Dicyclopentadiene (cas 77-73-6)
Dicyclopentadiene (DCPD) Comprehensive Information
Basic Chemical Properties
| Parameter | Details |
|---|---|
| Chemical Formula | C₁₀H₁₂ |
| CAS Number | 77-73-6 |
| Molecular Weight | 132.20 g/mol |
| Physical Properties | White crystalline solid or colorless liquid (above boiling point), camphor-like odor, density 0.979 g/cm³, melting point 31.5–33.6°C, boiling point 170°C (decomposes). |
| Solubility | Insoluble in water; soluble in ethanol, ether, and carbon tetrachloride. |
| Stability | Prone to self-polymerization into CPD at room temperature; depolymerizes to cyclopentadiene (CPD) at >140°C. |
Core Applications
- Polymer Materials Synthesis
- Ethylene-Propylene-Diene Monomer (EPDM): Acts as a third monomer to enhance weather resistance and elasticity.
- Epoxy Resin Curing Agent: Reacts with maleic anhydride to produce nadic anhydride, used in coatings and adhesives.
- Polydicyclopentadiene (PDCP): Thermosetting resin for automotive parts and industrial equipment.
- Fine Chemical Intermediates
- Pesticides: Synthesis of aldrin, dieldrin, and chlorinated hydrocarbons.
- Pharmaceuticals: Intermediate for α-cyclopentadienyl mandelic acid methyl ester.
- Flavors & Additives: Used in fragrances, flame retardants, and paper sizing agents.
- Energy & Fuels
- High-Energy Fuels: Hydrogenated DCPD for rocket propellants.
- Petroleum Resins: Applied in inks, coatings, and rubber fillers.
- Emerging Materials
- Cycloolefin Copolymers (COC/COP): High-purity DCPD (>99.5%) is critical for producing optical materials used in smartphone screens and medical tubing.
Safety & Handling
- Hazard Classification:
- Flammable liquid (Category 2), irritant to skin/eyes (H315, H319), and respiratory system (H335).
- Precautions:
- Use explosion-proof ventilation; avoid open flames and static discharge.
- Wear chemical-resistant gloves, goggles, and respiratory protection.
- Storage:
- Store in cool, ventilated areas away from oxidizers and strong acids/bases.
Production & Technical Advances
- Raw Material Sources
- Primarily derived from C5 fraction separation in petroleum cracking; minor extraction from C9 fractions.
- High-Purity Synthesis
- Dimerization-Depolymerization-Dimerization (DDD) Process:
- Depolymerization: Gas-phase cracking (superior to liquid-phase due to reduced coke formation).
- Key Challenge: Minimizing high-polymer byproducts and optimizing reactor design (inert gas protection, upward flow).
- Dimerization-Depolymerization-Dimerization (DDD) Process:
- Major Suppliers
Market Trends
- Demand Drivers:
- COC/COP materials: Projected 42,000 tons demand in China by 2025.
- Pricing:
- Industrial-grade DCPD: $10–50/kg (82%-95% purity); high-purity (>99%) costs higher.
Regulatory Compliance
- HS Code: 2933.39.90 (heterocyclic compounds).
- Transport: UN 2048, packaging Class III, requires explosion-proof containers.
Research Insights
- Synergy with Cyclopentene: Partial hydrogenation yields cyclopentene for 1,5-trans-polycyclopentene production.
- Patents: Over 20 patents cover synthesis methods (e.g., microbial fermentation, enzymatic modification).
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