Patent GB-190122583-A (GB)
Title: Improvements in the Manufacture or Production of Anthraquinone Derivatives.
Inventor: NEWTON HENRY EDWARD
Filed: 1901-11-08
Granted: 1902-10-02
Abstract: 22,583. Newton, H. E., [Farbenfabriken vorm. F. Bayer & Co.]. Nov. 8. Dyes, artificial; halogen- and nitroalkylamidoanthraquinones.-Anthraquinone derivatives, which contain nitro or halogen groups in addition to alkyl amido groups and are valuable intermediate compounds for the production of dyes, are produced by the action of halogens, or agents giving off halogens, or nitrating-agents, on secondary and tertiary alkylamidoanthraquinones, or derivatives thereof such as sulphonic acids. The nitration of tertiary alkylamidoanthraquinones results in some cases in the production of nitrated secondary alkylamidoanthraquinones. The nitro products are basic, but less so than the parent substances. Examples are given in which the following compounds are prepared :-alpha1alpha2 - bromomonomethylamidoanthraquinone, and a greenish-blue dye by reaction thereof with p-toluidine; a dibromo derivative of monomethylamidoanthraquinone, and a dyestuff therefrom by condensation with p-toluidine; alpha1alpha3- dibromo - alpha2alpha4 - dimethyldiamidoanthraquinone and a green dye by reaction therewith on p-toluidine; alpha1alpha4-dibromo-alpha2alpha3- dimethyldiamidoanthraquinone; alpha1alpha4 - dibromoalpha1alpha3 - nitromethylamidoanthraquinone; bromomethylamidoanthraquinone sulphonic acid, which dyes unmordanted wool bluish-red shades ; alpha1alpha2- chloromethylamidoanthraquinone; p - bromodimethylamidoanthraquinone perbromide ; p-bromodimethylamidoanthraquinone, and bluish -green dyes therefrom by reaction with primary aromatic amines; bromo-alpha1alpha3- and alpha1alpha4-tetramethyldiamidoanthraquinones and their perbromides; bromo - alpha1alpha4 - nitrodimethylamidoanthraquinone ; bromodimethylamidoanthraquinone sulphonic acid; p - chlorodimethylamidoanthraquinone ; p - nitromonomethylamidoanthraquinone; alpha1alpha3- dinitro - alpha2alpha4 - tetramethyldiamidoanthraquinone; alpha1alpha4 - dibromo - alpha2alpha3- dimethylamidoanthraquinone; alpha1alpha3 - dinitro - alpha4 - ethyl- or methylamidoanthraquinone; alpha1alpha4-dinitroalkylamidoanthraquinones; alpha1alpha2- and alpha1#1-monomethylamidomononitroanthraquinones from alpha - dimethylamidoanthraquinone, and similar compounds from alpha1alpha3- and alpha1-alpha4 tetramethyldiamidoanthraquinones; alpha1 - monomethylamido - #1 - alpha2 - dinitroanthraquinone from alpha-dimethylamidoanthraquinone, or o-, or p-nitroalpha-monomethylamidoanthraquinone, and a green dye by heating the product with p-toluidine. The perbromides above mentioned are produced when an excess of bromine is employed in some cases, or when the operation is conducted in chloroform solution, or when gaseous bromine is used in closed vessels. The perbromides are deprived of two atoms of bromine by treatment with halogen absorbing-agents, such as ammonia, bisulphites, or the like. The splitting off of an alkyl group from tertiary alkylamidoanthraquinones above referred to, which occurs when nitric acid is used as a nitrating agent, is prevented by using nitric acid in presence of sulphuric acid. In this manner, alpha1 - dimethylamido - alpha3- mononitroanthraquinone, and alpha1-dimethylamidoalpha4 - mononitroanthraquinone are produced from dimethylamidoanthraquinone.