CH206093A - Process for the preparation of a pseudonaphthazimide. - Google Patents
Process for the preparation of a pseudonaphthazimide.Info
- Publication number
- CH206093A CH206093A CH206093DA CH206093A CH 206093 A CH206093 A CH 206093A CH 206093D A CH206093D A CH 206093DA CH 206093 A CH206093 A CH 206093A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- parts
- sulfo
- diazo compound
- oxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 10
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 229950000244 sulfanilic acid Drugs 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HXXMONHYPKNZHE-UHFFFAOYSA-N 4-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 HXXMONHYPKNZHE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Psendonaphthazimids. Es wurde gefunden, dass man das 2-Oxy- 2'-(4"- sulfo)-phenyl -3.4-pseudonaphtbazimid der Formel
EMI0001.0007
erhalten kann, wenn man 1-Aminonaphtbalin- 3-sulfonsäure, die Diazoverbindung der Sul- fanilsäure, ein Oxydationsmittel und Ätzal- kalien derart aufeinander einwirken lässt,
dass die Diazoverbindung in die 2-Stellung des Naphthalinkerns eingreift, das Ätzalkali den Ersatz der Sulfogruppe des Naphtbalin- kerns durch die OH-Gruppe bewirkt, und dass die Einwirkung des Oxydationsmittels UDMit- telbar nach der stattgefundenen Einwirkung der Diazoverbindung der Sulfanilsäure statt findet.
Das 2-Oxy-2'-[4"-sulfojphenyl-3.4- pseudonaphthazimid stellt ein farbloses Pulver dar; es kann zur Herstellung von Farbstoffen verwendet werden.
<I>Beispiel:</I> <B>223</B> Teile 1-Aminonaphthalin-3-sulfonsäure werden in 4500 Teilen Wasser suspendiert und mit einer Diazolösung aus<B>173</B> Teilen Sulfanilsäure versetzt. Hierauf gibt man nach und nach<B>500</B> Teile Natriumacetat zu, rührt bis die Diazoreaktion verschwunden ist<B>'</B> fügt so viel Natriumhydroxyd. zu, bis klare Lö sung entsteht und filtriert von etwaigen Ver unreinigungen ab. Aus dem Filtrat wird der gebildete Farbstoff durch Essigsäurezusatz abgeschieden.
<B>818</B> Teile des so erhaltenen Azofarbstoffes werden in<B>5000</B> Teilen Wasser unter Zusatz von 300 Teilen 30%iger Natriumhydroxyd- lösung gelöst und bei<B>50-550</B> mit 1200 Gewichtsteilen einer Natriumliypocliloritlö- sung versetzt,
die 12% aktives Chlor ent- hält. Die 2'-(4"-sulfo)-phenyl-3.4-pseudonaph- thazimid-2-sulfoiisäure wird mit Kochsalz abgeschieden und filtriert.
<B>125</B> Teile der 2'-(4"-sulfo)-pheiiyl-3.4- pseudonaphthazimid-2-sulioiisäui-e werden nun im Autoklaven zusammen mit<B>375</B> Teilen Kaliumhydroxyd, <B>150</B> Teilen Natriumhydro- xyd und 40 Teilen Wasser unter Druck er hitzt, wobei die Temperatur allmählich auf etwa 200<B>0</B> gebracht wird. Man rührt einige Zeit bei dieser Temperatur weiter und lässt dann abkühlen.
Der Autoklaveninhalt wird in Wasser gelöst, die alkalische Lösung mit Überschüssiger Salzsäure versetzt und das abgeschiedene 2-Oxy-2'-(4"-sulfo)-phenyl-3.4- pseudonaplitliazimid filtriert.
Process for the preparation of a psendonaphthazimide. It has been found that 2-oxy-2 '- (4 "- sulfo) -phenyl -3.4-pseudonaphthobazimide of the formula
EMI0001.0007
can be obtained if 1-aminonaphthbalin-3-sulfonic acid, the diazo compound of sulfanilic acid, an oxidizing agent and caustic alkalis are allowed to act on one another
that the diazo compound engages in the 2-position of the naphthalene nucleus, the caustic alkali causes the sulfo group of the naphthalene nucleus to be replaced by the OH group, and that the action of the oxidizing agent UDM takes place immediately after the action of the diazo compound of the sulfanilic acid has taken place.
The 2-oxy-2 '- [4 "-sulfojphenyl-3.4-pseudonaphthazimide is a colorless powder; it can be used for the production of dyes.
<I> Example: </I> <B> 223 </B> parts of 1-aminonaphthalene-3-sulfonic acid are suspended in 4500 parts of water and a diazo solution of <B> 173 </B> parts of sulfanilic acid is added. <B> 500 </B> parts of sodium acetate are then gradually added, and the mixture is stirred until the diazo reaction has disappeared. <B> '</B> as much sodium hydroxide is added. until a clear solution is produced and any impurities are filtered off. The dye formed is separated off from the filtrate by adding acetic acid.
<B> 818 </B> parts of the azo dye thus obtained are dissolved in <B> 5000 </B> parts of water with the addition of 300 parts of 30% strength sodium hydroxide solution and at <B> 50-550 </B> with 1200 parts by weight of a sodium liypoclilorite solution added,
which contains 12% active chlorine. The 2 '- (4 "-sulfo) -phenyl-3,4-pseudonaphthazimide-2-sulfoiic acid is separated off with common salt and filtered.
<B> 125 </B> parts of the 2 '- (4 "-sulfo) -pheiiyl-3.4-pseudonaphthazimide-2-sulioiisäui-e are now placed in the autoclave together with <B> 375 </B> parts of potassium hydroxide, <B > 150 parts of sodium hydroxide and 40 parts of water are heated under pressure, the temperature gradually being brought to about 200. The mixture is stirred for a while at this temperature and then allowed to cool.
The contents of the autoclave are dissolved in water, excess hydrochloric acid is added to the alkaline solution and the 2-oxy-2 '- (4 "-sulfo) -phenyl-3.4-pseudonaplitliazimide which has separated out is filtered.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH206093T | 1937-06-30 | ||
| CH201620T | 1937-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206093A true CH206093A (en) | 1939-07-15 |
Family
ID=25723727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206093D CH206093A (en) | 1937-06-30 | 1937-06-30 | Process for the preparation of a pseudonaphthazimide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206093A (en) |
-
1937
- 1937-06-30 CH CH206093D patent/CH206093A/en unknown
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