CH123735A - Process for the preparation of 3-phenylamino-1.8-naphtsultam-6-sulfonic acid. - Google Patents
Process for the preparation of 3-phenylamino-1.8-naphtsultam-6-sulfonic acid.Info
- Publication number
- CH123735A CH123735A CH123735DA CH123735A CH 123735 A CH123735 A CH 123735A CH 123735D A CH123735D A CH 123735DA CH 123735 A CH123735 A CH 123735A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- naphtsultam
- aniline
- phenylamino
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 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 claims description 2
- 159000000009 barium salts Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- -1 sulpho group Chemical group 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Darstellung von 3-Phenylamino-1.8-naphtsultam-6-sulfosäure. Es wurde gefunden, dass solche 1. 8-Napht- sultamsulfosäuren, welche eine Sulfogruppe in 3-Stellung zum Sultamstickstoff enthalten, beim Erhitzen mit aromatischen Aminen die 3-ständige Sulfogruppe gegen den Aryla- minrest austauschen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur .Herstellung der 3-Phenyl- amino-l.8-ziaphtsultam-6-sulfosäure; das Ver fahren gemäss der Erfindung ist dadurch gekennzeichnet, dass man eine 1.8-Naphtsul- tampolysulfosäure mit einer Sultogruppe in 3-Stellung, zum Beispiel die 1.8-Naphtsul- tam-3.6-disulfosäure, mit Anilin, zweck mässig unter Zusatz eines Anilinsalzes und eines Verdünnungsmittels, erhitzt.
Unter Entwicklung von Schwefeldioxyd wird die 3-ständige Sulfogruppe gegen den Anilinrest ausgetauscht. Die Wirkung der Anilinsalze ist anscheinend eine katalytische. Die 3-Phe- nylamino-l.8-naphtsultam-6-sulfosiiure dient als Zwischenprodukt für die Herstellung von Farbstoffen.
<I>Beispiel</I> 387 Gewichtsteile des sauren Natrium salzes der 1.8-Naphtsultam-3.6-disulfosäure (siehe Dr essel und Kothe, Ber. 27, 2149 [1894]) werden mit 1200 Gewichtsteilen Ani lin und 200 Gewichtsteilen Salzsäure 191/2 B6 48 Stunden auf 130-1401 erwärmt.
Das Reaktionsprodukt wird in Eis und über schüssige verdünnte Salzsäure gegossen, das abgeschiedene Anilinsalz der 3-Phenylamino- 1. 8-naphtsultam-6-sulfosäure abgenutscht und ausgewaschen. Um es ganz rein zu erhalten, kristallisiert man es zweckmässig aus sehr verdünnter Essigsäure um. Man erhält es dann in kleinen Prismen, welche bei 277 bis 278 schmelzen.
Die Verbindung ist leicht löslich in Essig säure und Alkohol, schwer in Wasser. Mit verdünnter Natronlauge oder Natriumacetat- lösung wird sie zerlegt und man erhält aus der von der organischen Base befreiten Lösung durch Aussalzen das Natriumsalz der 3-Phenylamino-l. 8-naphtsultam- 6 - sulfosäure als gelbes kristallinisches Pulver, das leicht in Alkohol und Wasser löslich ist.
Die 3-Phe- nylamino-l.8-naphtsultam-6-sulfosäure bildet ein schwer lösliches Bariumsalz, leicht lös liche Natrium- und Kaliumsalze ; letzteres kristallisiert in gelben Prismen und ist zur Reinigung der Säure geeignet. Die freie Säure stellt ein in Wasser leicht lösliches gelb liches Pulver dar.
Das Verfahren gemäss der Erfindung kann auch mit der äquivalenten Menge der in den Ber. d. deutschen chem. Ges. 27, 2149 beschreibenen 1.8-Naphtsultari-3.4(?)-6-tri- sulfosäure ausgeführt werden, da die labile 9-(?)-ständige Sulfogruppe bei der Reaktion abgespalten und dasselbe Endprodukt des Verfahrens hierbei erzeugt wird.
Process for the preparation of 3-phenylamino-1.8-naphtsultam-6-sulfonic acid. It has been found that 1,8-naphthosultamsulphonic acids which contain a sulpho group in the 3-position to the sultam nitrogen exchange the 3-position sulpho group for the arylamine residue when heated with aromatic amines.
The subject of the present patent is a process for producing 3-phenylamino-1,8-ziaphtsultam-6-sulfonic acid; the method according to the invention is characterized in that one 1.8-naphthosultampolysulfonic acid with a sulto group in the 3-position, for example 1.8-naphthosultam-3.6-disulfonic acid, with aniline, advantageously with the addition of an aniline salt and one Diluent, heated.
The 3-position sulfo group is exchanged for the aniline residue with the evolution of sulfur dioxide. The effect of the aniline salts is apparently catalytic. The 3-phenylamino-1.8-naphtsultam-6-sulfonic acid is used as an intermediate for the production of dyes.
<I> Example </I> 387 parts by weight of the acidic sodium salt of 1.8-naphtsultam-3.6-disulfonic acid (see Dr essel and Kothe, Ber. 27, 2149 [1894]) are mixed with 1200 parts by weight of aniline and 200 parts by weight of hydrochloric acid 191 / 2 B6 heated to 130-1401 for 48 hours.
The reaction product is poured into ice and excess dilute hydrochloric acid, and the precipitated aniline salt of 3-phenylamino-1,8-naphtsultam-6-sulfonic acid is suction filtered and washed out. To get it completely pure, it is expediently recrystallized from very dilute acetic acid. It is then obtained in small prisms which melt at 277 to 278.
The compound is easily soluble in acetic acid and alcohol, difficult in water. It is broken down with dilute sodium hydroxide solution or sodium acetate solution and the sodium salt of 3-phenylamino-1 is obtained from the solution freed from the organic base by salting out. 8-naphtsultam- 6 - sulfonic acid as a yellow crystalline powder that is easily soluble in alcohol and water.
The 3-phenylamino-1.8-naphtsultam-6-sulfonic acid forms a barium salt that is difficult to dissolve, as well as sodium and potassium salts which are easily soluble; the latter crystallizes in yellow prisms and is suitable for cleaning the acid. The free acid is a yellowish powder that is easily soluble in water.
The method according to the invention can also with the equivalent amount of the Ber. d. German chem. Ges. 27, 2149 described 1.8-Naphtsultari-3.4 (?) - 6-trisulphonic acid, since the labile 9 - (?) - sulfo group is split off during the reaction and the same end product of the process is produced.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH123735T | 1926-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH123735A true CH123735A (en) | 1927-12-16 |
Family
ID=4382389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH123735D CH123735A (en) | 1926-08-31 | 1926-08-31 | Process for the preparation of 3-phenylamino-1.8-naphtsultam-6-sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH123735A (en) |
-
1926
- 1926-08-31 CH CH123735D patent/CH123735A/en unknown
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