Patent GB-182487-A (GB)
IPC: C07B35/04
Filed: 1922-06-30
Abstract: The oxidation of aromatic organic compounds is effected by free oxygen under the influence of light in the presence of anthraquinone or its substitution products, for example chloranthraquinones.  By addition of substances which react with the oxidation products, derivatives thereof, such as salts and esters, may be directly obtained.  The following examples are given:-(1) toluene containing anthraquinone is oxidized by air, under the influence of light, to benzoic acid together with smaller amounts of benzaldehyde, dibenzyl, isohydrobenzoin, and hydrobenzoin; by further oxidation the hydrobenzoins also yield benzoid acid; by addition of acetic anhydride to the toluene benzyl acetate results directly; (2) the three toluic acids are similarly obtained from the three xylenes, acetophenone from ethylbenzene, and naphthalene carboxylic acids from methylnaphthalenes; (3) b -anthraquinone carboxylic acid and some b : b 1-dianthraquinonylethane are obtained by action of air and light upon b -methylanthraquinone in glacial acetic acid solution.  The Specification as open to inspection under Sect. 91 (3) (a) mentions the acid chlorides and anhydrides of fatty and aromatic carboxylic acids as substances capable of reacting with the oxidation products when formed, and describes the oxidation of benzyl alcohol to benzoic acid, hydroquinone to quinhydrone, 1-methoxy-2-methylanthraquinone to 1-oxyanthraquinone-2-carboxylic acid, and 1-chloro-4-methylanthraquinone to a mixture of 1-chloroanthraquinone-4-carboxylic acid and 4 : 41-dichloro-1 : 11-dianthraquinonylethane.  This subject-matter does not appear in the Specification as accepted.ALSO:The oxidation of aromatic organic compounds is effected by free oxygen under the influence of light in the presence of anthraquinone or its substitution products, for example chloranthraquinones.  By addition of substances which react with the oxidation products, derivatives thereof, such as salts and esters, may be directly obtained.  The following examples are given:-(1) toluene containing anthraquinone is oxidized by air, under the influence of light, to benzoic acid together with smaller amounts of benzaldehyde, dibenzyl, isohydrobenzoin, and hydrobenzoin; by further oxidation the hydrobenzoins also yield benzoic acid; by addition of acetic anhydride to the toluene benzyl acetate results directly; (2) the three toluic acids are similarly obtained from the three xylenes, acetophenone from ethylbenzene, and naphthalene carboxylic acids from methylnaphthalenes; (3) b -anthraquinone carboxylic acid and some b : b 1-dianthraquinonylethane are obtained by action of air and light upon b -methylanthraquinone in glacial acetic acid solution.  The Specification as open to inspection under Sect. 91 (3) (a) mentions the acid chlorides and anhydrides of fatty and aromatic carboxylic acids as substances capable of reacting with the oxidation products when formed, and describes the oxidation of benzyl alcohol to benzoic acid, hydroquinone to quinhydrone, 1-methoxy-2-methylanthraquinone to 1-oxyanthraquinone-2-carboxylic acid, and 1-chloro-4-methylanthraquinone to a mixture of 1-chloroanthraquinone-4-carboxylic acid and 4 : 41-dichloro-1 : 11-dianthraquinonylethane.  This subject-matter does not appear in the Specification as accepted.