Dicyclopentadiene

Dicyclopentadiene[1]
Names
IUPAC name
Tricyclo[5.2.1.02,6]deca-3,8-diene
Other names
1,3-Dicyclopentadiene, Bicyclopentadiene, 3a,4,7,7a-Tetrahydro-4,7-methanoindene
Identifiers
3D model (JSmol)
Abbreviations DCPD
1904092
ChemSpider
ECHA InfoCard 100.000.958
EC Number 201-052-9
KEGG
MeSH Dicyclopentadiene
RTECS number PC1050000
UNII
UN number UN 2048
Properties
C10H12
Molar mass 132.20 g/mol
Appearance Colorless, crystalline solid[2]
Odor disagreeable, camphor-like[2]
Density 0.978 g/cm3
Melting point 32.5 °C (90.5 °F; 305.6 K)
Boiling point 170 °C (338 °F; 443 K)
0.02%[2]
Solubility very soluble in ethyl ether, ethanol
soluble in acetone, dichloromethane, ethyl acetate, n-hexane, toluene
log P 2.78
Vapor pressure 180 Pa (20 °C)[2]
Hazards
NFPA 704
Flammability code 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., gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
1
Flash point 32 °C (90 °F; 305 K)
503 °C (937 °F; 776 K)
Explosive limits 0.8%-6.3%[2]
US health exposure limits (NIOSH):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 5 ppm (30 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a clear light yellow color liquid with an acrid 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 179 kilotonnes (395 million pounds).

Reactivity

When heated above 150 °C, dicyclopentadiene undergoes a retro-Diels-Alder reaction to yield cyclopentadiene. The reaction is reversible and at room temperature cyclopentadiene dimerizes over the course of hours at room temperature to reform dicyclopentadiene. Cyclopentadiene is a precursor to metallocenes in organometallic chemistry.

Hydrogenation of dicyclopentadiene gives endo-tetrahydrodicyclopentadiene, which on reaction with aluminium chloride at elevated temperature rearranges to adamantane.[3]

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. The "norbornene double bond" participates.[4] Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.

Hydrogenation of dicyclopentadiene gives TH-dimer, which has been employed as a fuel in military applications.

References

  1. ↑ Merck Index, 11th Edition, 2744
  2. 1 2 3 4 5 6 7 8 "NIOSH Pocket Guide to Chemical Hazards #0204". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Paul von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas (1973). "Adamantane". Organic Syntheses. ; Collective Volume, 5, p. 16
  4. ↑ 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.
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