CH207300A - Process for the preparation of a quaternary aminobenzylacylamine. - Google Patents
Process for the preparation of a quaternary aminobenzylacylamine.Info
- Publication number
- CH207300A CH207300A CH207300DA CH207300A CH 207300 A CH207300 A CH 207300A CH 207300D A CH207300D A CH 207300DA CH 207300 A CH207300 A CH 207300A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary
- preparation
- aminobenzylacylamine
- methylbenzylamino
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 p- (methylbenzylamino) -benzylsulfanilic acid Chemical compound 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- LCTOXAHEDJCUII-UHFFFAOYSA-N n-carbamoyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(N)=O LCTOXAHEDJCUII-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000004902 Softening Agent Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Verfahren zur Darstellung eines quaternären Aminobenzylaeylamins. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines quater- nären Aminobenzylacylamins der Formel
EMI0001.0006
dadurch gekennzeiehnet, dass man Stearoyl- harnstoff, erhältlich durch Einwirkung von Stearinsäurechlorid auf Harnstoff, mit p-(Me- thylbenzylamino)-benzylsulfanilsäure umsetzt und den erhaltenen N-p-(Methylbenzylamino)
- benzyl-N'-stearoylharnstoff durch Einwirkung von Dimetbylsulfat in die entsprechende quaternäre Verbindung umwandelt.
Die neue Verbindung, eine braune, wachs artige Masse, eignet sich als Netz-, Disper- gier- und Emulgiermittel, insbesondere aber als Weichmachungsmittel für Baumwolle oder umgefällte Zellulose.
Beispiel: 120 Teile Stearoylharnstoff, dargestellt in bekannter Weise aus Stearinsäurechlorid und Harnstoff, und 150 Teile p-(lylethylbenzyl- amino)-benzylsulfanilsäure werden zusammen mit 280 Teilen konzentriertem Ammoniak und 120 Teilen Wasser während 6 Stunden bei 150 im Autoklaven erhitzt. Nach dem Erkalten wird die Reaktionsmasse abgesaugt und mit Wasser dachgewaschen. Gegebenen falls wird zur Reinigung in heissem Amyl- alkohol aufgenommen, das Wasser abgetrennt und die amylalkoholische Lösung filtriert.
Nach dem Abdestillieren des Lösungsmittels erhält man den neuen Körper als braune, wachsartige Masse.
Die quaternäre Ammoniumverbindung er hält man durch Erhitzen von 20 Teilen des Amides mit 10 Volumteilen Dimethylsulfat, bis das Produkt in heissem Wasser klar lös lich ist, als braune, wachsartige Masse.
Process for the preparation of a quaternary aminobenzylaeylamine. The present patent relates to a process for the preparation of a quaternary aminobenzylacylamine of the formula
EMI0001.0006
characterized in that stearoyl urea, obtainable by the action of stearic acid chloride on urea, is reacted with p- (methylbenzylamino) -benzylsulfanilic acid and the resulting N-p- (methylbenzylamino)
- converts benzyl-N'-stearoylurea into the corresponding quaternary compound by the action of dimethyl sulfate.
The new compound, a brown, waxy mass, is suitable as a wetting, dispersing and emulsifying agent, but especially as a softening agent for cotton or reprecipitated cellulose.
Example: 120 parts of stearoylurea, prepared in a known manner from stearic acid chloride and urea, and 150 parts of p- (lylethylbenzyl-amino) -benzylsulfanilic acid are heated together with 280 parts of concentrated ammonia and 120 parts of water for 6 hours at 150 in an autoclave. After cooling, the reaction mass is filtered off with suction and the roof is washed with water. If necessary, it is taken up in hot amyl alcohol for cleaning, the water is separated off and the amyl alcoholic solution is filtered.
After the solvent has been distilled off, the new body is obtained as a brown, waxy mass.
The quaternary ammonium compound is kept by heating 20 parts of the amide with 10 parts by volume of dimethyl sulfate until the product is clearly soluble in hot water, as a brown, waxy mass.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH207300T | 1938-06-10 | ||
| CH199452T | 1939-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207300A true CH207300A (en) | 1939-10-15 |
Family
ID=25723270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207300D CH207300A (en) | 1938-06-10 | 1938-06-10 | Process for the preparation of a quaternary aminobenzylacylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207300A (en) |
-
1938
- 1938-06-10 CH CH207300D patent/CH207300A/en unknown
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