CH99043A - Process for the preparation of 1-5-diaminoanthraquinone. - Google Patents
Process for the preparation of 1-5-diaminoanthraquinone.Info
- Publication number
- CH99043A CH99043A CH99043DA CH99043A CH 99043 A CH99043 A CH 99043A CH 99043D A CH99043D A CH 99043DA CH 99043 A CH99043 A CH 99043A
- Authority
- CH
- Switzerland
- Prior art keywords
- diaminoanthraquinone
- preparation
- oxidizing agent
- ammonia
- anthraquinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- LIBWRRJGKWQFSD-UHFFFAOYSA-M sodium;2-nitrobenzenesulfonate Chemical group [Na+].[O-][N+](=O)C1=CC=CC=C1S([O-])(=O)=O LIBWRRJGKWQFSD-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- -1 dichromates Chemical compound 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé pour la préparation de la 1-h-diaminoanthraquinone. Le brevet allemand no 256515 protège un procédé de fabrication des amino et diamino- antliraquinones en général. Ce procédé con siste à chauffer les acides .anthraquinone- mono ou disulfoniques avec de l'ammoniaque sous pression en ajoutant à la masse de réac tion, des ,agents d'oxydation inorganiques, du genre du bioxyde de manganèse, des oxydes de cuivre, des bichromates, de l'acide arséni- que ou de l'oxyde d'argent.
L'adjonction de ces oxydants a pour effet une amélioration de rendement.
Les brevets suisses no 74747 et 90622 décrivent un procédé pour la préparation de l'a et -de la f-monoaminoantbraquinone à par tir des acides a et fl-authraquinone-monosul- foniques et de l'ammonia.qne dans lesquels les agents d'oxydation inorganiques sont rempla cés par des agents d'oxydation organiques. Ces derniers ont l'avantage de donner direc tement sans extraction, l'a et la fl-amino- anthra.quinone pure.
L'inventeur a, trouvé que si l'on remplace les acides a et fl-monosulfoniques par de l'a cide anthra,quino@ne-1.-5-clisulfonique et que l'on chauffe ce dernier acide avec de l'ammo- raque sous pression, en présence d'un agent d'oxydation organique, comme par exemple ,des dérivés nitrosulfonés de la série aroma tique, on obtient directement de la 1-5 diamino-anthraquinone sous une forme beau coup plus pure et avec un meilleur rendement que si l'on emploie des agents d'oxydation inorganique.
De plus, tandis que la -diaminoanthraqui- none-1-5 ne peut pas être obtenue à l'état pur sans faire intervenir un procédé -d'extrac tion, lorsque l'on travaille en présence -d'oxy dants inorganiques, cette extraction devient souvent inutile lorsque l'on emploie les oxy dants organiques.
Ce nouveau procédé de préparation de la 1-5-diaminoanthraquinone, qui fait précisé ment l'objet de la présente invention, peut être exécuté, par exemple, comme suit: On chauffe dans un autoclave un mélange de<B>100</B> parties d'acide anthraquinone-1-5- disulfonique sous forme de son sel de sodium avec 900 parties d'ammoniaque à 25 % et 100 parties @de nitro-benzène-sulfonate .de so dium. La température est de<B>170'</B> et la durée du chauffage de 20 heures. On filtre le contenu de l'autoclave après refroidissement.
La 1-5-diaminoanthra.qui- none est obtenue directement à l'état pur et sous forme de beaux cristaux après lavage à l'eau bouillante.
On pourra remplacer le nitrobenzène-sul- fonate de sodium par d'autres dérivés -de la. série aromatique et l'on pourra faire varier dans de certaines limites les quantités de réactifs ainsi que la température indiquées ci-dessus sans influencer sensiblement le ré sultat final.
Process for the preparation of 1-h-diaminoanthraquinone. German Patent No. 256515 protects a process for the manufacture of amino and diaminoantliraquinones in general. This process consists in heating the .anthraquinone-mono or disulfonic acids with pressurized ammonia by adding to the reaction mass, inorganic oxidizing agents, such as manganese dioxide, copper oxides, dichromates, arsenic acid or silver oxide.
The addition of these oxidants has the effect of improving the yield.
Swiss Patents Nos. 74747 and 90622 describe a process for the preparation of α and β-monoaminoantbraquinone from α and β-authraquinone-monosulfonic acids and ammonia. Inorganic oxidation are replaced by organic oxidizing agents. The latter have the advantage of giving, directly without extraction, pure α and α-amino-anthra.quinone.
The inventor has found that if one replaces the α and fl-monosulfonic acids with anthra, quino @ ne-1.-5-clisulfonic acid and that the latter acid is heated with ammonia under pressure, in the presence of an organic oxidizing agent, such as, for example, nitrosulfonated derivatives of the aromatic series, 1-5 diamino-anthraquinone is obtained directly in a much purer form and with better yield than if inorganic oxidizing agents are used.
In addition, while -diaminoanthraquinone-1-5 cannot be obtained in the pure state without involving an extraction process, when working in the presence of inorganic oxides, this extraction often becomes unnecessary when organic oxidants are employed.
This new process for the preparation of 1-5-diaminoanthraquinone, which is precisely the object of the present invention, can be carried out, for example, as follows: A mixture of <B> 100 </ B is heated in an autoclave. > parts of anthraquinone-1-5- disulphonic acid in the form of its sodium salt with 900 parts of 25% ammonia and 100 parts of sodium nitro-benzene-sulphonate. The temperature is <B> 170 '</B> and the heating time is 20 hours. The contents of the autoclave are filtered after cooling.
1-5-diaminoanthra.quinone is obtained directly in the pure state and in the form of beautiful crystals after washing with boiling water.
Sodium nitrobenzene sulphonate can be replaced by other derivatives of the. aromatic series and it is possible to vary within certain limits the quantities of reagents as well as the temperature indicated above without appreciably influencing the final result.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH99043T | 1922-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH99043A true CH99043A (en) | 1923-05-01 |
Family
ID=4356942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH99043D CH99043A (en) | 1922-03-02 | 1922-03-02 | Process for the preparation of 1-5-diaminoanthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH99043A (en) |
-
1922
- 1922-03-02 CH CH99043D patent/CH99043A/en unknown
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