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Cyclopentene

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Cyclopentene Basic information

Product Name:
Cyclopentene
CAS:
142-29-0
MF:
C5H8
MW:
68.12
EINECS:
205-532-9
Mol File:
142-29-0.mol
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Cyclopentene Chemical Properties

Melting point:
−135 °C(lit.)
Boiling point:
44-46 °C(lit.)
Density 
0.771 g/mL at 25 °C(lit.)
vapor pressure 
20.89 psi ( 55 °C)
refractive index 
n20/D 1.421(lit.)
Flash point:
<−30 °F
storage temp. 
0-6°C
solubility 
water: soluble0.535g/L at 25°C
form 
Liquid
color 
Colorless
Water Solubility 
immiscible
Sensitive 
Air Sensitive
BRN 
635707
Henry's Law Constant
6.3 x 10-2 atm?m3/mol at 25 °C (Hine and Mookerjee, 1975)
Stability:
Stable. Highly flammable. Incompatible with strong oxidizing agents. Store cold.
InChIKey
LPIQUOYDBNQMRZ-UHFFFAOYSA-N
CAS DataBase Reference
142-29-0(CAS DataBase Reference)
NIST Chemistry Reference
Cyclopentene(142-29-0)
EPA Substance Registry System
Cyclopentene (142-29-0)
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Safety Information

Hazard Codes 
F,Xn
Risk Statements 
11-21/22-36/37/38-65-67-52/53-38
Safety Statements 
9-16-26-33-36-62-61-36/37
RIDADR 
UN 2246 3/PG 2
WGK Germany 
3
RTECS 
GY5950000
10-23
Autoignition Temperature
743 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29021990
Toxicity
Acute oral LD50 for rats is 1,656 mg/kg (quoted, RTECS, 1985).

MSDS

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Cyclopentene Usage And Synthesis

Chemical Properties

colourless liquid with a petrol-like odour

Physical properties

Clear, colorless, watery, very flammable liquid with a characteristic sweet, petroleum-like odor.

Uses

Cross-linking agent; organic synthesis; solvent; extracting agent.

Production Methods

Cyclopentene is present in coal tar, cigarette smoke, and automobile emissions. It is also detected in air close to forests and as a decomposition product of polypropylene. It is used as a raw material in chemical synthesis.

Definition

ChEBI: A cycloalkene that is cyclopentane having one endocyclic double bond.

General Description

A colorless liquid. Less dense than water and insoluble in water. Flash point below 0°F. Vapors heavier than air. Inhalation of high concentrations may be narcotic. Used to make rubber and plastics.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Cyclopentene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Health Hazard

May be harmful by inhalation, ingestion, or skin absorption. May cause eye and skin irritation.

Fire Hazard

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback. Explosion may occur under fire condition.

Safety Profile

Moderately toxic by ingestion and skin contact. A very dangerous fire hazard when exposed to flame or heat; can react with oxidning materials. Keep away from heat and open flame. To fight fire, use foam, CO2, dry chemical.

Source

Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of cyclopentene was 7.8 mg/kg of pine burned. Emission rates of cyclopentene were not measured during the combustion of oak and eucalyptus.
California Phase II reformulated gasoline contained cyclopentene at a concentration of 1,120 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 480 and 31,700 μg/km, respectively (Schauer et al., 2002).
Given that cyclopentene is prepared from cyclohepentanol, the latter may be present as an impurity.

Environmental Fate

Biological. Cyclopentene may be oxidized by microbes to cyclopentanol, which may oxidize to cyclopentanone (Dugan, 1972).
Photolytic. The following rate constants were reported for the reaction of cyclopentene with OH radicals in the atmosphere: 6.39 x 10-11 cm3/molecule?sec (Atkinson et al., 1983), 4.99 x 10-11 cm3/molecule?sec at 298 K (Rogers, 1989), 4.0 x 10-10 cm3/molecule?sec (Atkinson, 1990) and 6.70 x 10-11 cm3/molecule?sec (Sablji? and Güsten, 1990); with ozone in the atmosphere: 8.13 x 10-16 at 298 K (Japar et al., 1974) and 9.69 x 10-16 cm3/molecule?sec at 294 K (Adeniji et al., 1981); with NO3 in the atmosphere: 4.6 x 10-13 cm3/molecule?sec at 298 K (Atkinson, 1990) and 5.81 x 10-13 cm3/molecule?sec at 298 K (Sablji? and Güsten, 1990).
Chemical/Physical. Gaseous products formed from the reaction of cyclopentene with ozone were (% yield): formic acid, carbon monoxide, carbon dioxide, ethylene , formaldehyde, and butanal. Particulate products identified include succinic acid, glutaraldehyde, 5-oxopentanoic acid, and glutaric acid (Hatakeyama et al., 1987).
At elevated temperatures, rupture of the C-C bond occurs forming molecular hydrogen and cyclopentadiene (95% yield) as the principal products (Rice and Murphy, 1942).

Purification Methods

Free cyclopentene from hydroperoxide by refluxing with cupric stearate. Fractionally distil it from Na. It can be chromatographed on a Dowex 710-Chromosorb W GLC column. Methods for cyclohexene should be applicable here. Also, it has been washed with 1M NaOH solution followed by water. It was dried over anhydrous Na2SO4, distilled over powdered NaOH under nitrogen, and passed through neutral alumina before use [Woon et al. J Am Chem Soc 108 7990 1986]. It was distilled in a dry nitrogen atmosphere from powdered fused NaOH through a Vigreux column (p 11), and then passed through activated neutral alumina before use [Wong et al. J Am Chem Soc 109 3428 1987]. [Beilstein 5 IV 209.]

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