CH207302A - Process for the preparation of a quaternary aminobenzylacylamine. - Google Patents
Process for the preparation of a quaternary aminobenzylacylamine.Info
- Publication number
- CH207302A CH207302A CH207302DA CH207302A CH 207302 A CH207302 A CH 207302A CH 207302D A CH207302D A CH 207302DA CH 207302 A CH207302 A CH 207302A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary
- preparation
- aminobenzylacylamine
- heptadecylurea
- 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
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- ZZUXQMKCDKYDRB-UHFFFAOYSA-N heptadecylurea Chemical compound CCCCCCCCCCCCCCCCCNC(N)=O ZZUXQMKCDKYDRB-UHFFFAOYSA-N 0.000 claims description 3
- YNURTLLQUYRULT-UHFFFAOYSA-N CCN(CC)C1(C=CC(S(O)(=O)=O)=C(CC2=CC=CC=C2)C1)N Chemical compound CCN(CC)C1(C=CC(S(O)(=O)=O)=C(CC2=CC=CC=C2)C1)N YNURTLLQUYRULT-UHFFFAOYSA-N 0.000 claims description 2
- 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 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 238000006243 chemical reaction Methods 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
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 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
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 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 qua- ternären Aminobenzylacylamins der Formel
EMI0001.0006
dadurch gekennzeichnet, dass man Heptade- cylharnstoff, erhältlich aus Reptadecylamin und Kaliumcyanat,
mit p-Diäthylaminobeii- zylsulfanilsäure umsetzt und den erhaltenen N - p - Diäthylaminobenzyl - N'- heptadecyl- harnstoff durch Einwirkung von Dimethyl- sulfat in die entsprechende quaternäre Ver bindung 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: 112 Teile Heptadecylharnstoff, dargestellt aus Heptadecylamin und Naliumcyanat, und <B>128</B> Teile p-Diäthyl-aminobenzylsulfanilsäure werden zusammen mit 280. Teilen konzen triertem Ammoniak und 120 Teilen Wasser während 6 Stunden bei 150 im Autoklaven erhitzt. Nach dem Erkalten wird die Reak tionsmasse abgesaugt und mit Wasser nach gewaschen. Gegebenenfalls wird zur Reini gung in heissem Amylalkohol aufgenommen, das Wasser abgetrennt und die amylalko- holische Lösung filtriert.
Nach dem Abdestil- lieren 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 9 Vol.-Teilen Dimethylsulfat, bis das Produkt in heissem Wasser klar lös lich ist, als braune, wachsartige, in Wasser leicht lösliche 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 heptadecylurea, obtainable from reptadecylamine and potassium cyanate,
with p-diethylaminobeiizylsulfanilic acid and converts the resulting N - p - diethylaminobenzyl - N'-heptadecyl urea 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: 112 parts of heptadecylurea, prepared from heptadecylamine and sodium cyanate, and 128 parts of p-diethylaminobenzylsulfanilic acid are heated in an autoclave together with 280 parts of concentrated ammonia and 120 parts of water for 6 hours at 150. After cooling, the reac tion mass is filtered off and 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 9 parts by volume of dimethyl sulfate until the product is clearly soluble in hot water, as a brown, waxy mass that is readily soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH207302T | 1938-06-10 | ||
| CH199452T | 1939-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207302A true CH207302A (en) | 1939-10-15 |
Family
ID=25723272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207302D CH207302A (en) | 1938-06-10 | 1938-06-10 | Process for the preparation of a quaternary aminobenzylacylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207302A (en) |
-
1938
- 1938-06-10 CH CH207302D patent/CH207302A/en unknown
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