DE455955C - Process for the preparation of benzanthrone derivatives - Google Patents

Description

Process for the preparation of benzanthrone derivatives. In the further processing of the process of the main patent 453 280 it was found that even Bz-2-aroyloxybenzanthrones when treated with acidic condensation agents are converted into oxy compounds of dibenzpyrenquinone or its substitution products, homologues or analogs. So you get z. B. from the benzoate of Bz-2-oxybenzanthrone when fused with aluminum chloride the i-oxy-3 # 4 # 8 # 9-dibenzpyrenquinone in the sense of the following scheme Some of the compounds obtained in this way are already vat dyes or valuable intermediates for the production of such. There are z. B. obtained by etherifying the oxy groups valuable yellow to orange-yellow vat dyes. Examples. i. io parts by weight of Bz-2-Benzoyloxybenz- anthron (available from Bz-z-Oxybenzanthron by benzoylation according to S. chott -en -Bau - man, yellow crystals from chlorobenzene, FP 215 to 216 °, solution color in concentrated Sulfuric acid reddish brown with brown fluo- rescence) are melted in at 180 ° Mixture of 5o parts by weight of A1Cls and 10 parts by weight of sodium chloride and with stirring for 1/2 hour to 22o to 24o ° heated. After cooling down, the Melt cake crushed and diluted with Boiled hydrochloric acid. The product represents dried a red-brown powder, almost insoluble in organic solvents, soluble in concentrated sulfuric acid with red- purple color. From the ld.rs, Chroten Hydro- sülfitküpe, cotton turns a strong reddish brown stained. Strikes when dabbed with acids the color changes to yellow. io parts by weight of the i-oxy- 3 - 4 - 8 - 9-clibenzpyrenquinones are used with 100 parts by weight of nitrobenzene, 5 parts by weight share soda and 10 parts by weight p-toluene sulfonic acid methyl ester for 6 hours at i8o ° @ ex- Bitzt and filtered simmering hot. When calculating th. the 1-methoxy-3 # 4 # 8 # 9- dibenzpyrenquinone in golden yellow crystals the end. These are sucked off with alcohol washed and dried. The product eats only in high-boiling organic solutions medium soluble with yellow-brown color; in con- centered sulfuric acid dissolves, "it dissolves with bluish-red color. From the cherry red Hydrosulfite vat is made in real cotton stained yellow tones. 2. If you use instead of the p-toluene sulfonic acid methyl ester the corresponding Ethyl ester, then one obtains the i-ethoxy- 3-4 # 8 # 9-dibenzpyrenquinone. It is in Example i described methyl derivative in its properties are very similar. 3. If one takes in place of the in example i applied benzoate of Bz-2-Oxyb; enz- anthrons the p-toluyl; acid ester of Bz-2-oxy- benzanthrons (represented by heating equal parts of p-toluic acid chloride and Bz- 2-Oxyb, enzanthron at 16o °, from chlorobenzene yellow-brown crystals FP 212 to 213 °, in concentrated sulfuric acid brown-red with brown fluorescence) and proceeds in the rest, as indicated in example i, is obtained the 1-oxy-3 # 4-methylbenz-8 # 9-b.enz- pyrenequinone, which in its properties is yours Oxydibenzpyrenquinone of Example i is the same. Methylation gives you one real yellow vat dye, whose own properties with those of the example i hold essentially. to match.

Claims (1)

PATENT CLAIM: Procedure for the representation of B: enz- anthrone derivatives according to patent 453 280, that characterized by that Inzr Bz- 2-aroyloxybenzanthrones with acidic con- treatment agents and the hold oxy compounds if necessary alkylated.