Acenaphthene


Acenaphthene is a polycyclic aromatic hydrocarbon consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

Production and reactions

Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot. Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene.
Like other arenes, acenaphthene forms complexes with low valent metal centers. One example is Mn3]+.

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners. Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.