DE855565C - Process for the preparation of carbonic acid amides - Google Patents

Process for the preparation of carbonic acid amides

Info

Publication number
DE855565C
DE855565C DEB5998D DEB0005998D DE855565C DE 855565 C DE855565 C DE 855565C DE B5998 D DEB5998 D DE B5998D DE B0005998 D DEB0005998 D DE B0005998D DE 855565 C DE855565 C DE 855565C
Authority
DE
Germany
Prior art keywords
preparation
carbonic acid
acid amides
acid
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
DEB5998D
Other languages
German (de)
Inventor
Ernst Dr Ploetz
Erwin Dr Weinhardt
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 DEB5998D priority Critical patent/DE855565C/en
Application granted granted Critical
Publication of DE855565C publication Critical patent/DE855565C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom

Landscapes

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

Description

Verfahren zur Herstellung von Carbonsäureamiden Es wurde gefunden, daß man a-i - 2-Alkyleniminocarbonsäureamide erhält, wenn man a-Alkyleniminocarbonsäureester niedrigmolekularer Alkohole mit .lmmoniak oder primären und sekundären Aminen umsetzt.Process for the preparation of carboxamides It has been found that a-i - 2-alkyleniminocarboxamides are obtained if you get a-Alkyleniminocarbonsäureester low molecular weight alcohols with ammonia or primary and secondary amines.

Als a-i - 2-Alkyleniminocarbonsäureester eignen sich beispielsweise die Ester der Äthyleniminoessigäure, der a-i - 2-Propyleniminobuttersäure oder der a-Äthyleniminostearinsäure mit Methyl-, Äthyl-oder Propylalkohol. Geeignete Amine sind z. 13. Ammoniak, Methylamin, Äthylamin, Butylamin, Octodecylamin, Dimethylamin, Dipropylamin, Octodecylmethylamin, Äthylendiamin, N - N'-Dimethylhexamethylendiamin, Hexamethylenimin, Morpholin oder Piperazin.As a-i-2-alkyleniminocarboxylic acid esters, for example, are suitable the esters of ethyleneiminoacetic acid, a-i - 2-propyleneiminobutyric acid or the a-Ethyleniminostearic acid with methyl, ethyl or propyl alcohol. Suitable amines are z. 13. Ammonia, methylamine, ethylamine, butylamine, octodecylamine, dimethylamine, Dipropylamine, octodecylmethylamine, ethylenediamine, N - N'-dimethylhexamethylenediamine, Hexamethyleneimine, morpholine or piperazine.

Die Umsetzung erfolgt je nach der Reaktionsfä@higkeit derAmine und der Ester bei gewöhnlicher oder mäßig erhöhter Temperatur, gegebenenfalls unter Kühlung oder gelindem Erwärmen. Man kann in An- oder Abwesenheit indifferenter Lösungsmittel, wie Alkohol, Benzol, Chloroform oder Tetrahv_ drofuran, arbeiten.The reaction takes place depending on the reactivity of the amines and the ester at ordinary or moderately elevated temperature, optionally below Cooling or gentle heating. In the presence or absence of inert solvents, how Alcohol, benzene, chloroform or tetrahydrofuran work.

Die erhaltenen Produkte sind farblose Flüssigkeiten oder kristalline Stoffe, die sich in organischen Lösungsmitteln und teilweise auch in Wasser lösen. In der Wärme oder durch Zusatz geringer Mengen Säure polymerisieren sie zu in Wasser und in organischen Lösungsmitteln unlöslichen Produkten.The products obtained are colorless liquids or crystalline Substances that dissolve in organic solvents and sometimes also in water. When heated or when small amounts of acid are added, they polymerize into water and products insoluble in organic solvents.

Bei der großen Reaktionsfähigkeit des i - 2-A1-,kyleniminringeswar es überraschend, daß bei der Umsetzung von a-i # 2-Alkyleniminocarbonsäureest)ern mit Aminen nur die Estergruppe reagiert und der Alkyleniminring unverändert bleibt.The high reactivity of the i-2-A1, kylenimine ring was it is surprising that in the implementation of a-i # 2-Alkyleniminocarbonsäureest) ern only the ester group reacts with amines and the alkylenimine ring remains unchanged.

Die a-i # 2-Alkyleniminocarbonsäureamide sollen als Zwischenprodukte für die Herstellung von Textilhilfsmitteln verwendet werden.The a-i # 2-alkyleniminocarboxamides are said to be intermediates used for the production of textile auxiliaries.

Die im folgenden Beispiel genannten Teile sind Gewichtsteile. Beispiel Zu einem Gemisch aus 3o Teilen Äthylendiamin und ioo Teilen Benzol läßt man .bei 1o bis 20° 129 Teile Äthyleniminoessigsäureäthylester zufließen. Nach einstündigem Nachrühren bei gewöhnlicher Temperatur und Stehenlas;en über I`Tacht wird das in Kristallen abgeschiedene Umsetzungsprodukt abgesaugt. Es schmilzt nach Umlösen aus Alkohol bei 58° und ist in Wasser sehr gut löslich.The parts mentioned in the following example are parts by weight. example To a mixture of 30 parts of ethylenediamine and 100 parts of benzene one leaves .bei 1o to 20 ° 129 parts of ethyleniminoacetate flow in. After an hour Stir at normal temperature and let it stand; after about eight hours, this is done in Crystals deposited reaction product sucked off. It melts out after dissolving Alcohol at 58 ° and is very soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Carbonsäureamiden, dadurch gekennzeichnet, daß man a-i # 2-Alkyleniminocarbonsäureester niedrigmolekularer Alkohole mit Ammoniak oder primären und sekundären Aminen umsetzt.PATENT CLAIM: Process for the production of carboxamides, thereby characterized in that one a-i # 2-Alkyleniminocarbonsäureester of low molecular weight Reacts alcohols with ammonia or primary and secondary amines.
DEB5998D 1942-12-17 1942-12-17 Process for the preparation of carbonic acid amides Expired DE855565C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB5998D DE855565C (en) 1942-12-17 1942-12-17 Process for the preparation of carbonic acid amides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB5998D DE855565C (en) 1942-12-17 1942-12-17 Process for the preparation of carbonic acid amides

Publications (1)

Publication Number Publication Date
DE855565C true DE855565C (en) 1952-11-13

Family

ID=6954304

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB5998D Expired DE855565C (en) 1942-12-17 1942-12-17 Process for the preparation of carbonic acid amides

Country Status (1)

Country Link
DE (1) DE855565C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1010846B (en) * 1954-12-21 1957-06-19 Hermann Schoepe Dipl Ing Tire seal for tubeless tires

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1010846B (en) * 1954-12-21 1957-06-19 Hermann Schoepe Dipl Ing Tire seal for tubeless tires

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