Dicyclopentadiene

  • 3a, 4,7,7 a -tetrahydro- 4 ,7- methanoindene
  • Tricyclo [ 5.2.1.02,6 ] deca -3 ,8-diene
  • TCD
  • DCPD
  • Dimeric cyclopentadiene

Colorless to pale-yellow solid with campherähnlichem odor

Liquid to solid, technical grade

Endo form: 0.98 g · cm -3

Endo form: 32 ° C

Endo form: 170 ° C

3 hPa (20 ° C)

Practically insoluble in water

1.5050 ( 35 ° C)

Risk

0.5 ml · m-3 and 2.7 mg · m-3

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Commercially available dicyclopentadiene ( IUPAC name: tricyclo [ 5,2,1,02,6 ] deca -3 ,8 -diene) is a colorless to pale yellow liquid and is a member of the dienes. Very pure dicyclopentadiene is a solid.

It is the dimer of cyclopentadiene, from which it is formed by Diels- Alder reaction. Due to the geometry of the dicyclopentadiene molecule two stereoisomeric forms are possible: the endo - and exo - dicyclopentadiene. The Diels -Alder reaction, a mixture of both forms is produced. The Diels -Alder reaction is also an equilibrium reaction, isomerically pure, solid at room temperature exo- dicyclopentadiene mixture therefore is gradually returns to a endo / and then again contains traces of cyclopentadiene and other Diels-Alder adducts.

At 170 ° C, a rapid decomposition of dicyclopentadiene to cyclopentadiene is taking place, which is also favored by the addition of a catalyst such as iron powder. By separation by distillation of the monomer can be produced synthetically this. The flash point of the dimer is 32 ° C, at the ignition temperature of 503 ° C. In water it is insoluble. Dicyclopentadiene is stabilized with butylphenol. The mixture of dicyclopentadiene isomers smells very unpleasant terpene to campherähnlich.

At a volume fraction of 0.8 to 6.3 percent in air, it forms explosive mixtures. Dicyclopentadiene is hazardous to water ( WGK 2). Dicyclopentadiene is harmful, dangerous for the environment and highly flammable.

Use

Dicyclopentadiene is used as the starting material for the production of other chemical compounds (eg TCD amines and alcohols). Fully hydrogenated dicyclopentadiene can be rearranged with aluminum chloride to adamantane. Tetrahydro- dicyclopentadiene serves as a jet fuel JP- tenth

CAS registry number PubChem Vapor pressure Dangerous Substances Directive (67/548/EEC) Dimer (chemistry) Diels–Alder reaction CRC Handbook of Chemistry and Physics
8156
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