GB394990A - Manufacture of halogen derivatives of the benzophenone and anthraquinone series - Google Patents
Manufacture of halogen derivatives of the benzophenone and anthraquinone seriesInfo
- Publication number
- GB394990A GB394990A GB3590731A GB3590731A GB394990A GB 394990 A GB394990 A GB 394990A GB 3590731 A GB3590731 A GB 3590731A GB 3590731 A GB3590731 A GB 3590731A GB 394990 A GB394990 A GB 394990A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ring
- carboxylic acid
- aldehyde
- action
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C66/00—Quinone carboxylic acids
- C07C66/02—Anthraquinone carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/38—Quinones containing —CHO or non—quinoid keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Benzophenone and anthraquinone derivatives.--A halogenmethylbenzophenone of the formula <FORM:0394990/IV/1> wherein R stands for a residue of the benzene series which may be substituted, but is unsubstituted in one o-position to the CO-group, is reacted with halogen under conditions such that the methyl hydrogen atoms are completely or nearly completely exchanged for halogen atoms, and the product is subjected to the action of a saponifying and ring-closing agent, so as to form the corresponding halogenanthraquinone-carboxylic acid or aldehyde. By treating the halogenated products with an agent having a saponifying action only, such as caustic soda, halogenbenzophenone-carboxylic acid or aldehyde derivatives are obtained, and these may then be subjected to the action of a ring-closing agent to yield the corresponding anthraquinone derivatives. Advantageous halogenation conditions comprise the presence of an indifferent diluent, such as trichlorobenzene, whilst exposing the mixture to the light of a mercury vapour lamp. In examples: (1) 2 : 5-dimethyl-4-chlorbenzophenone (prepared by condensing 1 : 4-dimethyl-3-chlorobenzene with benzoyl chloride) is chlorinated in trichlorbenzene at 170-180 DEG C. whilst exposing to ultra-violet to give a o -hexachloro derivative; treating this product with concentrated sulphuric acid yields 2-chloranthraquinone-3-carboxylic acid, whereas by using caustic soda 4-chlorbenzophenone-3 : 6-dicarboxylic acid is first obtained and this can then be ring-closed as above; the chlorination process can be interrupted when the o -pentachloro derivative is formed, and this, on ring-closing by means of sulphuric acid, yields a mixture of 2-chloranthraquinone-3-carboxylic acid and aldehyde which are separated by adding sodium carbonate; (2) 2 : 5 : 4<1>-trimethyl-4 : 5<1>-dichlorobenzophenone (prepared by condensing 2-chloro-p-xylene with 3-chloro-4-methylbenzoic acid chloride) is chlorinated as in (1) and the product treated with concentrated sulphuric acid to give 2 : 6-dichloroanthraquinone-3 : 7-dicarboxylic acid; the 2 : 7-dichloranthraquinone-3 : 6-dicarboxylic acid is similarly prepared from 2 : 5 : 5<1>-trimethyl-4 : 4<1>-dichlorbenzophenone. Specification 10790/13 (as open to inspection under Sect. 91), [Class 2 (iii), Dyes &c.], is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3590731A GB394990A (en) | 1931-12-29 | 1931-12-29 | Manufacture of halogen derivatives of the benzophenone and anthraquinone series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3590731A GB394990A (en) | 1931-12-29 | 1931-12-29 | Manufacture of halogen derivatives of the benzophenone and anthraquinone series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB394990A true GB394990A (en) | 1933-06-29 |
Family
ID=10382864
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3590731A Expired GB394990A (en) | 1931-12-29 | 1931-12-29 | Manufacture of halogen derivatives of the benzophenone and anthraquinone series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB394990A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0111120A2 (en) * | 1982-11-10 | 1984-06-20 | BASF Aktiengesellschaft | Process for the preparation of anthraquinones |
-
1931
- 1931-12-29 GB GB3590731A patent/GB394990A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0111120A2 (en) * | 1982-11-10 | 1984-06-20 | BASF Aktiengesellschaft | Process for the preparation of anthraquinones |
EP0111120A3 (en) * | 1982-11-10 | 1985-12-04 | Basf Aktiengesellschaft | Process for the preparation of anthraquinones |
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