BE357270A - - Google Patents
Info
- Publication number
- BE357270A BE357270A BE357270DA BE357270A BE 357270 A BE357270 A BE 357270A BE 357270D A BE357270D A BE 357270DA BE 357270 A BE357270 A BE 357270A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- carbazol
- oxy
- acids
- oxycarbazols
- Prior art date
Links
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- -1 alkali metal salts Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- RSAZYXZUJROYKR-UHFFFAOYSA-N Indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-Nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Description
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EMI1.1
ItFroduction deacides 0 arbo liques du-carbazol" @ Les acides oxycarboxyliques du carbazol n"ont pas été décrits jusqu'à présent dans la littérature chimique.
Or on a trouvé, qu'on peut obtenir facilement par action de l'acide carbonique sur des sels de métaux
EMI1.2
alcalins doxyoarbazols ou sur des o7,yea, azole en
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présence d'hydroxydes ou de carbonates des métaux alca-
EMI2.1
lins, des acides oxycarbr,ique5 du carbazol-
Les nouveaux acides oxycarboxyliques du carbazol sont des produits intermédiaires précieux pour la produc- tion de colorants.
Exemple:
115 parties en poids de 2-oxycarbazol sont pulvéri- sée finement avec 350 parties en poids de bicarbonate de potassium et introduites dans un autoclave en ajoutant des billes de verre- Puis on introduit sous pression de l'acide carbonique et on maintient à une température de 275 et à une pression de 25 atm. pendant 20 heures.
Après quoi on laisse refroidir, on reprend le produit de réaction avec de l'eau, on filtre et on rend la solu-
EMI2.2
tion acide. Ltacide 2-oxy-carbazol--o-carboxylique se sépare sous forme d'une masse colorée faiblement jaune.
On essore, lave et fait sécher cette masse. Le produit brut, fondant à 266-267 C consiste en 2-isomères des
EMI2.3
acides 2-oxy-ca.rbazol- ortho-carboxyliques-.
Le mélange peut être séparé par recristallisation dans l'alcool. A partir de celui-ci on obtient un acide difficilement soluble, en gros prismes d'une couleur jaune tirant sur le vert, qui a probablement la consti-
EMI2.4
tution d'un acide 2-oxy-carbazol-J-aarboxylique> fon- en/
EMI2.5
dant à 273 - 274C'tdégageant de l'acide carbonique. Il
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donne une coloration bleue avec du chlorure de fer,, et la solution alcaline présente une fluorescence violette.
Avec des composés diazoiques il se combine pour former des colorants azoiques. Il ne forme pas 1'indophénol avec du para-nitroso-phénol en solution d'acide sul- furique. Il est soluble dans l'acide sulfurique avec une couleur jaune. En acétylant on obtient l'acide acé- tylique correspondant, se cristallisant dans;l'acide acétique glacial en aiguilles fondant à 272 C. L'ortho- anisidide, préparée d'après des méthodes usuelles, se cristallise dans le benzène ou dans. l'alcool méthy-. lique en longes prismes d'un point de fusion de 204-206 C. L'acide isomère qui a probablement la structure d'un acide 2-oxy-carbazol-l-carboxylique se cristallise de 1'eau-mère concentrée. Il fond à 271-272 C après recristallisation dans le xylène.
L'acide, ayant une couleur jaune pâle, donne une colo- ration bleue avec du chlorure de fer ; tout générale- ment, ses propriétés sont très semblables à celles de - avec l'acide isomère. Mais en contradiction l'acide mentionnée dtabord, l'acide 2-oxy-carbazol-1-carboxy- lique se condense avec le para-nitrophénol pour donner un indophénol bleu en solution acide. L'ortho-anisi- dide se cristallise dans le xylène et a un?oint de fusion de 192-193 C.
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EMI1.1
Production of 0-arbolic acids of carbazol "The oxycarboxylic acids of carbazol have not heretofore been described in the chemical literature.
Now we have found that we can easily obtain by the action of carbonic acid on metal salts
EMI1.2
alkaline doxyoarbazols or on o7, yea, azole in
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presence of hydroxides or carbonates of alka-
EMI2.1
linins, oxycarbr acids, carbazol ic5
The new oxycarboxylic acids of carbazol are valuable intermediates for the production of dyes.
Example:
115 parts by weight of 2-oxycarbazol are finely pulverized with 350 parts by weight of potassium bicarbonate and introduced into an autoclave by adding glass beads. Carbonic acid is then introduced under pressure and the temperature is maintained at a temperature of 275 and at a pressure of 25 atm. for 20 hours.
After which it is allowed to cool, the reaction product is taken up with water, filtered and the solution is made up.
EMI2.2
acid tion. The 2-oxy-carbazol - o-carboxylic acid separates out as a faint yellow colored mass.
This mass is filtered off, washed and dried. The crude product, melting at 266-267 C, consists of 2-isomers of
EMI2.3
2-oxy-ca.rbazol- ortho-carboxylic acids-.
The mixture can be separated by recrystallization from alcohol. From this we obtain a hardly soluble acid, in large prisms of a yellow color tending to green, which probably has the consti-
EMI2.4
tution of a 2-oxy-carbazol-J-aarboxylic acid> melting /
EMI2.5
at 273 - 274C't, liberating carbonic acid. he
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gives a blue coloration with iron chloride, and the alkaline solution fluoresces purple.
With diazo compounds it combines to form azo dyes. It does not form indophenol with para-nitroso-phenol in sulfuric acid solution. It is soluble in sulfuric acid with a yellow color. By acetylation, the corresponding acetylic acid is obtained, crystallizing from glacial acetic acid in needles, melting at 272 C. Orthoanisidide, prepared according to the usual methods, crystallizes in benzene or in. methyl alcohol. Lic in long prisms with a melting point of 204-206 C. The isomeric acid which probably has the structure of a 2-oxy-carbazol-1-carboxylic acid crystallizes from concentrated mother water. It melts at 271-272 C after recrystallization from xylene.
The acid, having a pale yellow color, gives a blue color with chloride of iron; generally, its properties are very similar to those of - with isomeric acid. But in contrast to the acid mentioned above, 2-oxy-carbazol-1-carboxylic acid condenses with para-nitrophenol to give a blue indophenol in acidic solution. Ortho-anisidide crystallizes in xylene and has a melting point of 192-193 C.
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
BE357270A true BE357270A (en) |
Family
ID=31180
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE357270D BE357270A (en) |
Country Status (1)
Country | Link |
---|---|
BE (1) | BE357270A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0110239A1 (en) * | 1982-11-27 | 1984-06-13 | Bayer Ag | Process for the preparation of 2-hydroxy-carbazole-1-carboxylic acid |
-
0
- BE BE357270D patent/BE357270A/fr unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0110239A1 (en) * | 1982-11-27 | 1984-06-13 | Bayer Ag | Process for the preparation of 2-hydroxy-carbazole-1-carboxylic acid |
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