DE858250C - Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones - Google Patents

Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones

Info

Publication number
DE858250C
DE858250C DEB6844D DEB0006844D DE858250C DE 858250 C DE858250 C DE 858250C DE B6844 D DEB6844 D DE B6844D DE B0006844 D DEB0006844 D DE B0006844D DE 858250 C DE858250 C DE 858250C
Authority
DE
Germany
Prior art keywords
pyrrolidones
preparation
oxy group
containing derivatives
parts
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
DEB6844D
Other languages
German (de)
Inventor
Hans Dr Nienburg
Curt Dr Schuster
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 DEB6844D priority Critical patent/DE858250C/en
Application granted granted Critical
Publication of DE858250C publication Critical patent/DE858250C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Description

Verfahren zur Herstellung von oxygruppenhaltigen Derivaten von a-Pyrrolidonen Es ist bekannt, daß man N-A1ky1-a-pyrrolidone erhält, wenn man y-Butyrolacton mit primären Alkylaminen längere Zeit unter Druck auf höhere Temperaturen erhitzt.Process for the preparation of oxy group-containing derivatives of α-pyrrolidones It is known that N-A1ky1-a-pyrrolidone is obtained when y-butyrolactone is used with primary alkylamines heated to higher temperatures under pressure for a long time.

Es wurde nun gefunden, daß man in guter Ausbeute wertvolle oxygruppenhaltige Derivate von a-Pyrrolidonen erhält, wenn man y-Butyrolacton oder seine Alkylderivate mit aliphatischen oder aromatischen Oxyaminen mit primärer Aminogruppe auf Temperaturen über 2oo° erhitzt.It has now been found that valuable oxy groups can be obtained in good yield Derivatives of α-pyrrolidones are obtained when using γ-butyrolactone or its alkyl derivatives with aliphatic or aromatic oxyamines with a primary amino group at temperatures heated over 2oo °.

Als Ausgangsstoffekommen einerseitsy-Butyrolacton oder die Lactone der i-, 2- oder 3-Alkyl-3-oxybuttersäuren, andererseits z. B. Monoäthanolamin, 2-Oxypropylamin-i, S-Aminopentanol-i, 4-Oxybutylamin-i oder aromatische Oxyamine, wie p-Aminophenol, in Betracht.On the one hand, butyrolactone or lactones are used as starting materials the i-, 2- or 3-alkyl-3-oxybutyric acids, on the other hand, for. B. monoethanolamine, 2-oxypropylamine-i, S-aminopentanol-i, 4-oxybutylamine-i or aromatic oxyamines such as p-aminophenol, into consideration.

Man kann die Umsetzungsteilnehmer für sich oder nach Zugabe indifferenter Lösungs- oder Verdünnungsmittel umsetzen. Zweckmäßig verwendet man äquivalente Mengen der einzelnen Teilnehmer.The reaction participants can be indifferent either by themselves or after addition React solvents or thinners. It is expedient to use equivalent amounts of the individual participants.

Es ist überraschend, daß bei der Umsetzung nur die Amino- und nicht auch die Oxygruppen der Oxyamine in Reaktion treten.It is surprising that in the implementation only the amino and not the oxy groups of the oxyamines also react.

Die erhaltenen N-(Oxyalkyl)- bzw. -(Oxyaryl)-a-pyrrolidone sind dickflüssige Öle oder, feste Verbindungen, die sich sowohl in organischen Lösungsmitteln wie auch in Wasser leicht lösen bzw. verteilen. Sie sind wertvolle Zwischenprodukte, insbesondere für Textilhilfsmittel, Weichmacher und Kunststoffe.The resulting N- (oxyalkyl) - or - (oxyaryl) -a-pyrrolidones are viscous Oils or, solid compounds, both in organic solvents how Easily dissolve or distribute even in water. They are valuable intermediate products, especially for textile auxiliaries, plasticizers and plastics.

Die in den folgenden Beispi61en verwendeten Teile sind Gewichtsteile.The parts used in the following examples are parts by weight.

Beispiel i Man erhitzt 86 Teile y-Butyrolacton und 6i Teile Äthanolamin im Druckgefäß 5 Stunden auf 22O°. Dann wird das Umsetzungsprodukt destilliert. Nach einem Vorlauf von Wasser geht das entstandene N-(ß-Oxyäthyl)-a-pyrrolidon unter io mm Druck bei 172 bis i75° über. Die Ausbeute beträgt 105 Teile. Das Erzeugnis ist ein dickflüssiges, in Wasser, Benzol, Alkoholen, Estern, Ketonen und Chlorkohlenwasserstoffen lösliches 01. Beispiel 2 Man erhitzt 86 Teile y-Butyrolacton, wie im Beispiel i, mit io9 Teilen p-Aminophenol. Bei der Aufarbeitung erhält man in einer Ausbeute von 85 °/o d. Th. das N-(4'-Oxyphen@11)-a-pyrrolidon vom Schmelzpunkt i6i bis i62'.EXAMPLE i 86 parts of γ-butyrolactone and 61 parts of ethanolamine are heated in a pressure vessel to 220 ° for 5 hours. Then the reaction product is distilled. After a first run of water, the resulting N- (ß-oxyethyl) -a-pyrrolidone passes over under 10 mm pressure at 172 to 175 °. The yield is 105 parts. The product is a viscous oil which is soluble in water, benzene, alcohols, esters, ketones and chlorinated hydrocarbons . Example 2 86 parts of y-butyrolactone are heated, as in Example 1, with 10 9 parts of p-aminophenol. Working up gives a yield of 85 ° / o d. Th. The N- (4'-oxyphene @ 11) -a-pyrrolidone from melting point i6i to i62 '.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von oxygruppenhaltigen Derivaten von a-Pyrrolidonen, dadurch gekennzeichnet, daß man y-Butyrolacton oder seine Alkylderivate mit aliphatischen oder aromatischen Oxyaminen mit primärer Aminogruppe auf Temperaturen über 200° erhitzt. Claim: Process for the preparation of oxy-containing derivatives of α-pyrrolidones, characterized in that γ-butyrolactone or its alkyl derivatives with aliphatic or aromatic oxyamines with primary amino groups are heated to temperatures above 200 °.
DEB6844D 1944-04-18 1944-04-18 Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones Expired DE858250C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB6844D DE858250C (en) 1944-04-18 1944-04-18 Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB6844D DE858250C (en) 1944-04-18 1944-04-18 Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones

Publications (1)

Publication Number Publication Date
DE858250C true DE858250C (en) 1952-12-04

Family

ID=6954921

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB6844D Expired DE858250C (en) 1944-04-18 1944-04-18 Process for the preparation of oxy group-containing derivatives of ª ‡ -pyrrolidones

Country Status (1)

Country Link
DE (1) DE858250C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1228263B (en) * 1960-04-13 1966-11-10 Gen Aniline & Film Corp Process for the preparation of N- [1, 3-dioxypropyl- (2)] -morpholonen- (3)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1228263B (en) * 1960-04-13 1966-11-10 Gen Aniline & Film Corp Process for the preparation of N- [1, 3-dioxypropyl- (2)] -morpholonen- (3)

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