CH129787A - 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
- CH129787A CH129787A CH129787DA CH129787A CH 129787 A CH129787 A CH 129787A CH 129787D A CH129787D A CH 129787DA CH 129787 A CH129787 A CH 129787A
- Authority
- CH
- Switzerland
- Prior art keywords
- ammonium compound
- preparation
- aromatic amine
- 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
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl sulfuric acid Chemical compound 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 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
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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 Gruppen 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 Rückfuss zu Ende geführt wird.
Die sonst schwer isolierbaren Ammonium verbindungen werden hierbei als alkylschwefel- saure bezw. arylsulfosaure Salze in fester Form erhalten.
Vorliegendes Patent bezieht sich auf die Darstellung einer Ammoniumverbindung aus m, m'-Dichlortetramethyl-p, p'-diaminodiphe- nylmethan durch Einwirkung von Dimethyl- sulfat im molekularen Verhältnis.
Die so erhaltene Ammoniumverbindung schmilzt bei ungefähr 218' unter Gasentwick lung.
Beispiel: 65 Teile von m, m'-Dichlor tetramethyl-p, p'-diaminodiphenylmethan, das bei 276-277 136 mm siedet, werden in 90 kg Monochlorbenzol gelöst. Zu der fast bis zum Sieden erhitzten Lösung lässt man 51 kg Dimethylsulfat so langsam zulaufen, dass die Flüssigkeit durch die Reaktionswärme in mässigem Sieden ge halten wird. Schon während des Zulaufen lassens tritt gristallabscheidung ein. Man rührt dann noch bei der gleichen Temperatur einige Zeit weiter und filtriert die Ammonium verbindung nach dem Erkalten ab.
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 one is in the o- or. O- and p- positions halogenated dialkylarylamines with sulfuric acid alkyl esters or aryl sulfo acid alkyl esters in reaction.
Since the introduction of negative groups in the o- or. o- and p-positions the basicity of the tertiary amines and as a result their reactivity is considerably reduced, 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 refluxing to be led.
The ammonium compounds, which are otherwise difficult to isolate, are referred to as alkyl sulfuric acid or. aryl sulfonic acid salts obtained in solid form.
The present patent relates to the preparation of an ammonium compound from m, m'-dichlorotetramethyl-p, p'-diaminodiphenylmethane by the action of dimethyl sulfate in the molecular ratio.
The ammonium compound thus obtained melts at about 218 'with evolution of gas.
Example: 65 parts of m, m'-dichlorotetramethyl-p, p'-diaminodiphenylmethane, which boils at 276-277 136 mm, are dissolved in 90 kg of monochlorobenzene. 51 kg of dimethyl sulfate are allowed to run in slowly enough to keep the liquid at a moderate boiling point due to the heat of reaction. Granular separation occurs as soon as it is allowed to flow. The mixture is then stirred for some time at the same temperature and the ammonium compound is filtered off after cooling.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128226T CH128226A (en) | 1927-04-25 | 1927-04-25 | Process for the preparation of an ammonium compound of a halogenated aromatic amine. |
| CH129787T | 1927-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH129787A true CH129787A (en) | 1929-01-02 |
Family
ID=25711058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH129787D CH129787A (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) | CH129787A (en) |
-
1927
- 1927-04-25 CH CH129787D patent/CH129787A/en unknown
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