Dicyclopentadiene
From Wikipedia, the free encyclopedia
| Dicyclopentadiene[1] | |
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| IUPAC name | 3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene |
| Other names | 1,3-Dicyclopentadiene |
| Identifiers | |
| CAS number | [77-73-6] |
| SMILES | C13C=CC(C3)C2C1C=CC2 |
| Properties | |
| Molecular formula | C10H12 |
| Molar mass | 132.20 g/mol |
| Density | 0.98 g/cm3 |
| Melting point |
32.5 °C |
| Boiling point |
170 °C |
| Hazards | |
| NFPA 704 |
 3
1
1
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| Flash point | 32 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Dicyclopentadiene, abbreviated DCPD, is the chemical compound with the formula C10H12. 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 pounds (179 gigagrams).[2]
[edit] 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.[3]
Dicyclopentadiene is a monomer in polymerization reactions for example as copolymer with ethylene or styrene utilizing only the norbornene double bond.[4]. Polydicyclopentadiene is the homopolymer.
[edit] References
- ^ Merck Index, 11th Edition, 2744.
- ^ Chemical Profiles-Dicyclopentadiene
- ^ Organic Syntheses, Coll. Vol. 5, p.16 (1973); Vol. 42, p.8 (1962). Link
- ^ 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
