CH212563A - Process for the preparation of a quaternary aminoacetic acid amide derivative. - Google Patents
Process for the preparation of a quaternary aminoacetic acid amide derivative.Info
- Publication number
- CH212563A CH212563A CH212563DA CH212563A CH 212563 A CH212563 A CH 212563A CH 212563D A CH212563D A CH 212563DA CH 212563 A CH212563 A CH 212563A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary
- preparation
- amide derivative
- acid amide
- aminoacetic acid
- Prior art date
Links
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 dimethylaminoacetic acid-p-dodecylanilide Chemical compound 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 2
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- RFGYILSFZGENSS-UHFFFAOYSA-N ClCC(=O)NC1=CC=C(C=C1)CCCCCCCCCCCC Chemical compound ClCC(=O)NC1=CC=C(C=C1)CCCCCCCCCCCC RFGYILSFZGENSS-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines quaternären Aminoessigsäureamidderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines- quater- nären Aminoessigsäureamidderivates, da durch gekennzeichnet, dass man Chloressig- säure-p-dodecylanilid mit Dimethylamin um setzt und das erhaltene Dimethylaminoessig- säure-p-dodecylanilid mit Dimethylsulfat in die quaternäre Verbindung überführt.
Die neue Verbindung, eine halbfeste Masse, ist in Wasser klar löslich und eignet sich als Weichmachungsmittel.
<I>Beispiel:</I> Zu 1 Mol. p-Dodecylanilin, dargestellt nach der britischen Patentschrift Nr. 4682'26, lässt man langsam 1,2 Mol. Chloracetylchlo- rid zutropfen und rührt während 12 Stun den bei<B>90-100'.</B> Dann nimmt man in Äther auf, wäscht mit Wasser gut aus und trägt das nach Verjagen des Äthers hinterbleibende 01 in 1000 Volumteile 20%ige Dimethyl- aminlösung ein. Die Lösung erwärmt sieh selbst auf ca. 40 und wird für 24 Stun- den bei dieser Temperatur gehalten.
Durch Ausäthern der wässrigen Emulsion gewinnt man das Dimethylaminoessigsäure-p-dodecyl- anilid.
35 Teile Dimethylaminoessigsäure-p- dodecylanilid werden mit 12,5 Teilen Di- methylsulfat verrührt, wobei beträchtliche Selbsterwärmung auftritt. Man erhitzt einige Stunden auf<B>100'</B> und erhält schliesslich eine halbfeste Masse, die in Wasser klar löslich ist.
Process for the preparation of a quaternary aminoacetic acid amide derivative. The present patent relates to a process for the preparation of a quaternary aminoacetic acid amide derivative, characterized in that chloroacetic acid p-dodecylanilide is reacted with dimethylamine and the dimethylaminoacetic acid p-dodecylanilide obtained is converted into the quaternary compound with dimethyl sulfate .
The new compound, a semi-solid mass, is clearly soluble in water and is suitable as a plasticizer.
<I> Example: </I> 1.2 mol of chloroacetyl chloride are slowly added dropwise to 1 mol of p-dodecylaniline, prepared according to British patent specification No. 4682'26, and the mixture is stirred for 12 hours at <B> 90-100 '. </B> Then take up in ether, wash well with water and add the oil that remains after the ether has been chased away in 1000 parts by volume of 20% dimethylamine solution. The solution itself heats up to approx. 40 and is kept at this temperature for 24 hours.
The dimethylaminoacetic acid p-dodecyl anilide is obtained by etherifying the aqueous emulsion.
35 parts of dimethylaminoacetic acid-p-dodecylanilide are stirred with 12.5 parts of dimethyl sulfate, with considerable self-heating occurring. The mixture is heated to <B> 100 '</B> for a few hours and finally a semi-solid mass is obtained which is clearly soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198052X | 1935-12-23 | ||
| CH212563T | 1938-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212563A true CH212563A (en) | 1940-11-30 |
Family
ID=25725275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212563D CH212563A (en) | 1935-12-23 | 1938-12-30 | Process for the preparation of a quaternary aminoacetic acid amide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH212563A (en) |
-
1938
- 1938-12-30 CH CH212563D patent/CH212563A/en unknown
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