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Home > Encyclopedia > Cyclopentadiene

Cyclopentadiene

pharmaceutical raw materials
Cyclopentadiene structure

Cyclopentadiene 

structure
  • CAS No:

    542-92-7

  • Formula:

    C5H6

  • Chemical Name:

    Cyclopentadiene

  • Synonyms:

    1,3-Cyclopentadiene;R-Pentine;Pentole;Pyropentylene;Cyclopentadiene;26912-33-4;2351150-22-4

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

colourless liquid Cyclopentadiene is a flammable, colorless liq- uid with a sweet odor, like turpentine. 1,3-Cyclopentadiene is a colorless liquid that dimerizes easily in the presence of peroxides and trichloroacetic acid to a colorless solid.


Cyclopentadiene is a colorless liquid with an irritating, terpene-like odor. Bp: 42.5°C; Flash point: 77°F. Density: 0.805 g cm-3.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Colorless liquid with an irritating, terpene-like odor.


Cyclopentadiene is a colorless liquid with an irritating, terpene-like odor. Bp: 42.5°C; Flash point: 77°F. Density: 0.805 g cm-3.|Cyclopentadiene is a cycloalkadiene.|A group of alicyclic hydrocarbons with the general formula R-C5H9.

Cyclopentadiene Basic Attributes

66.10114

66.10

208-835-4

5DFH9434HF

0857

1993

DTXSID0027191

Colorless liquid

Characteristics

0

1.79

Cyclopentadiene is a colorless liquid with an irritating, terpene-like odor. Bp: 42.5°C; Flash point: 77°F. Density: 0.805 g cm-3.

0.8021 g/cm3 @ Temp: 20 °C

-85 °C

41.5-42.1 °C @ Press: 760 Torr

-32.2±13.0 °C

1.503

10.3 mM at 25 °C (shake flask-UV spectrophotometry, Streitwieser and Nebenzahl, 1976)

Monomer may largely be prevented from dimerizing by storage at -80 deg C or below.

381 at 20.6 °C, 735 at 40.6 °C, 1,380 at 60.9 °C (Stoeck and Roscher, 1977)

Relative vapour density (air = 1): 2.3

Oral-rat LD50: 113 mg/kg; Oral-Mouse LD50: 800 mg/kg

It is flammable in case of open flame, high temperature, oxidant; strong decomposition at high temperature; burning produces irritating smoke

The substance can readily form explosive peroxides on contact with air. The substance will readily polymerize to dimer with fire or explosion hazard. The reaction is accelerated by peroxides or trichloroacetic acid.

MONOMERIC FORM HAS TERPENE ODOR IN VAPOR STATE

Henry's Law constant = 2.12X10-2 atm-cu m/mol at 25 °C (est)

MP: -85 °C. Density: 0.8235 at 0 °C/4 °C; 0.8131 at 10 °C/4 °C; 0.7966 at 25 °C/4 °C; 0.7914 at 30 °C/4 °C|Cyclopentadiene polymerizes to dicyclopentadiene on standing; accelerated by peroxides or trichloroacetic acid.|Dimer has camphor-like odor. /dicyclopentadiene/|Cyclopentadiene undergoes self-condensation in a Diels-Alder reaction. /Cyclopentadiene/|Hydroxyl radical reaction rate constant = 1.4X10-10 cu cm/molec-sec at 25 °C (est)|Ozone radical reaction rate constant = 3.2X10-16 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air No rapid reaction with water

Hydrocarbons, Aliphatic Unsaturated

Highly Flammable

CYCLOPENTADIENE is incompatible with strong oxidizing agents. Ignites on contact with oxygen (O2) and ozone (O3). Explodes on contact with fuming nitric acid or a mixture of sulfuric acid and nitrogen tetroxide. Reacts vigorously on contact with potassium hydroxide and other strong bases. Mixtures with air are explosive. Presents a moderate explosion hazard when exposed to heat or flame. Decomposes violently at high temperature and pressure. May form explosive peroxides in storage. Undergoes a spontaneous dimerization at room temperature to give DICYCLOPENTADIENE (C10H12, CAS No: 77-73-6), which is a low-melting solid (melting point: 32.5° C). The reaction is strongly exothermic (Hazardous Chemicals Desk Reference, p. 360 (1987)), but occurs sufficiently slowly that cyclopentadiene can be said to be stable at room temperature. The dimerization accounts for the partial or complete solidification of liquid cyclopentadiene in storage. Polymerization occurs more rapidly and extensively at higher temperatures. When heated to 180-200° C, cyclopentadiene gives polycyclopentadiene, a white waxy solid. Stronger heating breaks down polycyclopentadiene and re-generates the monomeric cyclopentadiene as a vapor. The vapor decomposes violently at higher temperatures and pressures.

640 °C

8.56 eV

Class IC Flammable Liquid: Fl.P. at or above 73°F and below 100°F.

The vapour is heavier than air.

Safety Information

III

3.2

1993

GY1000000

Storehouse ventilated at low temperature and dry; stored separately from oxidants and acids; should not be stored for a long time to prevent polymerization

High temperature, open flame mixed with air can be explosive

Stable at room temperature. Incompatible with oxidizing agents, acids and a wide variety of other compounds. May form peroxides in storage. May undergo spontaneous polymerisation. Decomposes on heating. Highly flammable. Mixtures with air are explosive.

P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501

H225

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Incineration

Reacts vigorously on contact with potassium hydroxide.|Contact with the ethanolic base /eg potassium hydroxide/ causes vigorously exothermic resin formation.|Incompatible with nitric acid; oxides of nitrogen; oxygen; sulfuric acid.|Dienes and acetylene derivatives are hypergolic on contact with concn nitric acid, ignition delay being 1 ms. Cyclopentadiene reacts explosively with fuming nitric acid, igniting under nitrogen ...|For more Hazardous Reactivities and Incompatibilities (Complete) data for 1,3-CYCLOPENTADIENE (9 total), please visit the HSDB record page.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Flammable. Above 25 °C explosive vapour/air mixtures may be formed.|Flammable - 3rd degree

|Danger|H226 (99.62%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 266 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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 SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet should be immediately removed due to its flammability hazard(i.e. for liquids with flash point Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Respirator Recommendations: Up to 750 ppm:[Table#3935]|Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions:[Table#3936]|For more Personal Protective Equipment (PPE) (Complete) data for 1,3-CYCLOPENTADIENE (6 total), please visit the HSDB record page.|(See protection codes)

A dangerous fire hazard when exposed to heat or flame.

Moderate explosion hazard in the form of gas when exposed to heat or by chemical reaction.|Studies on the fire & explosion hazard properties of petroleum cyclopentadiene. These products can be incl into group a of class 2 dangerously explosive mixtures. Explosion proof equipment is required in mfr.|Dimerization is highly exothermic, the rate increasing rapidly with temperature, and may cause rupture of a closed uncooled container ... The polymerization of the undiluted diene may become explosive within the range 0 to 40 °C and at pressures up to 340 bar ...|Above 25 °C explosive vapor/air mixtures may be formed.|The substance can readily form explosive peroxides on contact with air. The substance will readily polymerize to dimer with fire or explosion hazard. The reaction is accelerated by peroxides or trichloroacetic acid.

Powder, aqueous film-forming foams (AFFF), foam, carbon dioxide ... Keep drums, etc, cool by spraying with water.|Dry chemical, carbon dioxide, foam

The vapor is heavier than air ... A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place (extra personal protection: self-contained breathing apparatus).|1. Remove ... ignition sources. 2. Ventilate area of spill. ... 3. For small quantity, allow material to dimerize, collect on paper or other material. Evaporate in safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear hood ductwork. Burn paper in suitable location. ... 3. Large quantities may be reclaimed or dissolved in appropriate solvent & atomized in suitable combustion chamber. ... Should not be allowed to enter confined space, such as sewer, because of possibility of an explosion.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|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. Ensure that the local ventilation moves the contaminant away from the worker.|The worker should immediately wash the skin when it becomes contaminated.|For more Preventive Measures (Complete) data for 1,3-CYCLOPENTADIENE (7 total), please visit the HSDB record page.

Flammable liquids, n.o.s. require a label "FLAMMABLE LIQUIDS". Quantity limitations: Passenger aircraft/rail: 60L; Cargo aircraft only: 220L. It falls in Hazard Class 3 and Packin Group III.

Exposure can irritate the eyes, skin, and respiratory tract. Skin contact causes a burning sensation and rash.|1,3-Cyclopentadiene is irritating to eyes and mucous membranes. It has caused contact dermatitis and sensitization.|ACUTE ... SYMPTOMS: Inhalation--cough and sore throat; Eyes--redness and pain.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 75 ppm (200 mg/cu m).

Recommended Exposure Limit: 10 Hr Time-Weighted avg: 75 ppm (200 mg/cu m).

Personal protection: self-contained breathing apparatus. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Separated from strong oxidants, strong acids and potassium hydroxide. Cooled. Store only if stabilized.

A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes and respiratory tract.

NO open flames, NO sparks and NO smoking. Above 25 °C use a closed system, ventilation and explosion-proof electrical equipment.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

1,3-Cyclopentadiene was detected in the concentration range of 10-100 ug/L, in one out of 63 effluents from US industries(1). 1,3-Cyclopentadiene has been detected in stack emissions from waste incineration(2), and in emissions from polymer manufacture, polymer combustion, and biomass combustion(3). 1,3-Cyclopentadiene was reported in the atmosphere near an oil fire at 0.061 mg/cu m(4). Median concentrations in fireplace smoke of 1,3-cyclopentadiene were measured in mg/kg dry fuel used: 29.39 from soft wood, 35.05 from hard wood and synthetic wood 0.93; and measured from hard wood burned in wood stoves at 80.90(5). In the production of vertically aligned multi-walled carbon nanotubes, 1,3-cyclopentadiene emissions from the pre-heat step were 4.7 ppmV at 690 °C to 17.6 ppmV at 1040 °C(6).|1,3-Cyclopentadiene emissions from three types of fuel were found at 0.003% in average gasoline, 0.002% in EPA certified gasoline and at 0% in 85% methanol gasoline(1). Four-stroke lawn mower studies showed 0.21% of total emissions where 1,3-cyclopentadiene with regular gasoline and 0.16% with reformulated gasoline(2). Single cylinder engines found 1,3-cyclopentadiene emissions present only when using 1-hexene fuel and a 50/50 by volume mixture of n-hexane/toluene for fuel(3). 1,3-Cyclopentadiene had an annual minimum emission from automobiles of 0.412 ppm from 5,094 vehicles and maximum of 1.206 ppm from 6,600 vehicles(4).

1,3-Cyclopentadiene was detected in the gas phase of tobacco smoke at levels ranging from 0.06-7 ug/cigarette, with the amount of cyclopentadiene increasing with increasing tar delivery(1).

Toxicity

highly toxic

IDENTIFICATION AND USE: 1,3-Cyclopentadiene is a colorless liquid with an unpleasant odor. It is used as a starter compound in the manufacturing of resins and in organic synthesis as a starting material for synthetic prostaglandins, chlorinated insecticides, and formation of sandwich compounds by chelation. HUMAN EXPOSURE AND TOXICITY: Human exposure may occur during the manufacturing process. Short term exposure: exposure can irritate the eyes, skin, and respiratory tract. Skin contact causes a burning sensation and rash. Long term exposure: exposure may damage the liver and kidneys. Exposure can cause a skin allergy to develop. If allergy develops, even low exposures may cause symptoms. No further human studies could be located. ANIMAL STUDIES: Exposure to 1,3-Cyclopentadiene vapors produce CNS depression in the frog in 10 minutes, with a complete recovery in 70 minutes. In rats, 35 repeated daily 7-hour exposures to cyclopentadiene during a period of 53 days at an average concentration of 500 ppm resulted in mild injury to both liver and kidneys described as centrilobular, cloudy swelling of liver cells and cloudy vacuolization of renal tubular epithelium. In contrast, repeated daily exposures at 250 ppm produced no effects in rabbits, rats, guinea pigs, and dogs. In rabbits, subcutaneous injection of 3 cc was a CNS depressing dose with fatal convulsions; however, injections of 0.5 to 1.0 cc did not induce CNS depression. Signs and symptoms during CNS depression included primary motor unrest and a decreased intermittent respiration rate prior to death. The liquid caused marked local irritation, exudates in the pleural and peritoneal cavities, and hyperemia of the kidneys.

An added stabilizer or inhibitor can influence the toxicological properties of this substance.

LC50 Rat inhalation 39 mg/L/1 hr|LC50 Mouse inhalation 15 mg/L/1 hr

1,3-Cyclopentadiene's production and use as a starting material for synthetic prostaglandins, for chlorinated insecticides, and the formation of sandwich compounds by chelation, for example, cyclopentadienyl iron dicarbonyl dimer(1), may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a structure estimation method(2), indicates that 1,3-cyclopentadiene is expected to have high mobility in soil(SRC). Volatilization of 1,3-cyclopentadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-2 atm-cu m/mole(SRC), based upon its vapor pressure, 435 mm Hg(3), and water solubility, 1800 mg/L(4). 1,3-Cyclopentadiene is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2014).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a structure estimation method(2), indicates that 1,3-cyclopentadiene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.1X10-2 atm-cu m/mole(SRC), derived from its vapor pressure, 435 mm Hg(4), and water solubility, 1800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 hours and 3.2 days, respectively(SRC). Olefins, as a general class, are susceptible to reaction with photochemically-produced hydroxyl radicals and singlet oxygen in natural waters(6). Half-lives are typically on the order of 13-14 days for olefins reacting with hydroxyl radicals and 40 days for cyclic olefins reacting with singlet oxygen(6). According to a classification scheme(7), an estimated BCF of 14(SRC), from an estimated log Kow of 2.25(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,3-Cyclopentadiene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data in water were not available(SRC, 2014).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-cyclopentadiene, which has a vapor pressure of 435 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-cyclopentadiene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.5 hours(SRC), calculated from its rate constant of 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase 1,3-cyclopentadiene is also degraded by reaction with ozone(SRC); the half-life for this reaction is estimated to be 52 minutes(SRC), calculated from its rate constant of 3.2X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Reaction of 1,3-cyclopentadiene with nitrate radicals in the night time atmosphere may also be a relevant removal mechanism(4).

The rate constant for the vapor-phase reaction of 1,3-cyclopentadiene with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,3-cyclopentadiene with ozone has been estimated as 3.2X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 52 min at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Reaction of 1,3-cyclopentadiene with nitrate radicals in the night time atmosphere may also be a relevant removal mechanism(2). Reaction of 1,3-cyclopentadiene with atomic oxygen in air is expected to be too slow to be environmentally relevant (estimated half-life 5.9 days)(3). Highly concentrated solutions of 1,3-cyclopentadiene, such as those which may occur in spill situations or landfills(SRC), are expected to polymerize spontaneously and exothermally to dicyclopentadiene(4). 1,3-Cyclopentadiene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Olefins, as a general class, are susceptible to reaction with photochemically-produced hydroxyl radicals and singlet oxygen in natural waters(5). Half-lives are typically on the order of 13-14 days for olefins reacting with hydroxyl radicals and 40 days for cyclic olefins reacting with singlet oxygen(5).

An estimated BCF of 14 was calculated in fish for 1,3-cyclopentadiene(SRC), using an estimated log Kow of 2.25(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,3-cyclopentadiene can be estimated to be 80(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,3-cyclopentadiene is expected to have high mobility in soil.

The Henry's Law constant for 1,3-cyclopentadiene is estimated as 2.1X10-2 atm-cu m/mole(SRC) derived from its vapor pressure, 435 mm Hg(1), and water solubility, 1800 mg/L(2). This Henry's Law constant indicates that 1,3-cyclopentadiene is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2.4 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 3.2 days(SRC). 1,3-Cyclopentadiene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1,3-Cyclopentadiene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: 1,3-Cyclopentadiene was qualitatively identified in drinking water at unspecified locations in the US(1-2). 1,3-Cyclopentadiene was detected at a concentration of 0.36 ppb in polluted drinking water from Czechoslovakia(3).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 1,3-cyclopentadiene is 1-99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 51 workers (none of these were female) were potentially exposed to 1,3-cyclopentadiene in the US(1). Occupational exposure to 1,3-cyclopentadiene may occur through inhalation and dermal contact with this compound at workplaces where 1,3-cyclopentadiene is produced or used. Monitoring data indicate that the general population may be exposed to 1,3-cyclopentadiene via inhalation of ambient air, ingestion of contaminated drinking water, and dermal contact(SRC).

Drug Information

Routes of Entry: Inhalation, ingestion, skin and/or eye contact.|The substance can be absorbed into the body by inhalation.

Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, nose Target Organs: Eyes, respiratory system (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

FIRST AID: Inhalation--Fresh air, rest. Refer for medical attention. Skin--Remove contaminated clothes. Rinse and then wash skin with water and soap. Eyes--First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. Ingestion--Rinse mouth. Refer for medical attention.|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

/SIGNS AND SYMPTOMS/ Short Term Exposure: Exposure can irritate the eyes, skin, and respiratory tract. Skin contact causes a burning sensation and rash.|/SIGNS AND SYMPTOMS/ Human sensory response was distinctly unfavorable at both 250 and 500 ppm cyclopentadiene in terms of irritating, objectionable odor.|/SIGNS AND SYMPTOMS/ Long Term Exposure: Exposure may damage the liver and kidneys. Exposure can cause a skin allergy to develop. If allergy develops, even low exposures may cause symptoms.

Cyclopentadiene

The substance can be absorbed into the body by inhalation.|inhalation, ingestion, skin and/or eye contact

irritation eyes, nose


Cough. Sore throat.


Redness. Pain.

Eyes, respiratory system

Cyclopentadiene Use and Manufacturing

Methods of Manufacturing

The preparation method is to obtain pure cyclopentadiene dimer from the coal tar benzene prefraction fraction, and obtain cyclopentadiene monomer through high temperature cracking and fractionation. Add cyclopentadiene dimer to the dimer cracking kettle heated by heat-carrying oil circulation. When the kettle temperature reaches 165 ℃, the pyrolysis of the dimer is significantly accelerated, through the packing tower directly connected to the pyrolysis kettle Fractionation. Cyclopentadiene is distilled from the top of the tower, the amount of cooling water is controlled, and the fraction with a top temperature of 39-43°C is the desired product. The yield of cyclopentadiene is about 58%. This process is a batch process medium temperature cracking. If it is replaced by continuous pipeline high temperature cracking, the reaction yield can reach more than 90%.

Uses

manufacture of resins; in organic synthesis as the diene in the Diels-Alder reaction producing sesquiterpenes, synthetic alkaloids, camphors.


Intermediates


Plastic and rubber products not covered elsewhere

Production

500,000 - 1,000,000 lb|(1984) 4.39X10+10 g|1,3-Cyclopentadiene is listed as a High Production Volume (HPV) chemical (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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#3938]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,3-Cyclopentadiene. Aggregated National Production Volume: 1 to < 10 million pounds.|Non-confidential 2014 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,3-Cyclopentadiene. National Production Volume: 510,714 lb/yr.

Hydrocarbon resin systems, 50%; Unsaturated polyester resins, 27%; EPDM elastomers, 13%; Miscellaneous, including chemical synthesis, flame retardants, pesticides and agricultural chemicals, 10% (1984)

High purity commercial form is supplied as a dimer, dicyclopentadiene

All other basic organic chemical manufacturing|1,3-Cyclopentadiene: ACTIVE|SP - indicates a substance that is identified in a proposed Significant New Use Rule.|/The dimer/ ... is a more convenient form in which to handle cyclopentadiene, and is easily depolymerized by distilling at atmospheric pressure. /Cyclopentadiene dimer/

Method: NIOSH 2523; Procedure: gas chromatography with flame ionization detector; Analyte: 1,3-cyclopentadiene; Matrix: air; Detection Limit: 0.01 mg/sample.|A method is proposed for determining cyclopentadiene in air of production facilities. This method is based on the formation of green or blue dianione from the interaction of cyclopentadiene with 1,4-dinitrobenzene in medium of dimethylformamide in presence of alkali.|Sensitivity of a thin-layer chromatographic method for cyclopentadiene in the air of coumarone-indene resin processing shops is 0.5 ug. This method is based on the formation of mercury acetate derivative in anhydrous solution of mercury acetate.

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:66.10
XLogP3:1.8
Exact Mass:66.0469501914
Monoisotopic Mass:66.0469501914
Heavy Atom Count:5
Complexity:58.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Related Drugs

Recommended Suppliers of Cyclopentadiene

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