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Acenaphthylene

Acenaphthalene Tricyclo[6.3.1.04,12]dodeca-1(12),2,4,6,8,10-hexaene Tricyclo[6.3.1.04,12]dodecahexaene 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. 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.

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).

It functions as a ligand for some organometallic compounds.

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.

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.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (June 18, 2018). "CRC Handbook of Chemistry and Physics". CRC Press.
  3. (2000). "Hydrocarbons".
  4. (1996-01-01). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews.
  5. (2005). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Carbonyl Cluster as the Catalyst". Organic Syntheses.
  6. Ullmann, 4th ed., 21, 70
  7. (2017). "Toxicity of repeated 28-day oral administration of acenaphthylene in rats". Fundamental Toxicological Sciences.
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polycyclic-aromatic-hydrocarbons tricyclic-compounds acenaphthylenes
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