DE538450C - Process for the preparation of carbazole-2,7-disulfonic acid - Google Patents
Process for the preparation of carbazole-2,7-disulfonic acidInfo
- Publication number
- DE538450C DE538450C DE1930538450D DE538450DD DE538450C DE 538450 C DE538450 C DE 538450C DE 1930538450 D DE1930538450 D DE 1930538450D DE 538450D D DE538450D D DE 538450DD DE 538450 C DE538450 C DE 538450C
- Authority
- DE
- Germany
- Prior art keywords
- disulfonic acid
- carbazole
- preparation
- water
- diaminodiphenyl
- 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
Links
- XMFMKIFROZLSOL-UHFFFAOYSA-N 9h-carbazole-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C3=CC=C(S(=O)(=O)O)C=C3NC2=C1 XMFMKIFROZLSOL-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- -1 acids carbazoles Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- QAFJHDNFUMKVIE-UHFFFAOYSA-N 2,2'-dinitrobiphenyl Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1[N+]([O-])=O QAFJHDNFUMKVIE-UHFFFAOYSA-N 0.000 description 1
- HOLGXWDGCVTMTB-UHFFFAOYSA-N 2-(2-aminophenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1N HOLGXWDGCVTMTB-UHFFFAOYSA-N 0.000 description 1
- JPJAVZPZMFGPNP-UHFFFAOYSA-N 9h-carbazole-1,2-disulfonic acid Chemical compound C1=CC=C2NC3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C2=C1 JPJAVZPZMFGPNP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung von Carbazol-2, 7-disulfosäure Es ist bekannt, daß man aus 2, 2'-Diaminodiphenylderivaten durch Erhitzen mit Mineralsäuren Carbazole herstellen kann.Process for the preparation of carbazole-2, 7-disulfonic acid It is known that from 2,2'-diaminodiphenyl derivatives by heating with mineral acids carbazoles can produce.
Überträgt man diese Methode auf 2, 2'-Diaminodiphenyl-4, 4'-disulfosäure, dann erhält man nicht die erwartete Carbazoldisulfosäure, sondern es entsteht unter Abspaltung der Sulfogruppen Carbazol. Ebenfalls findet schon eine Abspaltung der Sulfogruppen beim Erhitzen mit Wasser auf 18o' statt unter Bildung von Carbazol.If this method is applied to 2,2'-diaminodiphenyl-4, 4'-disulfonic acid, then one does not get the expected carbazole disulphonic acid, but it arises under Splitting off of the sulfo groups carbazole. There is also a spin-off of Sulpho groups when heated with water to 18o 'instead of forming carbazole.
Es wurde nun gefunden, daß man den Carbazolringschluß so leiten kann, daß die Sulfogruppen erhalten bleiben, nämlich dadurch; daß man 2, 2'-Diaminodiphenyl-4"4- 'disulfosäure mit Wasser unter Zusatz von Salzen oder etwa so viel Alkali, als zurAbsättigungeiner Sulfogruppe nötig ist, auf Temperaturen von über 15o° erhitzt. Als Salze kommen für das Verfahren wasserlösliche Salze, wie Ammoniumsulfat, Ammoniumchlorid, Natriumsulfat, Natriumkarbonat, saures Natriumphosphat, in Frage, ausgenommen solche, die eine chemische Veränderung der gebildeten Carbazol-2, 7-disulfosäure bewirken, wie z. B. Salpeter. Die neue Carbazol-2, 7-disulfosäure ist ein wertvolles Farbstoffzwischenprodukt. Beispiel i 327 Gewichtsteile 2, 2'-Diaminodiphenyl-4, 4'-disulfosäure werden mit 1500 Gewichtsteilen Wasser und 40 Gewichtsteilen Ätznatron bis zum Verschwinden der Diaminoverbindung auf etwa 18o ° erhitzt. Mit Kochsalz fällt aus der erkalteten Lösung das Salz der Carbazol-2, 7-disulfosäure in feinen Nadeln. Das Natronsalz ist in heißem Wasser sehr leicht löslich.It has now been found that the carbazole ring closure can be conducted in such a way that the sulfo groups are retained, namely by; that 2, 2'-diaminodiphenyl-4 "4- 'disulfonic acid with water with the addition of salts or about as much alkali as is necessary to saturate a sulfo group, heated to temperatures above 150 °. The salts used for the process are water-soluble salts, such as ammonium sulfate, ammonium chloride, sodium sulfate, sodium carbonate, acidic sodium phosphate, with the exception of those that cause a chemical change in the carbazole-2, 7-disulfonic acid formed, such as nitric, which is the new carbazole-2, 7-disulfonic acid a valuable dye intermediate. example i 327 parts by weight of 2, 2'-diaminodiphenyl-4, 4'-disulfonic acid are heated with 1500 parts by weight of water and 40 parts by weight of caustic soda until the disappearance of the diamino compound to about 18o °. with saline falls from the cooled solution, the Salt of carbazole-2, 7-disulfonic acid in fine needles.The sodium salt is very easily soluble in hot water.
Die als Ausgangsmaterial dienende 2, 2'-Diaminodiphenyl-4, 4'-disulfosäure gewinnt man durch Reduktion aus der 2, 2'-Dinitrodiphenyl 4" 4!-disulfosäure, die z. B. nach dem Verfahren des Patents 126 961 hergestellt werden kann. Sie ist in kaltem Wasser schwer löslich und bildet eine schwer lösliche Tetrazoverbindung. Beispiel 2 327 Gewichtsteile a, 2'-Diaminodiphenyl-4, 4'-disulfosäure werden mit i ooo Gewichtsteilen Wasser und 25o Gewichtsteilen Ammoniumsulfat 15 Stunden auf 18o ° erhitzt. Die noch warme Lösung wird mit i ooo Gewichtsteilen Wasser verdünnt und mit Natronlauge schwach alkalisch gestellt. Das Salz der Carbazol-2, 7-disulfosäure fällt beim Aussahen mit Natriumchlorid als dicker Kristallbrei aus.The 2, 2'-diaminodiphenyl-4, 4'-disulfonic acid used as starting material is obtained by reduction from the 2,2'-dinitrodiphenyl 4 "4! -disulfonic acid, the z. B. can be prepared by the method of patent 126,961. she is in sparingly soluble in cold water and forms a sparingly soluble tetrazo compound. Example 2 327 parts by weight of a, 2'-diaminodiphenyl-4, 4'-disulfonic acid are mixed with 100 parts by weight of water and 250 parts by weight of ammonium sulfate for 15 hours Heated to 18o °. The still warm solution is diluted with 100 parts by weight of water and made weakly alkaline with sodium hydroxide solution. The salt of carbazole-2, 7-disulfonic acid when viewed with sodium chloride, precipitates as a thick crystal slurry.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE538450T | 1930-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE538450C true DE538450C (en) | 1931-11-13 |
Family
ID=6558143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930538450D Expired DE538450C (en) | 1930-05-22 | 1930-05-22 | Process for the preparation of carbazole-2,7-disulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE538450C (en) |
-
1930
- 1930-05-22 DE DE1930538450D patent/DE538450C/en not_active Expired
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