CH209578A - Process for the preparation of a quinhydron. - Google Patents
Process for the preparation of a quinhydron.Info
- Publication number
- CH209578A CH209578A CH209578DA CH209578A CH 209578 A CH209578 A CH 209578A CH 209578D A CH209578D A CH 209578DA CH 209578 A CH209578 A CH 209578A
- Authority
- CH
- Switzerland
- Prior art keywords
- flavanthrone
- quinhydron
- parts
- preparation
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 6
- BDJXVNRFAQSMAA-UHFFFAOYSA-N quinhydrone Chemical compound OC1=CC=C(O)C=C1.O=C1C=CC(=O)C=C1 BDJXVNRFAQSMAA-UHFFFAOYSA-N 0.000 claims description 3
- 229940052881 quinhydrone Drugs 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/20—Flavanthrones
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
- C09B5/56—Preparation from starting materials already containing the indanthrene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr.<B>207513.</B> Verfahren zur Herstellung eines Chinhydrons. Es ist allgemein bekannt, dass sich Benzo- chinon sowie verschiedene andere einfach zusammengesetzte Chinone in Chinhydrone überführen lassen.
Diese Chinhydrone sind meist als Molekülverbindungen zwischen dem Chinon und dem entsprechendenHydrochinon, d. h. der Verbindung, in der beide Ketogrup- pen des Chinons zu Hydroxylgruppen redu ziert sind, aufgefasst worden.
Diese Chinhy- drone konnten beispielsweise durch Umsetzen von Chinonen mit Hydrochinonen, in man eben Fällen auch durch partielle Reduktion der Chinone oder partielle Oxydation der Hy- drochinone, d. h. allgemein durch partielle Veränderung der Oxydationsstufe des .einen in den Chinhydronen enthaltenen Bestandteils erhalten werden.
Hierbei kann immer ange nommen werden, dass' sich intermediär die eine Komponente aus der andern bildet und hierauf mit dieser in Reaktion tritt.
Es ist auch schon die Auffassung ver treten worden, dass es sich bei den Chinhy- dronen nicht um Molekülverbindungen, son- dern um in monomolekularer Form vorliegende Zwischenstufen zwischen der mindestens zwei Ketogruppen enthaltenden Verbindung und derjenigen Verbindung handle, in denen die getogruppen bis zu Hydroxylgruppen reduziert sind.
Unbekümmert um die beson dere Deutungsweise der Chinhydrone sind die Möglichkeiten zu ihrer Herstellung stets die selben.
Es wurde nun gefunden, @dass ein neues und wertvolles Chinhydron aus. dem entspre chenden Chinon hergestellt werden kann, wenn man als Chinon Flavanthron wählt und die Leukoverbindung des genannten Farb stoffes auf den Farbstoff einwirken lässt.
Das neue Chinhyd:ron ist ein braunes, sandiges Pulver, dass sich in konzentrierter Schwefelsäure mit olivgrüner Farbe löst und Baumwolle aus dunkelblauvioletter Küpe in gelben Tönen färbt. Es lässt sich sehr leicht verküpen.
Die Einwirkung der Lukoverbindung des Flavanthrons auf Flavanthron kann in Ge- genwart von organischen Lösungs- bezw. Verdünnungsmitteln, wie zum Beispiel Alko hol, durchgeführt werden, zweckmässig aber in wässerigem Medium bei niederer oder vorzugsweise erhöhter Temperatur, beispieIs- weise bei etwa<B>30-80'</B> C, vorteilhaft in ätza-lkalischem Medium.
Beispiel: 21 Teile Flavanthron (Schultz, Farbstoff tabellen, 7. Auflage, Nr. 1241) werden in einem Gemisch von 700 Teilen Alkohol, 150 Teilen Wasser und 50 Teilen 10%iger Na tronlauge suspendiert und bei Gegenwart von Nickelkatalysator so lange mit Wasserstof f geschüttelt, bis die Aufnahme pro 1 Mol Flavanthron 1 Mol Wasserstoff beträgt.
Nach dem Entfernen des Katalysators durch Filtra tion bei 35-40' unter Wasserstoff wird zu der tief violettblauen Lösung des Dihydro- flavanthrons ein durch Mahlen von 10 Teilen Flavanthron mit 100 Teilen Alkobol herge- stellter Farbstoffteig zugegeben, worauf man die Suspension i/2 Stunde bei 70-75 rührt, auf 40-45' abkühlt, unter Wasserstoff ab saugt, mit viel luftfreiem Wasser wäscht und bei<B>80-100'</B> trocknet.
Man erhält 21 Teile braunes Chinhydron neben unverändertem, nicht in Reaktion getretenen Dihydroflavan- thron im Filtrat.
<B> Additional patent </B> to main patent no. <B> 207513. </B> Process for the production of a quinhydron. It is generally known that benzoquinone and various other simply composed quinones can be converted into quinhydrons.
These quinhydrons are mostly found as molecular compounds between the quinone and the corresponding hydroquinone, i.e. H. the compound in which both keto groups of the quinone are reduced to hydroxyl groups.
These quinhydrones could, for example, by reacting quinones with hydroquinones, in some cases also by partial reduction of the quinones or partial oxidation of the hydroquinones, ie. H. can generally be obtained by partially changing the oxidation state of the component contained in the quinhydrons.
It can always be assumed here that one component is formed as an intermediate from the other and then reacts with it.
The view has also been taken that quinhydrones are not molecular compounds, but rather intermediate stages present in monomolecular form between the compound containing at least two keto groups and the compound in which the geto groups up to hydroxyl groups are reduced.
Irrespective of the particular way quinhydrons are interpreted, the ways in which they can be produced are always the same.
It has now been found @that a new and valuable quinhydrone from. the corre sponding quinone can be produced if you choose flavanthrone as the quinone and the leuco compound of the dye mentioned can act on the dye.
The new quinhydron is a brown, sandy powder that dissolves in concentrated sulfuric acid with an olive green color and dyes cotton from a dark blue-violet vat in yellow tones. It is very easy to shred.
The effect of the luco compound of the flavanthrone on the flavanthrone can in the presence of organic solutions or. Diluents, such as, for example, alcohol, are carried out, but expediently in an aqueous medium at a lower or preferably elevated temperature, for example at about 30-80 ° C., advantageously in an alkaline medium.
Example: 21 parts of flavanthrone (Schultz, dyestuff tables, 7th edition, No. 1241) are suspended in a mixture of 700 parts of alcohol, 150 parts of water and 50 parts of 10% sodium hydroxide solution and, in the presence of a nickel catalyst, for so long with hydrogen shaken until the uptake per 1 mole of flavanthrone is 1 mole of hydrogen.
After the catalyst has been removed by filtration at 35-40 'under hydrogen, a dye paste prepared by grinding 10 parts of flavanthrone with 100 parts of alcohol is added to the deep violet-blue solution of the dihydroflavanthrone, whereupon the suspension is added for 1/2 hour Stir at 70-75, cool to 40-45 ', suction under hydrogen, wash with plenty of air-free water and dry at <B> 80-100' </B>.
21 parts of brown quinhydrone are obtained in the filtrate in addition to unchanged, unreacted dihydroflavanthrone.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH209578T | 1937-12-06 | ||
| CH207513T | 1937-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209578A true CH209578A (en) | 1940-04-15 |
Family
ID=25724422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209578D CH209578A (en) | 1937-12-06 | 1937-12-06 | Process for the preparation of a quinhydron. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209578A (en) |
-
1937
- 1937-12-06 CH CH209578D patent/CH209578A/en unknown
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