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Dicyclopentadiene



Dicyclopentadiene[1]
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
 
Flash point 114 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.

Additional recommended knowledge

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dicyclopentadiene". A list of authors is available in Wikipedia.
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