1,3-Dicyclopentadiene, Bicyclopentadiene, 3a,4,7,7a-Tetrahydro-4,7-methanoindene
3D model (JSmol)
|UN number||UN 2048|
|Molar mass||132.20 g/mol|
|Appearance||Colorless, crystalline solid|
|Melting point||32.5 °C (90.5 °F; 305.6 K)|
|Boiling point||170 °C (338 °F; 443 K)|
|Solubility||very soluble in ethyl ether, ethanol |
soluble in acetone, dichloromethane, ethyl acetate, n-hexane, toluene
|Vapor pressure||180 Pa (20 °C)|
|Flash point||32 °C (90 °F; 305 K)|
|503 °C (937 °F; 776 K)|
|US health exposure limits (NIOSH):|
|TWA 5 ppm (30 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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).
When heated above 150 °C, dicyclopentadiene undergoes a retro-Diels-Alder reaction to yield cyclopentadiene. The reaction is reversible and at room temperature cyclopentadiene dimerizes over the course of hours at room temperature to reform dicyclopentadiene. Cyclopentadiene is a precursor to metallocenes in organometallic chemistry.
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. The "norbornene double bond" participates. Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.
Hydrogenation of dicyclopentadiene gives TH-dimer, which has been employed as a fuel in military applications.
- Merck Index, 11th Edition, 2744
- "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.; Collective Volume, 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.