Dicyclopentadiene

"DCPD" redirects here. For District of Columbia police, see Metropolitan Police Department of the District of Columbia and United States Capitol Police.
Dicyclopentadiene[1]
Stereo wireframe model of dicyclopentadiene.
endo‑Dicyclopentadiene (left) exo‑Dicyclopentadiene (right)
Ball and stick model of dicyclopentadiene
Ball-and-stick model of endo‑Dicyclopentadiene
Names
IUPAC name
Tricyclo[5.2.1.02,6]deca-3,8-diene
Other names
1,3-Dicyclopentadiene, Bicyclopentadiene, 3a,4,7,7a-Tetrahydro-1H-4,7-methanoindene
  • endo isomer: (3aR*,4S*,7R*,7aS*)-
  • exo isomer: (3aS*,4S*,7R*,7aR*)-
Identifiers
3D model (JSmol)
Abbreviations DCPD
1904092
ChemSpider
ECHA InfoCard 100.000.958 Edit this at Wikidata
EC Number
  • 201-052-9
KEGG
MeSH Dicyclopentadiene
RTECS number
  • PC1050000
UNII
UN number UN 2048
  • InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2 checkY
    Key: HECLRDQVFMWTQS-UHFFFAOYSA-N checkY
  • 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
  • C1C=CC2C1C3CC2C=C3
Properties
C10H12
Molar mass 132.20 g/mol
Appearance Colorless, crystalline solid[2]
Odor 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 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point 32 °C (90 °F; 305 K)
503 °C (937 °F; 776 K)
Explosive limits 0.8%-6.3%[2]
NIOSH (US health exposure limits):
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 checkY☒N ?)

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced 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).

DCPD was discovered as a C10H12 hydrocarbon among the products of pyrolysis of phenol by Henry Roscoe, who didn't identify the structure (that was made during the following decade) but accurately assumed that it was a dimer of some C5H6 hydrocarbon.[3]

  1. ^ Merck Index, 11th Edition, 2744
  2. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0204". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Levandowski, B. J.; Raines, R. T. (2021). "Click Chemistry with Cyclopentadiene". Chemical Reviews. 121 (12): 6777–6801. doi:10.1021/acs.chemrev.0c01055. PMC 8222071. PMID 33651602.