Dicyclopentadiene
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| Names | |
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| IUPAC name
Tricyclo[5.2.1.02,6]deca-3,8-diene
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| Other names
1,3-Dicyclopentadiene, Bicyclopentadiene, 3a,4,7,7a-Tetrahydro-4,7-methanoindene
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | DCPD |
| 1904092 | |
| ChemSpider | |
| ECHA InfoCard | 100.000.958 |
| EC Number |
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| KEGG | |
| MeSH | Dicyclopentadiene |
PubChem CID
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| RTECS number |
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| UNII |
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| UN number | UN 2048 |
CompTox Dashboard (EPA)
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| Properties | |
| C10H12 | |
| Molar mass | 132.20 g/mol |
| Appearance | Colorless, crystalline solid[2] |
| Odor | disagreeable, camphor-like[2] |
| Density | 0.978 g/cm3 |
| Melting point | 32.5 °C (90.5 °F; 305.6 K) |
| Boiling point | 170 °C (338 °F; 443 K) |
| 0.02%[2] | |
| Solubility | very soluble in ethyl ether, ethanol soluble in acetone, dichloromethane, ethyl acetate, n-hexane, toluene |
| log P | 2.78 |
| Vapor pressure | 180 Pa (20 °C)[2] |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 32 °C (90 °F; 305 K) |
| 503 °C (937 °F; 776 K) | |
| Explosive limits | 0.8%-6.3%[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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none[2] |
REL (Recommended)
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TWA 5 ppm (30 mg/m3)[2] |
IDLH (Immediate danger)
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N.D.[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a clear light yellow color liquid with an acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints.
The top seven suppliers worldwide together had an annual capacity in 2001 of 179 kilotonnes (395 million pounds).
Reactivity
When heated above 150 °C, dicyclopentadiene undergoes a retro-Diels-Alder reaction to yield cyclopentadiene, a popular ligand in inorganic chemistry. The reaction is reversible and at room temperature cyclopentadiene slowly dimerizes to reform dicyclopentadiene.
Hydrogenation of dicyclopentadiene gives endo-tetrahydrodicyclopentadiene which on reaction with aluminium chloride at elevated temperature rearranges to adamantane.[3]
Dicyclopentadiene can be used as a monomer in polymerization reactions, either in olefin polymerization or in ring-opening metathesis polymerization. For example, using olefin polymerization catalysts, copolymers can be formed with ethylene or styrene by polymerizing only the norbornene double bond.[4] Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.
References
- ^ Merck Index, 11th Edition, 2744
- ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0204". National Institute for Occupational Safety and Health (NIOSH).
- ^ Paul von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas (1973). "Adamantane". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 16. - ^ Li, Xiaofang; Hou, Zhaomin (2005). "Scandium-Catalyzed Copolymerization of Ethylene with Dicyclopentadiene and Terpolymerization of Ethylene, Dicyclopentadiene, and Styrene". Macromolecules. 38 (16): 6767. doi:10.1021/ma051323o.