Acenaphthylene

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.[2] Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.

Not to be confused with Acenaphthene.
Acenaphthylene
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Acenaphthylene[1]
Other names
Cyclopenta[de]naphthalene
Acenaphthalene
Tricyclo[6.3.1.04,12]dodeca-1(12),2,4,6,8,10-hexaene
Tricyclo[6.3.1.04,12]dodecahexaene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.380
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 C12H8
Molar mass 152.196 g·mol−1
Appearance Yellow crystals
Density 0.8987 g cm−3
Melting point 91.8 °C (197.2 °F; 364.9 K)
Boiling point 280 °C (536 °F; 553 K)
Solubility in water
 Insoluble
Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Solubility in benzene very soluble
Solubility in chloroform soluble
Thermochemistry
Enthalpy of vaporization (ΔfHvap)
 69 kJ/mol
Enthalpy of sublimation (ΔfHsublim)
 71.06 kJ/mol
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H302, H310, H315, H319, H330, H335
GHS precautionary statements
 P260, P261, P262, P264, P270, P271, P280, P284, P301+312, P302+350, P302+352, P304+340, P305+351+338, P310, P312, P320, P321, P322, P330, P332+313, P337+313, P361, P362, P363, P403+233
Flash point 122 °C (252 °F; 395 K)
Related compounds
Related compounds
 acenaphthene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Occurrence

Acenaphthylene occurs as about 2% of coal tar. It is produced industrially by gas phase dehydrogenation of acenaphthene.[2]

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). [3]

It functions as a ligand for some organometallic compounds.[4]

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. [5]

Toxicity

The no-observed-effect-level of acenaphthylene after repeated 28-day oral administration to both male and female rats was found to be 4 mg/kg/day.[6]

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 210. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4.
  2. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
  3. N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x
  4. Motoyama, Yukihiro; Itonaga, Chikara; Ishida, Toshiki; Takasaki, Mikihiro; Nagashima, Hideo (2005). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Cluster as the Catalyst". 82: 188. doi:10.15227/orgsyn.082.0188. Cite journal requires |journal= (help)
  5. Ullmann, 4th ed., 21, 70
  6. Tanabe, S.; et al. (2017). "Toxicity of repeated 28-day oral administration of acenaphthylene in rats". Fundamental Toxicological Sciences. 4 (6): 247–259. doi:10.2131/fts.4.247.
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