CH306990A - Process for the preparation of ethylene urea-N, N'-dipropionic acid. - Google Patents
Process for the preparation of ethylene urea-N, N'-dipropionic acid.Info
- Publication number
- CH306990A CH306990A CH306990DA CH306990A CH 306990 A CH306990 A CH 306990A CH 306990D A CH306990D A CH 306990DA CH 306990 A CH306990 A CH 306990A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethylene urea
- dipropionic acid
- acid
- preparation
- added
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Äthylenharnstoff.N,N'.dipropionsäure. Es wurde gefunden, dass man neue Dipro- pionsä.uren der heteroc5-elisehen Reihe erhält, wenn man an heterocyclische Verbindungen, welche zwei NH-Gruppen und mindestens eine CO- oder CS-Gruppe im Ring enthalten, Acrylsäure oder deren Substitutionsprodukte bzw.
funktionelle Derivate dieser Säuren an lagert und die so erhaltenen N-Substitutions- produkte der heterocy clisehen Verbindungen gegebenenfalls zu den betreffenden N,N'-Di- propionsäuren verseift.
Die so erhaltenen. neuen Verbindungen sind infolge der in ihnen enthaltenen Grup pen, z. B. der Carboxylgruppen, zu weiteren Umsetzungen befähigt und stellen deshalb werkvolle Zwischenprodukte der chemischen Industrie, z. B. zur Herstellung von Farb stoffen. Textilhilfsmitteln, Heilmitteln, Kunst stoffen, dar. Bei geeigneter Wahl der Aus gangsmaterialien besitzen sie auch selbst be reits therapeutisch wertvolle Eigenschaften.
Gegenstand der vorliegenden Erfindung ist. nun ein Verfahren zur Herstellung von Ulrvlenharnstoff - N,N' - dipropionsäure, wel- clres dadurch gekennzeichnet ist, dass man an ä.thvlenlrarnstoff ein Derivat der Aerylsättre, das an Stelle der Carboxylgruppe einen zu einer solchen verseifbaren Rest enthält,
an lagert und das so erhaltene N-Substit.utions- produkt des Äthylenharnstoffes zur entspre- ehenden N-N'-Dipropionsäure verseift. Die so erhaltene Äthylenhainstoff-N,N'-di- propionsäure stellt eine farblose, kristalline Substanz vom Schmelzpunkt 120-122 dar.
<I>Beispiel:</I> Zu einer Suspension von 172 Teilen Äthy- lenharnstoff und 17 Teilen gepulvertem Ätz natron in 400 Teilen Dioxan lässt man unter gutem Rühren bei 45-50 langsam 212 Teile Acrylnitril zufliessen. Die Mischung wird noch etwa 12 Stunden bei etwa 45-50 gehalten, wobei der lithylenharnstoff unter Bildung von N,1\"-Di-(f-cyan-äthyl)-äthylenharnstoff in Lösung geht. 1lfan kühlt, nun auf etwa 20 ab, neutralisiert mit 50 /oi-er Schwefelsäure und destilliert das Dioxan ab.
Der Rückstand wird mit heissem Methanol digeriert und die methanolische Lösung vom Glaubersalz abfil- triert. Aus dem Filtrat gewinnt man nach dem Verdampfen des Lösungsmittels durch Vakuumdestillation den N,N' - Di - (ss - eyan- äthyl)-äthylenlrarnstoff als Öl vom Kp.l :230 bis 238 , das beim Abkühlen zu farblosen Kri stallen erstarrt.
Der N,N'-Di-(ss-cya.n-äthyl)-äthylenharn- stoff liefert. bei der Verseifunu, die zum Bei spiel sauer oder alkalisch in üblieher Weise durehgeführt werden kann, in guter Ausbeute die Äthylenharrrstoff-N,N'-dipropionsättre vom Sehmelzpunkt 120-122 und der Formel
EMI0002.0001
Ersetzt man das Acrylnitril ziem Beispiel durch Acrylsäureäthylester, so erhält man nach Verseifung die gleiche Säure.
Process for the production of ethylene urea.N, N'.dipropionic acid. It has been found that new dipropionic acids of the heteroc5-elisehen series are obtained when acrylic acid or its substitution products or their substitution products are added to heterocyclic compounds which contain two NH groups and at least one CO or CS group in the ring.
functional derivatives of these acids are added and the N-substitution products of the heterocyclic compounds thus obtained are optionally saponified to give the relevant N, N'-propionic acids.
The thus obtained. new compounds are pen due to the groups contained in them, z. B. the carboxyl groups, capable of further reactions and are therefore valuable intermediates in the chemical industry, z. B. for the production of color materials. Textile auxiliaries, remedies, synthetic materials. With a suitable choice of starting materials, they also have therapeutically valuable properties themselves.
The subject of the present invention is. Now a process for the production of ulcer urea - N, N '- dipropionic acid, which is characterized in that a derivative of aeryl saturation is added to the ethereal urea which, instead of the carboxyl group, contains a residue which can be saponified to form such a substance,
and the resulting N-substitution product of the ethylene urea is saponified to give the corresponding N-N'-dipropionic acid. The Ethylenhainstoff-N, N'-propionic acid thus obtained is a colorless, crystalline substance with a melting point of 120-122.
<I> Example: </I> 212 parts of acrylonitrile are slowly added to a suspension of 172 parts of ethylene urea and 17 parts of powdered caustic soda in 400 parts of dioxane with thorough stirring at 45-50. The mixture is kept at about 45-50 for about 12 hours, the lithylenurea dissolving with the formation of N, 1 \ "- di- (f-cyano-ethyl) -ethylene urea. 1lfan cools, now down to about 20, neutralized with 50% sulfuric acid and the dioxane is distilled off.
The residue is digested with hot methanol and the methanolic solution is filtered off from the Glauber's salt. After evaporation of the solvent by vacuum distillation, the N, N '- di - (ss - eyan-ethyl) -äthylenlrarnstoff is obtained from the filtrate as an oil with a boiling point of 230 to 238, which solidifies to colorless crystals on cooling.
The N, N'-di- (ss-cya.n-ethyl) -ethylene urea supplies. in the case of saponification, which can be carried out in the usual acidic or alkaline manner, for example, the ethylene urea-N, N'-dipropionate from the melting point 120-122 and the formula in good yield
EMI0002.0001
If the acrylonitrile is replaced by ethyl acrylate, for example, the same acid is obtained after saponification.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE306990X | 1951-03-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH306990A true CH306990A (en) | 1955-05-15 |
Family
ID=6121291
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH306990D CH306990A (en) | 1951-03-06 | 1952-03-05 | Process for the preparation of ethylene urea-N, N'-dipropionic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH306990A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2972618A (en) * | 1956-12-05 | 1961-02-21 | Rohm & Haas | Adducts of heterocyclic amides |
US3021338A (en) * | 1956-12-05 | 1962-02-13 | Rohm & Haas | Adducts of heterocyclic amides |
-
1952
- 1952-03-05 CH CH306990D patent/CH306990A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2972618A (en) * | 1956-12-05 | 1961-02-21 | Rohm & Haas | Adducts of heterocyclic amides |
US3021338A (en) * | 1956-12-05 | 1962-02-13 | Rohm & Haas | Adducts of heterocyclic amides |
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