Patent GB-338747-A (GB)
Title: Manufacture of halogenated 3:4:8:9- or 4:5:8:9-dibenzopyrene-quinones
Filed: 1929-12-04
Abstract: 338,747. I. G. Farbenindustrie Akt.- Ges. Dec. 4, 1928, [Convention date]. Dibenzpyrenequinones. - Halogenated dibenzpyrenequinones are made by causing halogen or a halogenating agent to react in an alkalialuminium chloride melt with a 3: 4: 8: 9-dibenzpyrene-5: 10-quinone or a 4: 5: 8: 9-dibenzpyrene-3:10-quinone, or with a ketone capable of being transformed into such a pyrenequinone by ring closure. The products may be after-treated with a hypochlorite to improve the shades of the dyeings. In examples, (1) 1 : 5-dibenzoylnaphthalene is converted into the dibenzpyrenequinone in a sodium-aluminium chloride melt while introducing oxygen according to Specification 293,768, and bromine is then introduced in the melt, yielding a dibrom derivative, which, after oxidation with an alkali hypochlorite solution, dyes cotton clear golden orange tints identical with those of the bromo-3 : 4 : 8 : 9-dibenzpyrenequinones obtained by the process of Specification 310,891: by varying the quantity of bromine used more highly brominated products dyeing in somewhat more reddish tints are obtained, (2) chlorine is introduced into a melt of 1 : 5-dibenzoylnaphthalene prepared according to example 5 of Specification 293,768; di-. tri-, tetra- and more highly chlorinated 3 : 4 : 8 : 9-dibenzpyrene-5-10-quinone, are obtained, (3) bromine vapour, undiluted or mixed with air or oxygen, is passed into a melt of 2-benzoylbenzanthrone prepared according to Specification 287,050; the product is identical with the dibrom- 4 : 5 : 8 : 9-dibenzpyrene-3 : 10-quinone obtained according to Specification 287,845, (4) by using chlorine instead of bromine in example 3, a dt- or poly - chlor - 4 : 3 : 8 : 9-dibenzpyrene-3 : 10- quinone is obtained; the dichlor derivative dyes cotton in clear orange tints, and (5) diclilor- 4 : 5 : 8 : 9-dibenzpyrene-3 : 10-quinone, made by condensation of 1: 4-di(p-chlorbenzoyl)-naphthalene by means of sodium-aluminium chloride while introducing air, is brominated in potassiumaluminium chloride; the brominated dichlor derivative obtained dves cotton in clear scarlet tints. The Specification, as open to inspection under Sect. 91 (3) (a) states that the hydrochloric acid set free during the ring closure, or the aluminium chloride, may serve as chlorinating agents in the presence of oxygen at raised temperatures and includes further examples according to which (6) 1 : 5-dibenzoylnaphthalene in sodium-aluminium chloride is treated with sulphuryl chloride; mono-, di- and tri-chlor-3 : 4 : 8 : 9-dibenzpyrene- 5 : 10-quinones are obtained, (7) the melt containing brominated 3 : 4 : 8 : 9-dibenzpyrene- 5 : : 10-quinone obtained according to example 1 is further treated with sulphuryl chloride; the product, which is fast to bromine and chlorine, dyes cotton golden-yellow tints, (8) 4 : 5 : 8 : 9-dibenzpyrene-3 : 10-quinone is chlorinated with sulphuryl chloride in sodium-aluminium chloride, (9) after the formation of the 4 : 5 : 8 : 9-dibenzpyrene-3 : 10-quinone in a sodium-aluminium chloride melt is complete, the temperature of the melt is raised while passing a further quantity of oxygen therethrough, or with addition of a solid oxidizing agent to the melt; mono- or polychlor derivatives are obtained according to the duration of the treatment, and (10) 3 : 4 : 8 : 9- dibenzpyrene-5 : 10-quinone! is treated with iodine in a sodium-aluminium chloride melt; an iodo derivative is obtained. This subject-matter does not appear in the Specification as accepted.