CH217132A - Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. - Google Patents
Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative.Info
- Publication number
- CH217132A CH217132A CH217132DA CH217132A CH 217132 A CH217132 A CH 217132A CH 217132D A CH217132D A CH 217132DA CH 217132 A CH217132 A CH 217132A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- soluble
- molecular weight
- higher molecular
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 α-substituted benzylamine Chemical class 0.000 title claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- IOXCQANOOMEVDN-UHFFFAOYSA-N 1-phenyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCC(N)C1=CC=CC=C1 IOXCQANOOMEVDN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DBLXXVQTWJFJFI-UHFFFAOYSA-N 1-phenyloctadecan-1-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)C1=CC=CC=C1 DBLXXVQTWJFJFI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen, höhermolekularen, a-substituierten Benzylaminderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser löslichen, höhermolekularen, a-substituierten Benzylaminderivates, dadurch gekennzeich net, dass man a-Heptadecyl-benzylamin, er hältlich durch katalytische Reaktion von Stearophenon in Gegenwart von Ammoniak,
mit Dimethylsulfat in die quaternäre Ammo- niumverbindung überführt.
Die neue Verbindung, eine helle, zähe Paste, ist in Wasser leicht löslich unter Bil dung stark schäumender Lösungen, und kann als Desinfektionsmittel verwendet werden.
<I>Beispiel:</I> 1 Mol. Stearophenon, hergestellt aus Stea- rinsäurechlorid und Benzol mit Aluminium chlorid, nach der Methode von Friedel-Crafts, wird in alkoholischem Ammoniak (dreifacher Überschuss) gelöst und im Autoklav bei 110 Atm. und 80 bis<B>90'</B> katalytisch hy driert.
Nach dem Abfiltrieren des Kataly- sators und Abdampfen des Alkohols wird das rohe a-Heptadecyl-benzylamin im Vakuum destilliert, Kp.o" 210 bis 212 .
In 800 Volumteilen trockenem Chlorben zol wird 1/2 Mol. a-Heptadecyl-benzylamin gelöst, 120 Teile feste Soda zugesetzt und bei 90 bis<B>100'</B> langsam<B>130</B> Teile Dimethyl- sulfat eingetropft. Nach 12 Stunden wird das Ganze mit dem gleichen Volumen Wasser vermengt und das Chlorbenzol durch Wasser dampfdestillation entfernt. Durch Ausäthern des Rückstandes und nachfolgende Vakuum destillation gewinnt man das reine a-Hepta- decyl-benzyl-dimethylamin, KP.,)., 223 .
1/2 Mol. a-Heptadecyl-benzyl-dimethyl- amin wird in 800 Volumteilen trockenem Chlorbenzol gelöst, bei<B>1001</B> 65 Teile Di- methylsulfat zugetropft und das Ganze bei dieser Temperatur mehrere Stunden gerührt. Hierauf wird das Chlorbenzol durch Wasser dampfdestillation entfernt und die klare Lö sung der quaternären Ammoniumverbindung zur Trockne verdampft.
Es hinterbleibt eine helle, zähe Paste, die in Wasser leicht lös- lieh ist unter Bildung stark schäumender Lö sungen.
Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. The subject of the present patent is a process for the preparation of a water-soluble, higher molecular weight, a-substituted benzylamine derivative, characterized in that one-heptadecyl-benzylamine, it is obtainable by catalytic reaction of stearophenone in the presence of ammonia
converted into the quaternary ammonium compound with dimethyl sulfate.
The new compound, a light-colored, viscous paste, is easily soluble in water with the formation of strong foaming solutions and can be used as a disinfectant.
<I> Example: </I> 1 mol. Stearophenone, produced from stearic acid chloride and benzene with aluminum chloride, according to the Friedel-Crafts method, is dissolved in alcoholic ammonia (three-fold excess) and placed in an autoclave at 110 atm. and 80 to <B> 90 '</B> catalytically hydrogenated.
After the catalyst has been filtered off and the alcohol has been evaporated off, the crude α-heptadecylbenzylamine is distilled in vacuo, boiling point 210 to 212.
1/2 mole of a-heptadecylbenzylamine is dissolved in 800 parts by volume of dry chlorobenzene, 120 parts of solid soda are added and, at 90 to 100 parts, slowly 130 parts of dimethyl sulfate are added dripped in. After 12 hours, the whole thing is mixed with the same volume of water and the chlorobenzene is removed by steam distillation. The pure a-heptadecylbenzyldimethylamine, KP.,)., 223 is obtained by etherifying the residue and then vacuum distillation.
1/2 mole of a-heptadecylbenzyldimethylamine is dissolved in 800 parts by volume of dry chlorobenzene, 65 parts of dimethyl sulfate are added dropwise at 1001 and the whole is stirred at this temperature for several hours. The chlorobenzene is then removed by steam distillation and the clear solution of the quaternary ammonium compound is evaporated to dryness.
What remains is a light, viscous paste which is easily soluble in water with the formation of strongly foaming solutions.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217132T | 1938-11-25 | ||
| CH214904T | 1941-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217132A true CH217132A (en) | 1941-09-30 |
Family
ID=25725642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217132D CH217132A (en) | 1938-11-25 | 1938-11-25 | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217132A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467708A (en) * | 1965-10-21 | 1969-09-16 | Armour Ind Chem Co | Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds |
-
1938
- 1938-11-25 CH CH217132D patent/CH217132A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467708A (en) * | 1965-10-21 | 1969-09-16 | Armour Ind Chem Co | Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds |
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