Anthracene

Keywords

anthracene

[CAS: 120-12-7]. A colorless solid; melting point 218°C, blue ßu-

orescence when pure; insoluble in water, slightly soluble in alcohol
or ether, soluble in hot benzene, slightly soluble in cold benzene;
transformed by sunlight into para-anthracene (C14 H10 )2 .
Anthracene reacts: (1) With oxidizing agents, e.g., sodium dichro-
mate plus sulfuric acid, to form anthraquinone, C6 H4 (CO)2 C6 H.
(2) With chlorine in water or in dilute acetic acid below 250°C
to form anthraquinol and anthraquinone, at higher temperatures
9,10-dichloroanthracene. The reaction varies with the temperature
and with the solvent used. The reaction has been studied using,
as solvent, benzene, chloroform, alcohol, carbon disulÞde, ether,
glacial acetic acid, and also without solvent by heating. Bromine
reacts similarly to chlorine. (3) With concentrated sulfuric acid
to form various anthracene sulfonic acids. (4) With nitric acid,
to form nitroanthracenes and anthraquinone. (5) With picric acid
(1)HO·C6 H2 (NO2 )3 (2,4,6) to form red crystalline anthracene picrate,
melting point 138°C.

Anthracene is obtained from coal tar in the fraction distilling be-

tween 300° and 400°C. This fraction contains 5–10% anthracene,
from which, by fractional crystallization followed by crystallization
from solvents, such as oleic acid, and washing with such solvents as
pyridine, relatively pure anthracene is obtained. It may be detected
by the formation of a blue-violet coloration on fusion with mellitic
acid. Anthracene derivatives, especially anthraquinone, are impor-
tant in dye chemistry.

Van Nostrand’s Encyclopedia of Chemistry, Copyright © 2005 John Wiley & Sons, Inc. 1