Related Searches: Dicyclopentadiene

Dicyclopentadiene(CAS No. 77-73-6)

Dicyclopentadiene C10H12 (cas 77-73-6) Molecular Structure

77-73-6 Structure

Identification and Related Records

【Name】
Dicyclopentadiene
【CAS Registry number】
77-73-6
【Synonyms】
4,7-Methanoindene,3a,4,7,7a-tetrahydro- (7CI,8CI)
3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene
3a,4,7,7a-Tetrahydro-4,7-methanoindene
Bicyclopentadiene
Biscyclopentadiene
Cyclopentadiene dimer
DCPD 103
Dicyclopentadiene
JP 10
NSC 7352
Prometa XP100
Tricyclo[4.3.1.02,5]deca-3,7-diene
Tricyclo[5.2.1.02,6]deca-3,8-diene
Ultrene
【EINECS(EC#)】
201-052-9
【Molecular Formula】
C10H12 (Products with the same molecular formula)
【Molecular Weight】
132.2023
【Inchi】
InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2/t7?,8?,9-,10+/m1/s1
【InChIKey】
HECLRDQVFMWTQS-BMNUFHGDSA-N
【Canonical SMILES】
C1C=CC2C1C3CC2C=C3
【MOL File】
77-73-6.mol

Chemical and Physical Properties

【Appearance】
colourless crystals with a camphor-like odour
【Density】
0.982
【Melting Point】
-1℃
【Boiling Point】
170℃
【Refractive Index】
1.51-1.512
【Flash Point】
26℃
【Solubilities】
Insoluble
【Color/Form】
Colorless crystalline solid [Note: A liquid above 90 degrees F]
【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.
【HS Code】
29021990
【Storage temp】
Flammables area
【Spectral properties】
MAX ABSORPTION (ISOOCTANE): 217 NM (LOG E= 1.4); SADTLER REF NUMBER: 1143 (IR, PRISM)
Iindex of refraction = 1.505 at 35 deg C
IR: 1262 (Coblentz Society Spectral Collection)
NMR: 6494 (Sadtler Research Laboratories Spectral Collection)
MASS: 628 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:132.20228 [g/mol]
Molecular Formula:C10H12
XLogP3-AA:2.5
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:132.0939
MonoIsotopic Mass:132.0939
Topological Polar Surface Area:0
Heavy Atom Count:10
Formal Charge:0
Complexity:212
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:4
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Ring Count:2
Effective Rotor Count:0.4
Conformer Sampling RMSD:0.4
CID Conformer Count:3

Safety and Handling

【Hazard Codes】
F:Flammable
【Risk Statements】
R11;R20/22;R36/37/38;R51/53
【Safety Statements 】
S36/37;S61
【HazardClass】
3
【Safety】
Hazard Codes:F,Xn,N
Risk Statements:11-20/22-36/37/38-51/53
11:Highly Flammable
20/22:Harmful by inhalation and if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements:36/37-61
36/37:Wear suitable protective clothing and gloves
61:Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR:UN 2048 3/PG 3
WGK Germany:3
HazardClass:3
PackingGroup:III
HS Code:29021990
Hazardous Substances Data:77-73-6(Hazardous Substances Data)
【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
Dicyclopentadiene causes mild to severe eye, skin, and respiratory tract irritation, and severe response of the eyes and skin result from 24-hour exposure.
... Eye and skin irritation from the undiluted material is relatively minor.
【Cleanup Methods】
Remove all ignition sources. Personal protection: A/P2 filter respirator for organic vapour and harmful dust. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers, then remove to safe place.
Collect with a brush onto a paper sheet. Place in an iron pan in hood. Burn the paper.
【Transport】
UN 2048
【Fire Fighting Procedures】
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
To fight fire use alcohol foam.
【Fire Potential】
Flammable; fire hazard
Dangerous fire hazard when exposed to heat or flame...
【Formulations/Preparations】
65%, 85%, 95% grades
Suspension concentrate
Grades or purity: 97%
【DOT Emergency Guidelines】
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
【Reactivities and Incompatibilities】
Above 32 deg C explosive vapor/air mixtures may be formed ... /Dicyclopentadiene/ can form explosive peroxides.
... Can react with oxidizing materials.
Oxidizers [Note: Depolymerizes at boiling point and forms two molecules of cyclopentadiene. Must be inhibited and maintained under an inert atmosphere to prevent polymerization].
Dienes and acetylene derivatives are hypergolic and contact with concn nitric acid, ignition delay being 1 ms ... Dicyclopentadiene is highly hypergolic with red or white fuming nitric acid, also in presence of sulfuric acid.
【Other Preventative Measures】
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water to knock down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amt of water or soap and water.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
NO open flames, NO sparks, and NO smoking. Above 32 deg C use a closed system, ventilation, and explosion-proof electrical equipment. Do not eat, drink, or smoke during work.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Personnel protection: ... Wear appropriate chemical protective gloves, boots, and goggles.
Air-supplied mask in confined areas, rubber gloves, safety glasses.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possbility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Ventilation (not if powder), local exhaust, or breathing protection ... Personal protection: A/P2 filter respirator for organic vapor and harmful dust.
【Specification】

colourless crystals with a camphor-like odour
Safety Statements:36/37-61
36/37:Wear suitable protective clothing and gloves
61:Avoid release to the environment. Refer to special instructions safety data sheet
【Octanol/Water Partition Coefficient】
log Kow = 3.16 (est)
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration.
Dicyclopentadiene a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
The following wastewater treatment technologies have been investigated for dicyclopentadiene: Activated carbon.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

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.
The distillate /of the total cracked product/ is heated to a temp of about 100 deg C to convert monomeric cyclopentadiene to dicyclopentadiene. Depending on the temp and concn, the heat soaking operation is 5-24 hr. The dicyclopentadiene, which boils higher than the unreacted hydrocarbons of the distillate, is recovered as distillation bottoms.
U.S. Exports

(1984) 1.49X10+10 g
U.S. Imports

(1986) 4.08X10+7 lb
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1972) 4.14X10+10 G
(1984) 4.59X10+10 g
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >100 million-500 million 1990 >100 million-500 million 1994 >100 million-500 million 1998 >100 million-500 million 2002 >50 million-100 million
Consumption Patterns

30% AS A CHEM INTERMED CYCLODIENE PESTICIDES (INCL ENDRIN, ALDRIN, & DIELDRIN); 30% AS A MONOMER FOR ETHYLENE-PROPYLENE TERPOLYMER ELASTOMERS; 30% AS A FIRE RETARDANT & CURING AGENT IN OTHER ELASTOMERS; 10% IN MISC APPLICATIONS (INCL AS A DRYER & HARDENER IN LINSEED & SOYBEAN OIL) (1973)
Hydrocarbon resin systems, 50%; Unsaturated polyester resins, 27%; ethylene-propylene dienemonomer elastomers, 13%; Miscellaneous, including chemical synthesis, flame retardants, pesticides, and agricultural chemicals, 10% (1984)
CHEMICAL PROFILE: Dicyclopentadiene. Hydrocarbon resin systems, 40%; unsaturated polyester resins, 35%; EPDM elastomers, 15%; miscellaneous, including pesticides, flame retardants and chemical synthesis, 10%.
CHEMICAL PROFILE: Dicyclopentadiene. Demand: 1986: 110 million lb; 1987: 115 million lb; 1991 /projected/: 140 million lb. (Includes imports, which were 40 million lb in 1986.)
【Usage】

Monomer for ethylene-propylene terpolymer elastomers, dryer & hardener in linseed & soybean oil, curing agent in other elastomers.

Biomedical Effects and Toxicity

【Pharmacological Action】
LIQUID OR SOLID: Irritating to skin and eyes.
【Biomedical Effects and Toxicity】
In general, although some dicyclopentadiene can be exhaled unchanged, most of that absorbed is hydroxylated in the liver, undergoes glucuronide conjugation, and is excreted in the urine.
When given by oral administration to lactating cows urine and feces contained 86% of administered dose with only trace amounts being secreted in milk. Some may have been eliminated in gaseous form. Compound was extensively absorbed from GI tract. [WAYNE G, OEHLER DD; BULL ENVIRON CONTAM TOXICOL 24 (5): 662-70 (1980)] PubMed Abstract
Dicyclopentadiene is predicted to be rapidly absorbed and distributed following any route of administration. It is extensively absorbed from the GI tract.
The substance can be absorbed into the body by inhalation and by ingestion.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
AEROBIC: Very slow biotransformation of dicyclopentadiene was observed when it was inoculated with soil and water obtained from the Rocky Mountain Arsenal(1). It is listed as being degradation resistant in consideration for the Chemical Substances Control Law of Japan(2). Two field studies in Alberta, Canada found biodegradation rates of 37-57% in 266 days and not appreciable to 60% in 116 days(3).

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