CH214902A - Process for the preparation of a new quaternary ammonium salt. - Google Patents
Process for the preparation of a new quaternary ammonium salt.Info
- Publication number
- CH214902A CH214902A CH214902DA CH214902A CH 214902 A CH214902 A CH 214902A CH 214902D A CH214902D A CH 214902DA CH 214902 A CH214902 A CH 214902A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- ammonium salt
- preparation
- new
- new quaternary
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen quaternären Ammoniumsalzes. Es wurde gefunden, dass ein neues qua- ternäres Ammoniumsalz der Formel
EMI0001.0006
dadurch erhalten wird,,dass man Pyridin mit der Chlormethylverbindung des Distearyl- diaminomethans der Formel
EMI0001.0012
zur Umsetzung bringt.
Die neue Verbindung bildet einen weissen Festkörper, der in Benzol und Alkohol (lös lich ist. Er löst sich in Wasser unter Bil dung von Lösungen, die beim Schütteln schäumen. Werden diese Lösungen gekocht, dann werden sie allmählich trübe und ver lieren ihre Schäumkraft; gegebenenfalls bil det sich ein Niederschlag. Die neue Verbin dung kann zum Wasserabstossendmachen von Textilien verwendet werden.
Bei der praktischen Durchführung des Verfahrens werden zweckmässig die genannte Chlormethylverbindung und das Pyridin vermischt, vorteilhaft in Gegenwart eines Lösungs- oder eines Verdünnungsmittels. Es entwickelt sich Wärme, und es ist vorteilhaft, das Amin langsam hinzuzufügen und den Reaktionsbehälter zu kühlen.
Beispiel: Das Ausgangsmaterial für dieses Bei spiel wird in folgender Weise dargestellt: 29 Teile Distearyldiaminomethan (siehe franz. Patentschrift Nr. 782330), in Form von Pulver, und 6 Teile Paraformaldehyd werden: mit 150 Teilen Benzol gemischt. Das Gemisch wird gerührt und auf GO C er wärmt. Trockener Chlorwasserstoff wird so lange eingeleitet, bis, nachdem eine Probe auf Zimmertemperatur abgekühlt wurde, sieh nichts Festes mehr abscheidet.
Man lä.sst Glas Gemisch sich setzen, worauf es: sich in zwei Schichten trennt. Die untere wässrige Schicht wird entfernt und nicht weiter verwertet. Das Benzol aus der obern Schicht wird unter vermindertem Druck abdestilliert. Auf diese Weise erhält man eine Chlormethylverbin- dung der folgenden Formel
EMI0002.0010
Sie ist ein niedrig schmelzender, wachsarti ger Festkörper.
Diese Chlormethylverbindung wird in 200 Teilen Äthylacetat gelöst und diese Lö sung allmählich mit 9 Teilen Pyridin ge mischt. Ein weisser Niederschlag scheidet aus. Dieser wird abfiltriert und getrocknet. Auf diese Weise erhält man das neue qua- ternäre Ammoniumsalz in Form eines weissen Pulvers, das sich in heissem Wasser löst, unter Bildung klarer schäumender Lösungen, ,die bei längerem Kochen trübe werden und zu schäumen aufhören.
Die Verbindung hat folgende Formel:
EMI0002.0020
Process for the preparation of a new quaternary ammonium salt. It has been found that a new quaternary ammonium salt of the formula
EMI0001.0006
is obtained by using pyridine with the chloromethyl compound of distearyl diaminomethane of the formula
EMI0001.0012
brings to implementation.
The new compound forms a white solid that is soluble in benzene and alcohol (. It dissolves in water to form solutions that foam when shaken. If these solutions are boiled, they gradually become cloudy and lose their foaming power; If necessary, a precipitate forms.The new compound can be used to make textiles water-repellent.
When carrying out the process in practice, the above-mentioned chloromethyl compound and the pyridine are advantageously mixed, advantageously in the presence of a solvent or a diluent. Heat will evolve and it will be beneficial to add the amine slowly and cool the reaction vessel.
Example: The starting material for this example is shown in the following way: 29 parts of distearyldiaminomethane (see French Patent No. 782330), in the form of powder, and 6 parts of paraformaldehyde are: mixed with 150 parts of benzene. The mixture is stirred and warmed to GO C. Dry hydrogen chloride is passed in until, after a sample has been cooled to room temperature, nothing solid can be seen.
You let the glass mixture sit down, whereupon it: separates into two layers. The lower aqueous layer is removed and not recycled. The benzene from the upper layer is distilled off under reduced pressure. In this way, a chloromethyl compound of the following formula is obtained
EMI0002.0010
It is a low-melting, waxy solid.
This chloromethyl compound is dissolved in 200 parts of ethyl acetate and this solution is gradually mixed with 9 parts of pyridine. A white precipitate separates out. This is filtered off and dried. In this way, the new quaternary ammonium salt is obtained in the form of a white powder that dissolves in hot water, forming clear, foaming solutions that become cloudy and stop foaming when boiled for a long time.
The compound has the following formula:
EMI0002.0020
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB214902X | 1938-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214902A true CH214902A (en) | 1941-05-31 |
Family
ID=10163806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214902D CH214902A (en) | 1938-07-29 | 1939-07-27 | Process for the preparation of a new quaternary ammonium salt. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214902A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE891258C (en) * | 1942-09-29 | 1953-09-28 | Hoechst Ag | Process for the preparation of quaternary ammonium or isothiuronium salts |
-
1939
- 1939-07-27 CH CH214902D patent/CH214902A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE891258C (en) * | 1942-09-29 | 1953-09-28 | Hoechst Ag | Process for the preparation of quaternary ammonium or isothiuronium salts |
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