GB629706A - Process for the manufacture of halogenated derivatives of the naphthoquinone series - Google Patents
Process for the manufacture of halogenated derivatives of the naphthoquinone seriesInfo
- Publication number
- GB629706A GB629706A GB1967347A GB1967347A GB629706A GB 629706 A GB629706 A GB 629706A GB 1967347 A GB1967347 A GB 1967347A GB 1967347 A GB1967347 A GB 1967347A GB 629706 A GB629706 A GB 629706A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthoquinone
- dihydroxy
- halogenated
- imines
- hydroxy
- 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
Halogenated 5 : 8-dihydroxy-1 : 4-naphthoquinone-imines-(1) of the general formula <FORM:0629706/IV (b)/1> where at least one of the positions X is halogenated, are prepared by hydrolysis of a halogenated amino - hydroxy - 1 : 4 - naphthoquinone-imine-(1) during or after its formation, to replace the amino group by a hydroxy group. The halogenated amino-hydroxy-1 : 4-naphthoqyinone-imines-(1) used as starting materials may be prepared by halogenation of aminohydroxy - 1 : 4 - naphthoquinone - imines or by halogenation of the reduction products of a : a -dinitronaphthalenes during or after the reduction process in sulphuric acid. The hydrolysis may be carried out with aqueous mineral acids or mixtures of acids such as sulphuric acid and glacial acetic acid. In examples: (1) and (2) 1 : 5-dinitronaphthalene is reduced with sulphur in strong sulphuric acid, the reaction mixture is diluted with water and treated with bromine in the presence of iodine as a catalyst, and on pouring into a large volume of water dibrom-5 : 8-dihydroxy-1 : 4-naphthoquinone-imine-(1) or a mixture thereof with other halogenated 5 : 8-dihydroxy-1 : 4-naphthoquinone-imines-(1) is obtained; (3) tribrom-5-amino-8-hydroxy-1 : 4-naphthoquinoneimine-(1) is treated with a mixture of sulphuric and glacial acetic acid to give tribrom-5 : 8-dihydroxy - 1 : 4 - naphthoquinone - imine - (1) and dibrom - 5 : 8 - dihydroxy - 1 : 4 - naphthoquinone-imine-(1). Specification 606,008 is referred to.ALSO:Halogenated - 5 : 8 - dihydroxy - 1 : 4-naphthoquinone - imines - (1) of the general formula <FORM:0629706/IV (c)/1> where at least one of the positions X is halogenated are prepared by hydrolysis of a halogenated amino - hydroxy - 1 : 4 - naphthoquinone imine-(1) during or after its formation, to replace the amino group by a hydroxy group. The halogenated amino-hydroxy-4 : 4-naphthoquinone imines-(1) used as starting materials may be prepared by halogenation of aminohydroxy - 1 : 4 - naphthoquinone imines or halogenation of the reduction products of a : a -dinitronaphthalenes during or after the reduction process in sulphuric acid. The hydrolysis may be carried out with aqueous mineral acids or mixtures of acids such as sulphuric acid and glacial acetic acid. The products dye cellulose acetate artificial silk and nylon violet to reddish-blue. In examples: (1) and (2) 1 : 5-dinitronaphthalene is reduced with sulphur in strong sulphuric acid, the reaction mixture is diluted with water and treated with bromine in the presence of iodine as a catalyst and on pouring into a large volume of water dibrom-5 : 8-dihydroxy-1 : 4-naphthoquinone imine-(1) or a mixture thereof with other halogenated 5 : 8-dihydroxy-1 : 4-naphthoquinine-imines-(1) is obtained; (3) tribrom - 5 - amino - 8 - hydroxy - 1 : 4 - naphquinone-imine-(1) is treated with a mixture of sulphuric and glacial acetic acid to give tribrom-5 : 8 - dihydroxy - 1 : 4 - naphthoquinoneimine-(1) and dibrom - 5 : 8 - dihydroxy-1 : 4 - naphthoquinoneimine-(1). Specification 606,008 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1967347A GB629706A (en) | 1947-07-22 | 1947-07-22 | Process for the manufacture of halogenated derivatives of the naphthoquinone series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1967347A GB629706A (en) | 1947-07-22 | 1947-07-22 | Process for the manufacture of halogenated derivatives of the naphthoquinone series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB629706A true GB629706A (en) | 1949-09-27 |
Family
ID=10133281
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1967347A Expired GB629706A (en) | 1947-07-22 | 1947-07-22 | Process for the manufacture of halogenated derivatives of the naphthoquinone series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB629706A (en) |
-
1947
- 1947-07-22 GB GB1967347A patent/GB629706A/en not_active Expired
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