Dicyclopentadiene
Encyclopedia
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 resin
s, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints. It is also a kind of high-energy fuel.
The top seven suppliers worldwide together had an annual capacity in 2001 of 395 million pounds (179 kilotonnes).
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
.
Dicyclopentadiene is a monomer
in polymerization
reactions for example as copolymer with ethylene
or styrene utilizing only the norbornene
double bond. Polydicyclopentadiene
is the homopolymer.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with formula C10H12. At room temperature, it is a white crystalline solid with a camphor
Camphor
Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula C10H16O. It is found in wood of the camphor laurel , a large evergreen tree found in Asia and also of Dryobalanops aromatica, a giant of the Bornean forests...
-like odor. Its energy density
Energy density
Energy density is a term used for the amount of energy stored in a given system or region of space per unit volume. Often only the useful or extractable energy is quantified, which is to say that chemically inaccessible energy such as rest mass energy is ignored...
is 10,975 Wh
Watt-hour
The kilowatt hour, or kilowatt-hour, is a unit of energy equal to 1000 watt hours or 3.6 megajoules.For constant power, energy in watt hours is the product of power in watts and time in hours...
/l.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha
Naphtha
Naphtha normally refers to a number of different flammable liquid mixtures of hydrocarbons, i.e., a component of natural gas condensate or a distillation product from petroleum, coal tar or peat boiling in a certain range and containing certain hydrocarbons. It is a broad term covering among the...
and gas oils to ethylene
Ethylene
Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...
. The major use is in resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...
s, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints. It is also a kind of high-energy fuel.
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 reactionDiels-Alder reaction
The Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...
to yield cyclopentadiene
Cyclopentadiene
Cyclopentadiene is an organic compound with the formula C5H6. This colorless liquid has a strong and unpleasant odor. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction...
, a popular ligand in inorganic chemistry. The reaction is reversible and at room temperature cyclopentadiene slowly dimerizes to reform dicyclopentadiene.
Hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
of dicyclopentadiene gives endo-tetrahydrodicyclopentadiene which on reaction with aluminium chloride
Aluminium chloride
Aluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...
at elevated temperature rearranges to adamantane
Adamantane
Adamantane is a colorless, crystalline chemical compound with a camphor-like odor. With a formula C10H16, it is a cycloalkane and also the simplest diamondoid. Adamantane molecules consist of three cyclohexane rings arranged in the "armchair" configuration. It is unique in that it is both rigid...
.
Dicyclopentadiene is a monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...
in polymerization
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...
reactions for example as copolymer with ethylene
Ethylene
Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...
or styrene utilizing only the norbornene
Norbornene
Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the para position...
double bond. Polydicyclopentadiene
Polydicyclopentadiene
Polydicyclopentadiene is a polymer which is formed through ring opening metathesis polymerisation of dicyclopentadiene . The difference between the various systems lies in the type of catalyst used to create the polymer, but the final polymer properties are similar...
is the homopolymer.