CH129785A - Process for the preparation of an ammonium compound of a halogenated aromatic amine. - Google Patents
Process for the preparation of an ammonium compound of a halogenated aromatic amine.Info
- Publication number
- CH129785A CH129785A CH129785DA CH129785A CH 129785 A CH129785 A CH 129785A CH 129785D A CH129785D A CH 129785DA CH 129785 A CH129785 A CH 129785A
- Authority
- CH
- Switzerland
- Prior art keywords
- ammonium compound
- aromatic amine
- preparation
- halogenated aromatic
- reaction
- Prior art date
Links
- 150000003868 ammonium compounds Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 150000004982 aromatic amines Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- QDCPXCIPVQJVDD-UHFFFAOYSA-N 2-chloro-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1Cl QDCPXCIPVQJVDD-UHFFFAOYSA-N 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Ammoniumverbindung eines halogenierten aromatischen Amins. Es wurde gefunden, dass für Alkylierungs- zwecke besonders geeignete Ammoniumver- bindungen aromatischer Amine erhalten wer den,
wenn man in der o- bezw. o- und p Stellung halogenierte Dialkylarylamine mit schwefelsauren Alkylestern oder Arylsulfo- säurealkylestern in Reaktion bringt.
Da durch die Einführung von negativen (sruppen in die o- bezw. o- und p-Stellung die Basicität der tertiären Amine und infolge dessen ihre Reaktionsfähigkeit erheblich herab gesetzt wird, war die Möglichkeit eines glatten Reaktionsverlaufes nicht vorauszusehen.
Das Verfahren wird in der Weise ausge führt, dass die beiden Komponenten in mole kularem Verhältnis entweder direkt oder in geeigneten Lösungsmitteln wie Toluol, Mono chlorbenzol und ähnlichen zusammengebracht werden, worauf die Reaktion entweder durch längeres Rühren bei gewöhnlicher Temperatur oder durch Erhitzen unter Rückfluss zu Ende geführt wird.
Die sonst schwer isolierbaren Ammonium verbindungen werden hierbei als alky1schwefel- saure beziehungsweise arylsulfosaure Salze in fester Form erhalten.
Vorliegendes Patent bezieht sich auf die Darstellung einer Ammoniumverbin- dung aus o-Chlordimethylanilin durch Ein wirkung von Dimethylstilfat im molekularen Verhältnis.
Die so erhaltene Ammoniumverbindung ist eine gelbliche kristallinische Masse. <I>Beispiel:</I> <B>15,5</B> Teile von o-Chlordimethylanilin wer den mit 14,5 kg Dimethylsulfat gemischt. Aus der zunächst klaren Lösung scheidet sich nach einiger Zeit unter Erwärmen ein Öl ab. Lm die Reaktion zu Ende zu führen, lässt man die Temperatur auf 115-120 steigen und belässt darin noch bei etwa 100 , bis eine Wasser verdünnte Probe mit überschüs siger Natronlauge fast klar bleibt. Beim Er kalten erstarrt das Reaktionsprodukt zu einer gelblichen kristallinischen Masse der neuen Amoniumverbindung.
Process for the preparation of an ammonium compound of a halogenated aromatic amine. It has been found that ammonium compounds of aromatic amines which are particularly suitable for alkylation purposes are obtained,
if you are in the o- or. O- and p-position halogenated dialkylarylamines with sulfuric acid alkyl esters or aryl sulfo acid alkyl esters in reaction.
Since the introduction of negative groups in the o, o and p positions considerably reduces the basicity of the tertiary amines and, as a result, their reactivity, the possibility of a smooth course of the reaction could not be foreseen.
The process is carried out in such a way that the two components are brought together in a molecular ratio either directly or in suitable solvents such as toluene, monochlorobenzene and the like, whereupon the reaction is completed either by prolonged stirring at ordinary temperature or by heating under reflux to be led.
The ammonium compounds, which are otherwise difficult to isolate, are obtained in solid form as alky1sulfuric acid or arylsulfonic acid salts.
The present patent relates to the preparation of an ammonium compound from o-chlorodimethylaniline by the action of dimethyl stilfate in the molecular ratio.
The ammonium compound thus obtained is a yellowish crystalline mass. <I> Example: </I> <B> 15.5 </B> parts of o-chlorodimethylaniline are mixed with 14.5 kg of dimethyl sulfate. After a while, an oil separates out of the initially clear solution with heating. In order to complete the reaction, the temperature is allowed to rise to 115-120 and is left there at about 100 until a sample diluted with water with excess sodium hydroxide solution remains almost clear. When it is cold, the reaction product solidifies to form a yellowish crystalline mass of the new ammonium compound.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH129785T | 1927-04-25 | ||
| CH128226T CH128226A (en) | 1927-04-25 | 1927-04-25 | Process for the preparation of an ammonium compound of a halogenated aromatic amine. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH129785A true CH129785A (en) | 1929-01-02 |
Family
ID=25711056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH129785D CH129785A (en) | 1927-04-25 | 1927-04-25 | Process for the preparation of an ammonium compound of a halogenated aromatic amine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH129785A (en) |
-
1927
- 1927-04-25 CH CH129785D patent/CH129785A/en unknown
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