1911 Encyclopædia Britannica/Anthracene

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ANTHRACENE (from the Greek ἄνθραξ, coal), C14H10, a hydrocarbon obtained from the fraction of the coal-tar distillate boiling between 270° and 400° C. This high boiling fraction is allowed to stand for some days, when it partially solidifies. It is then separated in a centrifugal machine, the low melting-point impurities are removed by means of hot water, and the residue is finally hot-pressed. The crude anthracene cake is purified by treatment with the higher pyridine bases, the operation being carried out in large steam-jacketed boilers. The whole mass dissolves on heating, and the anthracene crystallizes out on cooling. The crystallized anthracene is then removed by a centrifugal separator and the process of solution in the pyridine bases is repeated. Finally the anthracene is purified by sublimation.

Many synthetical processes for the preparation of anthracene and its derivatives are known. It is formed by the condensation of acetylene tetrabromide with benzene in the presence of aluminium chloride:—

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and similarly from methylene dibromide and benzene, and also when benzyl chloride is heated with aluminium chloride to 200° C. By condensing ortho-brombenzyl bromide with sodium, C. L. Jackson and J. F. White (Ber., 1879, 12, p. 1965) obtained dihydro-anthracene

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Anthracene has also been obtained by heating ortho-tolylphenyl ketone with zinc dust

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Anthracene crystallizes in colourless monoclinic tables which show a fine blue fluorescence. It melts at 213° C. and boils at 351° C. It is insoluble in water, sparingly soluble in alcohol and ether, but readily soluble in hot benzene. It unites with picric acid to form a picrate, C14H10·C6H2(NO2)3·OH, which crystallizes in needles, melting at 138° C. On exposure to sunlight a solution of anthracene in benzene or xylene deposits para-anthracene (C14H10)2, which melts at 244° C. and passes back into the ordinary form. Chlorine and bromine form both addition and substitution products with anthracene; the addition product, anthracene dichloride, C14H10Cl2, being formed when chlorine is passed into a cold solution of anthracene in carbon bisulphide. On treatment with potash, it forms the substitution product, monochlor-anthracene, C14H9Cl. Nitro-anthracenes are not as yet known. The mono-oxyanthracenes (anthrols), C14H9OH or 1911 Britannica - Anthracene3.png (α) and (β) resemble the phenols, whilst 1911 Britannica - Anthracene4.png (γ) (anthranol) is a reduction product of anthraquinone. β-anthrol and anthranol give the corresponding amino compounds (anthramines) when heated with ammonia.

Numerous sulphonic acids of anthracene are known, a monosulphonic acid being obtained with dilute sulphuric acid, whilst concentrated sulphuric acid produces mixtures of the anthracene disulphonic acids. By the action of sodium amalgam on an alcoholic solution of anthracene, an anthracene dihydride, C14H12, is obtained, whilst by the use of stronger reducing agents, such as hydriodic acid and amorphous phosphorus, hydrides of composition C14H16 and C14H24 are produced.

Methyl and phenyl anthracenes are known; phenyl anthranol (phthalidin) being somewhat closely related to the phenolphthaleins (q.v.). Oxidizing agents convert anthracene into anthraquinone (q.v.); the production of this substance by oxidizing anthracene in glacial acetic acid solution, with chromic acid, is the usual method employed for the estimation of anthracene.