|PubChem||, (6R) , (1S,7R)|
|ChemSpider||, (2H12) , (6R) , (1S,7R)|
|UN number||UN 2048|
|Jmol-3D images||Image 1|
|Molar mass||132.20 g/mol|
|Melting point||32.5 °C|
|Boiling point||170 °C|
|Flash point||32 °C (90 °F; 305 K)|
|Except where noted otherwise, 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 white crystalline solid with a camphor-like 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 395 million pounds (179 kilotonnes).
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.
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. Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.
- Merck Index, 11th Edition, 2744
- Paul von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas (1973), "Adamantane", Org. Synth.; Coll. Vol. 5: 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.