AT45592B - Process for the preparation of anthraquinone derivatives. - Google Patents
Process for the preparation of anthraquinone derivatives.Info
- Publication number
- AT45592B AT45592B AT45592DA AT45592B AT 45592 B AT45592 B AT 45592B AT 45592D A AT45592D A AT 45592DA AT 45592 B AT45592 B AT 45592B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- anthraquinone
- anthraquinone derivatives
- mercaptans
- sodium
- Prior art date
Links
- 238000000034 method Methods 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 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 150000002019 disulfides Chemical class 0.000 claims description 3
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Anthrachinonderivaten.
In dem Stammpatente Nr. 41169 und dessen erstem Zusatzpatente Nr. 43879 wurde gezeigt, dass sich Halogenanthrachinone durch Einwirkung von Schwefelalkalien, wobei Halogen gegen die SH-Gruppe ausgetauscht wird, in Merkaptane bezw. die entsprechenden Disulfide überführen lassen. Lässt man statt auf Halogenanthrachinone auf Nitroanthrachinone Schwefelalkalien einwirken, so verläuft die Reaktion anders, indem kein Austausch der negativen Gruppe gegen SH, sondern Reduktion der Nitrogruppe eintritt. Nur in einem Falle (deutsche Patentschrift Nr. 73684 bezw. Nr. 77720), wo ein sehr kompliziertes Nitroanthrachinonderivat zur Anwendung gelangt, wird die Nitrogruppe durch SH ersetzt.
Es wurde nun gefunden, dass die Anthrachionsulfosäuren und deren Derivate im allgemeinen ein anderes Verhalten zeigen wie die Nitroanthrachinone, wo anscheinend noch verschiedene andere Gruppen vorhanden sein müssen um einen Austausch der Nitrogruppe zu ermöglichen, indem sie beim Behandeln mit Schwefelalkalien ein den Halogenanthrachinone analoges Verhalten zeigen und die Sulfogruppe gleichfalls unter Bildung von Merkaptanen bezw. Disulfiden austauschen.
Die so erhaltenen Merkaptane sind als Farbstoffe verwendbar.
Beispiel 1.
15 kg Ânthrachinon-oc-sulfosaures Kali werden mit 100 leg einer Lösung von Natriumsulfhydrat (280/0) und 100 kg Alkohol 24 Stunden am Rückflusskühler gekocht. Die
EMI1.1
aus dem Natriumsalz des im Zusatzpatente Nr. 43879, Beispiel I, beschriebenen 1-Thioanthrachinons und dessen Disulfid.
Beispiel II.
20 kg Anthrachinon-l b-disulfosaures Natron werden mit einer Lösung von 250 k. g kristallisiertem Schwefelnatrium in 60 kg Wasser gekocht. Die Schmelze färbt sich bald dunkel und nach Verlauf von etwa 24 Stunden hat sich das Natronsalz des 1'5-Dithio- anthrachinons vollständig abgeschieden. Man saugt letzteres ab, wäscht mit Kochsalzlösung aus und erhält es durch Umkristallisieren aus heissem, alkalihaltigem Wasser und Abscheidung mit Kochsalz in dunkelbraunen Nadeln. Sie losen sich in Alkali rotbraun, in konzentrierter Schwefelsäure rot.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of anthraquinone derivatives.
In the parent patent no. 41169 and its first additional patent no. 43879 it was shown that halogenanthraquinones are converted into mercaptans respectively by the action of sulfur alkalis, with halogen being exchanged for the SH group. let transfer the corresponding disulfides. If, instead of haloanthraquinones, alkaline nitroanthraquinones are allowed to act, the reaction proceeds differently in that there is no exchange of the negative group for SH, but a reduction of the nitro group. Only in one case (German Patent No. 73684 and No. 77720), where a very complicated nitroanthraquinone derivative is used, is the nitro group replaced by SH.
It has now been found that the anthraquinone sulfonic acids and their derivatives generally show a different behavior than the nitroanthraquinones, where apparently various other groups must also be present in order to enable the nitro group to be exchanged by showing a behavior analogous to the haloanthraquinones when treated with alkaline sulfur and the sulfo group likewise with the formation of mercaptans respectively. Exchange disulfides.
The mercaptans thus obtained can be used as dyes.
Example 1.
15 kg of anthraquinone-oc-sulfosaures Kali are boiled with 100 leg of a solution of sodium sulfhydrate (280/0) and 100 kg of alcohol for 24 hours on the reflux condenser. The
EMI1.1
from the sodium salt of the 1-thioanthraquinone described in additional patent no. 43879, Example I, and its disulfide.
Example II.
20 kg of anthraquinone-1 b-disulfonic acid sodium are mixed with a solution of 250 k g of crystallized sodium sulphide boiled in 60 kg of water. The melt soon turns dark and after about 24 hours the sodium salt of the 1'5-dithioanthraquinone has completely deposited. The latter is filtered off with suction, washed with sodium chloride solution and obtained by recrystallization from hot, alkaline water and separation with sodium chloride in dark brown needles. They dissolve red-brown in alkali and red in concentrated sulfuric acid.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1908212857D DE212857C (en) | 1908-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT45592B true AT45592B (en) | 1911-01-10 |
Family
ID=5810252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT45592D AT45592B (en) | 1908-02-08 | 1909-02-22 | Process for the preparation of anthraquinone derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT45592B (en) |
-
1909
- 1909-02-22 AT AT45592D patent/AT45592B/en active
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