CH285995A - Process for the preparation of an anthraquinone vat dye. - Google Patents
Process for the preparation of an anthraquinone vat dye.Info
- Publication number
- CH285995A CH285995A CH285995DA CH285995A CH 285995 A CH285995 A CH 285995A CH 285995D A CH285995D A CH 285995DA CH 285995 A CH285995 A CH 285995A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- anthraquinone
- radical
- vat dye
- releases
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000984 vat dye Substances 0.000 title claims description 4
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 p-dichlorobenzoyl Chemical group 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonküpenfarbstoffes. Es wurde gefunden, da.ss man zu einem wertvollen Anthrachinonküpenfarbstoff ge langt, wenn man 1,4-Diamino-2-(m.p-diehlor- benzoyl )-anthraeliinon mit einem den p--,#le- thylbenzoylrest abgebenden Mittel behandelt.
Der neue Farbstoff, das 1-Amino-4-(p-me- thylbenzoyl-amino) -2- (m,p-dichlorbenzoyl <B>)</B> - anthraehinon, löst. sich in konz. Schwefelsäure mit grüner Farbe und liefert. auf Baumwolle reine, rotstichig blaue Töne von vorzüglieher Chlor- und Lichteehtheit.
Als den p-Methylbenzoylrest abgebende Mittel kommen vorzugsweise Halogenide, ins besondere das Chlorid der p-Methylbenzoe- säure, in Betracht. Die Umsetzung erfolgt zweekmässig in einem organischen Lösungsmit tel wie o-Dielilorbenzol und bei erhöhter Tem peratur.
gegebenenfalls unter Zusatz eines säurebindenden Mittels wie Pyridin. Nach dem vorliegenden Verfahren wird nur die in der 4-Stellung des Anthrachinonrestes befindliehe Aminogruppe in der angegebenen Weise acy - liert, während die in 1.-Stellung befindliche Aminogruppe zufolge der Anwesenheit der Ketogrnppe in 2-Stellung unverändert bleibt.
<I>Beispiel:</I> Zu einer Suspension von 3 Teilen 1,4-Di- amino-2-(m,p-diehlorbenzoyl)-anthrachinon in 90 Volumteilen o-Dichlorbenzol und 3 Volum- teilen Pyridin lässt man unter Rühren 1,7 Teile p-Methylbenzoesäurechlorid zutropfen und er hitzt darauf 1 Stunde auf 110 bis 115 . Nach dem Abkühlen auf 70 bis 80 wird der in blauen Nadeln kristallisierte Farbstoff abfil- triert und getrocknet.
Das 1.,4-Diamino-2-(in,p-dichlorbenzoyl)- anthraehinon, welches nach dem Umkristalli- sieren aus o-Diehlorbenzol blaue Nadeln vom Schmelzpunkt 243 (unkorr.) bildet, kann nach folgender Methode erhalten werden 1,4 -Diehloranthrachinon-2-carbonsäurechlorid wird nach der Friedel-Craftsschen Methode mit, o-Dichlorbenzol umgesetzt.
Das so erhält liche 1,4-Diehlor-2- (m,p-diehlorbenzoyl)-an- thrachinon wird hierauf mittels p-Toluolsul- fonsäureamid in das 1,4-Di-(p-tol.itolsulfamino)- 2-(m,p-chlorbenzovl )-anthrachinon umgewan delt und in diesem die Toluolsulfaminogrup- pen durch Behandlung mit konz. Schwefel .,Hure verseift.
Process for the preparation of an anthraquinone vat dye. It has been found that a valuable anthraquinone vat dye is obtained if 1,4-diamino-2- (m.p-diehlorbenzoyl) -anthraeliinone is treated with an agent which releases the p-, #ethylbenzoyl radical.
The new dye that dissolves 1-amino-4- (p-methylbenzoyl-amino) -2- (m, p-dichlorobenzoyl <B>) </B> - anthraehinone. in conc. Sulfuric acid with green color and supplies. on cotton pure, reddish-tinged blue tones with excellent resistance to chlorine and light.
Preferred agents for releasing the p-methylbenzoyl radical are halides, in particular the chloride of p-methylbenzoic acid. The reaction takes place in an organic solvent such as o-dielilobenzene and at an elevated temperature.
optionally with the addition of an acid-binding agent such as pyridine. According to the present process, only the amino group in the 4-position of the anthraquinone residue is acylated in the manner indicated, while the amino group in the 1-position remains unchanged due to the presence of the keto group in the 2-position.
<I> Example: </I> A suspension of 3 parts 1,4-di-amino-2- (m, p-dichlorobenzoyl) -anthraquinone in 90 parts by volume of o-dichlorobenzene and 3 parts by volume of pyridine is added with stirring 1.7 parts of p-methylbenzoic acid chloride are added dropwise and it is then heated to 110 to 115 for 1 hour. After cooling to 70 to 80, the dye which has crystallized in blue needles is filtered off and dried.
The 1st, 4-diamino-2- (in, p-dichlorobenzoyl) - anthraehinone, which after recrystallization from o-diehlobenzene forms blue needles with a melting point of 243 (uncorr.), Can be obtained by the following method: 1,4 -Diehloranthraquinone-2-carboxylic acid chloride is reacted with o-dichlorobenzene according to the Friedel-Crafts method.
The 1,4-diehlor-2- (m, p-diehlobenzoyl) -anthrachinone thus obtained is then converted into 1,4-di- (p-tol.itolsulfamino) - 2- (using p-toluenesulfonic acid amide) m, p-chlorobenzovl) -anthraquinone converted and in this the toluene sulfamino groups by treatment with conc. Sulfur., Whore saponified.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280188T | 1948-01-30 | ||
| CH285995T | 1948-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH285995A true CH285995A (en) | 1952-09-30 |
Family
ID=25731995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285995D CH285995A (en) | 1948-01-30 | 1948-12-29 | Process for the preparation of an anthraquinone vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH285995A (en) |
-
1948
- 1948-12-29 CH CH285995D patent/CH285995A/en unknown
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