Dicyclopentadiene

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Dicyclopentadiene^[1]


IUPAC name Tricyclo[5.2.1.0^2,6]deca-3,8-diene
Other names 1,3-Dicyclopentadiene
Identifiers
Abbreviations	DCPD
CAS number	77-73-6^Y
PubChem	6492 ^Y, 6428576 (6R) ^Y, 10396885 (1S,7R) ^Y
ChemSpider	6247^Y, 24532442 (²H₁₂) ^Y, 4933978 (6R) ^Y, 8572323 (1S,7R) ^Y
EC number	247-724-5
UN number	UN 2048
KEGG	C14411^Y
MeSH	Dicyclopentadiene
RTECS number	PC1050000
Beilstein Reference	1904092
Jmol-3D images	Image 1
SMILES C1C=CC2C1C3CC2C=C3
InChI InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2^Y Key: HECLRDQVFMWTQS-UHFFFAOYSA-N^Y InChI=1/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2 Key: HECLRDQVFMWTQS-UHFFFAOYAO
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	32 °C; 90 °F; 305 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C₁₀H₁₂. At room temperature, it is a white crystalline solid with a camphor-like 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.

The top seven suppliers worldwide together had an annual capacity in 2001 of 395 million pounds (179 kilotonnes).

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.^[2]

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.^[3] Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.

References

↑ Merck Index, 11th Edition, 2744
↑ Paul von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas (1973), "Adamantane", Org. Synth. ; Coll. Vol. 5: 16
↑ Li, Xiaofang; Hou, Zhaomin (2005). "Scandium-Catalyzed Copolymerization of Ethylene with Dicyclopentadiene and Terpolymerization of Ethylene, Dicyclopentadiene, and Styrene". Macromolecules 38 (16): 6767. doi:10.1021/ma051323o.

External links

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