DE723498C - Process for the preparation of aliphatic oxyaldehydes and oxyketones - Google Patents

Process for the preparation of aliphatic oxyaldehydes and oxyketones

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Publication number
DE723498C
DE723498C DEI63527D DEI0063527D DE723498C DE 723498 C DE723498 C DE 723498C DE I63527 D DEI63527 D DE I63527D DE I0063527 D DEI0063527 D DE I0063527D DE 723498 C DE723498 C DE 723498C
Authority
DE
Germany
Prior art keywords
aliphatic
oxyketones
water
oxyaldehydes
weight
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
DEI63527D
Other languages
German (de)
Inventor
Dr Walter Bock
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI63527D priority Critical patent/DE723498C/en
Application granted granted Critical
Publication of DE723498C publication Critical patent/DE723498C/en
Expired legal-status Critical Current

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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
    • C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
    • 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

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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 von aliphatischen Oxyaldehyden und Oxyketonen Es ist bekannt, Methydenketone in alkalischen Mitteln mit Wasser zu behandeln. Als Hauptprodukt dieser Reaktion erhält man unter Kondensation von zwei Molekülen des angewandten Methylenketoni O:ktadionol bzw. seine Homologen. Daneben tritt auch in untergeordnetem Maße bei Anwendung von Methylvinylketon Anlagerung von Wasser ein unter Bildung von ß-Ketobutylallcohod. Ferner hat man a-ß-ungesättigte, wasserunlösliche Ketone im wässerigen alkalischen Mittel in Gegenwart von Formaldehyd behandelt. Hierbei erhält man unter weitgehender Kondensation harzartige Produkte.Process for the preparation of aliphatic oxyaldehydes and oxyketones It is known to treat methylene ketones in alkaline agents with water. as The main product of this reaction is obtained with the condensation of two molecules of applied Methylenketoni O: ktadionol or its homologues. Next to it also occurs to a lesser extent when using methyl vinyl ketone, water build-up one with the formation of ß-ketobutylallcohod. Furthermore, there are a-ß-unsaturated, water-insoluble ones Ketones treated in an aqueous alkaline agent in the presence of formaldehyde. Resin-like products are obtained with extensive condensation.

Es wurde die Beobachtung gemacht, daß aliphatische a-ß-ungesättiigte Ketone oder Aldehyde, welche ganz oder teilweise wasserlöslicb. sind, in wässerigem, alkalischem Mittel bei Gegenwart von Formaldehyd leicht Wasser anlagern und in die gesättigten Oxyketone oder Aldehyde übergehen. Diese Wirkung des Formaldehyds .ist überraschend und gestattet, die Oxyketone oder Aldehyde in guter Ausbeute und Reinheit herzustellen.It was observed that aliphatic α-β-unsaturates Ketones or aldehydes which are wholly or partly water-soluble. are, in watery, alkaline agent in the presence of formaldehyde easily accumulate water and into the Pass over saturated oxyketones or aldehydes. This effect of formaldehyde. Is Surprisingly and permitted, the oxyketones or aldehydes in good yield and purity to manufacture.

Die Behandlung wird zweckmäßig bei nicht erhöhten Temperaturen von -io bis + 25' und einer H-Ionenkonzentration von pa 8 bis io durchgeführt, wobei die verschiedensten basisch wirkenden Stoffe verwendet "werden können. Die Aufarbeitung kann z. B. in der Weise erfolgen, d,aß man das Umsetzungsgemisch neutralisiert oder schwach ansäuert und der Destillation unterwirft. Die nicht umgesetzten Anteile an Ausgangsverbindung sowie der angewandte Formaldehyd können für .den nächsten Einsatz eingesetzt werden. Beispiel i Eine Lösung von 28o Gewichtsteilen Methylvinyllceton in 56o Gewichtsteilen 27°1oigem wässerigem Formaldehyd wird bei -io° mit Zoo Gewichtsteilen einer gesättigten Calciumhydroxydlösung versetzt. Man läßt die Temperatur o° nicht übersteigen und rührt 2o bis 24 Stunden nach. Es werden 16o bis 17o Gewichtsteile einer Fraktion vom Kp2, 85 bis 88° erhalten, die aus ß-Ketobutylalkohol CHs-CO-CH@-CH.OH besteht.The treatment is expediently carried out at not elevated temperatures of -io to + 25 ' and an H ion concentration of pa 8 to 10, it being possible to use a wide variety of basic substances. d, the reaction mixture was neutralized or weakly acidified and subjected to distillation. The unreacted proportions of starting compound and the formaldehyde used can be used for the next use. Example i A solution of 28o parts by weight of methylvinyl acetone in 56o parts by weight of 27 ° 10% aqueous formaldehyde zoo parts by weight of a saturated calcium hydroxide solution are added at -io °. The temperature is not allowed to exceed 0 ° and the mixture is subsequently stirred for 20 to 24 hours. 16o to 17o parts by weight of a fraction of bp2.85 to 88 ° are obtained, which from ß- Ketobutyl alcohol CHs-CO-CH@-CH.OH consists.

Arbeitet man (unter Beibehaltung der Wassermenge) mit der halben Menge Formaldehyd, so erhält man ß-Ketobutylalkohol ebenfalls noch in guter Ausbeute.If you work with half the amount (while maintaining the amount of water) Formaldehyde, ß-ketobutyl alcohol is also still obtained in good yield.

Beispiel 2 Eine Mischung von 28o Gewichtsteilen Crotonaldehyd und 56o Gewichtsteilen 27°jai.gem wässerigem Formaldehyd wird auf o° abgekühlt und tropfenweise mit einer wässerigen Lösung von 2 Gewichtsteilen Trimethylamin in 5o Gewichtsteilen Wasser versetzt. Man läßt die Temperatur 5° nicht übersteigen und rührt 2d. Stunden nach. Es wurden 15o bis ido Gewichtsteile einer Fraktion vom Kp_5 84 bis 90° erhalten, die im wesentlichen aus Aldol besteht.Example 2 A mixture of 28o parts by weight of crotonaldehyde and 56o parts by weight of 27 ° jai.gem aqueous formaldehyde is cooled to 0 ° and an aqueous solution of 2 parts by weight of trimethylamine in 50 parts by weight of water is added dropwise. The temperature is not allowed to exceed 5 ° and the mixture is stirred for 2 days. Hours after. 150 to ido parts by weight of a fraction with a bp of 84 to 90 ° were obtained, consisting essentially of aldol consists.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von aliphatischen Oxyalde-hyden und OZyketonen durch Anlagerung von Wasser an a-ß-ungesättigte Aldehyde und Ketone, dadurch gekennzeichnet, daß man a-ß-ungesättigte Aldehyde oder Ketone mit mehr als drei Kohlenstoffatomen, die in Wasser ganz oder teilweise löslich sind, ;in Gegenwart von Formaldehyd bei nicht erhöhten Temperaturen in wässerigem, alkalischem Mittel behandelt.PATENT CLAIM: Process for the production of aliphatic Oxyalde-hyden and O-cyketones due to the addition of water to α-ß-unsaturated aldehydes and ketones, characterized in that one a-ß-unsaturated aldehydes or ketones with more than three carbon atoms fully or partially soluble in water; in the presence of formaldehyde at non-elevated temperatures in an aqueous, alkaline medium treated.
DEI63527D 1939-01-19 1939-01-19 Process for the preparation of aliphatic oxyaldehydes and oxyketones Expired DE723498C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI63527D DE723498C (en) 1939-01-19 1939-01-19 Process for the preparation of aliphatic oxyaldehydes and oxyketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI63527D DE723498C (en) 1939-01-19 1939-01-19 Process for the preparation of aliphatic oxyaldehydes and oxyketones

Publications (1)

Publication Number Publication Date
DE723498C true DE723498C (en) 1942-08-18

Family

ID=7195923

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI63527D Expired DE723498C (en) 1939-01-19 1939-01-19 Process for the preparation of aliphatic oxyaldehydes and oxyketones

Country Status (1)

Country Link
DE (1) DE723498C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001038292A2 (en) * 1999-11-25 2001-05-31 Basf Aktiengesellschaft Method for producing optically active amines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001038292A2 (en) * 1999-11-25 2001-05-31 Basf Aktiengesellschaft Method for producing optically active amines
WO2001038292A3 (en) * 1999-11-25 2002-02-28 Basf Ag Method for producing optically active amines
US7078226B1 (en) 1999-11-25 2006-07-18 Basf Aktiengesellschaft Method for producing optically active amines
US7358396B2 (en) 1999-11-25 2008-04-15 Basf Aktiengesellschaft Preparation of optically active amines

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