ANTHRACENE

EC / List no.: 204-371-1
CAS no.: 120-12-7
Mol. formula: C14H10

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. 
Anthracene is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. 
Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.

Occurrence and production
Coal tar, which contains around 1.5% anthracene, remains a major source of this material.
 Common impurities are phenanthrene and carbazole. 
The mineral form of anthracene is called freitalite and is related to a coal deposit.
A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction.

Reactions
Reduction
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Hydrogenation gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.

Cycloadditions
The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] cycloaddition. 
Anthracene reverts to anthracene thermally or with UV irradiation below 300 nm. 
Substituted anthracene derivatives behave similarly. 
The reaction is affected by the presence of oxygen.

With electrophiles
Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate

Electrophilic substitution of anthracene occurs at the 9 position. 
For example, formylation affords 9-anthracenecarboxaldehyde. Substitution at other positions is effected indirectly, for example starting with anthroquinone.
Bromination of anthracene gives 9,10-dibromoanthracene

Uses:
Anthracene is converted mainly to anthraquinone, a precursor to dyes.

Niche
Anthracene, a wide band-gap organic semiconductor is used as a scintillator for detectors of high energy photons, electrons and alpha particles. 
Plastics, such as polyvinyltoluene, can be doped with anthracene to produce a plastic scintillator that is approximately water-equivalent for use in radiation therapy dosimetry. 
Anthracene's emission spectrum peaks at between 400 nm and 440 nm.

Anthracene is also used in wood preservatives, insecticides, and coating materials.

Anthracene is commonly used as a UV tracer in conformal coatings applied to printed wiring boards. 
The anthracene tracer allows the conformal coating to be inspected under UV light.
Anthracene also used in manufacturing of anthraquinone.

Derivatives

False-color AFM image of anthracene diradical, where hydrogen atoms are removed at carbons 9 and 10
A variety of anthracene derivatives find specialized uses. 
Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol) are pharmacologically active. 
Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene.

Occurrence
Anthracene, as many other polycyclic aromatic hydrocarbons, is generated during combustion processes. 
Exposure to humans happens mainly through tobacco smoke and ingestion of food contaminated with combustion products.

Description    
Anthracene is one of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). 
PAHs are often found together in groups of two ormore. 
They can exist inmore than 100 different combinations, but the most common are treated as a group of 15. 
PAHs are found naturally in the environment but they can also be made synthetically. 
Anthracene can vary in appearance from a colorless to pale yellow crystal-like solid.
 PAHs are created when products like coal, oil, gas, and garbage are burned but the burning process is not complete. 
Very little information is available on the individual chemicals within the PAH group; the majority of the information is for the entire PAH group. 
Anthracene is a solid white to yellow crystal, has a weak aromatic odor, and sinks in water. 

Its characteristics are 
boiling point, 3421°C; 
melting point, 2181°C; 
molecular weight, 178.22; 
density/specific gravity, 1.25 at 27 and 41°C; 
octanol–water coefficient, 4.45. 
Anthracene is soluble in absolute alcohol and organic solvents. 
Maximum absorption occurs at 218 nm.

Chemical Properties    
ANTHRACENE is a colorless solid; 
melting point 218 °C, blue fluorescence 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 (C14H10)2.

Anthracene is colorless, to pale yellow crystalline solid with a bluish fluorescence. 
PAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons.

Physical properties    
White to yellow crystalline flakes or crystals with a bluish or violet fluorescence and a weak aromatic odor. 
Impurities (naphthacene, tetracene) impart a yellowish color with green fluorescence.

Uses:
Anthracene has been shown to be soluble in a variety of binary and ternary mixtures of cyclohexanone, ethyl acetate, and methanol 1,2.
Anthracene is an aromatic hydrocarbonwith three fused rings, and is obtained by the distillationof crude oils. 
The main useis in the manufacture of dyes.Anthracene is an important source of dyestuffs.
    
Most of the PAHs are used to conduct research. 
Like most PAHs, anthracene is used to make dyes, plastics, and pesticides. 
Anthracene has been used to make smoke screens and scintillation counter crystals. 
(A scintillation counter is used to detect or count the number of sparks or flashes that occur over a period of time.)

Production Methods    
Anthracene is obtained from coal tar in the fraction distilling between 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. 
Anthracene may be detected by the formation of a blue-violet coloration on fusion with mellitic acid. Anthracene derivatives, especially anthraquinone, are important in dye chemistry.

Definition    
(C14H10) A 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 AROMATIC COMPOUNDS.

Purification Methods    
Likely impurities are anthraquinone, anthrone, carbazole, fluorene, 9,10-dihydroanthracene, tetracene and bianthryl. 
Carbazole is removed by continuous-adsorption chromatography using a neutral alumina column and eluting with n-hexane. 
The solvent is evaporated, and anthracene is sublimed under vacuum, then purified by zone refining, under N2 in darkness or non-actinic light. 
Anthracene 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. 
Anthracene 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 . 
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.
Anthracene has been chromatographed on alumina, recrystallised from n-hexane and sublimed under reduced pressure. 
Alternatively, recrystallise it from cyclohexane, chromatograph it on alumina with n-hexane as eluent, and recrystallise two more times . 
Anthracene is fluorescent and forms a picrate complex, m 139o, on mixing the components in CHCl3 or *C6H6, but decomposes on attempted crystallization.

Anthracene is anthracene, also called paranaphthalene or green oil, a solid polycyclic aromatic hydrocarbon (PAH) consisting of three benzene rings derived from coal-tar, is the simplest tricyclic aromatic hydrocarbon. 
Anthracene is on the EPA's priority pollutant list. 
Anthracene is ubiquitous in the environment as a product of incomplete combustion of fossil fuels. 
Anthracene has been identified in surface and drinking water, ambient air, exhaust emissions, smoke of cigarettes and cigars, and in smoked foods and edible aquatic organisms. 
Anthracene is primarily used as an intermediate in the production of dyes, smoke screens, scintillation counter crystals, and in organic semiconductor research. 
Although a large body of literature exists on the toxicity of PAHs, data for anthracene are limited. 
Prolonged exposure causes variety of topical and systemic adverse reactions. 
Carcinogenicity bioassays with anthracene generally gave negative results.

Anthracene is a white to yellow solid with a weak aromatic odor. 
Sinks in water.

Anthracene is a natural product found in Festuca rubra, Lolium arundinaceum, and other organisms with data available.

Methods of Manufacturing
High-temperature coal tar contains, on average, 1.5% of anthracene.
Continuous tar distillation concentrates the anthracene in the fraction boiling between 300 and 360 °C (anthracene oil I). 
This oil amounts to 15 - 20% of the raw tar and contains about 7% anthracene.
Anthracene is cooled to 20 - 30 °C and then centrifuged. 
About 10-15 % of the crude anthracene oil I is obtained as a yellow-green crystalline material with an anthracene content of 20 - 35% (anthracene residues). 
These residues, which also contain 40 - 50% phenanthrene and 12-20% carbazole, are crystallized or distilled. Distillation yields a crude product containing 45 - 55% anthracene (50s anthracene). 
A 50s anthracene with an improved quality can be produced by two-step continuous column distillation. 
The crude 50s anthracene then is purified by recrystallization from selective solvents and by distillation. 
Repeated recrystallization from a three- to fourfold excess of pyridine produces anthracene (95% purity) from the 50s anthracene in 80% yield relative to the anthracene content.
Anthracene can be separated from the higher-boiling carbazole by distillation with lower-boiling hydrocarbon fractions as reflux medium or by azeotropic distillation with ethylene glycol. 
Azeotropic distillation also is used to separate the anthracene-accompanying tetracene and to obtain very pure anthracene for scintillation counting.

Anthracene is one of the smaller polynuclear aromatic hydrocarbons. 
(The only smaller one is naphthalene.) 
Anthracene was isolated from coal tar in 1832 by pioneering French chemists Jean-Baptiste Dumas and Auguste Laurent.

Anthracene can be synthesized by the Elbs reaction, in which o-tolyl phenyl ketone is dehydrated at 400–450 ºC. But most commercial anthracene is still recovered from coal tar.

In commerce, anthracene is mainly used as a starting material for the manufacture of 9,10-anthraquinone, which in turn is used to make colorants such as the red dye alizarin. 
More recently, crystalline anthracene was found to be a useful wide band-gap semiconductor in devices such as organic field-effect transistors and scintillators for detecting high-energy subatomic particles. 

What is anthracene? 
Anthracene is one of a group of chemicals called polycyclic aromatic hydrocarbons, PAHs for short.  
PAHs are often found together in groups of two or more.  
They can exist in over 100 different combinations but the most common are treated as a group of 15.  
PAHs are found naturally in the environment but they can also be man-made.  
Anthracene can vary in appearance from a colorless to pale yellow crystal-like solid. 
PAHs are created when products like coal, oil, gas, and garbage are burned but the burning process is not complete.  
Very little information is available on the individual chemicals within the PAH group. 
Most of the information available is for the PAH group as a whole.  
Information specific to anthracene is included in this fact sheet when available. 

What is anthracene used for? 
Most of the PAHs are used to conduct research. 
Like most PAHs, anthracene is used to make dyes, plastics and pesticides.  
Anthracene has been used to make smoke screens and scintillation counter crystals.  
A scintillation counter is used to detect or count the number of sparks or flashes that occur over a period of time. 

Anthracene derivatives are useful in preparing stable blue-emitting organic electroluminescence devices. 
Anthracene is oxidized to anthracene cis-1,2-dihydrodiol by Mycobacterium sp. strain PYR-12. 
Anthracene forms bis-adducts by [4+2]-cycloaddition reaction with [5,6]-fullerene C60.

Application
Anthracene has been shown to be soluble in a variety of binary and ternary mixtures of cyclohexanone, ethyl acetate, and methanol 
Anthracene was used to study the photodimerization reaction of anthracene in supercritical CO2.

About Anthracene
Helpful information
Anthracene is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.

Anthracene is used at industrial sites and in manufacturing.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Anthracene is most likely to be released to the environment.

Article service life
ECHA has no public registered data on the routes by which Anthracene is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using Anthracene. 
ECHA has no public registered data on the routes by which Anthracene is most likely to be released to the environment.

Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the routes by which Anthracene is most likely to be released to the environment.

Uses at industrial sites
Anthracene is used in the following products: laboratory chemicals and pharmaceuticals.
Anthracene has an industrial use resulting in manufacture of another substance (use of intermediates).
Anthracene is used for the manufacture of: chemicals.
Release to the environment of Anthracene can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).

Manufacture
Release to the environment of Anthracene can occur from industrial use: manufacturing of the substance.

IUPAC NAMES:
Anthracen
Anthracene
anthracene
Anthracene
anthracene

SYNONYMS:
Anthracen
Coal tar pitch volatiles:anthracene
coaltarpitchvolatiles:anthracene
Crudeanthracene
p-Naphthalene
Sterilite hop defoliant
Tetra Olive N2G
tetraoliven2g
Anthracene, 99.0%
anthracene solution
ANTHRACENE,PRACTICAL
ANTHRACENE,REAGENT
ANTHRAZENE
ANTHRACENE: 99.9%
Anthracene, 90+%
Anthracene Zone Refined (number of passes:30)
ANTHRACENE extrapure scintillation grade
Anthracene, tech. 90+%
Anthracene, melting point 215-218°C
Anthracene,crude
Anthracene ReagentPlus(R), 99%
Anthracene, standard for GC,>=99.5%(GC)
Anthracene 50
Anthracene reagent grade, 97%
Anthracene sublimed grade, >=99%
SKIRROW SELECTIVE MEDIUM 90MM
Anthracene Standard
Green oil Paranaphtalene Anthracene blue fluorescence
Anthracene, 98.5%
Anthracence
jingen
Anthracene blue fluorescence
anthracene, pure
Anthracenepract
Anthracenescintillationgrade
Anthracene;Green oil ; Paranaphtalene; Paranaphtalene; Anthracene blue fluorescence; Green oil
ANTHRACENE, 5000MG, NEAT
ANTHRACENE, ZONE-REFINED, 99+%
ANTHRACENE, FOR SCINTILLATION
1,2-DIBROMOETHANE, 1X1ML, MEOH, 5000UG/M L
ANTHRACENE, REAGENTPLUS, 99%
ANTHRACENE APPROX. 98%
ANTHRACENE OEKANAL, 250 MG
ANTHRACENE REAGENTPLUS(TM) 99%
ANTHRACENE, 1X1ML, ACET, 1000UG/ML
ANTHRACENE 99+%
ANTHRACENE, 1X1ML, MEOH, 200UG/ML
Anthracene, scintillation grade, 99+%
ANTHRACENE 99% FOR SCINTILLATION
ANTHRACENE PURE 98%
Anthracene(High Purity)
Anthracene 98 %
GREEN OIL
CI NO 10790
CI 10790
ANTHRACENE
ANTHRACENE, SCINTILLATOR
ANTHRACIN