CH139366A - Process for the preparation of 4-di (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid. - Google Patents
Process for the preparation of 4-di (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid.Info
- Publication number
- CH139366A CH139366A CH139366DA CH139366A CH 139366 A CH139366 A CH 139366A CH 139366D A CH139366D A CH 139366DA CH 139366 A CH139366 A CH 139366A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- amino
- oxybenzene
- preparation
- oxyethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- 238000005187 foaming Methods 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 4-[Di(ogyäthyl)]-amino-l-oxybenzol-2-carbonsänre. Wie gefunden wurde, kann man 4-[Di- (oxyäthyl)]-atnin o -1- oxybenzol -2-carbon säure darstellen, wenn man 1 111o1 4-Amino-l-oxy- betizol-2-carbonsäure mit 2 Mol eines Ha- logenhydrins des Glykols kondensiert.
Die neue Verbindung bildet farblose Kristalle, sie zersetzt sich bei etwa 18311 C unter Aufschäumen und löst sich leicht in Wasser, Säuren, Alkalien, wenig in Alkohol, kaum in Äther und Aceton. Sie kann unter anderem als photographischer Entwickler Verwendung finden.
<I>Beispiel:</I> 153 Teile 4-Amino-l-oxybenzol-2-carbon- säure werden mit 300 Teilen Äthylenchlor- hydrin innig verrührt, worauf nach Erwärmen auf etwa<B>---0</B> C unter Rühren allmählich 290 Teile einer 10-normalen Natriumhydroxyd- lösung zugetropft werden. Sobald die Masse verflüssigt ist, steigert man die Temperatur langsam derart, dass der Siedepunkt bei Zu gabe der letzten Menge Natriumhydroxy d erreicht ist. Nach kurzer Zeit ist das Na- triumhydroxyd verbraucht.
Man säuert mit einer Mineralsäure schwach an, destilliert im Vakuum Wasser und überschüssiges Äthylen- chlorhydrin ab und zieht aus dem Rückstand die 4-[Di(oxyäthyl)]-amino-l-ogybenzol-2-car- bonsäure mit heissem Alkohol aus. Beim Erkalten scheidet sie sieh aus der Lösung in fast farblosen Kristallen ab.
Process for the preparation of 4- [di (ogyäthyl)] - amino-1-oxybenzene-2-carboxylic acid. As has been found, you can 4- [Di- (oxyethyl)] - atnin o -1-oxybenzene -2-carboxylic acid, if you 1 111o1 4-amino-1-oxy betizol-2-carboxylic acid with 2 mol of one Halohydrins of the glycol condensed.
The new compound forms colorless crystals, it decomposes at about 18311 C with foaming and dissolves easily in water, acids, alkalis, little in alcohol, hardly in ether and acetone. Among other things, it can be used as a photographic developer.
<I> Example: </I> 153 parts of 4-amino-1-oxybenzene-2-carboxylic acid are intimately stirred with 300 parts of ethylene chlorohydrin, whereupon after heating to about <B> --- 0 </B> C. 290 parts of a 10 normal sodium hydroxide solution are gradually added dropwise with stirring. As soon as the mass has liquefied, the temperature is slowly increased so that the boiling point is reached when the last amount of sodium hydroxide is added. The sodium hydroxide is used up after a short time.
It is acidified weakly with a mineral acid, water and excess ethylene chlorohydrin are distilled off in vacuo and the 4- [di (oxyethyl)] amino-1-ogybenzene-2-carboxylic acid is extracted from the residue with hot alcohol. When it cools down, it separates out of the solution in almost colorless crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH132029T | 1927-10-25 | ||
| DE139366X | 1927-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139366A true CH139366A (en) | 1930-04-15 |
Family
ID=25711735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139366D CH139366A (en) | 1927-10-25 | 1928-09-27 | Process for the preparation of 4-di (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139366A (en) |
-
1928
- 1928-09-27 CH CH139366D patent/CH139366A/en unknown
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