CH159868A - Process for the preparation of a condensation product of the anthraquinone series. - Google Patents
Process for the preparation of a condensation product of the anthraquinone series.Info
- Publication number
- CH159868A CH159868A CH159868DA CH159868A CH 159868 A CH159868 A CH 159868A CH 159868D A CH159868D A CH 159868DA CH 159868 A CH159868 A CH 159868A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- condensation product
- anthraquinone series
- phenoxyquinizarin
- phenol
- Prior art date
Links
- 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 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Anthrachinonreihe. Im Hauptpatent ist ein Verfahren zur Darstellung eines neuen Kondensationspro duktes der Anthrachinonreihe beschrieben, das dadurch gekennzeichnet ist, dass man auf 2-Halogenchinizariri Phenol einwirken lässt, und das so erhältliche 2-Phenoxychinizarin mit einem stilfierenden Mittel bis zur Auf- iiahnie von 2-Sulfogruppen behandelt.
Gegenstand vorliegenden Patentes ist nun ein Verfahren zur Darstellung eines Konden sationsproduktes der Anthrachinonreihe, da durch gekennzeichnet, dass man 2-Halogen- chinizarin mit Phenol umsetzt und das so erhältliche 2-Pherioxychinizai in mit einem stilfierenden Mittel bis zur Aufnahme einer Sulfogruppe behandelt.
Die so erhaltene 2-Phenoxychinizai-in-Mono- sulfosäure soll insbesondere für die Herstel lung von Farblacken Verwendung finden. <I>Beispiel:</I> 15 Gewichtsteile 2-Bromcliinizarin, 7,5 Ge wichtsteile Natriumphenolat und 0,4 Gewichts- teile Kupferacetat werden in 150 Gewichts teilen Phenol unter Rühren zum Sieden er hitzt. Die anfänglich violett gefärbte dicke Schmelze wird allmählich orangefarben und dünnflüssig. Sobald unverändertes Ausgangs material nicht mehr nachzuweisen ist, wird abgekühlt und bei 70 C mit 300 Gewichts teilen Methanol verdünnt.
Das in schönen orangeroten Nädelchen ausgefallene 2-Phe- noxychinizarin wird bei Raumtemperatur ab gesaugt, ausgewaschen und getrocknet. Es kristallisiert aus Eisessig oder p-Chlortoluol in prachtvollen orangeroten Nadeln, die bei <B>209-2110</B> schmelzen.
Das so erhaltene 2-Phenoxychinizarin wird sulfiert durch Auflösung in der zehnfachen Menge einer Schwefelsäure, die zirka 2 0/0 freies SOs enthält. Isolierung der gebilde ten Sulfosäure wie üblich als Natriumsalz, das in Wasser löslich ist. Die Lösung der Sulfosäure in starker Schwefelsäure ist blau stichig rot.
Process for the preparation of a condensation product of the anthraquinone series. In the main patent, a process for the preparation of a new condensation product of the anthraquinone series is described, which is characterized in that phenol is allowed to act on 2-haloquinizarin, and the 2-phenoxyquinizarin thus obtainable with a styling agent up to the dissolution of 2-sulfo groups treated.
The subject of the present patent is a process for the preparation of a condensation product of the anthraquinone series, characterized in that 2-haloquinizarin is reacted with phenol and the thus obtainable 2-pherioxychinizai is treated with a styling agent until a sulfo group is taken up.
The 2-phenoxyquinizai-in-monosulfonic acid obtained in this way is said to be used in particular for the manufacture of colored lacquers. <I> Example: </I> 15 parts by weight of 2-bromoclinizarin, 7.5 parts by weight of sodium phenolate and 0.4 parts by weight of copper acetate are heated to boiling in 150 parts by weight of phenol with stirring. The thick melt, initially purple in color, gradually turns orange and runny. As soon as unchanged starting material can no longer be detected, the mixture is cooled and diluted at 70 C with 300 parts by weight of methanol.
The 2-phenoxyquinizarin, which has precipitated in beautiful orange-red needles, is sucked off, washed out and dried at room temperature. It crystallizes from glacial acetic acid or p-chlorotoluene in magnificent orange-red needles that melt at <B> 209-2110 </B>.
The 2-phenoxyquinizarin obtained in this way is sulfated by dissolving it in ten times the amount of a sulfuric acid which contains about 2% free SO 2. Isolation of the formed sulfonic acid as usual as a sodium salt, which is soluble in water. The solution of the sulfonic acid in strong sulfuric acid is blue, tinged red.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE159868X | 1930-06-04 | ||
| CH155460T | 1931-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH159868A true CH159868A (en) | 1933-01-31 |
Family
ID=25716601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH159868D CH159868A (en) | 1930-06-04 | 1931-06-03 | Process for the preparation of a condensation product of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH159868A (en) |
-
1931
- 1931-06-03 CH CH159868D patent/CH159868A/en unknown
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