Anthraquinone sulfonic Acids

Anthraquinone-1-sulfonic acid, 9 313-314 Anthraquinone-a,a -disulfonic acids, 9 314-315... 

The traditionally most important route to 1-aminoanthraquinone [1] proceeds via nucleophilic exchange of anthraquinone-1-sulfonic acid or 1-chloroanthraquinone with ammonia. Replacing ammonia by amines affords the corresponding alkyl or arylaminoanthraquinones. 

Chloroanihraquinone is an inlermediaie for manufacturing vat dyes such as Ci Vat Brown 1. 1-Chloroanihraquinone is prepared by chlorination of anthraquinone-1-sulfonic acid with. sodium chlorate in hydrochloric acid at elevated temperature. 

The presence of mercuric salts in the sulfonation mixtures favors the formation of anthraquinone-1-sulfonic acid further sulfonation leads to a complex mixture of disulfonic acids, chiefly 1,5 and 1,8 with lesser quantities of 1,6 and 1,7-isomers [11]. 

The novel vat dyes encouraged the development of processes for obtaining the important intermediate 1-aminoanthraquinone (49). The reaction involves replacement of the sulfonic acid group in anthraquinone-1-sulfonic acid by the amino group. It is achieved by heating the sulfonate with aqueous ammonia in the presence of sodium arsenate, which oxidizes the sulfite liberated to sulfate. 

Use of mercuric catalysts has created a serious pollution problem thereby limiting the manufacture of such acids. Other catalysts such as palladium or mthenium have been proposed (17). Nitration of anthraquinone has been studied intensively in an effort to obtain 1-nitroanthraquinone [82-94-8] suitable for the manufacture of 1-aniinoanthraquinone [82 5-1]. However, the nitration proceeds so rapidly that a mixture of mono- and dinitroanthraquinone is produced. It has not been possible, economically, to separate from this mixture 1-nitroanthraquinone in a yield and purity suitable for the manufacture of 1-arninoanthraquinone. Chlorination of anthraquinone cannot be used to manufacture 1-chloroanthraquinone [82-44-0] since polychlorinated products are formed readily. Consequently, 1-chloroanthraquinone is manufactured by reaction of anthraquinone-1-sulfonic acid [82-49-5] with sodium chlorate and hydrochloric acid (18). 

In presence of mercirry, one obtains the kinetically-controUed anthraquinone-1-sulfonic acid W. Langenbeck, W. Pritzkow, Lehrbuch der Organischen Chemie, Verlag Theodor Steinkopfif, Dresden, 21st. Edn., (1969) 173. 

The main use of anthraquinone-1-sulfonic acid is in the production of 1-amino-anthraquinone. Production of 1-aminoanthraquinone by way of sulfonic acid is diminishing, because of the involved use of mercury. In its place, nitration of anthraquinone, followed by the reduction of 1-nitroanthraquinone, is becoming increasingly common, as is pressure ammonolysis. 

Dyes, Dye Intermediates, and Naphthalene. Several thousand different synthetic dyes are known, having a total worldwide consumption of 298 million kg/yr (see Dyes AND dye intermediates). Many dyes contain some form of sulfonate as —SO H, —SO Na, or —SO2NH2. Acid dyes, solvent dyes, basic dyes, disperse dyes, fiber-reactive dyes, and vat dyes can have one or more sulfonic acid groups incorporated into their molecular stmcture. The raw materials used for the manufacture of dyes are mainly aromatic hydrocarbons (67—74) and include ben2ene, toluene, naphthalene, anthracene, pyrene, phenol (qv), pyridine, and carba2ole. Anthraquinone sulfonic acid is an important dye intermediate and is prepared by sulfonation of anthraquinone using sulfur trioxide and sulfuric acid. 

Aluminium hydroxide Unknown s Anthraquinone sulfonic acid Unknown 1... 

There are several cases of hydroxylation according to the hidden-radical mechanism, within a solvent cage. As assumed (Fomin and Skuratova 1978), hydroxylation of the anthraquinone sulfonic acids (AQ—SO3H) proceeds by such a reticent pathway, and OH radicals attack the substrate anion-radicals in the solvent cage. Anthraquinone hydroxyl derivatives are the final products of the reaction. In the specific case of DMSO as a solvenf, hydroxyl radicals give complexes with the solvent and lose their ability to react with the anthraquinone sulfonic acid anion-radicals (Bil kis and Shein 1975). The reaction stops after an anion-radical is formed ... 

In this field, several authors have reported the complete removal of organic pollutants, such as formaldehyde (Do and Chen 1993), aniline (Brillas et al. 1996), phenol (Alvarez-Gallegos and Pletcher 1999), pesticides (Guivarch et al. 2003), herbicides (Boye et al. 2002), and industrial effluent containing naphthalene- and anthraquinone-sulfonic acids (Panizza and Cerisola 2001) by in situ electrogenerated hydrogen peroxide catalyzed by iron ions. 

The oxidation of a wide range of phenol and other biorefractory organic compounds (e.g., ethanol, aliphatic acids, naphthalene and anthraquinone sulfonic acids, aniline, nitrobenzene, etc.) on platinized titanium was also studied by Kotz et al. (Kotz et al. 1991 Stucki et al. 1991). The elimination of TOC was rather ineffective due to the leakage current for oxygen evolution, and the average EOI was about 0.05. 

The molten alkali can have the opposite effect and exert an imdizing action. Thus, it is well known that anthraquinone> -sulfonic acid does not yield hyditRyanthraquinone, but alizarin (l,2>dihydroxyanthraquinone). This reaction can be favored by the addition of an oxidizing agent. 

Ah zarin from anthraquinone- -sulfonic acid (NaOCl in alkali fusion ... 

Fig. 10. Mannich reaction on l-amino-2-anthraquinone sulfonic acid.

The sulfonic group present in anthraquinonc dyes is readily replaced by the Mannich reagent, as has been mentioned previously (see 10 in Sec. A. I) in particular, 1 -amino-and l-hydroxy-2-anthraquinone-sulfonic acids may occasionally be involved in the production of cyclic Mannich bases. Finally, the methyl group of dimelhylsulfite (CH,)2SOj may be similarly replaced by the dimethylaminomcthyl group giving OjS—CH —... 

Some 80 % of anthraquinone dyes are prepared via the anthraquinone sulfonic acids. In producing certain dyes, the sulfonic acid group is replaced by a hydroxyl group using high pressure fusion with lime [31.28]. 

Anthraquinone-2-sodium sulfonate 2-Anthraquinonesulfonate sodium Anthraquinone-2-sulfonate sodium salt 2-Anthraquinone sulfonic acid, sodium salt Anthraquinone-p-sulfonic acid sodium salt. 

Empiricai CsHgNaOsS Properties M.w. 240.20 Uses Electroplating brightening agent Sodium 2-anthraquinone sulfonate CAS 131-08-8 EINECS/ELINCS 205-009-5 Synonyms 2-Anthracenesulfonic acid, 9,10-dihydro-9,10-dioxo-, sodium salt 9,10-Anthraquinone-2-sodium sulfonate 2-Anthraquinonesulfonate sodium Anthraquinone-2-sulfonate sodium salt 2-Anthraquinone sulfonic acid, sodium salt Anthraquinone-p-sulfonic acid sodium salt ... 

Anthraquinone-sulfonic Acid suspension 20 60 8 Resistant <3 <0.5 Hostalen Hoechst Celanese Specimen 50X25X1 mm (2X1X0.04 in) from press-molded sheets to DIN 53455... 

Amino-4-(3-(b-hydroxyethylsulfonyl-phenylamino))anthraquinone-2-sulfonic acid [39582-26-8... 

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