CH259352A - Process for the preparation of an anthraquinone derivative. - Google Patents
Process for the preparation of an anthraquinone derivative.Info
- Publication number
- CH259352A CH259352A CH259352DA CH259352A CH 259352 A CH259352 A CH 259352A CH 259352D A CH259352D A CH 259352DA CH 259352 A CH259352 A CH 259352A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- anilido
- amino
- derivative
- exchangeable
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/60—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic radicals
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 253480. Verfahren zur Herstellung eines Anthraehinonabkömmlings. Es wurde gefunden, dass ein wertvoller Anthrachinonabkömmling hergestellt werden kann, wenn man ein in 2-,Stellung einen aus tauschbaren Substituenten enthaltendes 1- Amino-4-anilido-anthra,chinon mit Mitteln behandelt, die den austauschbaren Substi- tuenten durch eine Merkaptogruppe zu erset zen imstande sind und hierauf mit Mitteln, die die ss,
y-Dioxypropylgruppe einzuführen imstande sind.
Der neue Anthrachinonabkömmling, der 1- Amino - -anilido =anthrachinon@- 2-(ss,y-di- oxypropyl)-thioäther ist ein dunkelblaues Pulver, das sich in konz. Schwefelsäure, ganz verdünnt mit schmutzig grünlichblauer, bei höherer Konzentration mit rotstichig blauer Farbe und in Aceton mit blauer Farbe löst und Acetatkunstseide in kräftigen und licht echten blauen Tönen färbt.
Die als Ausgangsstoffe verwendeten 1 Amino-4-anilido-anthrachinone können als austauschbare Substituenten in 2-Stellung beispielsweise ein Halogenatom, insbesondere ein Bromatom, oder eine Sulfonsäuregruppe, enthalten. Als Mittel, die den austauschbaren Substituenten durch eine lvlerkaptogruppe zu ersetzen imstande sind, kommen beispiels weise Schwefelalkalien in Betracht, und zur Einführung der ss,y-Dioxypropylgruppe ist beispielsweise Glyzerinchlorhydrin brauch bar.
Die Durchführung der Reaktion kann in an sich bekannter Weise zum Beispiel in alko- holischem, wässerigem oder gemischt alkoho- lisch-wässerigem Medium, offen. oder unter Druck vorgenommen werden.
<I>Beispiel:</I> 100 g 1- Amino -- 4 - anilido-2-bromanthra- ehinon werden zusammen mit 300 cm' Me thylalkohol, 75 cm' Wasser, 0,75 g Soda, 200 em3 Natriumsulfhydratlösung mit einem Gehalt an 24,6 Vol.- % -j-- 3,6 % Na2S, 100 cm' 40 Vol.-%iger Natronlauge und 50 g Schwe fel 5 Stunden in einem Eisenautoklaven auf 90 erhitzt.
Man destilliert den Alkohol ab, spült mit 400 cm2 1 % iger Sodalösung nach, fällt das Merkaptan mit 200 g Kochsalz aus, kühlt wenn nötig auf 10 bis 15 und filtriert. Das Filtrat ist nur schwach gefärbt, aber nicht mehr blau. Man wäscht mit 800 cm' einer Lösung von 20 % Kochsalz und 1 Soda. frei von S-Ionen (Probe mit Bleiacetat).
Hierauf wird das Merkaptan sofort in 1000 cm' 1 % iger Sodalösung mit 30 cm' Glyzerinchlorhydrin erwärmt, bis die Lösung farblos wird (bei etwa 70 ), worauf man fil triert und mit. Wasser kalt auswäscht.
<B> Additional patent </B> to the main patent No. 253480. Process for the production of an anthraquinone derivative. It has been found that a valuable anthraquinone derivative can be produced if a 1-amino-4-anilido-anthra-quinone containing one of exchangeable substituents in the 2-, position is treated with agents which add a mercapto group to the exchangeable substituents are able to replace and then with funds that the SS,
are able to introduce y-dioxypropyl group.
The new anthraquinone derivative, the 1- amino - -anilido = anthraquinone @ - 2- (ss, y-di-oxypropyl) -thioether is a dark blue powder which is in conc. Sulfuric acid, completely diluted with dirty greenish-blue, dissolves in a higher concentration with a reddish blue color and in acetone with a blue color and dyes acetate silk in strong and light blue tones.
The 1-amino-4-anilido-anthraquinones used as starting materials can contain, for example, a halogen atom, in particular a bromine atom, or a sulfonic acid group, as exchangeable substituents in the 2-position. Suitable agents which are capable of replacing the exchangeable substituent with an intercapto group are, for example, alkaline sulfur, and glycerol chlorohydrin, for example, can be used to introduce the ε, γ-dioxypropyl group.
The reaction can be carried out in a manner known per se, for example in an alcoholic, aqueous or mixed alcoholic-aqueous medium, open. or under pressure.
<I> Example: </I> 100 g 1-amino-4-anilido-2-bromanthrahinone are mixed with 300 cm 'methyl alcohol, 75 cm' water, 0.75 g soda, 200 em3 sodium sulfhydrate solution with a Content of 24.6% by volume - 3.6% Na2S, 100 cm '40% by volume sodium hydroxide solution and 50 g sulfur heated to 90 for 5 hours in an iron autoclave.
The alcohol is distilled off, rinsed with 400 cm2 of 1% soda solution, the mercaptan is precipitated with 200 g of table salt, cooled to 10 to 15 if necessary and filtered. The filtrate is only slightly colored, but no longer blue. It is washed with 800 cm 'of a solution of 20% table salt and 1 soda. free of S ions (sample with lead acetate).
The mercaptan is then immediately heated in 1000 cm '1% sodium carbonate solution with 30 cm' glycerol chlorohydrin until the solution becomes colorless (at about 70), whereupon it is filtered and with. Washes cold water.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH259352T | 1944-01-13 | ||
CH253480T | 1944-01-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259352A true CH259352A (en) | 1949-01-15 |
Family
ID=25729761
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259352D CH259352A (en) | 1944-01-13 | 1944-01-13 | Process for the preparation of an anthraquinone derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259352A (en) |
-
1944
- 1944-01-13 CH CH259352D patent/CH259352A/en unknown
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