DE71157C - Process for the preparation of aiss3-naphthylenediamine-a * -sulfonic acid from a <^ 3-amidonaphthol-az-sulfonic acid - Google Patents
Process for the preparation of aiss3-naphthylenediamine-a * -sulfonic acid from a <^ 3-amidonaphthol-az-sulfonic acidInfo
- Publication number
- DE71157C DE71157C DENDAT71157D DE71157DA DE71157C DE 71157 C DE71157 C DE 71157C DE NDAT71157 D DENDAT71157 D DE NDAT71157D DE 71157D A DE71157D A DE 71157DA DE 71157 C DE71157 C DE 71157C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid
- naphthylenediamine
- preparation
- aiss3
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004571 lime Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification 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
- C07C309/47—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 having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
a2-sulfosäure.a 2 sulfonic acid.
Wird die a - Naphtylamin - a2 ß8 - disulfosäure (II. der Patentschrift Nr. 41957) mit Aetznatron verschmolzen, so entsteht als erstes Einwirkungsproduct die aj-Amido-ßg-Naphtol-^-monosulfosäure. Diese Säure ist in Wasser sehr schwer löslich. Ihre Salze sind leicht löslich und krystallisiren leicht. Die Fluorescenz ihrer Lösungen ist blauviolett. Durch Einwirkung von Ammoniak bei höherer Temperatur unter Druck entsteht leicht und quantitativ eine bis jetzt nicht bekannte Diamidonaphtalinsulfosäure.If the a - naphthylamine - a 2 ß 8 - disulfonic acid (II. Of patent specification No. 41957) is fused with caustic soda, the first product of action is the aj-amido-βg-naphthol - ^ - monosulfonic acid. This acid is very sparingly soluble in water. Their salts are easily soluble and readily crystallize. The fluorescence of their solutions is blue-violet. A previously unknown diamidonaphthalene sulfonic acid is easily and quantitatively formed by the action of ammonia at a higher temperature under pressure.
Zur Darstellung derselben verfährt man wie folgt:To display the same, proceed as follows:
100 kg a,-Amido-ßg-Naphtol-a2-monosulfosäure werden in einem Druckkessel mit 80 kg wässerigem Ammoniak vom spec. Gew. 0,910 bei einer Temperatur von 170 bis i8o° während 12 bis 15 Stunden erhitzt.100 kg of a, -amido-ß g -naphtol-a 2 -monosulfonic acid are in a pressure vessel with 80 kg of aqueous ammonia from the spec. Weight 0.910 heated at a temperature of 170 to 180 ° for 12 to 15 hours.
Nach dem Erkalten des Kessels ist der Inhalt desselben zu einer blätterig krystallinischen Masse erstarrt, bestehend aus dem Ammoniaksalz der neu entstandenen Naphtylendiaminsulfosäure. Die Säure kann sofort, ohne weitere Reinigung, zur Darstellung von Farbstoffen benutzt werden..After the kettle has cooled down, the contents of the kettle have become crystalline in the form of sheets The mass solidifies, consisting of the ammonia salt of the newly formed naphthylenediamine sulfonic acid. The acid can immediately, without further purification, to form dyes to be used..
Die freie Naphtylendiaminsulfosäure (at ß3 a2) ist in kaltem Wasser sehr schwer, in heifsem Wasser leichter löslich und bildet ein weifses Pulver. Aus heifs gesättigten wässerigen Lösungen scheidet sie sich in kleinen Nädelchen ab.The free naphthylenediamine sulfonic acid (a t ß 3 a 2 ) is very difficult in cold water, more easily soluble in hot water and forms a white powder. It is deposited in small needles from hot, saturated aqueous solutions.
Die Ammoniak-, Natron- und Kalksalze der Säure krystallisiren aus Wasser leicht in grofsen Tafeln und sind darin ziemlich schwer löslich.The ammonia, soda, and lime salts of acid easily crystallize from water to a large extent Tablets and are rather difficult to dissolve in them.
Die Naphtylendiaminsulfosäure nimmt beim Diazotiren 2 Mol. salpetrige Säure auf. Nach kurzem Stehen der Tetrazoverbindung beginnt jedoch schon bei o° eine lebhafte Gasentwickelung, indem eine Diazogruppe durch Hydroxyl ersetzt wird. Dementsprechend verbindet sich die Tetrazoverbindung auch nur mit 1 Mol. eines Naphtols, während die andere Diazogruppe durch Hydroxyl ersetzt wird. Die Tetrazoverbindung der Naphtylendiaminsulfosäure ist leicht löslich, dagegen scheidet sich die durch Ersatz einer Diazogruppe durch O H entstehende Diazonaphtolsulfosäure als Niederschlag ab. Die Naphtylendiaminsulfosäure verbindet sich sowohl in essigsaurer wie in alkalischer Lösung leicht mit Diazo- und Tetrazokörpern zu neuen Farbstoffen, von denen einige ein hervorragendes technisches Interesse bieten.The naphthylenediamine sulfonic acid takes up 2 moles of nitrous acid when diazotizing. After the tetrazo compound has stood still for a short time, however, vigorous evolution of gas begins at 0 °, as a diazo group is replaced by hydroxyl. Accordingly, the tetrazo compound only combines with 1 mole of a naphthol, while the other diazo group is replaced by hydroxyl. The tetrazo compound of naphthylenediaminesulphonic acid is easily soluble, whereas the diazonaphtholsulphonic acid formed by replacing a diazo group with OH separates out as a precipitate. Naphthylenediaminesulfonic acid combines easily with diazo and tetrazo bodies in both acetic and alkaline solutions to form new dyes, some of which are of outstanding technical interest.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE71157C true DE71157C (en) |
Family
ID=344483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT71157D Expired - Lifetime DE71157C (en) | Process for the preparation of aiss3-naphthylenediamine-a * -sulfonic acid from a <^ 3-amidonaphthol-az-sulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE71157C (en) |
-
0
- DE DENDAT71157D patent/DE71157C/en not_active Expired - Lifetime
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