AT53458B - Process for the preparation of vat dyes of the dianthraquinone series. - Google Patents
Process for the preparation of vat dyes of the dianthraquinone series.Info
- Publication number
- AT53458B AT53458B AT53458DA AT53458B AT 53458 B AT53458 B AT 53458B AT 53458D A AT53458D A AT 53458DA AT 53458 B AT53458 B AT 53458B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- series
- dianthraquinone
- vat dyes
- vat
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- MGRRGKWPEVFJSH-UHFFFAOYSA-N 10-(10-oxoanthracen-9-ylidene)anthracen-9-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C1=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MGRRGKWPEVFJSH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- CJADAVIATOALFB-UHFFFAOYSA-N helianthrone Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=C2C3=C1C=CC=C3C(=O)C1=CC=CC=C12 CJADAVIATOALFB-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Küpenfarbstoffen der Dianthrachinonreihe.
Es wurde gefunden, dass die nach den Patenten Nr. 41809,42716 und 44372 erhaltenen Anthrachinonderivate durch Einwirkung von Energie in Form chemisch aktiver Lichtstrahlen eine Kondensation zu 2 bis 6 Wasserstoffatome ärmeren Verbindungen der Helianthron- bzw. Naphtodianthronreihe und Zwischenprodukten, etwa der Formel
EMI1.1
erfahren. Die Reaktion erfolgt langsam bereits in der Kälte, rasch bei höherer Temperatur, am besten in Lösungsmitteln, wie Eisessig, Azetonöl, Pyridin und dgl. Die Reaktion kann auch durch Hindurchblasen von Luft oder Sauerstoff unterstützt und durch Katalysatoren beschleunigt werden.
Beispiel l. Bianthron (dargestellt nach den österreichischen Patenten Nr. 41809 und
EMI1.2
Oxydation) wird in Eisessig gelöst und mehrere Stunden unter Rückfluss im Sonnenlichte gekocht. Die Lösung trübt sich nach kurzer Zeit und scheidet quantitativ das in Eisessig schwer lösliche Oxydationsprodukt in chemisch reiner Form ab.
Letzteres bildet feine glänzende gelbe Nädelchen oder Schuppen, in allen gebräuchlichen organischen Lösungsmitteln sehr schwer, in konzentrierter Schwefelsäure leichter, mit karminroter Farbe und starker ziegelroter Fluoreszenz löslich. In stark alkalischer Hydrosulfitklipe, namentlich auf Zusatz von Zinkstaub, wird das Produkt in fleiscbfarbige Lösung gebracht und aus dieser Küpe Baumwolle gelb angefärbt.
Bei s pie I 2. Bianthron wird in der sechsfachen Menge Azetonöl suspendiert und unter stetem Turbinieren zum Kochen erhitzt. Die siedende, in steter Bewegung erhaltene Masse wird nun so lange mit einer 1000 kerzigen Bogenlampe bestrahlt, bis eine Probe des ab- filtrierten Reaktionsproduktes die unter Beispiel 1 beschriebene Reaktion mit Schwefelsäure in typischer Weise zeigt. Das Reaktionsprodukt erweist sich nach dem Umkristallisieren aus sehr viel Nitrobenzol als mit dem unter Beispiel 1 beschriebenen identisch.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of vat dyes of the dianthraquinone series.
It has been found that the anthraquinone derivatives obtained according to patents No. 41809, 42716 and 44372 condensation to form compounds of the helianthrone or naphthodianthrone series and intermediates, for example of the formula, which are poorer in hydrogen atoms from 2 to 6 hydrogen atoms
EMI1.1
Experienced. The reaction takes place slowly even in the cold, quickly at a higher temperature, preferably in solvents such as glacial acetic acid, acetone oil, pyridine and the like. The reaction can also be assisted by blowing air or oxygen through it and accelerated by catalysts.
Example l. Bianthron (shown according to Austrian patents No. 41809 and
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Oxidation) is dissolved in glacial acetic acid and refluxed for several hours in the sunlight. The solution becomes cloudy after a short time and quantitatively separates the oxidation product, which is sparingly soluble in glacial acetic acid, in chemically pure form.
The latter forms fine, shiny yellow needles or scales, very difficult in all common organic solvents, more easily soluble in concentrated sulfuric acid, with a carmine-red color and strong brick-red fluorescence. In a strongly alkaline hydrosulphite clip, namely with the addition of zinc dust, the product is brought into a flesh-colored solution and cotton is dyed yellow from this vat.
At pie I 2. Bianthron is suspended in six times the amount of acetone oil and heated to a boil with constant turbine operation. The boiling mass, obtained in constant motion, is then irradiated with a 1000-candle arc lamp until a sample of the filtered reaction product shows the reaction with sulfuric acid described in Example 1 in a typical manner. After recrystallization from a large amount of nitrobenzene, the reaction product turns out to be identical to that described under Example 1.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT53458T | 1911-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT53458B true AT53458B (en) | 1912-05-10 |
Family
ID=3574771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT53458D AT53458B (en) | 1911-02-04 | 1911-02-04 | Process for the preparation of vat dyes of the dianthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT53458B (en) |
-
1911
- 1911-02-04 AT AT53458D patent/AT53458B/en active
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