Dicyclopentadiene

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.

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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]

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 aluminum 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]

References

1. ^ Merck Index, 11th Edition, 2744.
2. ^ Chemical Profiles-Dicyclopentadiene
3. ^ Organic Syntheses, Coll. Vol. 5, p.16 (1973); Vol. 42, p.8 (1962). Link
4. ^ 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