CH211798A - Process for the preparation of a higher molecular weight α-substituted benzylamine sulfonic acid. - Google Patents
Process for the preparation of a higher molecular weight α-substituted benzylamine sulfonic acid.Info
- Publication number
- CH211798A CH211798A CH211798DA CH211798A CH 211798 A CH211798 A CH 211798A CH 211798D A CH211798D A CH 211798DA CH 211798 A CH211798 A CH 211798A
- Authority
- CH
- Switzerland
- Prior art keywords
- molecular weight
- sulfonic acid
- higher molecular
- preparation
- substituted benzylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 α-substituted benzylamine Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims 1
- 235000011941 Tilia x europaea Nutrition 0.000 claims 1
- 239000004571 lime Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Herstellung einer höher molekularen a-substituier ten Benzylaminsulfonsäure. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer höher molekularen a-substituierten Benzylaminsul- fonsäure, dadurch gekennzeichnet, dass man N-p-Toluolsul:fonyl-N-m-ethyl-a-undecylben- zylamin sulfiert.
Die neue Sulfonsäure bildet als Natrium- salz ein helles, in Wasser gut lösliches Pul ver. Sie kann als Wasch- und Netzmittel und als NalkseifenemulgatorVerwendung finden. <I>Beispiel:</I> 26,1 Teile a-Undecylbenzylamin werden in 100 Volumteilen absolutem Benzol und 50 Volumteilen Pyridin gelöst.
Dazu tropft man eine Lösung von 20 Teilen p-Toluol- sulfochlorid in 100 Volumteilen absolutem Benzol und kocht 5 Stunden unter Rückfluss. Nach dem Abkühlen entfernt man das Pyri- din durch Auswaschen mit verdünnter Salz säure und dampft das Benzol ab.
Den im Vakuum getrockneten Rückstand, das N-p- Toluolsulfonyl - a - undecylbenzylamin führt man in Gegenwart von Natronlauge mit 65 Teilen Dimethylsulfat in das N-p-To- luolsulfonyl-N-methyl-a-undecylbenzylamin über.
4$ Teile desselben werden gelöst in 120 Teilen Schwefelsäuremonohydrat und bei 0 bis 5 mit 40 Teilen 26 % igem Oleum versetzt. Man rührt so lange, bis eine Probe in Wasser klar löslich ist, giesst auf Eis und neutralisiert mit Natronlauge. Durch Ein dampfen der wässrigen Lösung erhält man das Natriumsalz der Sulfonsäure als ein helles, in Wasser gut lösliches Pulver.
Process for the preparation of a higher molecular weight α-substituted benzylamine sulfonic acid. The subject of the present patent is a process for the preparation of a higher molecular weight α-substituted benzylamine sulphonic acid, characterized in that N-p-toluenesulphonyl-N-m-ethyl-α-undecylbenzylamine is sulphated.
As a sodium salt, the new sulphonic acid forms a light-colored powder that is readily soluble in water. It can be used as a detergent and wetting agent and as a soap emulsifier. <I> Example: </I> 26.1 parts of a-undecylbenzylamine are dissolved in 100 parts by volume of absolute benzene and 50 parts by volume of pyridine.
A solution of 20 parts of p-toluenesulfochloride in 100 parts by volume of absolute benzene is added dropwise and the mixture is refluxed for 5 hours. After cooling, the pyridine is removed by washing with dilute hydrochloric acid and the benzene is evaporated off.
The residue, dried in vacuo, the N-p-toluenesulfonyl-a-undecylbenzylamine, is converted into N-p-toluenesulfonyl-N-methyl-a-undecylbenzylamine in the presence of sodium hydroxide solution with 65 parts of dimethyl sulfate.
4 parts of the same are dissolved in 120 parts of sulfuric acid monohydrate and 40 parts of 26% strength oleum are added at 0 to 5 parts. The mixture is stirred until a sample is clearly soluble in water, poured onto ice and neutralized with sodium hydroxide solution. By evaporating the aqueous solution, the sodium salt of sulfonic acid is obtained as a light-colored powder that is readily soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210340T | 1938-12-01 | ||
| CH211798T | 1938-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211798A true CH211798A (en) | 1940-10-15 |
Family
ID=25724823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211798D CH211798A (en) | 1938-12-01 | 1938-12-01 | Process for the preparation of a higher molecular weight α-substituted benzylamine sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211798A (en) |
-
1938
- 1938-12-01 CH CH211798D patent/CH211798A/en unknown
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