antracen

Antracen, more commonly known as anthracene in English, is a polycyclic aromatic hydrocarbon (PAH) with the chemical formula C14H10. It consists of three linearly fused benzene rings, giving a planar, symmetric molecule. Anthracene is part of the broader family of PAHs found in fossil fuels and related materials.

Occurrence and production

Anthracene occurs in coal tar and in some petroleum residues as a minor constituent. Industrial production of anthracene largely comes from distillation and purification of coal tar, with additional production from processing coal-distillation byproducts. It can also be derived from other PAHs through chemical transformations.

Physical and chemical properties

Anthracene is a colorless to pale yellow crystalline solid. It has a melting point around 216 °C and a high boiling point near 340–350 °C. It is practically insoluble in water but dissolves in many organic solvents such as benzene, toluene, and chloroform. The molecule is planar and relatively stable under normal conditions, though it can participate in characteristic PAH reactions.

Reactivity and derivatives

The 9,10-positions of anthracene are more reactive in certain chemical reactions, notably Diels–Alder reactions. Oxidation of anthracene yields anthraquinone, a widely used intermediate in dye manufacturing. Through various substitutions and oxidations, many anthracene derivatives are produced for dyes, pigments, and specialty chemicals.

Uses

Anthracene serves mainly as a precursor to dyes and pigments, particularly anthraquinone-derived dyes. It is also employed in organic electronics research as a model PAH and, in some contexts, in scintillation media.

Safety

As a polycyclic aromatic hydrocarbon, anthracene is considered a potential environmental and health hazard with long-term exposure. It is low in acute toxicity but can be harmful with prolonged contact or ingestion; handling typically requires standard protective measures and proper disposal in accordance with regulations.