Acenaphthene
Template:Distinguish Template:Chembox 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.<ref name=Ull/>
Production and reactions
Acenaphthene was prepared for the first time in 1866<ref>Template:Cite book</ref> 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.<ref>Template:Cite book</ref> 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 arenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3]+.<ref>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. {{#invoke:CS1 identifiers|main|_template=doi}}</ref>
Uses
It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners<ref name="Ull">Template:Ullmann</ref> (such as 1,4-bis(2-benzoxazolyl)naphthalene). Besides that, the anhydride is also the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. {{#invoke:CS1 identifiers|main|_template=doi}}</ref><ref>Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.{{#invoke:CS1 identifiers|main|_template=doi}}</ref>
