GB366055A - Improvements in the manufacture and production of chloro derivatives of the anthraquinonebenzacridone series - Google Patents
Improvements in the manufacture and production of chloro derivatives of the anthraquinonebenzacridone seriesInfo
- Publication number
- GB366055A GB366055A GB2225930A GB2225930A GB366055A GB 366055 A GB366055 A GB 366055A GB 2225930 A GB2225930 A GB 2225930A GB 2225930 A GB2225930 A GB 2225930A GB 366055 A GB366055 A GB 366055A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzacridone
- chloranthraquinone
- acid
- chlorine
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Chloranthraquinone-2.1-benzacridones are prepared by condensing 1-halogen (or nitro)-anthraquinone-2-carboxylic acids with 2.5-dichloraniline or a trichloraniline having a free o-position to the amino group, the product being further condensed to the acridone derivative. Or a 1-halogen (or nitro)-anthraquinone is condensed with an o-aminobenzoic acid substituted by chlorine in positions 3- and 6-, or containing three chlorine atoms, the product being further condensed to the acridone derivative. The above Bz-trichloro derivatives are also obtained by treating an anthraquinone-2.1-benzacridone substituted by chlorine in the Bz2-, Bz4, Bz2.3-, Bz3.4-, Bz4.5- or Bz2.5- positions, with chlorine or agents supplying chlorine in organic solvents in the absence of halogenating catalysts. In such halogenation process the initial materials must be freed from agents employed in their preparation and which may act as halogenating catalysts. The products dye orange to yellow-red shades and are particularly valuable in view of the fastness of the dyeings to alkali; details of the alkali heat treatment tests to which the dyeings conform are given. In examples (1) 1-chloranthraquinone-2-carboxylic acid is condensed with 3.4.5-trichloraniline in the presence of trichlorbenzene and boric acid, and the reaction product completely converted to Bz2.3.4-trichloranthraquinone-2.1-benzacridone by warming in chlorsulphonic acid or in nitrobenzene with phosphorus pentachloride; esters or amides of 1-chloranthraquinone-2-carboxylic acid or the corresponding 1-bromo derivative may be employed instead; (2) 1-chloranthraquinone-2-carboxylic acid is condensed with 2.5-dichloraniline and the product ring-closed by means of phosphorus pentachloride in nitrobenzene or by means of chlorsulphonic acid to give Bz2.5-dichloranthraquinone-2.1-benzacridone; (3) 1-chloranthraquinone-2-carboxylic acid-benzyl ester is condensed with 2.4.5-trichloraniline and the product ring-closed as in (2) to give Bz2.3.5-trichloranthraquinone-2.1-benzacridone; (4) 1-chloranthraquinone-2-carboxylic acid-benzyl ester is condensed with 2.3.5-trichloraniline and the product ring-closed to Bz2.4.5-trichloranthraquinone-2.1-benzacridone; (5) Bz3.4-dichloranthraquinone-2.1-benzacridone (prepared by condensing 1-chloranthraquinone with 4.5-dichloranthranilic acid and ring-closure to the acridone) is treated with chlorine in trichlorbenzene to give Bz3.4.5-trichloroanthraquinone-2.1-benzacridone; the same product is obtained by treatment with chlorine or sulphuryl chloride of Bz4-monochloro- or Bz4.5-dichloranthraquinone-2.1-benzacridone (these acridones being prepared by condensing 1-chloranthraquinone with 4-chloranthranilic acid and 3.4-dichloranthranilic acids respectively, followed by ring-closure to the acridones); (6) Bz2-chloranthraquinone-2.1-benzacridone (prepared by condensing 1-chloranthraquinone with 6-chloranthranilic acid followed by ring-closure to the acridone) is treated with chlorine in trichlorbenzene to give Bz2.3.5-trichloranthraquinone-2.1-benzacridone; the similar treatment of Bz2.3-dichloranthraquinone-2.1-benzacridone (prepared by condensing 1-chloranthraquinone with 5.6-dichloranthranilic acid followed by ring-closure to the acridone) yields the same product. Specifications 13907/09, 894/11, 260,588, 324,084, 338,182, [all in Class 2 (iii), Dyes &c.], 346,676, and 347,722 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2225930A GB366055A (en) | 1930-07-23 | 1930-07-23 | Improvements in the manufacture and production of chloro derivatives of the anthraquinonebenzacridone series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2225930A GB366055A (en) | 1930-07-23 | 1930-07-23 | Improvements in the manufacture and production of chloro derivatives of the anthraquinonebenzacridone series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB366055A true GB366055A (en) | 1932-01-25 |
Family
ID=10176463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2225930A Expired GB366055A (en) | 1930-07-23 | 1930-07-23 | Improvements in the manufacture and production of chloro derivatives of the anthraquinonebenzacridone series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB366055A (en) |
-
1930
- 1930-07-23 GB GB2225930A patent/GB366055A/en not_active Expired
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