DE224589C - - Google Patents

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Publication number
DE224589C
DE224589C DE1908224589D DE224589DA DE224589C DE 224589 C DE224589 C DE 224589C DE 1908224589 D DE1908224589 D DE 1908224589D DE 224589D A DE224589D A DE 224589DA DE 224589 C DE224589 C DE 224589C
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DE
Germany
Prior art keywords
red
mercaptan
anthraquinone
ether
parts
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Expired - Lifetime
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DE1908224589D
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German (de)
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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

KAISERLICHESIMPERIAL

PATENTAMT.PATENT OFFICE.

KLASSE 226. GRUPPE 2/3.CLASS 226. GROUP 2/3.

In der Patentschrift 116951 ist ein Verfahren zur Darstellung von Mercaptanätherri der Anthracenreihe beschrieben, welches darin besteht, daß man auf Nitroanthrachinone aromatische Mercaptane einwirken läßt.In patent specification 116951 is a method for the representation of mercaptan ether of the anthracene series described, which therein consists in allowing aromatic mercaptans to act on nitroanthraquinones.

Es wurde nun gefunden, daß man bei Anwendung der technisch leichter zugänglichen aliphatischen Mercaptane zu den Anthrachinonmercaptanalkyläthern gelangen kann, die sich als Farbstoffe durch ihre tiefere bzw. blauere Nuance vor den entsprechenden Aryläthern auszeichnen. Man kann ferner ganz allgemein negativ substituierte Anthrachinonderivate, also außer den Nitrokörpern Halogenverbindungen, Sulfosäuren usw. der bezeichneten Reaktion unterwerfen.It has now been found that when using the technically more accessible aliphatic mercaptans can reach the anthraquinone mercaptan alkyl ethers, which as dyes due to their deeper or bluer shade in front of the corresponding aryl ethers distinguish. You can also generally negatively substituted anthraquinone derivatives, thus, apart from the nitro bodies, halogen compounds, sulfonic acids, etc. of the designated ones Submit reaction.

Beispiel i.Example i.

10 Teile i-Amino-4-chloranthrachinon werden mit einer Lösung von 3 Teilen Äthylmercaptan und 2 Teilen Natriummetall in 100 Teilen Alkohol im Autoklaven 6 Stunden auf 75 ° erwärmt. Der i-Amino-4-mercaptanäthyläther, welcher sich beim Erkalten abscheidet, wird abgesaugt und aus Pyridin umkristallisiert.10 parts of i-amino-4-chloroanthraquinone will be with a solution of 3 parts of ethyl mercaptan and 2 parts of sodium metal in 100 parts Alcohol heated to 75 ° in the autoclave for 6 hours. The i-amino-4-mercaptan ethyl ether, which separates out on cooling is filtered off with suction and recrystallized from pyridine.

Analoge Produkte erhält man z. B. aus ι -Benzoylamino^-chloranthrachinon, 1 - Acetylamino - 4 - nitroanthrachinon, 1 -Amino - 2 · 4 - dibromanthrachinon, 1. 5-Diamino-4 · 8-dichloranthrachinon. Eigenschaften siehe Tabelle.Similar products are obtained z. B. from ι -Benzoylamino ^ -chloranthraquinone, 1 - acetylamino - 4 - nitroanthraquinone, 1-amino - 2 · 4 - dibromoanthraquinone, 1. 5-diamino-4 · 8-dichloroanthraquinone. See table for properties.

Der i-Benzoylamino-4-mercaptanäther und i-Acetylamino-4-mercaptanäther färben Wolle und Baumwolle in der Küpe rot.The i-Benzoylamino-4-mercaptanether and i-Acetylamino-4-mercaptan ether dye wool and cotton in the vat red.

Beispiel 2.Example 2.

10 Teile anthrachinon-i · 5-disulfosaures Natron werden mit einer Lösung von 2,5 Teilen Mercaptan in 20 Teilen Natronlauge von 340 Be. und 400 Teilen Wasser so lange auf 6o° erwärmt, bis keine unveränderte Anthrachinondisulfosäure mehr nachweisbar ist. Man läßt erkalten und saugt ab. Das Reaktionsprodukt besteht aus anthrachmon-i-mercaptanäther-5-sulfosaurem Natron neben Anthrachinon-i · 5-. dimercaptanäther, welche durch Umlösen aus heißem Wasser, worin letzterer unlöslich ist, getrennt werden. Das anthrachinon-i-mercaptanäther-5-sulfosaure Natron färbt Wolle in saurem Bade gelb.10 parts of anthraquinone-i · 5-disulfosaures soda with a solution of 2.5 parts of mercaptan in 20 parts of sodium hydroxide solution of 0 34 Be. and 400 parts of water heated to 60 ° until unchanged anthraquinone disulfonic acid can no longer be detected. Let it cool down and suck it off. The reaction product consists of anthraquinone-i-mercaptanether-5-sulfonic acid soda in addition to anthraquinone-i · 5-. dimercaptan ethers, which are separated by dissolving them from hot water in which the latter is insoluble. The anthraquinone-i-mercaptan-ether-5-sulfo acid dyes wool yellow in an acid bath.

Ersetzt man das anthrachinondisulfosaure Natron durch i-chlor-4-nitroanthrachinon-8-sulfosaures Kali (erhältlich durch Nitrieren der in der Patentschrift 205913, Beispiel 3, beschriebenen i-Chloranthrachinon-8-sulfosäure) und steigert die Temperatur auf etwa 95 °, so erhält man die Anthrachinon-i · 4-dimercaptanäther-8-sulfosäure, die sich als schwer lösliches Natronsalz in roten Nadeln abscheidet. Sie färbt Wolle in saurem Bade schön blaustichig rot.If you replace the anthraquinone disulfonic acid soda with i-chloro-4-nitroanthraquinone-8-sulfosaures Potash (obtainable by nitriding those described in Patent Specification 205913, Example 3 i-chloroanthraquinone-8-sulfonic acid) and increases the temperature to about 95 °, see above one obtains the anthraquinone-i · 4-dimercaptanether-8-sulfonic acid, which is deposited as a poorly soluble sodium salt in red needles. she dyes wool in an acidic bath with a beautiful bluish red tint.

Wie Äthylmercaptan verhalten sich die anderen aliphatischen Mercaptane, wie Methylmercaptan, Thioglykolsäure usw.The other aliphatic mercaptans behave like ethyl mercaptan, such as methyl mercaptan, Thioglycolic acid, etc.

In der folgenden Tabelle sind die Eigenschaften einer Anzahl der neuen Produkte angegeben: The following table shows the characteristics of a number of the new products:

AussehenAppearance Lösung
in
Chloroformsolution
in
chloroform Lösung
in konz.
Schwefelsäuresolution
in conc.
sulfuric acid i-Aminoanthrachinon-4-mercaptanätheri-Aminoanthraquinone-4-mercaptan ether bronzeglän
zende Prismenbronze gloss
prisms violettrotpurple red schmutzig blaudirty blue i-Benzoylaminoanthrachinon-4-mercaptanätheri-Benzoylaminoanthraquinone-4-mercaptan ether bronzige
Nadelnbronzy
Needles rotRed grüngreen i-Acetylaminoanthrachinon^-mercaptanätheri-Acetylaminoanthraquinone ^ mercaptan ether rote
KristalleRed
Crystals rotRed grüngreen ι-Aminoanthrachinon-2 · 4-dimercaptanätherι-Aminoanthraquinone-2 · 4-dimercaptanether granatrote
Blättchengarnet red
Leaflets rotviolettred-violet rotviolettred-violet ι · s-Diaminoanthrachinon^ · 8-dimercaptanätherι · s-Diaminoanthraquinone ^ · 8-dimercaptan ether stahlblaue
Blättchensteel blue
Leaflets violettviolet rotRed Anthrachinon-1 -mercaptanäther-5-sulfosaures
NatronAnthraquinone-1-mercaptan ether-5-sulfosaures
Baking soda orangefarbene
Blättchenorange
Leaflets orangegelb
(in Wasser)orange yellow
(in water) schmutzig violettdirty purple ι · 5-Anthrachinondimercaptanätherι · 5-anthraquinone dimercaptan ether gelbe
Blättchenyellow
Leaflets gelbyellow grüngreen Anthrachinon-1 · 4-dimercaptanäther-8-sulfosaures
NatronAnthraquinone-1 · 4-dimercaptanether-8-sulfosaures
Baking soda rote
NadelnRed
Needles rot
(in Wasser)Red
(in water) schmutzig violett.dirty purple.

Claims (1)

Patent-Anspruch : Verfahren zur Darstellung von Farbstoffen der Anthracenreihe, darin bestehend,Patent claim: Process for the preparation of dyes of the anthracene series, consisting of daß man auf negativ substituierte Anthrachinonderivate aliphatische Mercaptane einwirken läßt.that negatively substituted anthraquinone derivatives act on aliphatic mercaptans leaves.
DE1908224589D 1908-12-14 1908-12-14 Expired - Lifetime DE224589C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE224589T 1908-12-14

Publications (1)

Publication Number Publication Date
DE224589C true DE224589C (en)

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ID=8897574

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DE1908224589D Expired - Lifetime DE224589C (en) 1908-12-14 1908-12-14

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DE (1) DE224589C (en)
FR (1) FR410152A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998055446A1 (en) * 1997-06-03 1998-12-10 Eastman Chemical Company Process for the preparation of thioether-substituted aromatic ketones
US6096929A (en) * 1998-06-02 2000-08-01 Eastman Kodak Company Process for the preparation of thioether-substituted aromatic ketones
US6143935A (en) * 1997-06-03 2000-11-07 Eastman Chemical Company Process for the preparation of 1,3-dicarbonyl compounds
US6229051B1 (en) 1997-06-03 2001-05-08 Eastman Chemical Company Catalyst for oxidative NEF reaction using basic hydrogen peroxide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998055446A1 (en) * 1997-06-03 1998-12-10 Eastman Chemical Company Process for the preparation of thioether-substituted aromatic ketones
US6100431A (en) * 1997-06-03 2000-08-08 Eastman Chemical Company Process for the preparation of thioether-substituted aromatic ketones
US6143935A (en) * 1997-06-03 2000-11-07 Eastman Chemical Company Process for the preparation of 1,3-dicarbonyl compounds
US6229051B1 (en) 1997-06-03 2001-05-08 Eastman Chemical Company Catalyst for oxidative NEF reaction using basic hydrogen peroxide
US6096929A (en) * 1998-06-02 2000-08-01 Eastman Kodak Company Process for the preparation of thioether-substituted aromatic ketones

Also Published As

Publication number Publication date
FR410152A (en) 1910-05-13

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