CH148493A - Process for the preparation of a new dye of the anthraquinone acridone series. - Google Patents
Process for the preparation of a new dye of the anthraquinone acridone series.Info
- Publication number
- CH148493A CH148493A CH148493DA CH148493A CH 148493 A CH148493 A CH 148493A CH 148493D A CH148493D A CH 148493DA CH 148493 A CH148493 A CH 148493A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new dye
- parts
- carboxylic acid
- series
- Prior art date
Links
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 3
- -1 anthraquinone acridone series Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- SRYYQKDDYORYLD-UHFFFAOYSA-N O=C(C(C=C(C(C(C1=CC=CC=C11)=O)=C2C1=O)Cl)=C2Cl)OCC1=CC=CC=C1 Chemical compound O=C(C(C=C(C(C(C1=CC=CC=C11)=O)=C2C1=O)Cl)=C2Cl)OCC1=CC=CC=C1 SRYYQKDDYORYLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- DQNOIKMHTBFYTD-UHFFFAOYSA-N n,n,2,3-tetrachloroaniline Chemical compound ClN(Cl)C1=CC=CC(Cl)=C1Cl DQNOIKMHTBFYTD-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001256 steam distillation Methods 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 Darstellung eines neuen Farbstoffes der Antbrachinonaki#idonreihe. Es wurde gefunden, dass man einen neuen Farbstoff der Anthrachinonakridonreihe er halten kann, wenn man die 1-Tetrachlorani- lido-4-chloranthrachinon-2-carbonsäure, die durch Kondensation der 1 .4-Dichloranthra- chinon-2-carbonsäurebenzylester mit 2.3.4.5 Tetrachloranilin und Verseifung des entstan denen Esters hergestellt werden kann, mit wasserentziehenden Mitteln behandelt.
Der neue Farbstoff löst sich in konzen trierter Schwefelsäure mit orangeroter Farbe und liefert eine violette güpe, aus der Baum wolle in leuchtenden, blaustichigen Rosatönen gefärbt wird.
<I>Beispiel:</I> 22 Teile 1.4-Dichloranthrachinon-2-car- bonsäurebenzylester werden mit 10 Teilen 2 . 3 . 4. 5-Tetrachloranilin, 6 Teilen wasser freiem Natriumacetat, 0,3 Teilen Kupferoxyd und 25 Teilen Nitrobenzol 41/2 Stunden lang auf 180 bis 190 erwärmt. Nach dem Ab- kühlen trägt man die Schmelze in 200 Teile konzentrierte Schwefelsäure ein und rührt 1 Stunde lang bei 35 bis 40 C. Alsdann wird die Lösung in Wasser gegossen und das Nitrobenzol mit Wasserdampf abgetrieben.
22 Teile des erhaltenen Produktes werden mit 80 Teilen trockenem Nitrobenzol und 10 Teilen Essigsäurcanhydrid 1?#q Stunden lang bei 140 bis 145 C verrührt; darauf wird die Schmelze mit 80 Teilen trockenem Nitrobenzol verdünnt, worauf man bei 95 bis 100 C langsam 2,5 Teile konzentrierte Schwefelsäure hinzufügt. Man hält die Tem peratur zirka 3 Stunden lang auf gleicher Flöhe, lässt darnach erkalten und saugt das Reaktionsprodukt ab. Es wird mit Nitro- benzol gewaschen und durch Wasserdampf destillation von Nitrobenzol befreit.
Process for the preparation of a new dye of the Antbrachinonaki #idon series. It has been found that a new dye of the anthraquinone acridone series can be obtained if the 1-tetrachloroanilido-4-chloroanthraquinone-2-carboxylic acid is obtained by condensation of the 1,4-dichloroanthraquinone-2-carboxylic acid benzyl ester with 2.3. 4.5 Tetrachloroaniline and saponification of the resulting ester can be produced, treated with dehydrating agents.
The new dye dissolves in concentrated sulfuric acid with an orange-red color and produces a purple color from which cotton is dyed in bright, bluish pink tones.
<I> Example: </I> 22 parts of 1,4-dichloroanthraquinone-2-carboxylic acid benzyl ester are mixed with 10 parts of 2. 3. 4. 5-tetrachloroaniline, 6 parts of anhydrous sodium acetate, 0.3 parts of copper oxide and 25 parts of nitrobenzene were heated to 180-190 for 41/2 hours. After cooling, the melt is poured into 200 parts of concentrated sulfuric acid and stirred for 1 hour at 35 to 40 ° C. The solution is then poured into water and the nitrobenzene is driven off with steam.
22 parts of the product obtained are stirred with 80 parts of dry nitrobenzene and 10 parts of acetic anhydride for 1? #Q hours at 140 to 145 ° C .; The melt is then diluted with 80 parts of dry nitrobenzene, whereupon 2.5 parts of concentrated sulfuric acid are slowly added at 95 to 100.degree. The temperature is kept at the same level for about 3 hours, then left to cool and the reaction product is filtered off with suction. It is washed with nitrobenzene and freed from nitrobenzene by steam distillation.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE148493X | 1929-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH148493A true CH148493A (en) | 1931-07-31 |
Family
ID=5672735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148493D CH148493A (en) | 1929-04-29 | 1930-04-08 | Process for the preparation of a new dye of the anthraquinone acridone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH148493A (en) |
-
1930
- 1930-04-08 CH CH148493D patent/CH148493A/en unknown
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