CH184186A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH184186A CH184186A CH184186DA CH184186A CH 184186 A CH184186 A CH 184186A CH 184186D A CH184186D A CH 184186DA CH 184186 A CH184186 A CH 184186A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- anthraquinone series
- anthraquinone
- preparation
- soluble
- 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 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- YZXAXYKZKHTDAM-UHFFFAOYSA-N 1,4-dichloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=CC(Cl)=C3C(=O)C2=C1 YZXAXYKZKHTDAM-UHFFFAOYSA-N 0.000 description 1
- CAHGWVAXFJXDNI-UHFFFAOYSA-N 1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2Cl CAHGWVAXFJXDNI-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes der Anthraehinonreihe. Das Hauptpatent betrifft ein Verfahren zur Herstellung eines Farbstoffes der An- thrachinonreihe, bei dem der 1 .4-Di-p-tol- uidinoanthrachinon - 2 - cabonsäuremethylester solange mit einem sulfonierend wirken den Mittel behandelt wird, bis eine aufge arbeitete Probe völlig wasserlöslich gewor den ist.
Es wurde nun gefunden,, da3 man einen ähnlich wertvollen Farbstoff der Anthra.- chinonreihe erhalten kann, wenn man den 1 . 4-Di-(p-cycloheay lanilino)-anthrachinon- 2--carbonsäuremethylester solange mit einem sulfonierend wirkenden Mittel behandelt, bis eine aufgearbeitete Probe völlig wasserlös lich geworden ist.
Der erhaltene Farbstoff färbt Wolle aus schwach saurem Bade in klaren gelbstichig grünen Tönen von ausgezeichneten Echt- heitseigenschaften. Beispiel: 5 Teile <B>1.</B> 4-Di-(p-cyclohegylanilino)-an- thrachinon-2-carbonsäuremethylester (herge stellt zum Beispiel :durch Erhitzen des 1. 4- Dichloranthrachinon;
- 2 - carbonsäuremethyl- esters, der aus 1-Amino-2-methyl-4-chloran- thrachinon durch Diazotieren, Umsetzung der erhaltenen Diazoverbindung nach Sand meyer mit Kupferchlorür, Oxydation des so erhaltenen 1.4-Dichlor-2-methylanthrachi- nonsmit Braunstein in Schwefelsäure und anschliessende Veresterung gewonnen werden kann,
mit p-Cyclohegylanilin bei Gegenwart von wasserfreiem Natriumacetat und Kupfer acetat auf<B>150'</B> C) werden in 50 Teilen Schwefelsäuremonohydrat gelöst und bei einer Temperatur von etwa <B>10'</B> C so lange mit rauchender Schwefelsäure, enthaltend 23% S03, behandelt, bis eine aufgearbeitete Probe eben völlig wasserlöslich geworden ist. Man giesst danach auf Eis und salzt den ent standenen Farbstoff in der üblichen Weise aus.
Process for the preparation of a dye of the anthraquinone series. The main patent relates to a process for the production of a dye of the anthraquinone series, in which the 1 .4-di-p-toluidinoanthraquinone - 2 - cabonic acid methyl ester is treated with a sulfonating agent until a processed sample is completely water-soluble that is.
It has now been found that a similarly valuable dye of the anthraquinone series can be obtained if the 1. 4-Di- (p-cycloheay lanilino) -anthraquinone- 2- carboxylic acid methyl ester treated with a sulfonating agent until a processed sample has become completely water-soluble.
The dye obtained dyes wool from a weakly acidic bath in clear, yellowish green shades with excellent fastness properties. Example: 5 parts of methyl 4-di- (p-cyclohegylanilino) -anthrachinone-2-carboxylate (prepared for example: by heating the 1,4-dichloroanthraquinone;
- 2 - carboxylic acid methyl ester, which is derived from 1-amino-2-methyl-4-chloranothrachinone by diazotization, reaction of the resulting diazo compound according to Sand meyer with copper chloride, oxidation of the 1,4-dichloro-2-methylanthraquinone thus obtained with manganese dioxide in Sulfuric acid and subsequent esterification can be obtained,
with p-Cyclohegylaniline in the presence of anhydrous sodium acetate and copper acetate at <B> 150 '</B> C) are dissolved in 50 parts of sulfuric acid monohydrate and at a temperature of about <B> 10' </B> C for so long with smoking Sulfuric acid, containing 23% SO3, treated until a processed sample has just become completely water-soluble. It is then poured onto ice and the dye formed is salted out in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE184186X | 1934-02-01 | ||
| CH180697T | 1935-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184186A true CH184186A (en) | 1936-05-15 |
Family
ID=25720455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184186D CH184186A (en) | 1934-02-01 | 1935-01-16 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH184186A (en) |
-
1935
- 1935-01-16 CH CH184186D patent/CH184186A/en unknown
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