Anthracene - production and uses

Anthracene was first discovered in coal tar by Jean B.A. Dumas and Auguste Laurent in 1832. The importance of anthracene for industrial aromatic chemistry began with the synthesis of the dyestuff alizarin by Carl Graebe and Carl Th. Liebermann, as well as by William H. Perkin in 1868, replacing the natural dye produced from madder. Anthraquinone dyestuffs have remained the most important class of dyes, alongside azo-dyes, since the beginning of the chemistry of synthetic dyestuffs. 

From the time of the first alizarin synthesis, anthraquinone has been the most versatile anthracene derivative. This applies both for dye production and for the more recent applications of anthraquinone, as an additive (redox-catalyst) in wood pulping, and as a hydrogen carrier in H2O2 production. 

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Equimolar amounts of anthracene,/ -benzoquinone, and aluminum chloride give the faintly yellow adduct in 15 minutes. The product is unstable to heat turning yellow at 207°, turning red at 210°, and slowly charring. When 2 molar equivalents of anthracene are used, the bis adduct is obtained, mp 230°, unobtainable in the absence of the catalyst. 

In the case of the photoaddition of anthracene derivatives and tetracene, the cross-dimer is the major product isolated in all cases even when anthracene itself is used. 

NH3 Naphth2). If sodium is used in place of potassium, the product detonates as crystallisation starts. This is attributed to energetic expulsion of ammonia held endothermically in the growing crystal lattice. The same also occurs with anthracene and sodium, and nitrobenzene and barium. Caution in preparing and using these compounds is urged. 

Typical probes for the analysis of ionic solutes include 3-hydroxy-L-tyrosine (DOPA)24 and naphthalene-2-sulfonate,26 whereas those for use with uncharged solutes include nicotinamide,27 theophylline,28 and anthracene 29 Indirect detection is nonspecific and less suitable for the analysis of complex or impure samples, because unpurified biological samples, such as urine, contain a large number of hydrophilic solutes that will give problems such as extra system peaks. However, analyses of pharmaceutical products and quantification of impurities in substances are typical of applications.23... 

Together with benzene and naphthalene two other hydrocarbons are obtained from coal tar though in much smaller amounts. They are anthracene and phenanthrene, both of which have the formula CuHjo. Anthracene together with phenanthrene is present in the coal tar distillate which boils above 270°. The yield of anthracene is about 0.25 to 0.45 per cent of the tar. The crude distillate is purified by a second distillation and separated into two fractions (i) A product known as 50 per cent anthracene which is crystalline and still contains phenanthrene. (2) A less volatile non-crystalline oil known as anthracene oil. The 50 per cent anthracene is largely used, just as it is without further purification, in the preparation of alizarin, itsmost important derivative. To obtain pure anthracene from the crude 50 per cent product it is first redistilled after addition of potassium carbonate which forms a non-volatile compound with a constituent known as carbazole. 

Crude bromophenanthrene prepared by the bromination of technical (90%) phenanthrene and purified by distillation only was used by the submitters in this preparation. The an-thracene-9-aldehyde, which may be formed from the anthracene present as an impurity in 90% phenanthrene, does not form a sodimn bisulfite addition product and so will not contaminate the phenanthrene-9-aldehyde. The checkers used 9-bromophe-nanthrene, m.p. 54-56° (p. 20), exclusively, but without any advantage in yield. The submitters report yields of 55-60% from pure 9-bromophenanthrene. 

Introduction. The quinones are intermediate products in the oxidation of the aromatic nucleus. They may be prepared in some cases by the direct oxidation of aromatic hydrocarbons. For example, anthracene, naphthalene, and phenanthrene are oxidized to the corresponding quinones by chromic acid mixtures. Quinones are prepared more conveniently by oxidation of primary aromatic amines, particularly the p-substituted amines. p-Benzoquinone is obtained by the oxidation of aniline, p-toluidine, sulfanilic acid, p-aminophenol, and other similar compounds. Similarly the a-naph-thoquinone is obtained by oxidation of 1,4-aminonaphthol, and /9-naphthoquinone by the oxidation of 1,2-aminonaphthol. In the laboratory, although it is possible to prepare p-benzoquinone by the oxidation of aniline with acid-dichromate mixture, the method is tedious and the yield poor. Since hydroquinone is used extensively as a photographic developer and is made industrially, it is more convenient to prepare quinone by its oxidation. 

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