DE197496C - - Google Patents
Info
- Publication number
- DE197496C DE197496C DENDAT197496D DE197496DA DE197496C DE 197496 C DE197496 C DE 197496C DE NDAT197496 D DENDAT197496 D DE NDAT197496D DE 197496D A DE197496D A DE 197496DA DE 197496 C DE197496 C DE 197496C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfonic acid
- aminophenol
- phenol
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- XYTGREGNMWBPCM-UHFFFAOYSA-N C(=O)=C1C(C(=CC=C1)O)N Chemical compound C(=O)=C1C(C(=CC=C1)O)N XYTGREGNMWBPCM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 description 7
- 150000008049 diazo compounds Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- 210000004080 Milk Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 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
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 197496 -KLASSE 12.0. GRUPPE - JVl 197496 - CLASS 12.0. GROUP
Patentiert im Deutschen Reiche vom 22. März 1907 ab.Patented in the German Empire on March 22, 1907.
Post (Annalen 205, S. 51) hat durch Einwirkung von rauchender Schwefelsäure auf o-Aminophenol ausschließlich die 2-Amino-1-phenol-4-sulfosäure erhalten. Es wurde nun gefunden, daß eine von dieser verschiedene Säure entsteht, wenn man Carbonylo-aminophenol sulfiert und das Reaktionsprodukt mit verseifenden Mitteln behandelt. Die Diazoverbindung der neuen Säure verbindet sich glatt mit den üblichen Komponenten zu Farbstoffen, die sich vor denen aus der isomeren Säure durch ihre Intensität und Schönheit der Nuance auszeichnen.Post (Annalen 205, p. 51) has due to the action of fuming sulfuric acid o-aminophenol exclusively the 2-amino-1-phenol-4-sulfonic acid obtain. It has now been found that an acid different from this is formed when carbonylo-aminophenol is used sulfated and treated the reaction product with saponifying agents. The diazo compound of the new acid combines smoothly with the usual components to dyes that are distinguished from those from the isomeric acid by their intensity and beauty of the nuance.
Sulfierung von Carbonyl-o-aminophenol. Sulphation of carbonyl-o-aminophenol.
135 kg Carbonyl-o-aminophenol werden bei gewöhnlicher Temperatur in 300 kg Monohydrat gelöst und in diese Lösung 140 kg Oleum (63 Prozent) bei 5 bis 10° allmählich eingetragen. Nachdem die Sulfierung beendet ist, gießt man auf Eis, neutralisiert mit KaIkmilch, filtriert und dampft auf ein Volumen von 1000 1 ein. Man führt sodann in üblicher Weise das Calciumsalz in das Natriumsalz über und fällt letzteres durch Zufügen von Kochsalz aus. Man erhält es so in feinen weißen Nädelchen, die in reinem Wasser leicht löslich, in kochsalzhaltigem schwer löslich sind. ;■■■■■135 kg of carbonyl-o-aminophenol are used Ordinary temperature dissolved in 300 kg of monohydrate and 140 kg in this solution Gradually introduced oleum (63 percent) at 5 to 10 °. After the sulfation has ended is, it is poured onto ice, neutralized with milk milk, filtered and evaporated to volume from 1000 1 a. The calcium salt is then converted into the sodium salt in the usual way and the latter precipitates by adding table salt. It is obtained in fine white needles, those in pure Easily soluble in water, sparingly soluble in saline. ; ■■■■■
Verseifung von Carbonyl-o-aminophenol-5-sulfosäure. Saponification of carbonyl-o-aminophenol-5-sulfonic acid.
237 kg des nach Beispiel 1 erhaltenen Natriumsalzes der Ca'rbonyl-o-aminophenolsulfosäure werden in -750 1 Wasser gelöst und nach Zusatz von 250 kg; Natronlauge (400 Be.) unter Rückfluß gekocht, bis eine Probe keine Zunahme des Diazotiters mehr aufweist. Die klare Lösung wird mit Salzsäure neutralisiert und enthält nun das leicht lösliche Natriumsalz der neuen o-Aminophenolsulfosäure.237 kg of the sodium salt of Ca'rbonyl-o-aminophenolsulfonic acid obtained according to Example 1 are dissolved in -750 1 of water and, after addition of 250 kg; Sodium hydroxide solution (40 0 Be.) Boiled under reflux until a sample no longer shows any increase in the diazotiter. The clear solution is neutralized with hydrochloric acid and now contains the easily soluble sodium salt of the new o-aminophenol sulfonic acid.
Durch weiteren Zusatz von Salzsäure läßt sich die freie Säure in weißen Nadeln abscheiden, die in Wasser ziemlich leicht löslich sind. Mit Nitrit entsteht die in Lösung intensiv gelb gefärbte; Diazoverbindung, die sich aber nach einigem Stehen in langen, grünlichgrauen Nadeln aus der Lösung abscheidet. By adding more hydrochloric acid, the free acid can be separated out in white needles, which are fairly easily soluble in water. With nitrite, the one, which is intensely yellow in color in solution, is formed; Diazo compound that but after standing for some time it separates out of the solution in long, greenish-gray needles.
Die Tatsache, daß man aus der neuen Säure durch Verkochen ihrer' Diazoverbindung bei Gegenwart von Alkohol 1-Phenol-3-sulfosäure erhält, führt zu der Annahme, daß ihr die KonstitutionThe fact that the new acid can be obtained by boiling its' diazo compound Presence of alcohol 1-phenol-3-sulfonic acid receives leads to the assumption that you have the constitution
OHOH
I
ΐ I.
ΐ
6o6o
S Oo iZ- S Oo iZ-
NH,NH,
zukommt.comes to.
Die Unterschiede zwischen der neuen Säure und der bekannten 2 - Amino - 1 - phenol-The differences between the new acid and the well-known 2 - amino - 1 - phenol-
4-sulfosäure sind aus folgender Tabelle ersichtlich: 4-sulfonic acid can be seen from the following table:
boeder (Ann. 205, S. 51)transparent, colorless rhombic
boeder (Ann. 205, p. 51)
verbindungSolubility of the diazo
link
einigem Stehen oder durch Aus
salzen in langen Nadeln austhe diazo compound falls behind
some standing or by off
salt out in long needles
löslich und nicht aussalzbarthe diazo compound is easy
soluble and not saltable
verbindung beim Ver
kochen mit AlkoholBehavior of the diazo
connection at Ver
cook with alcohol
Claims (1)
Verfahren zur Darstellung der 2-Aminoi-phenol-5-sulfosäure, darin bestehend,Patent claim:
Process for the preparation of 2-Aminoi-phenol-5-sulfonic acid, consisting therein
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE197496C true DE197496C (en) |
Family
ID=460380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT197496D Active DE197496C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE197496C (en) |
-
0
- DE DENDAT197496D patent/DE197496C/de active Active
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