GB297129A - The manufacture of derivatives and condensation products of anthraquinone - Google Patents

Abstract

297,129. Carpmael, W., (I. G. Farbenindustrie Akt.-Ges.). May 12, 1927. Cinnamylideneanthrone or its derivatives are obtained by heating anthrone or its derivatives with cinnamic aldehyde or its addition products, such as the bisulphite compound, with or without an acid condensing-agent, such as sulphuric acid, zinc chloride, or phosphorus oxychloride. In an example, anthrone and cinnamic aldehyde are condensed in sulphuric acid solution; a-oxyanthrone or #-chloranthrone react similarly. Benzanthrotte or its derivatives are obtained by heating the cinnamylideneanthrones with aluminium chloride, the phenyl residue being split off; an example is given of the production of benzanthrone. Bz-1-Phenylbenzanthrone or its derivatives are obtained bv heating the cinnamylideneanthrones - to about 250-300‹ C., alone or in suspension or solution, e.g. in fused potassium bisulphate, or - a mixture of sodium and potassium acetates; according to examples, Bz-1-phenylbenzanthrone is obtained by heating' cinnamylideneanthrone alone, or in solution in alpha-chlornaphthalene, pphenetidine, or a molten mixture of potassium and sodium acetates; Bz-1-phenyl-alpha-oxybenzanthrone and Bz-1-phenyl-#-chlorbenzanthrone are prepared similarly. Alternatively, cinnamic aldehyde may be condensed with anthrone or its derivatives and the condensation products converted without isolation into the Bz-1-phenylbenzanthrones by further heating, with or without acid condensing-agents or solvents; according to examples, Bz-1-phenylbenzanthrone is obtained by heating anthrone with cinnamic aldehyde, then adding phosphorus oxychloride and heating further, or by heating anthrone and cinnamic aldehyde in a-chlornaphthalene or with potassium acetate and acetic anhydride, Bz-1-phenyl-a-oxybenzanthrone is obtained by heating a-oxyanthrone and cinnamic aldehyde with zinc chloride and Bz-1-phenyl-#-chlorbenzanthrone by heating #.chloranthrone and cinnamic aldehyde with achlornaphthalene and phosphorus oxychloride. Bz-2-Phenylbenzanthrone or its derivatives are obtained by isomerizing the Bz-1-phenylbenzanthrones by heating with aluminium chloride, or aluminium chloride and common salt; the melts containing the Bz-1-phenyl compounds may without isolation of the products be subjected to this further treatment; examples are given of the treatment of Bz-1-phenylbenzanthrone or the cinnamylideneanthrone melt containing it, and of Bz-1-phenyl-a-oxybenzanthrone and Bz-1-phenyl- #-chlorbenzanthrone. alpha-Oxyanthrone referred to above is prepared by reduction of a-oxyanthraquinone by means of copper or aluminium in sulphuric acid. #-Chloranthrone is prepared similarly from #- chloranthraquinone. Specification 1817/05 is referred to.