What Is Dicyclopentadiene?
Dicyclopentadiene, abbreviated as DCPD, is an organic compound with the chemical formula C10H12.
It has a molecular weight of 132.20, a melting point of 32.5°C, and a boiling point of 170°C. It is a colorless crystal or pale yellow powder at room temperature. It has a camphor-like aroma. Its density is 0.98 g/mL.
Structurally, endo and exo forms exist, but the CAS registry number for the mixture that does not distinguish between them is 77-73-6.
Dicyclopentadiene is soluble in organic solvents such as ethanol, ether, and benzene, and in acetic acid.
Uses of Dicyclopentadiene
Dicyclopentadiene’s main uses are in unsaturated polyester resins, coatings, and fragrances.
As a raw material for synthetic resins, dicyclopentadiene is used as a raw material for reaction injection molding resins and for various other resin materials such as epoxy, polyester, alkyd, and EP rubber, etc. It is called DCPD resin and is characterized by its rigidity and impact resistance. It is also used in inks, adhesives, or paints.
Dicyclopentadiene is also a useful organic synthetic compound. Cyclopentadiene, obtained by pyrolysis of dicyclopentadiene, is known as a conjugated diene that undergoes a Diels-Alder reaction with the parent diene agent.
It is also used industrially as a raw material for agrochemicals and insecticides.
Properties of Dicyclopentadiene
When dicyclopentadiene is heated above 150°C, the reverse Diels-Alder reaction yields cyclopentadiene. However, since this reaction is reversible, it slowly dimerizes back to dicyclopentadiene again at room temperature.
Hydrogenation of dicyclopentadiene also yields endo-tetrahydrodicyclopentadiene. When this compound is further heated with aluminum chloride, a rearrangement reaction occurs to form adamantane.
Types of Dicyclopentadiene
Dicyclopentadiene is commonly sold as a reagent product for research and development and as an industrial chemical. When used as a reagent product for research and development, it is mainly used as a raw material for organic synthesis, and is available in various capacities, including 25 mL, 500 mL, 100 g, 500 g, 1 kg, and 2.5 kg.
It is basically a reagent product that can be handled at room temperature. Industrial products are mainly used as a raw material for specialty resins and chemical synthesis products.
Other Information on Dicyclopentadiene
1. Production of Dicyclopentadiene
Dicyclopentadiene is a substance found in the low-boiling fractions of coal tar and in the by-products of naphtha thermal cracking. It is also co-produced in large quantities during the production of ethylene by steam cracking of naphtha and heavy oil.
2. Dicyclopentadiene and Polymerization
Dicyclopentadiene undergoes a polymerization reaction. Homopolymers of dicyclopentadiene are produced, and copolymerization with ethylene or styrene using only the norbornene double bond has also been reported. Both reactions are carried out in the presence of a catalyst. Ring-opening metathesis polymerization also produces polydicyclopentadiene.
Dicyclopentadiene is stable under normal storage conditions, but exposure to air can cause polymerization reactions. Therefore, it is generally stored in the presence of butyl hydroxytoluene (BHT) as an antioxidant.
3. Regulatory Information on Dicyclopentadiene
Dicyclopentadiene is known to be hazardous to human health due to its oral and dermal toxicity, skin irritation, potentially life-threatening by inhalation, eye irritation, damage to the respiratory system, liver, and kidneys, and possible drowsiness or dizziness. It is also a flammable substance with a low flash point of 26~38℃.