Back ثنائي حلقي البنتاديين Arabic Ditsiklopentadien Azerbaijani دیسیکلوپنتادیان AZB Dicyklopentadien Czech Dicyclopentadien German Diciclopentadieno Spanish دیسیکلوپنتادین Persian Disyklopentadieeni Finnish Dicyclopentadiène French Diciclopentadiene Italian
 endo‑Dicyclopentadiene (left) exo‑Dicyclopentadiene (right)
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 Ball-and-stick model of endo‑Dicyclopentadiene
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| Names | |
|---|---|
| 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-1H-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 | |
| 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 | 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 white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced 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).
DCPD was discovered in 1885 as a C10H12 hydrocarbon among the products of pyrolysis of phenol by Henry Roscoe, who didn't identify the structure (that was made during the following decade) but accurately assumed that it was a dimer of some C5H6 hydrocarbon.[3][4]
- ^ 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).
- ^ Levandowski, B. J.; Raines, R. T. (2021). "Click Chemistry with Cyclopentadiene". Chemical Reviews. 121 (12): 6777–6801. doi:10.1021/acs.chemrev.0c01055. PMC 8222071. PMID 33651602.
- ^ Roscoe, Henry E. (1885). "Note on the spontaneous polymerisation of volatile hydrocarbons at the ordinary atmospheric temperature". Journal of the Chemical Society, Transactions. 47 (0): 669–671. doi:10.1039/CT8854700669. ISSN 0368-1645.