GB664839A - Manufacture of anthraquinone derivatives - Google Patents

Abstract

1 - Aminoanthraquinone - 2 - sulphonic acids are made by heating the corresponding 1-aminoanthraquinones unsubstituted in the 2-position with a mixture of a sulphonating agent and a tertiary nitrogen base which is substantially not sulphonated under the reaction conditions, the whole or a part of the mixture being in the form of a labile addition product of the sulphonating agent and the tertiary base, and the said base being used in less than three molecular proportions per mol. of sulphonating agent. Examples describe the heating of the following substances with chlorsulphonic acid and pyridine, alone and in the presence of nitrobenzene, tetrachlorethane, or o - dicchlorbenzene; (1) 1 - aminoanthraquinone, (2) 1 - amino - 5 - methoxy - nitro -, sulpho-, or carboxyanthraquinone, (3) 1-amino-6 or 8-chloranthraquinone, (4) 1 - amino - 6,7 - dichloranthraquinone, (5) 1,5- or 1,8-diaminoanthraquinone. Also in examples, 1-amino-anthraquinone is heated in tetrachlorethane with pyridine and oleum or sulphur trioxide, and with quinoline and oleum. Dimethylamino-cyclohexane is specified as a base. The sulphonic acid may be brominated without isolation. A sample has been furnished under Sect. 2 (5) of the Acts of a product prepared by heating 1-aminoanthraquinone with triethylamine and oleum in tetrachlorethane.ALSO:1-Aminoanthraquinone-2-sulphonic acids are made by heating the corresponding 1-amino-anthraquinones unsubstituted in the 2-position with a mixture of a sulphonating agent and a tertiary nitrogen base which is substantially not sulphonated under the reaction conditions, the whole or a part of the mixture being in the form of a labile addition product of the sulphonating agent and the tertiary base, and the said base being used in less than three molecular proportions per mol. of sulphonating agent. Examples describe the heating of the following substances with chlorosulphonic acid and pyridine, alone and in the presence of nitrobenzene, tetrachlorethane, or o-dichlorbenzene; (1) 1-aminoanthraquinone; (2) 1-amino-5-methoxy-nitro-, sulpho- or carboxy-anthraquinone; (3) 1-amino-6 or 8-chloranthraquinone; (4) 1-amino-6,7-dichloranthraquinone; (5) 1.5- or 1.8-diamino-anthraquinone. Also in examples, 1-aminoanthraquinone is heated in tetrachlorethane with pyridine and oleum or sulphur trioxide, and with quinoline and oleum. Dimethylamino-cyclohexane is specified as a base. The sulphonic acid may be brominated without isolation. A sample has been furnished under Sect. 2 (5) of a product prepared by heating 1-amino-anthraquinone with triethylamine and oleum in tetrachlorethane.