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
77-73-6 YesY
1755-01-7 (endo) N
3D model (Jmol) Interactive image
Abbreviations DCPD
1904092
ChemSpider 6247 YesY
24532442 (2H12) YesY
4933978 (6R) YesY
8572323 (1S,7R) YesY
ECHA InfoCard 100.000.958
EC Number 201-052-9
KEGG C14411 YesY
MeSH Dicyclopentadiene
PubChem 6492
6428576 (6R)
10396885 (1S,7R)
RTECS number PC1050000
UNII 88Z4HUV8LI (endo) N
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., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special 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).
N verify (what is YesYN ?)
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, 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.[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 by polymerizing only the norbornene double bond.[4] Using ring-opening metathesis polymerization the homopolymer polydicyclopentadiene is formed.

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". Org. Synth.; Coll. Vol., 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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