Anthracene Chemical Properties,Uses,Production
Colourless Crystalline Solid
Anthracene is colorless, to pale yellow crystalline
solid with a bluish fluorescence. PAHs are compounds
containing multiple benzene rings and are also called polynuclear
Anthracene has been shown to be soluble in a variety of binary and ternary mixtures of cyclohexanone, ethyl acetate, and methanol 1,2.
Obtained from coal tar. It is an important source of dyestuffs
white crystalline solid used extensively in
the manufacture of dyes. Anthracene is
found in the heavy- and green-oil fractions
of crude oil and is obtained by fractional
crystallization. Its structure is benzene-like,
having three six-membered rings fused toanion gether. The reactions are characteristic of
anthracene: A white crystallinesolid, C14
; r.d. 1.28; m.p. 215.8°C;b.p. 341.4°C. It is an aromatic hydrocarbonwith three fused rings, and is obtained by the distillationof crude oils. The main useis in the manufacture of dyes.
White to yellow solid with a weak aromatic odor. Sinks in water.
Air & Water Reactions
Flammable. Insoluble in water.
Anthracene will spontaneously burst into flame on contact with chromic acid, and other strong oxidants.
A questionable carcinogen.
Carcinogenicity of anthracene is not known.Its toxicity is very low. An intraperitonealLD50 in mice is recorded at 430 mg/kg(NIOSH 1986).
Inhalation of dust irritates nose and throat. Contact with eyes causes irritation.
Anthracene is combustible.
Moderately toxic by
intraperitoneal route. A skin irritant and
allergen. Questionable carcinogen with
experimental neoplas tigenic and tumorigenic
data. Mutation data reported. Combustible
when exposed to heat, flame, or oxidizing
materials. Moderately explosive when exposed to flame, Ca(OCl)z, chromic acid.
To fight fire, use water, foam, CO2, water
spray or mist, dry chemical. Explodes on
contact with fluorine.
It is used as an intermediate in dye
stuffs (alizarin), insecticides, and wood preservatives; making
synthetic fibers, anthraquinone, and other chemicals.
May be present in coke oven emissions, diesel fuel, and
coal tar pitch volitiles.
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a oneway
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion,
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed.
As first aid for pulmonary edema, a doctor or authorized
paramedic may consider administering a drug or other
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Likely impurities are anthraquinone, anthrone, carbazole, fluorene, 9,10-dihydroanthracene, tetracene and bianthryl. Carbazole is removed by continuous-adsorption chromatography [see Sangster & Irvine J Phys Chem 24 670 1956] using a neutral alumina column and eluting with n-hexane. [Sherwood in Purification of Inorganic and Organic Materials, Zief (ed), Marcel Dekker, New York, 1969.] The solvent is evaporated, and anthracene is sublimed under vacuum, then purified by zone refining, under N2 in darkness or non-actinic light. It has also been purified by co-distillation with ethylene glycol (boils at 197.5o), from which it can be recovered by addition of water, followed by crystallisation from 95% EtOH, *benzene, toluene, a mixture of *benzene/xylene (4:1), or Et2O. It has also been chromatographed on alumina with pet ether in a dark room (to avoid photo-oxidation of adsorbed anthracene to anthraquinone). Other purification methods include sublimation in a N2 atmosphere (in some cases after refluxing with sodium), and recrystallisation from toluene [Gorman et al. J Am Chem Soc 107 4404 1985]. Anthracene has been crystallised from EtOH, chromatographed through alumina in hot *benzene (fume hood) and then sublimed in a vacuum in a pyrex tube that has been cleaned and baked at 100o. (For further details see Craig & Rajikan J Chem Soc, Faraday Trans 1 74 292 1978, and Williams & Zboinski J Chem Soc, Faraday Trans 1 74 611 1978.) It has been chromatographed on alumina, recrystallised from n-hexane and sublimed under reduced pressure. [Saltiel J Am Chem Soc 108 2674 1986, Masnori et al. J Am Chem Soc 108 1126 1986.] Alternatively, recrystallise it from cyclohexane, chromatograph it on alumina with n-hexane as eluent, and recrystallise two more times [Saltiel et al. J Am Chem Soc 109 1209 1987]. Anthracene is fluorescent and forms a picrate complex, m 139o, on mixing the components in CHCl3 or *C6H6, but decomposes on attempted crystallization. [Beilstein 5 IV 228.]
Finely dispersed powder may form
explosive mixture in air. Contact with strong oxidizers
(chlorates, nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, epoxides, chromic acid/or
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
Anthracene Preparation Products And Raw materials