CH217137A - 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
- CH217137A CH217137A CH217137DA CH217137A CH 217137 A CH217137 A CH 217137A CH 217137D A CH217137D A CH 217137DA CH 217137 A CH217137 A CH 217137A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- soluble
- molecular weight
- production
- higher molecular
- Prior art date
Links
- -1 α-substituted benzylamine Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen, höhermolekularen, a-substituierten Benzylaminderivates. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung eines wasserlöslichen, höhermolekularen, a-substi- tuierten Benzylaminderivates, dadurch ge kennzeichnet, dass man a-Undecyl-3,4-dime- thylbenzylamin (erhältlich durch Erhitzen von 3,
4-Dimethyllaurophenon mit Ammon- formia.t und nachfolgende Verseifung der ent standenen Formy lverbindung) mit Dimethyl- sulfat unter erschöpfender Methylierung in die quaternäre Ammoniumverbindung über führt.
Die neue Verbindung bildet ein helles 01, das in Wasser klar löslich ist und als Des infektionsmittel verwendet werden kann.
<I>Beispiel:</I> 196 Teile 3,4-Dimethyllaurophenon, dar gestellt aus destillierter Palmkernfettsäure, Fraktion Kp." 170 bis 220', und o-Xylol, werden mit 130 Teilen Ammonformiat, her gestellt durch Neutralisieren von 830 Teilen Ameisensäure<B>85</B>% mit 1080 Teilen Ammo- niak 25 % und Eindampfen auf zirka 900 bis 950 Teile, vermischt und 10 Stunden auf 180 bis<B>1.85'</B> erhitzt.
Die entstandene For- mylverbindimg des a-Undecyl-3,4-dimethyl- benzylamins wird mit konz. Salzsäure ver seift, das Amin mit Natronlauge in Freiheit gesetzt, ausgeäthert und destilliert. gp.:t,o 170 bis 225 . Das Amin ist ein helles, in verdünnter Salzsäure lösliches 01 mit basi schem Geruch.
i/2 Mol. a-Undecyl-3,4-dimethylbenzyl- amin wird gelöst in 500 Volumteilen trok- kenem Benzol und 110 Teile feste Soda darin aufgeschlämmt. Bei 75 bis<B>80'</B> lässt man langsam 195 Teile Dimethylsulfat zutrop- fen und rührt bei dieser Temperatur einige Stunden, bis sich die quaternäre Verbindung vollständig gebildet hat. Dieselbe wird mit Wasser dem Benzol entzogen.
Die klare, wässrige Lösung der quaternären Ammonium verbindung wird eingedampft. Es hinterbleibt ein helles 01, das in Wasser klar löslich ist und stark schäumt.
Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. The subject of the present additional patent is a process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative, characterized in that α-undecyl-3,4-dimethylbenzylamine (obtainable by heating 3,
4-Dimethyllaurophenone with ammonium formia.t and subsequent saponification of the formed formyl compound) with dimethyl sulphate with exhaustive methylation into the quaternary ammonium compound.
The new compound forms a light oil, which is clearly soluble in water and can be used as a disinfectant.
<I> Example: </I> 196 parts of 3,4-dimethyllaurophenone, made from distilled palm kernel fatty acid, fraction bp. "170 to 220 ', and o-xylene, are mixed with 130 parts of ammonium formate, made by neutralizing 830 parts Formic acid <B> 85 </B>% with 1080 parts of ammonia 25% and evaporation to about 900 to 950 parts, mixed and heated to 180 to <B> 1.85 '</B> for 10 hours.
The resulting formula compound of a-undecyl-3,4-dimethylbenzylamine is treated with conc. Hydrochloric acid is saponified, the amine is released with sodium hydroxide solution, etherified and distilled. gp.:t,o 170 to 225. The amine is a light-colored oil that is soluble in dilute hydrochloric acid and has a basic odor.
1/2 mol. of a-Undecyl-3,4-dimethylbenzylamine is dissolved in 500 parts by volume of dry benzene and 110 parts of solid soda and slurried therein. At 75 to 80, 195 parts of dimethyl sulfate are slowly added dropwise and the mixture is stirred at this temperature for a few hours until the quaternary compound has formed completely. The same is removed from the benzene with water.
The clear, aqueous solution of the quaternary ammonium compound is evaporated. A light oil remains, which is clearly soluble in water and foams strongly.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217137T | 1938-11-25 | ||
| CH214904T | 1941-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217137A true CH217137A (en) | 1941-09-30 |
Family
ID=25725647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217137D CH217137A (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) | CH217137A (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 CH217137D patent/CH217137A/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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