Cyclopentadiene

시클로펜타디엔 · 1,3-사이클로펜타디엔 · Cyclopentadiene · pyropentylene · pentole · r-pentine · JACS-542-92-7 · 2,4-Cyclopentadiene

식별자 및 물리적 특성

CAS No.	542-92-7
분자식	C5H6
평균 분자량	66.1 g/mol
단동위원소 질량	66.04695019 g/mol
SMILES	C1=CCC=C1
InChIKey	ZSWFCLXCOIISFI-UHFFFAOYSA-N
PubChem CID	7612
ChEMBL	CHEMBL3188826
ChEBI	CHEBI:30664
EC No.	208-835-4
DTXSID	DTXSID0027191
현지명	시클로펜타디엔

화학 및 물리적 성질

XLogP	1.8
극성 표면적	0
수소 결합 공여자 수	0
수소 결합 수용자 수	0
회전 가능 결합 수	0
무거운 원자 수	5
형식 전하	0
복잡도	58.1
물질 분류	Other Classes -> Aliphatics, UnsaturatedFlammable agents - 3rd degree
SpringerMaterials Properties	Coriolis coupling
냄새	MONOMERIC FORM HAS TERPENE ODOR IN VAPOR STATEIrritating terpene-like odor
밀도	0.8 (NIOSH, 2024) - Less dense than waterwill float0.8021 g/cu cm at 20 °CRelative density (water = 1): 0.8d40 0.8235d410 0.8131d420 0.8021d425 0.7966d430 0.7914
Color/Form	Colorless liquid
용해도	Insoluble (NIOSH, 2024)In water, 1,800 mg/L at 25 °CMiscible with carbon tetrachloridesoluble in carbon disulfide, aniline, acetic acid, liquid petrolatumSoluble in acetonemiscible with ethanol, ethyl ether, benzeneSolubility in water: insolubleMiscible with acetone, benzene, carbon tetrachloride, and ether. Soluble in acetic acid, aniline, and carbon disulfide (Windholz et al., 1983).
인화점	77 °F (NIOSH, 2024)77 °F (OPEN CUP)-20 °C(oc) 77 °F
끓는 점	107 °F at 760 mmHg (NIOSH, 2024)41 °C41.5-42.0 °Cbp760 41.5-42.0°
Decomposition	When heated to decomposition it emits acrid smoke and irritating fumes.It decomposes violently at high temperatures and pressures.
녹는점	-121 °F (NIOSH, 2024)-95.54 °C-85 °C-85°mp 32.5°
증기 밀도	(AIR= 1) AT BOILING POINT OF CYCLOPENTADIENE 2.3Relative vapor density (air = 1): 2.3
후각 역치	Odor Threshold Low: 1.8 [ppm]Low Threshold= 5.0 mg/cu mHigh threshold= 5.0 mg/cu m.
증기압	381 at 20.6 °C, 735 at 40.6 °C, 1,380 at 60.9 °C (Stoeck and Roscher, 1977)
굴절률	nD16 1.44632
pKa(산도 계수)	16(at 25℃)
물리적 상태	무색의 액체
용해도	25°C에서 10.3mM(진탕 플라스크-UV 분광광도법, Streitwieser 및 Nebenzahl, 1976)
헨리 상수	5.1 at 25 °C (approximate - calculated from water solubility and vapor pressure)
안정성	실온에서 안정함. 산화제, 산 및 다양한 기타 화합물과 호환되지 않습니다. 보관 시 과산화물을 형성할 수 있습니다. 자발적인 중합이 일어날 수 있습니다. 가열하면 분해됩니다. 가연성이 높습니다. 공기와의 혼합물은 폭발성이 있습니다.
InChI	InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2
InChIKey	ZSWFCLXCOIISFI-UHFFFAOYSA-N
SMILES	C1C=CC=C1
EPA	Cyclopentadiene (542-92-7)

화학적 성질

1,3-Cyclopentadiene is a colorless liquid that dimerizes easily in the presence of peroxides and trichloroacetic acid to a colorless solid.

안전 및 규제

GHS 분류	DangerH225 (28.2%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 372 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
규제 정보	Chemical: 1,3-Cyclopentadiene1,3-Cyclopentadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Cyclopentadiene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)SP - indicates a substance that is identified in a proposed Significant New Use Rule.Status: Active Update: 27-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34854Cyclopentadiene: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
운송 라벨(DOT)	Flammable Liquid
화재 위험	Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Flammable. Above 25 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers.
화재 가능성	A dangerous fire hazard when exposed to heat or flame.
건강 유해성	Excerpt from NIOSH Pocket Guide for Cyclopentadiene:
유해성 요약	Cyclopentadiene causes narcosis and liver injury in animal experiments. It has an irritating odor that is objectionable to workers. [ACGIH, 1987] A skin, eye, and respiratory tract irritant[ICSC]TLV and Documentation withdrawn. . . Since cyclopentadiene (CPD) dimerizes into DCPD [Dicyclopentadiene], we recommended using the TLV for DCPD if CPD is of concern. There is little information available on the toxicity of CPD. [ACGIH, 2019] See Dicyclopentadiene.
반응성 그룹	Hydrocarbons, Aliphatic Unsaturated
UN 분류	UN Hazard Class: 3UN Pack Group: III
TSCA 요건	Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 8/4/95Reporting date: 10/3/95.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cyclopentadiene is included on this list. Effective date: 8/4/95Sunset date: 6/30/98.
Reactivity Alerts	Highly Flammable
OSHA Standards	Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 75 ppm (200 mg/cu m).
Reactivity Profile	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.
소화	Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Use powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
응급 조치	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.Rinse mouth. Seek medical attention if you feel unwell.
응급 처치	Excerpt from NIOSH Pocket Guide for Cyclopentadiene:(General first aid procedures)
안전 보관	Fireproof. Store only if stabilized. Cooled. Separated from incompatible materials. See Chemical Dangers.
Firefighting Hazards	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.
소화 절차	Powder, aqueous film-forming foams (AFFF), foam, carbon dioxide ... Keep drums, etc, cool by spraying with water.Dry chemical, carbon dioxide, foam
보관 조건	A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.Fireproof. Separated from strong oxidants, strong acids, potassium hydroxide. Cooled. Store only if stabilized.Monomer may largely be prevented from dimerizing by storage at -80 °C or below.
정리 방법	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.
비화재 누출 대응	Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
처리 방법	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 qualitypotential migration in soil or watereffects on animal and plant lifeand 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
누출 처리	Evacuate danger area! Remove all ignition sources. Consult an expert! 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.
Preventive Measures	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.
상호 작용	An added stabilizer or inhibitor can influence the toxicological properties of this substance.
표적 장기	Eyes, respiratory system
환경 거동	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).
유해 작용	Neurotoxin - Acute solvent syndrome
노출 경로	The substance can be absorbed into the body by inhalation.inhalation, ingestion, skin and/or eye contact
독성 요약	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 convulsionshowever, 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.
Signs and Symptoms	Cough. Sore throat.Redness.Redness. Pain.Nausea. Vomiting.irritation eyes, nose
Effluent Concentrations	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 0.93and 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).
Medical Surveillance	If symptoms develop or overexposure is suspected, the following may be useful: liver and kidney function tests. Evaluation by a a qualified allergist, including careful exposure history and special testing, may help diagnose skin allergy.
Soil Adsorption/Mobility	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.
Human Toxicity Excerpts	/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.
Artificial Pollution Sources	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).
직업 노출 등급(OEB)	A
직업 노출 한계(OEL)	TWA: 75 ppm (200 mg/m3)
즉시 생명 위험 농도	750 ppm
TSCA 등재 상태	TSCA listed
운송 번호(UN)	1993
독성	LD50 of dimer orally in rats: 0.82 g/kg (Smyth)
포장분류	III
위험 등급	3.2
기존화학 물질	KE-09295
유해 물질 데이터	542-92-7(Hazardous Substances Data)

용도

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

일반 설명

1,3-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.

제조 및 합성 방법

생산 방법

This compound occurs in the C6–C8 petroleum distillation fraction, and in coke oven light oil fractions. It is produced by dehydrogenation of cyclopentadiene or monomerization of its dimer.