Isoprene (2-methyl-1,3-butadiene) (C₅H₈)

Isoprene (2-methyl-1,3-butadiene) (C₅H₈)

Synthetic rubber is produced by the polymerisation of isoprene.

Chemistry

Keywords

isoprene, 2-methylbutadiene, diene, alkadiene, conjugated double bond, polymerisation, addition, synthetic rubber, caoutchouc, carotenoids, polyisoprene, isoprene skeleton, polyenes, lycopene, latex, rubber, ebonite, Goodyear, organic chemistry, chemistry

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Scenes

Isoprene (2-methyl-1,3-butadiene) C₅H₈

Information

Molar mass: 68.11 g/mol

Melting point: -146 °C (-230.8 °F)

Boiling point: 34.1 °C (93.38 °F)

Relative steam density (air=1): 0.7

Heat of combustion: -3,182 kJ/mol

Properties

Isoprene is a colorless liquid with a low boiling point. It dissolves well in alcohol and ether but is insoluble in water. It is highly flammable.

It reacts with acid chlorides, alcohol, strong acids and bases. It is a strong oxidizing and reducing agent.

Occurrence and production

Isoprene is a component in many natural carbon compounds. Natural caoutchouc is built up from about 40,000 isoprene elements. Carotinoids are polyisoprenes containing 40 carbon atoms linked by conjugated double bonds. They are colored compounds, the best-known of them is beta-carotine which produces the typical orange color in carrots and is converted in our bodies into vitamin A. Carotinoids play an important role in photosynthesis; in the human body they can deactivate free radicals.

Isoprene can be produced during the raffination of crude oil or by using the Goodyear method: first dimerizing then pyrolyzing propylene.

Uses

Synthetic rubber can be produced by polymerizing isoprene.

Related items

1-butene (C₄H₈)

One of the isomers of butene.

2-methylbutane (C₅H₁₂)

One of the isomers of pentane, used as a solvent.

Butane (C₄H₁₀)

The fourth member in the homologous series of alkanes.

Cis-2-butene (C₄H₈)

A colorless, heavier-than-air gas. Its geometric isomer is trans-2-butene.

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