Acenaphthylene

Template:Distinguish Template:Chembox Acenaphthylene, a polycyclic aromatic hydrocarbon is an ortho- and peri-fused tricyclic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid.<ref name=Ullmanns/> Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.

Occurrence

Acenaphthylene occurs as about 2% of coal tar. It is produced industrially by gas phase dehydrogenation of acenaphthene.<ref name=Ullmanns>Template:Ullmann</ref>

Reactions

Hydrogenation gives the more saturated compound acenaphthene. Chemical reduction affords the radical anion sodium or potassium acenaphthalenide, which is used as a strong reductant (E = -2.26 V vs FC).<ref name="Connelly">Template:Cite journal</ref>

It functions as a ligand for some organometallic compounds.<ref>Template:Cite journal</ref>

Uses

Polymerisation of acenaphthylene with acetylene in the presence of a Lewis acid catalyst gives electrically conductive polymers. Acenaphthylene possesses excellent properties as an antioxidant in cross-linked polyethylene and ethylene-propylene rubber. Thermal trimerization of acenaphthylene leads to decacyclene, which can be further processed to sulfur dyes.<ref>Ullmann, 4th ed., 21, 70</ref>

Toxicity

The no-observed-adverse-effect-level of acenaphthylene after repeated 28-day oral administration to both male and female rats was found to be 4 mg/kg/day.<ref>Template:Cite journal</ref>

References

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