Acenaphthylene
Chemical compound
From Wikipedia, the free encyclopedia
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.[3] Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.
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| Names | |||
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| 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[citation needed] Tricyclo[6.3.1.04,12]dodecahexaene[citation needed] | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.380 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| 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) | ||
| Insoluble | |||
| Solubility in ethanol | very soluble | ||
| Solubility in diethyl ether | very soluble | ||
| Solubility in benzene | very soluble | ||
| Solubility in chloroform | soluble | ||
| Thermochemistry[2] | |||
Heat capacity (C) |
166.4 J mol−1 K−1 | ||
Enthalpy of fusion (ΔfH⦵fus) |
186.7 kJ/mol | ||
Enthalpy of vaporization (ΔfHvap) |
69 kJ/mol | ||
Enthalpy of sublimation (ΔfHsublim) |
71.06 kJ/mol | ||
| Hazards | |||
| GHS labelling: | |||
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| Danger | |||
| H302, H310, H315, H319, H330, H335 | |||
| P260, P262, P264, P270, P271, P280, P284, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501 | |||
| 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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Occurrence
Acenaphthylene occurs as about 2% of coal tar. It is produced industrially by gas phase dehydrogenation of acenaphthene.[3]
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).[4]
It functions as a ligand for some organometallic compounds.[5]
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.[6]
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.[7]