Dicyclopentadiene

At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids.

Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene.

[3][4] For many years the structure of dicyclopentadiene was thought to feature a cyclobutane ring as the fusion between the two subunits.

[5] The spontaneous dimerization of neat cyclopentadiene at room temperature to form dicyclopentadiene proceeds to around 50% conversion over 24 hours and yields the endo isomer in better than 99:1 ratio as the kinetically favored product (about 150:1 endo:exo at 80 °C).

The reaction is reversible and at room temperature cyclopentadiene dimerizes over the course of hours to re-form dicyclopentadiene.

In accord with the negative values of ΔH° and ΔS° for the Diels–Alder reaction, dissociation of dicyclopentadiene is more thermodynamically favorable at high temperatures.

[13] Hydrogenation of dicyclopentadiene gives tetrahydrodicyclopentadiene (C10H16), which is a component of jet fuel JP-10,[14] and rearranges to adamantane[15][16] with aluminium chloride or acid at elevated temperature.

Stereo wireframe model of dicyclopentadiene.
Stereo wireframe model of dicyclopentadiene.
Ball and stick model of dicyclopentadiene
Ball and stick model of dicyclopentadiene
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium Special hazards (white): no code