CH117776A - Process for the preparation of 1.1'-dianthraquinonyl-2.2'-dialdehyde. - Google Patents
Process for the preparation of 1.1'-dianthraquinonyl-2.2'-dialdehyde.Info
- Publication number
- CH117776A CH117776A CH117776DA CH117776A CH 117776 A CH117776 A CH 117776A CH 117776D A CH117776D A CH 117776DA CH 117776 A CH117776 A CH 117776A
- Authority
- CH
- Switzerland
- Prior art keywords
- dialdehyde
- preparation
- anthraquinone
- aldehyde
- dianthraquinonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- -1 copper halide Chemical class 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- LYVWMIHLNQLWAC-UHFFFAOYSA-N [Cl].[Cu] Chemical compound [Cl].[Cu] LYVWMIHLNQLWAC-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung des 1.1'-Diantlu achinonyl-2. 2'-dialdehyds. Im Schweizer Patent 56600 ist ein Ver fahren zur Darstellung von 1 .1'-Dianthrachi- nonyl-2.2'-dialdehyd beschrieben, das darin besteht, dass 1-Chlor-2-anthrachinonaldehyd mit halogenabspaltenden Dritteln, beispiels weise metallischem Kupfer behandelt wird.
Es hat sich nun gezeigt; dass der 1.1'- Diantbrachinonyl-2.2'-dialdehyd aus dem 1- Amino-2-anthrachinonaldehyd hergestellt wer den kann. Man verfährt zum Beispiel in der Weise, dass man die Diazoverbindung des 1-Amino-2-anthrachinonaldehyds in gelöster oder suspendierter Form mit einem Kupfer halogenür in Gegenwart von Wasser als Ver dünnungsmittel behandelt.
Statt des fertigen gupferhalogenürs kann man mit dem gleichen Erfolg auch ein Gemisch eines Cuprisalzes mit einem Reduktionsmittel verwenden, in welchem vor oder während der Reaktion Kupferhalogenür entsteht.
Beispiel: 10 Teile 1-Amino-2-anthrachinonaldehyd werden in schwefelsaurer Lösung diazotiert. Man verdünnt diese Lösung mit Eiswasser und lässt sie unter Rühren bei 90-9"0 in eine Kupferchlorürlauge einfliessen, die man durch Kochen einer Lösung von 17 Teilen Kupfersulfat, 8 Teilen Kochsalz und 7 Teilen Natriumbisulfit in 1000 Teilen Wasser bis zur Entfärbung und zum Aufhören der Ent wicklung von schwefliger Säure hergestellt hat. Der abgeschiedene Dialdehyd wird heiss abgesaugt und mit heissem Wasser ausge waschen.
Er kann durch Auskochen mit organischen Lösungsmitteln, beispielsweise Aceton, oder durch Umkristallisieren aus hoch siedenden Lösungsmitteln gereinigt werden.
Process for the preparation of the 1,1'-diantluoroquinonyl-2. 2'-dialdehyde. In the Swiss patent 56600 a process for the preparation of 1 .1'-Dianthraquinoneyl-2.2'-dialdehyde is described, which consists in that 1-chloro-2-anthraquinone aldehyde is treated with halogen-releasing thirds, for example metallic copper.
It has now been shown; that the 1.1'-diantbrachinonyl-2.2'-dialdehyde from the 1-amino-2-anthraquinone aldehyde can be produced. The procedure is, for example, that treating the diazo compound of 1-amino-2-anthraquinone aldehyde in dissolved or suspended form with a copper halogenur in the presence of water as a diluent.
Instead of the finished copper halide, a mixture of a cupric salt with a reducing agent can be used with the same success, in which copper halide is formed before or during the reaction.
Example: 10 parts of 1-amino-2-anthraquinone aldehyde are diazotized in a sulfuric acid solution. This solution is diluted with ice water and allowed to flow into a copper chlorine liquor with stirring at 90-9 "0, which is obtained by boiling a solution of 17 parts of copper sulfate, 8 parts of common salt and 7 parts of sodium bisulfite in 1000 parts of water until discoloration and cessation the development of sulphurous acid. The deposited dialdehyde is sucked off with hot water and washed out with hot water.
It can be cleaned by boiling with organic solvents, for example acetone, or by recrystallization from high-boiling solvents.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE117776X | 1924-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH117776A true CH117776A (en) | 1926-12-01 |
Family
ID=5655299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH117776D CH117776A (en) | 1924-08-20 | 1925-07-28 | Process for the preparation of 1.1'-dianthraquinonyl-2.2'-dialdehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH117776A (en) |
-
1925
- 1925-07-28 CH CH117776D patent/CH117776A/en unknown
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