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Dicyclopentadiene

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Dicyclopentadiene Basic information

Product Name:
Dicyclopentadiene
Synonyms:
  • 3,4,7,7-Tetrahydro-4,7-methano-1H-indene
  • 3a,4,7,7a-tetrahydro-7-methano-1h-indene
  • 3a,4,7,7a-tetrahydro-7-methanoindene
  • 4,7-methano-1H-indene,3a,4,7,7a-tetrahydro-
  • 4,7-methano-3a,4,7,7a-tetrahydro-1H-indene
  • 4,7-Methanoindene, 3a,4,7,7a-tetrahydro-
  • DCPD90%
  • ALPHA-DICYCLOPENTADIENE
CAS:
77-73-6
MF:
C10H12
MW:
132.2
EINECS:
201-052-9
Product Categories:
  • Pyridines
  • Chemical Synthesis
  • Cyclic
  • Organic Building Blocks
  • Pharmaceutical Intermediates
  • Alkenes
  • Building Blocks
Mol File:
77-73-6.mol
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Dicyclopentadiene Chemical Properties

Melting point:
33 °C(lit.)
Boiling point:
170 °C(lit.)
Density 
0.986 g/mL at 25 °C(lit.)
vapor pressure 
3 hPa (20 °C)
refractive index 
n20/D 1.511
Flash point:
114 °F
storage temp. 
Flammables area
form 
Liquid
Specific Gravity
0.968
color 
Clear
Odor
Camphor-like.
explosive limit
0.8-6.3%(V)
Water Solubility 
Immiscible with water.
FreezingPoint 
31.5℃
Hydrolytic Sensitivity
4: no reaction with water under neutral conditions
Merck 
14,2739
BRN 
1904092
Stability:
Stable at room temperature, but may form explosive peroxides if stored in contact with air. Incompatible with oxidizing agents. Decomposes on heating. Flammable. Mixtures of the vapour with air are explosive.
InChIKey
HECLRDQVFMWTQS-UHFFFAOYSA-N
CAS DataBase Reference
77-73-6(CAS DataBase Reference)
NIST Chemistry Reference
4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-(77-73-6)
EPA Substance Registry System
Dicyclopentadiene (77-73-6)
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Safety Information

Hazard Codes 
F,Xn,N,T
Risk Statements 
11-20/22-36/37/38-51/53-23-22-10
Safety Statements 
36/37-61-45-26
RIDADR 
UN 2048 3/PG 3
WGK Germany 
3
RTECS 
PC1050000
Autoignition Temperature
503 °C
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29021990
Hazardous Substances Data
77-73-6(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 353 mg/kg LD50 dermal Rabbit 4940 mg/kg

MSDS

  • Language:English Provider:DCPD
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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Dicyclopentadiene Usage And Synthesis

Chemical Properties

Cyclopentadiene is a crystalline solid or a liquid (above 32°C) with a disagreeable, camphor-like odor. The Odor Threshold is 0.011 (detectable); 0.020 ppm (recognizable).
cyclopentadiene, although a stable molecule, has a strong tendency to form the more stable dimer dicyclopentadiene. This dimerisation already takes place at room temperature and its rate rapidly increases with elevated temperatures. This reaction however is reversible too; dicyclopentadiene "cracks" at temperatures above 140°C to form two cyclopentadiene molecules. The physical properties of pure cyclopentadiene and dicyclopentadiene are given below as well as some product specific characteristics and compositions.

Uses

It is used in the synthesis of chlorinated hydrocarbon pesticides and ferrocene; in paint, varnish, and resin manufacture; in elastomers used as water pond liners, and as a repellent for animals such as hares, rabbits, and deer, in winter or in summer. It is applied in the form of impregnated strip on deciduous and coniferous trees, or by spraying around ornamental plants and shrubs.

Uses

Dicyclopentadiene or DCPD is the dimer of cyclopentadiene (CPD) formed by a DielsAlder addition reaction. DCPD products originate from high temperature cracking of petroleum fractions and are best characterized as highly reactive intermediates used for a wide range of resins, i. e. aromatic hydrocarbons, unsaturated polyesters, phenolics and epoxies.
Dicyclopentadiene RESIN GRADE  - Most used in aromatic hydrocarbon and unsaturated polyester resins.
Dicyclopentadiene, UPR Grade- Developed for use in unsaturated polyester resins.
Dicyclopentadiene HIGH PURITY- Suited for water-white resins and specialty applications.

Uses

As a chemical intermediate in the manufacture of pesticides; in the production of resin coatings, adhesives, and fuel additives

Production Methods

Dicyclopentadiene is produced by recovery from hydrocarbon streams from high temperature cracked petroleum fractions. It is also a by-product of the coke oven industry. Cyclopentadiene polymerizes to dicyclopentadiene on standing.

Production Methods

Dicyclopentadiene is produced by thermal cracking of petrochemical feedstocks or as a by-product of the coke oven industry. It is also formed by spontaneous dimerization of cyclopentadiene.

General Description

A liquid with an acrid odor. Flash point 90°F. The vapors are irritating to the eyes and respiratory system. Subject to polymerization if subjected to heat for prolonged periods or if contaminated. If the polymerization takes place inside a container, the container may violently rupture. Insoluble in water. Density 8.2 lb / gal. Used in paints, varnishes, as an intermediate in insecticides, as a flame retardant in plastics.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Dicyclopentadiene may react vigorously with oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. Can undergo exothermic polymierization reactions In the presence of various catalysts (such as acids) or initiators, if subjected to heat for prolonged periods, or if contaminated. Many undergo autoxidation upon exposure to the air to form explosive peroxides.

Health Hazard

LIQUID OR SOLID: Irritating to skin and eyes.

Fire Hazard

FLAMMABLE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur in presence of acids, but not hazardous; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by inhalation. Mildly toxic by skin contact. A severe skin and moderate eye irritant. Dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and fumes.

Potential Exposure

This compound is used in the manufacture of cyclopentadiene as a pesticide intermediate; in the production of ferrocene compounds; in paints, varnishes, and resin manufacture; in production of elastomers, resin systems, and polymers.

Carcinogenicity

Undiluted dicyclopentadiene caused minor irritation when applied to the skin of rabbits, and only trace injury occurred when instilled in the eye.
Dicyclopentadiene has a camphorlike odor with a 100% recognition threshold of 0.02ppm; however, there may not be noticeable irritation below 10ppm.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for dicyclopentadiene is 5ppm (27mg/m3).

Shipping

UN2048 Dicyclopentadiene must carry a “FLAMMABLE LIQUID” label. It falls in Hazard Class 3

Incompatibilities

Forms explosive mixture with air above flash point. Depolymerizes at boiling point and forms two molecules of cyclopentadiene; unless inhibited and maintained under inert atmosphere to prevent polymerization. Violent reaction with strong oxidizers; strong acids; strong bases. Can accumulate static electrical charges, and may cause ignition of its vapors

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

DicyclopentadieneSupplier

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