Styrene

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Styrene
Names
IUPAC name
Ethenylbenzene
Other names
Cinnamene
Diarex HF 77
Phenylethylene
Phenylethene
Styrol
Styrolene
Styropol
Vinylbenzene
Properties
C8H8
C6H5CH=CH2
Molar mass 104.15 g/mol
Appearance Colorless liquid
Odor Sweet, floral
Density 0.906 g/cm3 (20 °C)
Melting point −30 °C (−22 °F; 243 K)
Boiling point 145 °C (293 °F; 418 K)
0.05 g/100 ml (25 °C)
Solubility Miscible with acetone, benzene, ethanol, hexane, methanol, toluene
Vapor pressure 5 mmHg (20 °C)
Thermochemistry
Hazards
Safety data sheet Sigma-Aldrich
Flash point 31 °C (88 °F; 304 K)
Lethal dose or concentration (LD, LC):
6,000 mg/kg (rat, oral)
2,194 ppm (mouse, 4 hr)
5,543 ppm (rat, 4 hr)
Related compounds
Related compounds
Ethylbenzene
Phenylacetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Styrene, also known as ethenylbenzene, vinylbenzene and phenylethene, is an aromatic organic compound with the chemical formula C6H5CH=CH2. Polymerization of this compound yields polystyrene, a cheap and versatile polymer used in many every day items, ranging from cutlery to wall insulation.

Properties

Chemical

Upon exposure to light and air, styrene undergoes self-polymerization and oxidation with formation of peroxides.

Physical

Styrene is a colorless viscous liquid, with a sweet smell. It is insoluble in water, but miscible with organic solvents.

Availability

Styrene is sold by chemical suppliers.

Preparation

The easiest route to styrene is by cracking of polystyrene. This can be done by heating items made of polystyrene, such as plastic kitchen cutlery or other items, which must be made from polystyrene.[1] This reaction is not clean and also produces toluene, ethylbenzene, alpha-methylstyrene, beta-methylstyrene and higher products, which may contaminate even distilled samples.[2]

If styrofoam is all you have, you can shrink it to a solid mass by dissolving it in acetone, then dry it.[3]

Dehydrogenation of ethylbenzene will lead to styrene.

Styrene can be prepared via decarboxylation of cinnamic acid.[4]

Projects

Handling

Safety

Styrene is regarded as a "known carcinogen", especially in case of eye contact, but also in case of skin contact, of ingestion and of inhalation, according to several sources. Styrene is largely metabolized into styrene oxide in humans, resulting from oxidation by cytochrome P450. Styrene oxide is considered toxic, mutagenic, and possibly carcinogenic.

Storage

Styrene should be kept in closed bottles, in dark well ventilated places. Tert-butylcatechol is often used as preservative, to inhibit polymerization.

Disposal

Styrene should be mixed with a more flammable solvent and burned.

References

  1. https://www.thevespiary.org/library/Files_Uploaded_by_Users/no1uno/pdf/Toolkit/Acquisition/Chemical/Styrene/Cooley.Williams.Pyrolysis.of.Polystyrene.pdf
  2. Wheeler Scientific, YouTube 2024, "Doing Chemistry with a Styrofoam Box", https://www.youtube.com/watch?v=l6LdMYOx1ag
  3. Styrene from Styrofoam
  4. T. W. Abbott, John R. Johnson, Org. Synth. 1928, 8, 84, 10.15227/orgsyn.008.0084

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