Dicyclopentadiene
1742660
199895134
2008-03-21T19:44:11Z
Element16
6666894
changing "aluminum" to "aluminium" according to guidelines at [[WP:ALUM]]
{{Chembox new
| Name = Dicyclopentadiene
| Reference =<ref>''Merck Index'', 11th Edition, '''2744'''.</ref>
| ImageFile = Dicyclopentadiene.png
<!-- | ImageSize = 150px -->
| ImageName = Chemical structure of dicyclopentadiene.
| ImageFile1 = Dicyclopentadiene-3D-balls.png
<!-- | ImageSize1 = 150px -->
| ImageName1 = Ball-and-stick model of dicyclopentadiene
| IUPACName =<small>3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene</small>
| OtherNames = 1,3-Dicyclopentadiene
| Section1 = {{Chembox Identifiers
| CASNo = 77-73-6
| SMILES = C13C=CC(C3)C2C1C=CC2
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>10</sub>H<sub>12</sub>
| MolarMass = 132.20 g/mol
| Density = 0.98 g/cm<sup>3</sup>
| MeltingPt = 32.5 °C
| BoilingPt = 170 °C
}}
| Section7 = {{Chembox Hazards
| FlashPt = 32 °C
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 1
}}
}}
'''Dicyclopentadiene''', abbreviated '''DCPD''', is the [[chemical compound]] with the formula C<sub>10</sub>H<sub>12</sub>. At room temperature, it is a white crystalline solid with a [[camphor]]-like odor.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to [[ethylene]]. The major use is 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 [[pound (mass)|pounds]] (179 [[gigagram]]s).<ref> [http://www.the-innovation-group.com/ChemProfiles/Dicyclopentadiene.htm Chemical Profiles-Dicyclopentadiene]</ref>
==Reactivity==
When heated above 100 °C, dicyclopentadiene undergoes a retro-[[Diels-Alder reaction]] to yield [[cyclopentadiene]], a compound important in both organic and 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]].<ref>[[Organic Syntheses]], Coll. Vol. 5, p.16 (1973); Vol. 42, p.8 (1962). [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv5p0016 Link]</ref>
Dicyclopentadiene is a [[monomer]] in [[polymerization]] reactions for example as [[copolymer]] with [[ethylene]] or [[styrene]] utilizing only the [[norbornene]] double bond.<ref>''Scandium-Catalyzed Copolymerization of Ethylene with Dicyclopentadiene and Terpolymerization of Ethylene, Dicyclopentadiene, and Styrene'' Xiaofang Li and Zhaomin Hou Macromolecules; '''2005'''; 38(16) pp 6767 - 6769; (Communication to the Editor) {{DOI|0.1021/ma051323o}}</ref>. [[Polydicyclopentadiene]] is the homopolymer.
==References==
<references/>
==External links==
*[http://www.sciencelab.com/xMSDS-Dicyclopentadiene-9923741 MSDS for dicyclopentadiene]
*[http://www.inchem.org/documents/icsc/icsc/eics0873.htm Inchem fact sheet for dicyclopentadiene]
[[Category:hydrocarbons]]
[[Category:alkenes]]
[[Category:Monomers]]