CH215820A - Process for the preparation of a 1-oxy-4-acylaminonaphthalene-3-sulfonic acid. - Google Patents
Process for the preparation of a 1-oxy-4-acylaminonaphthalene-3-sulfonic acid.Info
- Publication number
- CH215820A CH215820A CH215820DA CH215820A CH 215820 A CH215820 A CH 215820A CH 215820D A CH215820D A CH 215820DA CH 215820 A CH215820 A CH 215820A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- acid
- sulfonic acid
- preparation
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 239000012345 acetylating agent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 acetyl- Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- HWAUAPHDMHWNCM-UHFFFAOYSA-N 4-acetamidonaphthalene-2-sulfonic acid Chemical group C1=CC=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 HWAUAPHDMHWNCM-UHFFFAOYSA-N 0.000 description 1
- LQBVQRPQACQWSC-UHFFFAOYSA-N 6-diazo-3-nitrocyclohexa-2,4-diene-1-sulfonic acid Chemical compound [N+](=O)([O-])C1=CC(C(C=C1)=[N+]=[N-])S(=O)(=O)O LQBVQRPQACQWSC-UHFFFAOYSA-N 0.000 description 1
- COYOYULJHHOUIV-UHFFFAOYSA-N CC(NC(C=C1C(OC(C)=O)=C2)=CC=C1C(NC(C)=O)=C2S(O)(=O)=O)=O Chemical compound CC(NC(C=C1C(OC(C)=O)=C2)=CC=C1C(NC(C)=O)=C2S(O)(=O)=O)=O COYOYULJHHOUIV-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 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
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Color Printing (AREA)
Description
Verfahren zur Herstellung einer 1-Oxy-4-acylaminonaphtalin-3-sulfonsäure. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 1-Oxy- 4,7 - di(acetylamino) -naphtalin- 3 - sulfonsäure. Das Verfahren ist dadurch gekennzeichnet, dass man auf 1-Oxy-4-amino-7-acetylamino- naphtalin-3-sulfonsäure ein acetylierendes Mit tel und auf das erhaltene Reaktionsprodukt ein verseifendes Mittel derart einwirken lässt,
dass die Acetylaminogruppen nicht angegriffen werden.
Die neue 1-Oxy-4,7-di(acetylamino)-naph- talin-3-sulfonsäure bildet ein in Wasser leicht lösliches Pulver; auch die Alkalisalze sind leicht wasserlöslich. Versetzt man eine sodaallka- lische Resorcinlösung mit einer wässerigen Lösung der Säure und giesst auf Filtrierpa- pier, so tritt keine Farbveränderung auf. Die Säure kuppelt mit Diazoverbindungen und soll zur Herstellung von Farbstoffen verwen det werden.
<I>Beispiel:</I> 50 Teile 1-Oxy-4-amino-7-acetylamino- naphtalin-3-sulfonsäure werden in ein Acety- Lierungsgemisch aus 150 Teilen Essigsäure- anhydrid und 27 Teilen wasserfreiem Natrium acetat bei 80 unter Rühren eingetragen, wo bei unter Selbsterwärmung auf ca. 100 Auf lösung eintritt. Man gibt weitere 50 Teile derselben Säure rasch hinzu. Die Temperatur steigt dadurch weiter auf ca.
120-125 und aus der Lösung scheidet sich nach kurzer Zeit die 1-Acetyloxy-4,7-di(acetylamino)-naph- talin-3-sulfonsäure aus. Man destilliert im Vakuum den Eisessig ab, löst die zurückblei bende Triacetylverbindung in wenig Wasser: auf, stellt mit Natronlauge phenolphtalein- alkalisch, fügt ca. 45 Teile Soda zu und er hitzt 15 Minuten auf 70 , wobei die Acetyl- oxygruppe verseift wird.
Nach Abkühlung wird mit Schwefelsäure neutral gestellt, 12, Stunden stehen gelassen und der sich aus scheidende Niederschlag gesammelt und ge- trocknet; er besteht aus der 1-Oxy-4,7-di- (acetylamino)-naphtalin-3-sulfonsäure, deren Gehalt durch Titration mit-p-Nitrodiazoben- . zollösung festgestellt werden kann.
Die bisher nicht beschriebene Säure bildet ein weisses, in Wasser leicht lösliches Pulver; auch die Alkalisalze sind leicht wasserlöslich. Versetzt man eine sodaalkalische Resorcinlö- sung mit einer wässerigen Lösung der Säure, so findet nach dem Aufgiessen auf Filtrier papier keine Farbveränderung statt.
Die zur Acetylierung verwendete, in der Literatur nicht beschriebene 1-Oxy-4-a.mino- 7-acetylaminonaphtaliu-3-sulfonsäure kann durch Reduktion des Azofarbstoffes gewonnen werden, den man bei der Kupplung von 4 Nitro-l-diazobenzol-2-sulfonsäure mit 1-Oxy- 7-acetylaminonaphtalin-3-sulfonsäure in Ge genwart von Soda erhält, wobei die Diazo- verbindung ausschliesslich in p-Stellung zur Hydroxy lgruppe eintritt.
Dadurch ist es mög lich, die Reduktion ohne Isolierung des Azo- farbstoffes vorzunehmen. Die 1-Oxy-4-amino- 7-acetylaminonaphtalin-3-sulfonsäure ist weder diazotierbar, noch kuppelt sie mit Diazover- bindungen. 3Tit sodaalkalischer Resorcinlösung auf Filtrierpapier gebracht, tritt allmählich eine intensive rote Färbung auf.
Process for the preparation of a 1-oxy-4-acylaminonaphthalene-3-sulfonic acid. The subject of the present patent is a process for the preparation of 1-oxy-4,7 - di (acetylamino) -naphthalene-3 - sulfonic acid. The process is characterized in that an acetylating agent is allowed to act on 1-oxy-4-amino-7-acetylamino-naphthalene-3-sulfonic acid and a saponifying agent is allowed to act on the reaction product obtained in such a way that
that the acetylamino groups are not attacked.
The new 1-oxy-4,7-di (acetylamino) -naphthalen-3-sulfonic acid forms a powder that is easily soluble in water; the alkali salts are also easily soluble in water. If an aqueous solution of the acid is added to a soda-alkaline resorcinol solution and poured onto filter paper, no color change occurs. The acid couples with diazo compounds and is said to be used for the production of dyes.
<I> Example: </I> 50 parts of 1-oxy-4-amino-7-acetylamino-naphthalene-3-sulfonic acid are added to an acetylation mixture of 150 parts of acetic anhydride and 27 parts of anhydrous sodium acetate at 80 ° with stirring entered, where with self-heating to approx. 100 resolution occurs. Another 50 parts of the same acid are added rapidly. The temperature rises further to approx.
120-125 and after a short time 1-acetyloxy-4,7-di (acetylamino) naphthalene-3-sulfonic acid separates out of the solution. The glacial acetic acid is distilled off in vacuo, the remaining triacetyl compound is dissolved in a little water, made phenolphthalein-alkaline with sodium hydroxide solution, approx. 45 parts of soda are added and it is heated to 70 for 15 minutes, the acetyl oxy group being saponified.
After cooling, it is made neutral with sulfuric acid, left to stand for 12 hours, and the precipitate which separates out is collected and dried; it consists of 1-oxy-4,7-di- (acetylamino) -naphthalene-3-sulfonic acid, the content of which is determined by titration with -p-nitrodiazobene-. Customs solution can be determined.
The acid not previously described forms a white powder that is easily soluble in water; The alkali salts are also easily soluble in water. If an aqueous solution of the acid is added to a soda-alkaline resorcinol solution, there will be no color change after pouring onto filter paper.
The 1-oxy-4-a.mino- 7-acetylaminonaphthalene-3-sulfonic acid used for the acetylation and not described in the literature can be obtained by reducing the azo dye which is obtained from the coupling of 4-nitro-l-diazobenzene-2- sulfonic acid with 1-oxy-7-acetylaminonaphthalene-3-sulfonic acid in the presence of soda, the diazo compound entering exclusively in the p-position to the hydroxyl group.
This makes it possible to carry out the reduction without isolating the azo dye. 1-Oxy-4-amino-7-acetylaminonaphthalene-3-sulfonic acid cannot be diazotized, nor does it couple with diazo compounds. 3Then applied to filter paper with a soda-alkaline resorcinol solution, an intense red color gradually appears.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212639T | 1939-04-05 | ||
| CH215820T | 1939-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215820A true CH215820A (en) | 1941-07-15 |
Family
ID=25725280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215820D CH215820A (en) | 1939-04-05 | 1939-04-05 | Process for the preparation of a 1-oxy-4-acylaminonaphthalene-3-sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215820A (en) |
-
1939
- 1939-04-05 CH CH215820D patent/CH215820A/en unknown
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