CH133699A - Process for the preparation of dichloroisodibenzanthrone. - Google Patents
Process for the preparation of dichloroisodibenzanthrone.Info
- Publication number
- CH133699A CH133699A CH133699DA CH133699A CH 133699 A CH133699 A CH 133699A CH 133699D A CH133699D A CH 133699DA CH 133699 A CH133699 A CH 133699A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- chlorobenzanthronyl
- water
- dichloroisodibenzanthrone
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/22—Dibenzanthrones; Isodibenzanthrones
- C09B3/24—Preparation by synthesis of the nucleus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Dichlorisodibenzanthron. In dem Hauptpatent 119233 ist ein Ver fahren zur Darstellung von Isodibenzanthron beschrieben, bei dem Bz1.Bz1'-Benzanthronyl- sulfid mit einem alkalischen Kondensations mittel behandelt wird, und gemäss dem Zu satzpatent Nr.
129191 erhält man 6.6'-Di- chlorisodibenzanthron dadurch, dass man das durch Einwirkung von Alkalipolysulfid auf 6-Chlor-Bz l-halogenbenzanthron erhältliche Dichlor-Bz1.Bz1'-benzanthronylsulfid mit al kalischen Kondensationsmitteln behandelt.
Es wurde nun gefunden, dass man das 6-6'Dichlorisodibenzanthron ebenfalls erhalten kann, wenn man ein solches 6-Chlorbenzan- thronylsulfid, das ausser dem 6-Chlorbenzan- thronylrest einen organischen Rest mit weniger als 17 Kohlenstoffatomen an das Schwefelatom gebunden enthält, mit einem alkalischen Kondensationsmittel, insbesondere alkoholischen Alkalien, behandelt.
Das in der üblichen Weise aufgearbeite Reaktionsgemisch liefert einen Farbstoff, der ein dunkelviolettes Pulver darstellt, das sich in Schwefelsäure mit grüner Farbe löst und aus blauer Hydro- sulfitküpe Baumwolle in blaustichigvioletten Tönen färbt. Die Färbungen zeichnen sich dadurch besonders aus, dass sie beim Befeuch ten mit Wasser praktisch nicht nach Rot umschlagen, im Gegensatz zu den mit Iso- dibenzanthron und seinen bisher bekannten Halogensubstitutionsprodukten erhältlichen Färbungen.
Der Farbstoff kann durch Auflösen in hochprozentiger Schwefelsäure, zum Beispiel Schwefelsäuremonohydrat und Verdünnen der Lösung mit Wasser, zweckmässig, durch Zu satz von mässig verdünnter Schwefelsäure leicht gereinigt werden.
<I>Beispiel:</I> 375 Teile Kaliumhydro$yd werden zu sammen mit 300 Teilen Äthylalkohol auf 140 erhitzt werden und solange gerührt, bis eine klare Schmelze entstanden ist. Hierauf lässt man auf<B>1100</B> abkühlen und trägt bei <B>110-1150</B> 75 Teile 6-Chlorbenzanthron-Bzl- p-thiol-resyläther vom Schmelzpunk 208 bis <B>205'</B> (erhalten durch 10-stündiges Erhitzen von 6-Bzl-Dichlorbenzanthron mit der be rechneten Menge p-Thiokresol und einem Überschuss von Pottasche in Trichlorbenzol bei 210-215 )
ein und rührt noch 2 Stunden bei 210-2150. Sodann verdünnt man die Schmelze mit viel Wasser, kocht auf und bläst den Farbstoff mit Luft aus. Der rohe Farbstoff wird abfiltriert und getrocknet. Zur Reinigung wird er in 10 Teilen Schwefel säuremonohydrat pro Teil Farbstoff gelöst und durch Zugabe von 5 Teilen Schwefel säure von 60 B6 pro Teil Farbstoff bei 70 fraktioniert gefällt.
Process for the preparation of dichloroisodibenzanthrone. In the main patent 119233 a process for the preparation of isodibenzanthrone is described in which Bz1.Bz1'-benzanthronyl sulfide is treated with an alkaline condensation agent, and according to the additional patent no.
129191, 6.6'-dichloroisodibenzanthrone is obtained by treating the dichloro-Bz1.Bz1'-benzanthronyl sulfide, which is obtained by the action of alkali polysulfide on 6-chloro-Bz 1-halobenzanthrone, with alkaline condensation agents.
It has now been found that 6-6'Dichlorisodibenzanthron can also be obtained if such a 6-chlorobenzanthronyl sulfide, which, in addition to the 6-chlorobenzanthronyl radical, contains an organic radical with fewer than 17 carbon atoms bonded to the sulfur atom treated with an alkaline condensing agent, in particular alcoholic alkalis.
The reaction mixture, worked up in the usual way, yields a dye which is a dark violet powder which dissolves in sulfuric acid with a green color and, from a blue hydrosulfite vat, dyes cotton in bluish violet tones. The colorations are particularly distinguished by the fact that they practically do not turn red when moistened with water, in contrast to the colorations obtainable with isodibenzanthrone and its previously known halogen substitution products.
The dye can be easily purified by dissolving it in high-percentage sulfuric acid, for example sulfuric acid monohydrate, and diluting the solution with water, expediently, by adding moderately dilute sulfuric acid.
<I> Example: </I> 375 parts of potassium hydroxide are heated to 140 together with 300 parts of ethyl alcohol and stirred until a clear melt has formed. It is then allowed to cool to <B> 1100 </B> and <B> 110-1150 </B> 75 parts of 6-chlorobenzanthrone-Bzl-p-thiol resyl ether with melting point 208 to <B> 205 ' B> (obtained by heating 6-Bzl-dichlorobenzanthrone for 10 hours with the calculated amount of p-thiocresol and an excess of potash in trichlorobenzene at 210-215)
and stir for a further 2 hours at 210-2150. The melt is then diluted with plenty of water, boiled and the dye is blown out with air. The crude dye is filtered off and dried. To clean it, it is dissolved in 10 parts of sulfuric acid monohydrate per part of dye and fractionally precipitated at 70 by adding 5 parts of sulfuric acid of 60 B6 per part of dye.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH119233T | 1927-12-05 | ||
| CH133699T | 1927-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133699A true CH133699A (en) | 1929-06-15 |
Family
ID=25709229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133699D CH133699A (en) | 1927-12-05 | 1927-12-05 | Process for the preparation of dichloroisodibenzanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133699A (en) |
-
1927
- 1927-12-05 CH CH133699D patent/CH133699A/en unknown
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