Anthraquinone 1-amino

In the anthraquinone series, apart from the special case of the amination of leucoquinizarin, sulfonic acid and nitro are the preferred leaving groups. 1-Aminoanthraquinone is manufactured from anthraquinone-l-sulfonic acid or 1-nitroanthraquinone, and 2-amino anthraquinone (betamine) from anthraquinone-2-sulfonic acid. 

In the first case (22), almost stoichiometric amounts of sulfuric acid or chlorosulfonic acid are used. The amine sulfate or the amine chlorosulfate is, first, formed and heated to about 180 or 130°C, respectively, to rearrange the salt. The introduction of the sulfonic acid group occurs only in the ortho position, and an almost quantitative amount of l-aminoanthraquinone-2-sulfonic acid is obtained. On the other hand, the use of oleum (23) requires a large excess of SO to complete the reaction, and inevitably produces over-sulfonated compound such as l-amino-anthraquinone-2,4-disulfonic acid. Addition of sodium sulfate reduces the byproduct to a certain extent. Improved processes have been proposed to make the isolation of the intermediate (19) uimecessary (24,25). 

The 2 -isomer is best formed by persulfate oxidation of 2-amino anthraquinone [Kirk Othmer 7 (1947), 9551... 

Dimethylamino-anthraquinone see Bis (methyl-amino)-anthraquinone 2 B148... 

Pigment Blue 60 [81-77-6] 69800 indanthrone intermolecular condensation of 2-amino-anthraquinone in presence of a strong inoiganic base and oxidizing agent... 

Acylaminoanthraquinones. Acylation of amino anthraquinones with benzoic acid or benzoyl chloride, for example, affords vat dyes with satisfactory affinity to cellulose fibers. The simplest dyes of this type, 1,4- and 1,5-dibenzoylaminoanthra-quinones, are no longer important. Bridging linkages, such as the dicarboxylic acids oxalic or phthalic acid, permit coupling of two anthraquinone units three amino anthraquinones may be combined by use of a triazine, such as cyanuric chloride. 

Previously, this was done with pyrolusite, but modem processes use arsenic acid (with 2-aminoanthraquinone) and sodium m-nitrobenzenesulfonate (with 1-amino-anthraquinone). The sulfite can ako be removed by precipitation with alkaline earth chlorides, e.g., barium chloride. The procedure given above has the advantage that it yields a product which is practically ash-free. The ammonium chloride is added to neutralize the alkali formed in the reaction (the arsenite forrned acts as free sodium hydroxide). The mother liquors, which contain arsenious acid, are poisonous, of course, and must be handled carefully. They are usually treated with milk ef lime to render them harmless. The toxicity of such waste products is frequently ovo emphasized if they are discharged into large streams, for example, ftey rarely poison the fish. In plant operations, the excess anunonia is collected and used over without further treataent For a general discussion of the sulfonation of anthraquinone, see page 56 ff. 

Aminoanthraquinone can be sulfonated relatively easily in the 2 position by treating it with fuming sulfuric acid in the presence of bisulfate. The l-aminoanthraquinone-2-sulfonic acid thus formed can also be prepared smoothly by baking the acid sulfate of 1-amino-anthraquinone at 200°C. It is a very important starting material for the preparation of valuable acid anthraquinone dyes. ... 

SYNS 2-AMINO-9,10-ANTHRACENEDIONE 2-AMINO-9,10-ANTHRAQUINONE P-AMINO-ANTHRAQUINONE P-ANTHRAQUINONYL-AiMINE NCI-C01876... 

CIBACET RED 3B CIBACET RED E3B CILLA FAST PINK BN C.I. 60710 O C.I. DISPERSE RED 15 O C.I. SOLVENT RED 53 DIACELLITON FAST PINK B DISPERSE FAST PINK B DISPERSE RED 15 DISPERSE RED 25 DISPERSOL ORANGE D-G DURANOL RED 2B FENACET FAST PINK B 1-HYDROXY-4-AMINO-ANTHRAQUINONE 4-HYDROXY-l-ANTHRA-QUINONYLAMINE INTERCHEM ACETATE PINK BLF INTERCHEM HISPERSE PINK BH MICROSETILE PINK BN NACELAN PINK B NEOSETILE PINK BN ORACET RED 3B PARA M PERLITON PINK 3B SERISOL FAST RED 2B SETACYL PINK 3B SUPRACET BRILLIANT RED 2B... 

In 1901 a most important discovery was made by Bohn. He endeavoured to make. e anthraquinone analogue of Indigo by fusing the substituted glycine, derived from 2 amino-anthraquinone, (13), with caustic soda. A blue vat dye was obtained, but instead of the anticipated product it was proved to be Indanthrone, (14), or Indanthren Blue RS(C.I. vatblue4) ... 

The early anthraquinone vat dyes were all blue or greenish-blue shades, but the fusion of 2 amino-anthraquinone at higher temperatures produced a yellow vat dye known as Flavanthrone or Indanthren Yellow G (C.I. VAT YELLOW 1), (19) ... 

Benzisoxazoles.- The thienylbenzisoxazole (343) is obtained from -chloronitro-benzene and 2-(cyanomethyl)thiophen or by the reaction of -nitrobenzaldehyde with thiophen in the presence of hydrogen chloride. 6H-Anthrall,9-cdjisoxaz-ol-6-one (344), prepared by the action of sodium azide on diazotized 1-amino-anthraquinone, is cleaved by triphenylphosphine or dimethylsulphoxide to the... 

To precipitate the desired potassium sulfonate, the filtrate [collected in receivers (3 and 3A), together with strong wash liquor] is transferred to the 20,000-liter rubber-lined precipitation tank (4) and the concentrated KCl solution is added. The temperature is maintained at 85°C to keep the byproduct 1,5-disulfonate in solution. The precipitated potassium sulfonate is isolated by continuous filtration on a rubber-covered rotary filter (5 and 6), where it is washed with 5 per cent potassium chloride solution and discharged at approximately 45 per hent solids content into a horizontal trough mixer (7), from which it is pumped to one of two 13,000-liter brick-lined paste storage tanks (8). The paste content is adjusted to 35 per cent solids and brought to neutrality with a small amount of soda ash solution, after which it is pumped either to an autoclave for conversion to 1-amino-anthraquinone or to the chlorinators for conversion to 1-chloroanthra-quinone. 

Aminoanthraquinone from 2-Chloroanthraquinone. By the use of potassium chlorate and ammonium nitrate as oxidants, it is possible to obtain directly a 2-amino-anthraquinone of 97.5-98.5 per cent purity. A copper catalyst is not essential but is sometimes used to moderate the conditions of the reaction. The only treatment required is a thorough washing of the 2-aminoanthraquinone with hot dilute aqueous ammonia or dilute sodium hydroxide. 

Description of Recovery System. In the preparation of 2-amino-anthraquinone, the excess ammonia can be recovered in the following manner (Fig. 8-29) at the end of the reaction, the gaseous constituents of the reaction mixture are gradually released through the line (2) by means of the needle valves (3 and 4) and allowed to expand to a pressure of about 50 psi. The expansion causes a considerable drop in temperature, and heat is eliminated as the gaseous products flow through the cooling coil (5), re-... 

It has been reported that y3-CD could improve the selectivity of the color reactions of various metal ions with triphenylmethane, xanthene acid dyes and some other coloring reagents. The effect of fi-CD on the association compound system of metal (Mo, Zn, Co)-thiocyanate basic dyes such as malachite green, crystal violet, rhodamine B, rhodamine 6G and butyhhodamine B, has been investigated and the result shows that /3-CD could contribute to a more sensitive and stable system which improve the solubility of the basic dyes and produce a favorable microenviromnent for the color reactions [63]. /3-CD could be employed to solubilize the 1,2-amino anthraquinone in water due to the formation of inclusion complex which acts as a ligand for metal ions could be used for the determination of palladium at trace levels by spectrophotometry. In the spectrophotometric determination of microamounts of Zn based on the Zn-dithizone color reaction, -CD could increase the apparent molar absorptivity at 538 nm by 8.37 times. In the presence of cr-CD, the determination sensitivity of copper in leaves based on the color reaction of Cu(II) and mesotetrakis (4-methoxy-3-sulfophenyl) porphyrin was enhanced by 50% in the spectrophotometric analysis [64,65]. 

Methoxy phcny lazo) -2-Naphthol Sudan Red G 1, 4 Diphenyl Toluidino Anthraquinone 2-(4-Dimethylamino Phen>4azo) Naphthalene 1-Amino Anthraquinone Fast red AI I, 4 EHmethylamino Anthraquinone, Fast blue B 4-Dimethylamino Azobenzene (for colored smoke mixtures) 1-Methylamino Anthraquinone... 

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