CH217133A - 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
- CH217133A CH217133A CH217133DA CH217133A CH 217133 A CH217133 A CH 217133A CH 217133D A CH217133D A CH 217133DA CH 217133 A CH217133 A CH 217133A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- soluble
- molecular weight
- higher molecular
- production
- Prior art date
Links
- -1 α-substituted benzylamine Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000000249 desinfective Effects 0.000 claims description 2
- 238000005187 foaming Methods 0.000 claims description 2
- 238000005755 formation reaction Methods 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N Ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BAQOOEPJROUOIU-UHFFFAOYSA-N 1-(4-methoxyphenyl)dodecan-1-one Chemical compound CCCCCCCCCCCC(=O)C1=CC=C(OC)C=C1 BAQOOEPJROUOIU-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- NPNZHCLGLGUIIB-UHFFFAOYSA-N CCCCCCCCCCCC(N(C)C)C1=CC=C(OC)C=C1 Chemical compound CCCCCCCCCCCC(N(C)C)C1=CC=C(OC)C=C1 NPNZHCLGLGUIIB-UHFFFAOYSA-N 0.000 description 1
- ONZXEBDDYUHTMZ-UHFFFAOYSA-N COC(CCC(=O)C1=CC=CC=C1)CCCCCCCC Chemical compound COC(CCC(=O)C1=CC=CC=C1)CCCCCCCC ONZXEBDDYUHTMZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Description
Verfahren zur Herstellung eines wasserlöslichen, höhermolekularen, a-substituier ten Benzylaminderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser löslichen, höhermolekularen, a-substituierten Benzylaminderivates, dadurch gekennzeich net,
dass man a-Undecyl-4-methoxybenzyl- amin (erhältlich durch Erhitzen von p-Me- thoxy-laurophenon mit Ammonformiat und nachfolgende Verseifung der entstandenen Formylverbindung) mit Dimethylsulfat in die quaternäre Ammoniumverbindung über führt.
Die neue Verbindung, ein helles, dickes 01, ist in Wasser leicht löslich unter Bildung stark schäumender Lösungen und kann als Desinfektionsmittel verwendet werden.
<I>Beispiel:</I> 100 Teile 4-Methoxy-laurophenon, darge stellt aus destillierter Palmkernfettsäure, Fraktion gp." 170 bis 220', und Anisol, werden mit 70 Teilen Ammonformiat, herge stellt durch Neutralisieren von 830 Teilen Ameisensäure<B>85%</B> mit 1080 Teilen Ammo- niak 25% und Eindampfen auf ca. 900 bis 950 Teile, vermischt und 10 Stunden auf 180 bis 185 erhitzt.
Die entstandene Formylverbindung des a-Undecyl-4-methoxy- benzylamins wird verseift, das freie Amin ausgeäthert und destilliert; gp.1,6 200 bis 250'. Das Amin ist ein helles, in verdünn ter Salzsäure lösliches Öl mit stark basischem Geruch.
1/2 Mol. a-Undecyl-4-methoxy-benzylamin wird gelöst in 700 Volumteilen trockenem Chlorbenzol und 120 Teile feste Soda darin aufgeschlämmt. Bei 100 lässt man langsam 130 Teile Dimethylsulfat zutropfen und rührt bei dieser Temperatur über Nacht.
Das aus geschiedene Natriumsulfat wird abfiltriert und zum Filtrat, das das a-Undecyl-4-me- thoxy-benzyldimethylamin enthält, nochmals 65 Teile Dimethylsulfat zugetropft. Nach mehrstündigem Erhitzen auf<B>100'</B> wird das Chlorbenzol durch Wasserdampfdestillation entfernt und die klare Lösung der quater- nären Ammoniumverbindung eingedampft.
Es hinterbleibt ein helles, dickes Öl, das in Wasser leicht löslich ist und dessen Lösungen stark schäumen.
Process for the preparation 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, α-substituted benzylamine derivative, characterized in that
that a-undecyl-4-methoxybenzylamine (obtainable by heating p-methoxy-laurophenone with ammonium formate and subsequent saponification of the resulting formyl compound) is converted into the quaternary ammonium compound with dimethyl sulfate.
The new compound, a light, thick 01, is easily soluble in water with the formation of strongly foaming solutions and can be used as a disinfectant.
<I> Example: </I> 100 parts of 4-methoxylaurophenone, made from distilled palm kernel fatty acid, fraction gp. "170 to 220", and anisole, are made with 70 parts of ammonium formate, produced by neutralizing 830 parts of formic acid B> 85% </B> with 1080 parts of ammonia 25% and evaporation to approx. 900 to 950 parts, mixed and heated to 180 to 185 for 10 hours.
The resulting formyl compound of a-undecyl-4-methoxybenzylamine is saponified, the free amine is extracted with ether and distilled; gp.1,6 200 to 250 '. The amine is a light-colored oil that is soluble in dilute hydrochloric acid and has a strong basic odor.
1/2 mol. Of a-Undecyl-4-methoxy-benzylamine is dissolved in 700 parts by volume of dry chlorobenzene and 120 parts of solid soda slurried therein. At 100, 130 parts of dimethyl sulfate are slowly added dropwise and the mixture is stirred at this temperature overnight.
The separated sodium sulfate is filtered off and a further 65 parts of dimethyl sulfate are added dropwise to the filtrate, which contains the α-undecyl-4-methoxy-benzyldimethylamine. After heating to <B> 100 '</B> for several hours, the chlorobenzene is removed by steam distillation and the clear solution of the quaternary ammonium compound is evaporated.
What remains is a light, thick oil that is easily soluble in water and the solutions of which foam strongly.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217133T | 1938-11-25 | ||
| CH214904T | 1941-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217133A true CH217133A (en) | 1941-09-30 |
Family
ID=25725643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217133D CH217133A (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) | CH217133A (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 CH217133D patent/CH217133A/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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