones with formaldehyde or formaldehyde-releasing agents Obtains oxyketones in the presence of alkalis or alkaline agents.
Es wurde nun gefunden, daß man die Kondensation von Ketonen mit Formaldehyd oder formaldehydabgebenden Mitteln zu Oxyketonen mit besonderem Vorteil durchführen kann, wenn man in neutralem wäßrigem Medium und in Abwesenheit von kondensierend wirkenden Stoffen bei Temperaturen zwischen etwa 5o und 200' arbeitet. Diese Arbeitsweise hat vor dem bisher gebräuchlichen Verfahren den Vorteil, daß eine Neutralisation der angewandten Kondensationsmittel und Entfernung der hierbei sich bildenden Salze in Fortfall kommt, und daß die in Gegenwart von Alkalien praktisch nicht vermeidbare Bildung von unlöslichen bzw. undestillierbaren Verbindungen auf ein Mindestmaß beschränkt wird.It has now been found that the condensation of ketones with formaldehyde or formaldehyde-releasing agents to oxyketones carry out with particular advantage can when in neutral aqueous medium and in the absence of condensing active substances at temperatures between about 5o and 200 'works. This way of working has the advantage over the previously customary process that neutralization the condensing agents used and the removal of the salts that are formed in the process in omission, and that that is practically unavoidable in the presence of alkalis Formation of insoluble or undistillable compounds limited to a minimum will.
Man erhält nach dem vorliegenden Verfahren in der Hauptsache Dioxyketone, selbst dann, wenn ein Überschuß des Ketons zur Anwendung kommt. Es empfiehlt sich, zur Erzielung einer guten Umsetzung einen Überschuß an Ketonen anzuwenden, die nach beendeter Reaktion leicht durch Destillation zurückgewonnen werden können.According to the present process, dioxyketones are mainly obtained, even if an excess of the ketone is used. It is advisable, to use an excess of ketones to achieve a good conversion, the after can be easily recovered by distillation after the reaction has ended.
Infolge ihrer reaktionsfähigen Gruppen sind die so erhaltenen Oxyketone zu den verschiedenartigsten Umsetzungen befähigt, sie stellen somit wertvolle Ausgangsprodukte für weitere organische Synthesen dar.As a result of their reactive groups, the oxyketones thus obtained are Capable of the most varied of reactions, they are therefore valuable starting products for further organic syntheses.
Bei dem beanspruchten Verfahren lagert sich das Formaldehyd an das Keton infolge der angewandten speziellen Reaktionsbedingungen unter Bildung einer neuen C-C-Bindung an, während bei der -im Chemischen Zentralblatt 1924, 2. Teil, S. zog beschriebenen Kondensation von p-Aminoacetophenon mit Formaldehyd in alkoholischer Lösung eine C-N-Bindung geschaffen wird. Beispiel x 8 kg Aceton und 4,2 kg 3o°/oigen wäßrigen Formaldehyds werden in einem Niederdruckgefäß 48 Stunden lang auf ioo° erhitzt. Der angewandte Überschuß an Aceton wird in einer Kolonne abdestilliert, worauf das Wasser unter vermindertem Druck abdestilllert wird. Man erhält das monomolekulare unsymmetrische Dimethylolaceton als nahezu farblose, leicht bewegliche Flüssigkeit in einer Ausbeute von etwa 76°/" der Theorie. Beispiel 2 Man erhitzt ein Gemisch von i kg Methyläthylketonmit 3 kg 3o°/oigem wäßrigem Formaldehyd 24 Stunden lang auf 12o ° und erhält beim Aufarbeiten in der üblichen Weise i,4 kg Dimethylolmethyläthylketon (Ausbeute = 78°/0 der Theorie).In the claimed process, the formaldehyde is deposited on the Ketone as a result of the special reaction conditions used to form a new C-C bond, while in the -im Chemischen Zentralblatt 1924, Part 2, S. drew described condensation of p-aminoacetophenone with formaldehyde in alcoholic Solution a C-N bond is created. Example x 8 kg of acetone and 4.2 kg of 30% aqueous formaldehyde are in a low pressure vessel for 48 hours at 100 ° heated. The excess acetone used is distilled off in a column, whereupon the water is distilled off under reduced pressure. You get the monomolecular asymmetrical dimethylolacetone as an almost colorless, easily mobile liquid in a yield of about 76% of theory. Example 2 A mixture is heated of 1 kg of methyl ethyl ketone with 3 kg of 30% aqueous formaldehyde for 24 hours to 12o ° and receives when working up in the usual way i, 4 kg of dimethylol methyl ethyl ketone (yield = 78% of theory).
Beispiel 3 Man erhitzt eine Mischung von 6,7 kg Aceton, i kg Trioxymetliylen und 3,4 kg einer 300/0igen wä.ßrigen Formaldehydlösung 24 Sunden: auf i20 ° und erhält beim Aufarbeiten in der üblichen Weise Dimethylolaceton in einer Ausbeute von über 7o0/0.Example 3 A mixture of 6.7 kg of acetone and 1 kg of trioxymethylene is heated and 3.4 kg of a 300/0 aqueous formaldehyde solution for 24 hours: to 120 ° and receives dimethylolacetone in one yield on working up in the usual manner of over 7o0 / 0.
Beispiel 4 Man erhitzt in einem Druckgefäß 2 kg Gyclohexanon mit 4 kg 300%igem wäßrigem Formaldehyd 24 Stunden lang auf i20 °. Man erhält 2,2 kg einer zähen, klebrigen, in Alkohol löslichen Masse.Example 4 2 kg of cyclohexanone are heated with 4 in a pressure vessel kg 300% aqueous formaldehyde for 24 hours at 120 °. 2.2 kg are obtained tough, sticky, alcohol-soluble mass.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41548D DE575949C (en) | 1931-05-14 | 1931-05-14 | Process for the preparation of oxyketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41548D DE575949C (en) | 1931-05-14 | 1931-05-14 | Process for the preparation of oxyketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE575949C true DE575949C (en) | 1933-05-05 |
Family
ID=7190571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI41548D Expired DE575949C (en) | 1931-05-14 | 1931-05-14 | Process for the preparation of oxyketones |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE575949C (en) |
-
1931
- 1931-05-14 DE DEI41548D patent/DE575949C/en not_active Expired
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