CH179955A - Process for the production of 2,3-diaminoanthraquinone. - Google Patents
Process for the production of 2,3-diaminoanthraquinone.Info
- Publication number
- CH179955A CH179955A CH179955DA CH179955A CH 179955 A CH179955 A CH 179955A CH 179955D A CH179955D A CH 179955DA CH 179955 A CH179955 A CH 179955A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- diaminoanthraquinone
- parts
- aqueous ammonia
- treated
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QLYNDPSMXHPWNH-UHFFFAOYSA-N 2,3-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(N)=C2 QLYNDPSMXHPWNH-UHFFFAOYSA-N 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- KPYPNTLKDIYIKB-UHFFFAOYSA-N 2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2 KPYPNTLKDIYIKB-UHFFFAOYSA-N 0.000 description 1
- VMOJFUJVEWWUAV-UHFFFAOYSA-N 2-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Cl)=C2 VMOJFUJVEWWUAV-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 2.3-Diaminoanthrachinon. Das Hauptpatent betrifft ein Verfahren zur Herstellung von 2- Amino-3-chloranthra- chinon, bei dem 2.3-Dichlor-anthrachinon mit wässerigem Ammoniak so lange behan delt wird, bis eine entnommene und auf gearbeitete Probe nach dem Umkristalli- sieren aus einem organischen Lösuno-smittel bei etwa 300 C schmilzt.
Es wurde nun gefunden, dass man in vor teilhafter Weise --1. 3-Diaminoanthrachinon erhalten kann, wenn man -). 3-Dichloranthra- chinon so lange mit wässerigem Ammoniak behandelt, bis eine entnommene und auf gearbeitete Probe chlorfrei ist. Es ist zweck mässig, hierbei höherkonzentriertes, beispiels weise -10 bis 50%iges wässeriges Ammonialz- zu verwenden. doch kann man auch die Um setzung mit verdünnterem, beispielsweise 10 bis 20 % igem Ammoniak ausführen.
Es ist vorteilhaft, die Behandlung in Gegenwart von Katalysatoren, insbesondere von Kupfer verbindungen, auszuführen. <I>Beispiel 1:</I> Man erhitzt 100 Teile 2 . 3-Dichloranthra- chinon mit 400 Teilen 50 % igem wässerigem Ammoniak und 3 Teilen Kupfersulfat 24 Stunden lang auf 205 C. Nach dem Ab kühlen saugt man ab, wäscht den Rückstand mit Wasser aus und trocknet. Das Reaktions produkt kann gewünschtenfalls durch frak tionierte Fällung aus seiner Lösung in kon zentrierter Schwefelsäure noch gereinigt wer den.
Beispiel <I>2:</I> 100 Teile 2. 3-Dichloranthrachinon wer den mit 2000 Teilen 25%igem Ammoniak und 10 Teilen kristallisiertem Kupfersulfat im Rührwerksautoklaven 30 Stunden lang auf 200' C erhitzt. Die Aufarbeitung er folgt wie im Beispiel 1.
Process for the production of 2,3-diaminoanthraquinone. The main patent relates to a process for the production of 2-amino-3-chloroanthraquinone in which 2,3-dichloro-anthraquinone is treated with aqueous ammonia until a sample taken and processed after recrystallization from an organic solution -smittel melts at about 300 C.
It has now been found that in a beneficial way --1. 3-diaminoanthraquinone can be obtained if one -). Treated 3-dichloroanthraquinone with aqueous ammonia until a sample taken and processed is chlorine-free. It is useful to use more concentrated, for example -10 to 50% aqueous ammonia. but you can also implement the implementation with more dilute, for example 10 to 20% ammonia.
It is advantageous to carry out the treatment in the presence of catalysts, in particular copper compounds. <I> Example 1: </I> 100 parts are heated 2. 3-dichloroanthraquinone with 400 parts of 50% aqueous ammonia and 3 parts of copper sulfate at 205 ° C. for 24 hours. After cooling, it is suctioned off, the residue is washed with water and dried. If desired, the reaction product can be purified by fractional precipitation from its solution in concentrated sulfuric acid.
Example <I> 2: </I> 100 parts of 2. 3-dichloroanthraquinone are heated to 200 ° C. for 30 hours in a stirrer autoclave with 2000 parts of 25% ammonia and 10 parts of crystallized copper sulfate. Working up he follows as in Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE179955X | 1933-06-21 | ||
| CH176028T | 1934-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH179955A true CH179955A (en) | 1935-09-30 |
Family
ID=25719779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH179955D CH179955A (en) | 1933-06-21 | 1934-05-26 | Process for the production of 2,3-diaminoanthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH179955A (en) |
-
1934
- 1934-05-26 CH CH179955D patent/CH179955A/en unknown
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