Acenaphthene

 ( Polycyclic Aromatic Hydrocarbons ) 

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) 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.

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Production and reactions Acenaphthene was prepared for the first time in 1866 by Marcellin Berthelot by reacting hot naphthalene vapours with acetylene, and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene in coal tar. 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 (and many other compounds).

Like other , acenaphthene forms complexes with low valent metal centers. One example is (η⁶-acenaphthene)Mn(CO)₃]⁺.S. B. Kim, S. Lotz, S. Sun, Y. K. Chung, R. D. Pike, D. A. Sweigart "Manganese Tricarbonyl Transfer (MTT) Agents" Inorganic Syntheses, 2010, Vol. 35, 109–128.

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Uses It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners (such as 1,4-bis(2-Benzoxazole)naphthalene). Besides that, the anhydride is also the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial and .K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.

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