CH135384A - Process for the preparation of an N-oxyethyl derivative of 4-amino-1-oxybenzene. - Google Patents
Process for the preparation of an N-oxyethyl derivative of 4-amino-1-oxybenzene.Info
- Publication number
- CH135384A CH135384A CH135384DA CH135384A CH 135384 A CH135384 A CH 135384A CH 135384D A CH135384D A CH 135384DA CH 135384 A CH135384 A CH 135384A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- oxybenzene
- oxyethyl
- preparation
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines N-Ogyäthylderivates des 4-Amino-l-ogybenzols. Nach dem Hauptpatent erhält man das 4-/Di-(oxyäthyl)/amino,-l-oxybenzol durch Kondensation von 4-Amino-l-oxybenzol mit der für die Bildung des Disubstitutionspro- duktes notwendigen Menge eines Halogen- hydrins des Glykols.
Wie nun weiter gefunden wurde, erhält man das 4-/Mono.-(oxyäthyl)/amino-l-oxyben- zol, wenn man eine entsprechend geringere Menge eines Halogenhy drins des Glykols mit 4-Amino-l-o_xybenzol kondensiert, gegebenen falls bei Anwesenheit von säurebindenden, sowie Verdünnungs- oder Lösungsmitteln.
Die neue Verbindung soll unter ande rem als Entwicklersubstanz in der Pho tographie Verwendung finden.
<I>Beispiel:</I> 110 Teile 4-Amino-l-oxybenzolwerden mit einer Lösung von 60 Teilen Kaliumhydroxyd in 500 Teilen Alkohol versetzt; es werden 81 Teile Äthylenchlorhydrin in 100 Teilen Alkohol zugegeben. Sehr bald beginnt die Ausscheidung von Kaliumchilorid,, die man durch Erhitzen. zum Sieden schnell beenden kann. Nach der Trennung von dem gebil deten Kaliumchlorid fällt man in der erkal teten alkoholischen Lösung das Reaktions produkt durch Zugabe von 46 bis 49 Teilen konzentrierter Schwefelsäure als Sulfat.
Durch Lösen in wenig heissem Wasser und Neutralisieren mit 10 %iger Natriumkarbo- natlösung gewinnt man beim Abkühlen ge ringe Mengen unverändertes 4-Amino-l-oxy- benzol zurück. Nach Absaugen wird die neue Base durch Extraktion des Filtrates in einem geeigneten Lösungsmittel in bräunlichen Kristallen erhalten, die man durch Umkri- stallisieren aus einem Essigäther-Chloroform- Gemisch rein in farblosen Kristallen vom Schmelzpunkt 96 bis 97 C erhält.
Sie ist das 4-Oxyäthylamino-l-oxybenzol, das leicht löslich in Wasser, Säuren" Alkalien, Alko hol, Essigäther, nicht löslich in Benzin und Benzol ist. Sie bindet als schwefelsaures Salz 1/2 Mol. Schwefelsäure, löslich in viel Alkohol, aus dem sie in feinen, langen Pris men kristallisiert.
Process for the preparation of an N-Ogyäthylderivates of 4-Amino-l-ogybenzene. According to the main patent, 4- / di- (oxyethyl) / amino, -l-oxybenzene is obtained by condensation of 4-amino-l-oxybenzene with the amount of a halohydrin of glycol necessary for the formation of the disubstitution product.
As has now also been found, the 4- / mono .- (oxyethyl) / amino-1-oxybenzene is obtained if a correspondingly smaller amount of a halogenohydin of the glycol is condensed with 4-amino-1-o_xybenzene, if appropriate in the presence of acid-binding agents as well as diluents or solvents.
The new compound is intended to be used, among other things, as a developer substance in photography.
<I> Example: </I> 110 parts of 4-amino-1-oxybenzene are mixed with a solution of 60 parts of potassium hydroxide in 500 parts of alcohol; 81 parts of ethylene chlorohydrin in 100 parts of alcohol are added. Very soon the excretion of potassium chloride begins, which is obtained by heating. can finish boiling quickly. After the separation of the potassium chloride formed, the reaction product is precipitated in the cold alcoholic solution as a sulfate by adding 46 to 49 parts of concentrated sulfuric acid.
By dissolving in a little hot water and neutralizing with 10% sodium carbonate solution, small amounts of unchanged 4-amino-1-oxybenzene are recovered on cooling. After suction filtration, the new base is obtained by extracting the filtrate in a suitable solvent in brownish crystals, which are obtained in pure colorless crystals with a melting point of 96 ° to 97 ° C. by recrystallization from an ethyl acetate-chloroform mixture.
It is 4-oxyäthylamino-1-oxybenzene, which is easily soluble in water, acids, alkalis, alcohol, acetic ether, not soluble in gasoline and benzene. As a sulfuric acid salt, it binds 1/2 mole of sulfuric acid, soluble in a lot of alcohol from which it crystallizes in fine, long prisms.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE135384X | 1926-11-19 | ||
| CH132029T | 1927-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH135384A true CH135384A (en) | 1929-09-15 |
Family
ID=25711732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH135384D CH135384A (en) | 1926-11-19 | 1927-10-25 | Process for the preparation of an N-oxyethyl derivative of 4-amino-1-oxybenzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH135384A (en) |
-
1927
- 1927-10-25 CH CH135384D patent/CH135384A/en unknown
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