Nfpa 170

Dicyclopentadiene


Dicyclopentadiene
IUPAC Name
tricyclo [5.2.1.02,6] Deca-3 ,8-diene
other names
1,3-dicyclopentadiene, DCPD
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CAS
Y 77-73-6
SMILES

C13C = CC (C3) CC2 = C2C1C
Properties
Molecular Formula
C10H12
Molar mass
132.20 g / mol
Density
0.98 g/cm3
Melting point
32.5 C
Boiling point
170 C
Risks
NFPA 704
3
1
1
Flashpoint
32 C
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Unless otherwise indicated, data are given for materials in their standard state (at 25 ° C, 100 kPa)
Infobox references
Dicyclopentadiene, DCPD short, is the chemical formula C10H12. At room temperature, it is a white crystalline solid with a camphor-like odor. Its energy density is 10,975 Wh / l. The dicyclopentadiene is co-produced in large quantities in the steam cracking of naphtha and gas oil to ethylene. The main use is to resins, particularly unsaturated polyester resins. It is also used in inks, glues and paints.
The seven major suppliers worldwide and has an annual capacity in 2001 of 395 million pounds (179 Gg).
Reactivity
When heated above 100 C, undergoes a reaction of dicyclopentadiene retro-Diels-Alder reaction of cyclopentadiene to give a compound important in both organic and inorganic chemistry. [Edit] The reaction is reversible at room temperature cyclopentadiene dimerizes slowly to reform dicyclopentadiene.
Hydrogenation gives endo-dicyclopentadiene tetrahydrodicyclopentadiene which react with aluminum chloride at elevated temperature rearranges to adamantane.
The dicyclopentadiene is a monomer in polymerization reactions such as ethylene and styrene using only the norbornene double bond .. Polydicyclopentadiene is the homopolymer.
References
^ Merck Index, 11th edition, 2744.
^ Chemical profiles of dicyclopentadiene
^ Organic Syntheses, Coll. Vol. 5, p.16 (1973), Vol. 42, p. 8 (1962). Link
^ Scandium-catalyzed copolymerization of ethylene with dicyclopentadiene terpolymerization ethylene, dicyclopentadiene, styrene and Xiaofang Li and Hou Zhaomin macromolecules, 2005, 38 (16) pp 6767-6769; (Communication to Editor) DOI: 0.1021/ma051323o
References
MSDS for dicyclopentadiene
Inchem sheet for dicyclopentadiene
Categories: Hydrocarbons | Alkenes | Monomers | energy density