CH233563A - Process for the production of acrylic acid diphenylamide. - Google Patents
Process for the production of acrylic acid diphenylamide.Info
- Publication number
- CH233563A CH233563A CH233563DA CH233563A CH 233563 A CH233563 A CH 233563A CH 233563D A CH233563D A CH 233563DA CH 233563 A CH233563 A CH 233563A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- acrylic acid
- diphenylamide
- acid diphenylamide
- alkalis
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Aerylsäurediphenylamid. Es wurde gefunden, dass Chlorpropion- säureamide beim Behandeln mit Alkalien oder alkalisch wirkenden Mitteln zweckmässig in wässriger Lösung oder Suspension in ein facher Reaktion die Salzsäure abspalten. Auf diese Weise können die technisch wichtigen Acrylsäureamide dargestellt werden.
Dies war überraschend, weil bekanntlich die ali- phatischen Säureamide, beispielsweise Acet- anilid, Propionsäureanilid oder andere ähn lich gebaute Amide der aliphatischen Säuren durch Alkalien sehr leicht verseift werden, so dass die Befürchtung bestand, dass die neue Reaktion nicht oder nur in untergeordnetem Masse eintreten würde.
Als Ausgangsmateria lien für die Herstellung der teils bekannten, teils neuen Acrylsäureamide verwendet man die ss-Chlorpropionsäureamide folgender Zu sammensetzung:
EMI0001.0020
wobei R, und R2 einen Alkyl-, Aralkyl-, Aryl- oder cycloaliphatischen Rest, R, ge gebenenfalls auch ein Wasserstoffatom be- deuten kann, ferner R ein Wasserstoffatom oder einen Alkylrest,
ferner
EMI0001.0031
gemeinsam einen heterocyclischen Rest.
Auf diese Weise können zum Beispiel fol gende Verbindungen hergestellt werden: Acrylsäure-anilid " -äthylamid " -butylamid " -octodecylamid,
" -diäthylamid " -dibutylamid " -benzylamid " -methylanilid " -cyclohegylamid " -dicyclohegylamid " -piperidid " -pyrrolidid " -carbazolidid " -teüahydrocarbazolidid. Gegenstand des Patentes ist ein Verfah ren zur Herstellung von Aerylsäurediphenyl- amid, das dadurch gekennzeichnet ist, dass man ss - Chlorpropionsäurediphenylamid mit alkalisch wirkenden Mitteln,
zum Beispiel Alkalien, behandelt, zweckmässig in wässri- gem Medium.
Die neue Verbindung ist fest, sie hat einen Schmelzpunkt von 87 bis 88 . Sie soll für die Herstellung von Kunststoffen ver wendet werden.
<I>Beispiel:</I> 12,97 Gewichtsteile f-Chlorpropionsä.ure- diphenylamid werden in eine Natronlauge aus 2,5 Gewichtsteilen etwa. 95 ö igem Na triumhydrogyd und 50 Gewichtsteilen Was ser eingetragen. Dann wird das Gemisch unter Schnellrühren so lange erhitzt, bis eine herausgenommene Probe in der Beilsteinreak- tion kein Chlor mehr anzeigt. Das zuerst feste Produkt verflüssigt sich allmählich und wird bei fortschreitender Reaktion wieder kristallin. Man lässt das Gemisch innerhalb 2 bis 3 Stunden erkalten, saugt das feste Produkt ab und wäscht es mit Wasser alkali- frei. Es wird im Vakuum bei 50 bis 60 getrocknet.
Die Ausbeute an rohem Acrylsäure- diphenylamid beträgt<B>10.9</B> Gewichtsteile vom Fp. 87 bis 88 (98% der Theorie).
Process for the production of aerylic acid diphenylamide. It has been found that chlorpropionic acid amides, when treated with alkalis or alkaline agents, expediently split off the hydrochloric acid in an aqueous solution or suspension in a single reaction. In this way the technically important acrylic acid amides can be prepared.
This was surprising because, as is known, the aliphatic acid amides, for example acetanilide, propionic anilide or other similarly structured amides of the aliphatic acids, are very easily saponified by alkalis, so that there was fear that the new reaction would not or only to a lesser extent would occur.
The ss-chloropropionic acid amides of the following composition are used as starting materials for the production of the partly known and partly new acrylic acid amides:
EMI0001.0020
where R, and R2 an alkyl, aralkyl, aryl or cycloaliphatic radical, R, ge can optionally also mean a hydrogen atom, furthermore R a hydrogen atom or an alkyl radical,
further
EMI0001.0031
together a heterocyclic radical.
In this way, for example, the following compounds can be prepared: Acrylic anilide "-äthylamid" -butylamid "-octodecylamid,
"-diäthylamid" -dibutylamid "-benzylamid" -methylanilid "-cyclohegylamid" -dicyclohegylamid "-piperidid" -pyrrolidid "-carbazolidid" -teüahydrocarbazolidid. The subject of the patent is a process for the production of Aerylsäurediphenyl- amid, which is characterized in that ss - Chlorpropionsäurediphenylamid with alkaline agents,
For example, treated alkalis, expediently in an aqueous medium.
The new compound is solid, it has a melting point of 87 to 88. It is intended to be used for the manufacture of plastics.
<I> Example: </I> 12.97 parts by weight of f-Chlorpropionsä.ure- diphenylamide are in a caustic soda solution from 2.5 parts by weight about. 95 igem sodium hydrogen and 50 parts by weight of water entered. The mixture is then heated with rapid stirring until a sample taken out of the Beilstein reaction no longer shows any chlorine. The initially solid product gradually liquefies and becomes crystalline again as the reaction proceeds. The mixture is allowed to cool within 2 to 3 hours, the solid product is filtered off with suction and washed with water to be free of alkali. It is dried at 50 to 60 in vacuo.
The yield of crude acrylic acid diphenylamide is 10.9 parts by weight of melting point 87 to 88 (98% of theory).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH236346T | 1942-03-17 | ||
| CH233563T | 1942-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233563A true CH233563A (en) | 1944-08-15 |
Family
ID=25727803
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233563D CH233563A (en) | 1942-03-17 | 1942-03-17 | Process for the production of acrylic acid diphenylamide. |
| CH236344D CH236344A (en) | 1942-03-17 | 1942-03-17 | Process for the preparation of acrylic acid n-butylamide. |
| CH236342D CH236342A (en) | 1942-03-17 | 1942-03-17 | Process for the production of acrylic anilide. |
| CH236345D CH236345A (en) | 1942-03-17 | 1942-03-17 | Process for the preparation of acrylic acid diisobutylamide. |
| CH236346D CH236346A (en) | 1942-03-17 | 1942-03-17 | Process for the production of methacrylic acid diphenylamide. |
| CH236343D CH236343A (en) | 1942-03-17 | 1942-03-17 | Process for the production of acrylic acid methylanilide. |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236344D CH236344A (en) | 1942-03-17 | 1942-03-17 | Process for the preparation of acrylic acid n-butylamide. |
| CH236342D CH236342A (en) | 1942-03-17 | 1942-03-17 | Process for the production of acrylic anilide. |
| CH236345D CH236345A (en) | 1942-03-17 | 1942-03-17 | Process for the preparation of acrylic acid diisobutylamide. |
| CH236346D CH236346A (en) | 1942-03-17 | 1942-03-17 | Process for the production of methacrylic acid diphenylamide. |
| CH236343D CH236343A (en) | 1942-03-17 | 1942-03-17 | Process for the production of acrylic acid methylanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (6) | CH233563A (en) |
-
1942
- 1942-03-17 CH CH233563D patent/CH233563A/en unknown
- 1942-03-17 CH CH236344D patent/CH236344A/en unknown
- 1942-03-17 CH CH236342D patent/CH236342A/en unknown
- 1942-03-17 CH CH236345D patent/CH236345A/en unknown
- 1942-03-17 CH CH236346D patent/CH236346A/en unknown
- 1942-03-17 CH CH236343D patent/CH236343A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH236345A (en) | 1945-01-31 |
| CH236344A (en) | 1945-01-31 |
| CH236342A (en) | 1945-01-31 |
| CH236343A (en) | 1945-01-31 |
| CH236346A (en) | 1945-01-31 |
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