CH215331A - Process for the preparation of an aminoarylsulfonic acid derivative. - Google Patents
Process for the preparation of an aminoarylsulfonic acid derivative.Info
- Publication number
- CH215331A CH215331A CH215331DA CH215331A CH 215331 A CH215331 A CH 215331A CH 215331D A CH215331D A CH 215331DA CH 215331 A CH215331 A CH 215331A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid derivative
- aminoarylsulfonic acid
- chloro
- sulfonic acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation 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
- 239000000835 fiber Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Aminoarylsulfonsäurederivates. Gegenstand des vorliegenden Zusatz patentes .ist ein Verfahren zur Heisstellung eines Aminoarylsulfonsäurederivates, da durch gekennzeichnet, @daB 2'-Chlor-4-lauroyl- aminodiphenyläther-2-sulfonsäure,
hergestellt zum Beispiel aus dem Chlorid der Palmkern- fettsäure und 2'-Chlor-4-aminodiphenyläther- 2-sulfons ure in Gegenwart eines säurebin- denden Mittels, in alkalischer Lösung ohlo- riert wird.
Die neue Verbindung bildet als Natrium- -salz ein helles Pulver, das in Wasser leicht löslich ist und das als wirksames Mottenmit- tel zur Behandlung tierischer Fasern benützt werden kann.
Beispiel: Durch Umsetzung von Palmkernfettsäurre- chlo@rid mit 2'-Chlor-4-aminodiphenyläther-2- sulfonsäure in Pyridin stellt man die als Ausgangsmaterial verwendete Acylverbin- dungdar. Das Rohprodukt wird von unver änderter Sulfonsäure durch Umlösen aus Alkohol befreit und eventuell entstandene Palmkernfettsäure mit Petroläther ausge zogen.
Das gereinigte Produkt enthält keine freie Aminogruppe, mehr.
23 Teile des obigen Kondenssationspro- @duktes werden mit Ader berechneten Soda- menge in<B>100</B> Volumteilen Wasser gelöst und bei 40-45 Chlor einsgeleitet, wobei die Reaktion durch Zutropfen von Natronlauge immer schwach alkalisch gehalten wird. Nach zirka 2 Stunden wird .die halogenierte Verbindung mittels Salzsäure -gefällt, in Äther aufgenommen',
dieser ,gewaschen und getrocknet. Nach dem Abdestillieren des Äthers bleibt ein pastenförmiger Rückstand zurück, der 1,3,2 % gebundenes Chlor enthält. Die neue Verbindung ist als Natriumsalz ein helles Pulver, das in Wasser leicht löslich ist und schäumende Lösungen erzeugt. Es kann. als wirksames Mottenmittel zur Be handlung von tierischen Fasern verwendet werden.
Process for the preparation of an aminoarylsulfonic acid derivative. The subject of the present additional patent is a process for the preparation of an aminoarylsulfonic acid derivative, characterized by @daB 2'-chloro-4-lauroyl-aminodiphenylether-2-sulfonic acid,
produced, for example, from the chloride of palm kernel fatty acid and 2'-chloro-4-aminodiphenyl ether-2-sulfonic acid in the presence of an acid-binding agent that is neutralized in an alkaline solution.
As a sodium salt, the new compound forms a light-colored powder which is easily soluble in water and which can be used as an effective moth remedy for treating animal fibers.
Example: The acyl compound used as the starting material is produced by reacting palm kernel fatty acid chloride with 2'-chloro-4-aminodiphenyl ether-2-sulfonic acid in pyridine. The crude product is freed from unchanged sulfonic acid by dissolving it from alcohol and any palm kernel fatty acid that has formed is extracted with petroleum ether.
The purified product no longer contains any free amino groups.
23 parts of the above condensation product are dissolved in 100 parts by volume of water using Ader's calculated amount of soda and fed in at 40-45 chlorine, the reaction always being kept slightly alkaline by adding sodium hydroxide solution dropwise. After about 2 hours, the halogenated compound is precipitated by means of hydrochloric acid and taken up in ether.
this one, washed and dried. After the ether has been distilled off, a paste-like residue remains which contains 1.3.2% bound chlorine. As a sodium salt, the new compound is a light-colored powder that is easily soluble in water and creates foaming solutions. It can. be used as an effective moth remedy for treating animal fibers.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213745T | 1938-12-31 | ||
| CH215331T | 1938-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215331A true CH215331A (en) | 1941-06-15 |
Family
ID=25725482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215331D CH215331A (en) | 1938-12-31 | 1938-12-31 | Process for the preparation of an aminoarylsulfonic acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215331A (en) |
-
1938
- 1938-12-31 CH CH215331D patent/CH215331A/en unknown
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