9,10-anthraquinone sulfonates

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. 

HCEH2O, pH=0.44 Na-P-hydroanthra-quinonesulfonate /P-anthraquinone-sulfonate, 1.8 mM 25 1.51-10" CF 62Losl... 

Anaerobic bio-reduction of azo dye is a nonspecific and presumably extracellular process and comprises of three different mechanisms by researchers (Fig. 1), including the direct enzymatic reduction, indirect/mediated reduction, and chemical reduction. A direct enzymatic reaction or a mediated/indirect reaction is catalyzed by biologically regenerated enzyme cofactors or other electron carriers. Moreover, azo dye chemical reduction can result from purely chemical reactions with biogenic bulk reductants like sulfide. These azo dye reduction mechanisms have been shown to be greatly accelerated by the addition of many redox-mediating compounds, such as anthraquinone-sulfonate (AQS) and anthraquinone-disulfonate (AQDS) [13-15],... 

The high surface charge on a micelle (10 volts/a or 300m-volts/micelle) can strongly participate in redox exchange reactions (11). For example, the equilibrium between anthraquinone sulfonate (AQS ) and duroquinone (DQ) and their reduced forms... 

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

Williams, S. J., Goodall, D. M., and Evans, K. P. (1993). Analysis of anthraquinone sulfonates — comparison of capillary electrophoresis with high-performance liquid-chromatography.. Chromatogr. 629, 379-384. 

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 ... 

Sodium hyposulfate (aqueous) 48 g Na2S20., 40 g NaOH, and 12 g anthraquinone sulfonate in 300 mL H20... 

Sodium anthraquinone sulfonate 2% sodium anthraquinone sulfonate in 1.5 M... 

Until fairly recently, preparation of almost 80 % of all important anthraquinones was based on anthraquinonesulfonic acids. However, nitration of anthraquinone is gaining in importance presently, a development triggered mainly by environmental considerations (e g., production of large volumes of waste dilute acids during anthraquinone sulfonation). However, great progress has been made recently in solving the problems associated with sulfonation. 

Kuk, W. K. and Huh, Y. D. (1997). Preferential intercalation of isomers of anthraquinone sulfonate ions into layered double hydroxides. J. Mater. Chem. 

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. 

This pale-yellow quaternary alkaloid, picrate mp 189°, [a]D of chloride — 930° (in water), was first isolated from a calabash curare (12) it was subsequently isolated from other calabash curare preparations (34, 35) and has been identified chromatographically in extracts from the bark of S. mitscherlichii (33) and other Strychnos species (7). The identification of C-fluorocurarine is greatly helped by its deep-blue fluorescence in UV-light. Analyses of the crystalline iodide and anthraquinone sulfonate showed its molecular formula to be C2oH23N20+ (12), which is in agreement with all subsequent work. The properties of C-fluorocurarine, particularly its low toxicity and high Rc values, suggest that it is a C20 alkaloid rather than a double molecule. This was confirmed (102) by application of the partial quaternization method to one of its derivatives (see subsequent discussion) the method cannot be applied to C-fluorocurarine itself, since on pyrolysis it is not smoothly demethylated to the... 

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 —... 

Fia. 84. Variation of a quinone-hydroquinone (anthraquinone sulfonate) puteutial with pH... 

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