CH170677A - Process for the preparation of a chloranthraquinone carboxylic acid. - Google Patents
Process for the preparation of a chloranthraquinone carboxylic acid.Info
- Publication number
- CH170677A CH170677A CH170677DA CH170677A CH 170677 A CH170677 A CH 170677A CH 170677D A CH170677D A CH 170677DA CH 170677 A CH170677 A CH 170677A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- chloranthraquinone
- carboxylic acid
- sulfuric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- NPOIYFMFHGQKIC-UHFFFAOYSA-N 2-chloro-9,10-dioxoanthracene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2C(=O)O NPOIYFMFHGQKIC-UHFFFAOYSA-N 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 chloranthraquinone carbonate Chemical compound 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GANDSBWEBNXLMG-UHFFFAOYSA-N 3-chloro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1Cl GANDSBWEBNXLMG-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Chloranthrachinonearbonsänre. Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung einer Chloranthra- chinoncarbonsäure, welches dadurch gekenn zeichnet ist, dass man 2. 0' .
4'-Trimethyl-4. 5'- dichlorbenzophenon in den Methylgruppen erschöpfend chloriert und die so erhaltene co-Chlorverbindung durch Behandlung mit konzentrierter Schwefelsäure in die 2.6-Di- chlor-3.7-anthrachinondicarbonsäure über führt.
Beispiel: 175 Gewichtsteile 2. 5 . 4'-Trimethy 1-4 . 5'- dichlorbenzophenon vom Schmelzpunkt 64', erhältlich durch Kondensation von 2-Chlor-p- gylol mit 3-Chlor-4-methylbenzoesäurechlorid nach Friedel-Crafts, werden in 175 Gewichts teilen Trichlorbenzol unter Belichten mit ultraviolettem Licht unter starkem Rühren bei 170 bis 180 in den Methylgruppen er schöpfend chloriert.
Beim Erkalten scheidet sich das in den Methylgruppen erschöpfend chlorierte Produkt kristallin ab (Schmelz- punkt 230 ). Es wird abgesaugt und mit etwas kaltem Benzol gewaschen.
200 Gewichtsteile des trockenen Chlo- rierungsproduktes werden in 2000 Gewichts teilen konzentrierter Schwefelsäure suspen diert. Dann wird langsam auf 170 bis 180 geheizt; unter starker Salzsäureentwicklung geht alles mit gelber Farbe in Lösung. Nach Abkühlen scheidet sich die bekannte in Schwefelsäure schwer lösliche 2. 6-Dichlor- 3. 7-anthrachinondicarbonsäure aus. Nach Ein giessen in Wasser, Absaugen und Trocknen erhält man die reine Säure in kristalliner Form. Sie ist in Soda leicht löslich und schmilzt oberhalb 360 .
Process for the preparation of a chloranthraquinone carbonate. The subject of the present patent is a process for the preparation of a chloranthraquinonecarboxylic acid, which is characterized in that one 2. 0 '.
4'-trimethyl-4. 5'-dichlorobenzophenone is exhaustively chlorinated in the methyl groups and the co-chlorine compound thus obtained is converted into the 2,6-dichloro-3,7-anthraquinonedicarboxylic acid by treatment with concentrated sulfuric acid.
Example: 175 parts by weight 2. 5. 4'-trimethyl 1-4. 5'-dichlorobenzophenone of melting point 64 ', obtainable by condensation of 2-chloro-p-gylene with 3-chloro-4-methylbenzoic acid chloride according to Friedel-Crafts, trichlorobenzene in 175 parts by weight under exposure to ultraviolet light with vigorous stirring at 170 to 180 in the methyl groups he chlorinated exhaustively.
On cooling, the product, which is exhaustively chlorinated in the methyl groups, separates out in crystalline form (melting point 230). It is filtered off with suction and washed with a little cold benzene.
200 parts by weight of the dry chlorination product are suspended in 2000 parts by weight of concentrated sulfuric acid. Then slowly heat to 170 to 180; with strong development of hydrochloric acid, everything dissolves with a yellow color. After cooling, the known 2,6-dichloro-3,7-anthraquinonedicarboxylic acid, which is sparingly soluble in sulfuric acid, separates out. After pouring into water, suction and drying, the pure acid is obtained in crystalline form. It is easily soluble in soda and melts above 360.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE170677X | 1931-11-13 | ||
| CH164545T | 1932-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH170677A true CH170677A (en) | 1934-07-15 |
Family
ID=25717970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH170677D CH170677A (en) | 1931-11-13 | 1932-11-11 | Process for the preparation of a chloranthraquinone carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH170677A (en) |
-
1932
- 1932-11-11 CH CH170677D patent/CH170677A/en unknown
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