DE57114C - Process for the preparation of a dioxynaphthalene monosulfonic acid from a-naphthylamine disulfonic acid - Google Patents
Process for the preparation of a dioxynaphthalene monosulfonic acid from a-naphthylamine disulfonic acidInfo
- Publication number
- DE57114C DE57114C DENDAT57114D DE57114DA DE57114C DE 57114 C DE57114 C DE 57114C DE NDAT57114 D DENDAT57114 D DE NDAT57114D DE 57114D A DE57114D A DE 57114DA DE 57114 C DE57114 C DE 57114C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dioxynaphthalene
- preparation
- monosulfonic
- naphthylamine disulfonic
- 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 title claims description 9
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002832 nitroso derivatives 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
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005987 sulfurization reaction 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die in der Patentschrift No. 41957 beschriebene a-Naphtylamindisulfosäure II, deren Kalksalz in 8oprocentigem Spiritus löslich ist, hat sich bis jetzt als technisch werthlos erwiesen.The method described in patent specification no. 41957 described a-naphthylamine disulfonic acid II, its lime salt is soluble in 8% alcohol has so far proven to be technically worthless.
Beim Schmelzen des Natronsalzes dieser Säure, welche nach dem im oben genannten Patent beschriebenen Sulfurirungsverfahren in ziemlich bedeutender Menge entsteht (ca. 30 pCt. des Sulfurirungsgemenges), mit Aetznatron kann sowohl die Amido- als auch eine Sulfogruppe mit Leichtigkeit entfernt und durch die Hydroxylgruppe ersetzt werden.When melting the sodium salt of this acid, which after the above The sulfurization process described in the patent is produced in a fairly significant amount (approx. 30 pCt. des Sulfurirgemenges), with caustic soda can both the amido and a sulfo group can be removed with ease and replaced with the hydroxyl group.
Die auf diese Art erhaltene Dioxynaphtaiinmonosulfosäure , welche, da das Ausgangsmaterial ein a - Naphtylaminderivat ist, eine Hydroxylgruppe in der α - Stellung besitzt, krystallisirt aus salzhaltigem Wasser in schmalen Blättchen, die in kaltem Wasser ziemlich schwer löslich sind.The Dioxynaphtaiinmonosulfosäure obtained in this way, which, because the starting material is an a - Naphtylaminderivat is a hydroxyl group at the α - position has, crystallizes from saline water in small flakes which are quite heavy soluble in cold water.
Ihr neutrales Natronsalz ist in Wasser und starkem Alkohol (95 pCt.) sehr leicht löslich und krystallisirt daraus ebenfalls in schmalen Blättchen.Its neutral sodium salt is very easily soluble in water and strong alcohol (95 pct.) and crystallizes from it likewise in narrow leaflets.
Eisenchlorid erzeugt in der wässerigen Lösung eine schwach grünlich blaue Färbung, die rasch in Braun übergeht.Ferric chloride produces a pale greenish blue color in the aqueous solution, which quickly turns brown.
In saurer Lösung erzeugt salpetrige Säure eine Nitrosoverbindung, welche schwer löslich ist und schon bei verhältnifsmäfsig geringer Concentration als gelbbraunes Pulver ausfällt.In acidic solution, nitrous acid produces a nitroso compound which is sparingly soluble and precipitates as a yellow-brown powder even at a relatively low concentration.
Mit Diazoverbindungen erzeugt die Dioxynaphtaiinmonosulfosäure werthvolle rothe bis blaue Azofarbstoffe.With diazo compounds, the dioxynaphthalene monosulfonic acid produces valuable red bis blue azo dyes.
Beispiel: 150 kg ct-naphtylamindisulfosaures Natron werden in eine auf i8o° erhitzte Lösung von 600 kg Aetznatron in 100 kg Wasser eingetragen und 6 bis 10 Stunden auf 200 bis 220° C. erhitzt. Es entweicht Ammoniak und fast zu gleicher Zeit wird eine Sulfogruppe abgespalten. Die Reaction ist beendigt, wenn in einer Probe keine a-Naphtylamindisulfosäure mehr· nachzuweisen ist. Die Schmelze wird alsdann in ca. 2000 1 heifsem Wasser gelöst, mit Salzsäure vollständig abgesättigt und heifs filtrirt. Nach dem Erkalten der klaren, nur wenig gelb gefärbten Lösung scheidet sich beinahe alle Dioxynaphtaiinmonosulfosäure in schönen Krystallen aus.Example: 150 kg of ct-naphthylamine disulfosaures Soda is in a heated to 180 ° solution of 600 kg of caustic soda in 100 kg of water entered and heated to 200 to 220 ° C. for 6 to 10 hours. Ammonia escapes and a sulfo group is split off at almost the same time. The reaction is ended when in no more a-naphthylamine disulfonic acid can be detected in a sample. The melt will then dissolved in about 2000 liters of hot water, completely saturated with hydrochloric acid and hot filtered. After the clear, only slightly yellow solution has cooled down, it almost separates all dioxynaphthalene monosulfonic acid in beautiful crystals.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE57114C true DE57114C (en) |
Family
ID=331498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT57114D Expired - Lifetime DE57114C (en) | Process for the preparation of a dioxynaphthalene monosulfonic acid from a-naphthylamine disulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE57114C (en) |
-
0
- DE DENDAT57114D patent/DE57114C/en not_active Expired - Lifetime
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