Abbreviations DCPD Molar mass 132.2 g/mol Melting point 32.5 °C | Formula C10H12 Density 980 kg/m³ Boiling point 170 °C | |
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Appearance Colorless, crystalline solid | ||
Dicyclopentadiene
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.
Contents
The top seven suppliers worldwide together had an annual capacity in 2001 of 179 kilotonnes (395 million pounds).
Reactivity
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.
Hydrogenation of dicyclopentadiene gives endo-tetrahydrodicyclopentadiene which on reaction with aluminium chloride at elevated temperature rearranges to adamantane.
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.
