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DE840090C - Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones - Google Patents

Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones

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Publication number
DE840090C
DE840090C DEB12726A DEB0012726A DE840090C DE 840090 C DE840090 C DE 840090C DE B12726 A DEB12726 A DE B12726A DE B0012726 A DEB0012726 A DE B0012726A DE 840090 C DE840090 C DE 840090C
Authority
DE
Germany
Prior art keywords
unsaturated aliphatic
aliphatic ketones
production
parts
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
Application number
DEB12726A
Other languages
German (de)
Inventor
Hans Dr Nienburg
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB12726A priority Critical patent/DE840090C/en
Application granted granted Critical
Publication of DE840090C publication Critical patent/DE840090C/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • 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

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

Description

Verfahren zur Herstellung a, j3-ungesättigter aliphatischer Ketone Es ist bekannt, a, ß-ungesättigte aliphatische Ketone durch Behandeln der entsprechenden gesättigten ß-Oxyketcme, wie man sie als Zwischenprodukt bei der alkalischen Kondensation von Ketonen mit Aldehyden erhält, mit wasserfreier Oxalsäure oder mit Jod in der Wärme herzustellen.Process for the preparation of α, j3-unsaturated aliphatic ketones It is known to obtain α, ß-unsaturated aliphatic ketones by treating the corresponding saturated ß-Oxyketcme, as they are an intermediate product in alkaline condensation obtained from ketones with aldehydes, with anhydrous oxalic acid or with iodine in the To produce heat.

Es wurde nun gefunden, daß man in sehr viel einfacherer Weise und mit besserer Ausbeute ß-Oxyketone in a, ß-ungesättigte Ketone überführen kann, wenn man dieß-Oxyketone in Anwesenheit von Wasser mit Dicarbonsä raren erhitzt.It has now been found that in a much simpler way and can convert ß-oxyketones into a, ß-unsaturated ketones with better yield, if one heated these oxyketones in the presence of water with Dicarbonsä rare.

Die Umsetzung läßt sich am einfachsten bewerkstelligen, indem man das ß-Oxyketon mit einer wäßrigcti Lösung einer Dicarbonsäure, z. B. Oxalsäure, Malonsäure oder Cyclohexandicarbonsäure, versetzt und einige Zeit zum Sieden unter Rückflußkühlung erhitzt, bis die Wasserabspaltung vollständig ist. Das ungesättigte Keton scheidet sich dann in der Regel als ölige Schicht von der wäßrigen Dicarbonsäurelösung ab. Man kann auch in geschlossenen Gefäßen unter erhöhtem Druck oberhalb des Siedepunktes des Reaktionsgemisches arbeiten.The easiest way to accomplish this is to have the ß-oxyketone with an aqueous solution of a dicarboxylic acid, z. B. oxalic acid, Malonic acid or cyclohexanedicarboxylic acid, added and left to boil for some time The reflux cooling is heated until the elimination of water is complete. The unsaturated one Ketone then separates as a rule as an oily layer from the aqueous dicarboxylic acid solution away. It can also be done in closed vessels under increased pressure above the boiling point of the reaction mixture work.

Die in dem nachstehenden Beispiel angegebenen Teile sind Gewichtsteile.The parts given in the example below are parts by weight.

Beispiel 55o Teile Heptanol-4-on-2 (Kp. 20 = 95 bis g9°), hergestellt durch Kondensation von Aceton mit n-Butyraldehyd in Gegenwart eines alkalischen Mittels, versetzt man mit einer Lösung von 38 Teilen Oxalsäure in i8o Teilen Wasser und erhitzt das Gemisch 3 Stunden zum Sieden unter RückfluBkühlung. Beim Erkalten des Reaktionsgemisches scheiden sich joo Teile rohes Butylidenaceton als ölige Schicht über der wäBrigen Lösung ab. Man trennt diese ab und fraktioniert sie unter einem Druck von 2o Torr. `eben einem Vorlauf und einer geringen Menge eines Destillationsrückstandes erhält man so 43o Teile Butylidenaceton (Kp. 2o = 6o bis 63°).Example 55o parts of heptanol-4-one-2 (bp. 20 = 95 to g9 °), prepared by condensation of acetone with n-butyraldehyde in the presence of an alkaline agent, are mixed with a solution of 38 parts of oxalic acid in 180 parts of water the mixture is refluxed for 3 hours. When the reaction mixture cools, 100 parts of crude butylidene acetone separate out as an oily layer over the aqueous solution. These are separated off and fractionated under a pressure of 20 Torr. With a forerun and a small amount of distillation residue, 43o parts of butylidene acetone (b.p. 20 = 60 to 63 ° ) are obtained .

Claims (1)

PATENTANSPRUCH: Verfahren 'zur Herstellung u, ß-ungesättigter aliphatischer Ketone, dadurch gekennzeichnet, daß man die entsprechenden ß-Oxyketone in Gegenwart von Wasser mit Dicarbonsäuren erhitzt. PATENT CLAIM: Process for the preparation of u, ß-unsaturated aliphatic ketones, characterized in that the corresponding ß-oxyketones are heated with dicarboxylic acids in the presence of water.
DEB12726A 1950-11-29 1950-11-29 Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones Expired DE840090C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB12726A DE840090C (en) 1950-11-29 1950-11-29 Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB12726A DE840090C (en) 1950-11-29 1950-11-29 Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones

Publications (1)

Publication Number Publication Date
DE840090C true DE840090C (en) 1952-05-26

Family

ID=6957251

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB12726A Expired DE840090C (en) 1950-11-29 1950-11-29 Process for the production of ª ‡, ª ‰ -unsaturated aliphatic ketones

Country Status (1)

Country Link
DE (1) DE840090C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002065A1 (en) * 1984-09-27 1986-04-10 Chevron Research Company Process for preparing 1,3-cyclohexanedione derivatives and intermediates therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002065A1 (en) * 1984-09-27 1986-04-10 Chevron Research Company Process for preparing 1,3-cyclohexanedione derivatives and intermediates therefor

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