Difference between revisions of "Styrene"
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| − | | OtherCompounds = [[Phenylacetylene]] | + | | OtherCompounds = [[Ethylbenzene]]<br>[[Phenylacetylene]] |
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| − | '''Styrene''', also known as '''ethenylbenzene''', '''vinylbenzene''' and '''phenylethene''', is an aromatic organic compound with the chemical formula '''C<sub>6</sub>H<sub>5</sub>CH=CH<sub>2</sub>'''. | + | '''Styrene''', also known as '''ethenylbenzene''', '''vinylbenzene''' and '''phenylethene''', is an aromatic organic compound with the chemical formula '''C<sub>6</sub>H<sub>5</sub>CH=CH<sub>2</sub>'''. Polymerization of this compound yields [[polystyrene]], a cheap and versatile polymer used in many every day items, ranging from cutlery to wall insulation. |
==Properties== | ==Properties== | ||
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==Preparation== | ==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 | + | 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.<ref>https://www.thevespiary.org/library/Files_Uploaded_by_Users/no1uno/pdf/Toolkit/Acquisition/Chemical/Styrene/Cooley.Williams.Pyrolysis.of.Polystyrene.pdf</ref> This reaction is not clean and also produces toluene, ethylbenzene, alpha-methylstyrene, beta-methylstyrene and higher products, which may contaminate even distilled samples.<ref>Wheeler Scientific, ''YouTube'' '''2024''', "Doing Chemistry with a Styrofoam Box", [https://www.youtube.com/watch?v=l6LdMYOx1ag https://www.youtube.com/watch?v=l6LdMYOx1ag]</ref> |
| − | + | If styrofoam is all you have, you can shrink it to a solid mass by dissolving it in acetone, then dry it.<ref>[https://www.youtube.com/watch?v=YfByQ190cOM Styrene from Styrofoam]</ref> | |
| − | Styrene can be prepared via decarboxylation of cinnamic acid. | + | Dehydrogenation of [[ethylbenzene]] will lead to styrene. |
| + | |||
| + | Styrene can be prepared via decarboxylation of cinnamic acid.<ref>T. W. Abbott, John R. Johnson, ''Org. Synth.'' '''1928''', 8, 84, [https://doi.org/10.15227/orgsyn.008.0084 10.15227/orgsyn.008.0084]</ref> | ||
==Projects== | ==Projects== | ||
*Make polystyrene | *Make polystyrene | ||
| + | *Make [[phenylacetylene]] | ||
*Make [[acetophenone]] | *Make [[acetophenone]] | ||
*Make ethylbenzene | *Make ethylbenzene | ||
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[[Category:Alkenes]] | [[Category:Alkenes]] | ||
[[Category:Fragrant compounds]] | [[Category:Fragrant compounds]] | ||
| − | [[Category: | + | [[Category:Liquids]] |
| − | + | ||
Latest revision as of 18:52, 22 February 2024
| 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): | |
| LD50 (Median dose)
|
6,000 mg/kg (rat, oral) |
| LC50 (Median concentration)
|
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.
Contents
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
- Make polystyrene
- Make phenylacetylene
- Make acetophenone
- Make ethylbenzene
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
- ↑ https://www.thevespiary.org/library/Files_Uploaded_by_Users/no1uno/pdf/Toolkit/Acquisition/Chemical/Styrene/Cooley.Williams.Pyrolysis.of.Polystyrene.pdf
- ↑ Wheeler Scientific, YouTube 2024, "Doing Chemistry with a Styrofoam Box", https://www.youtube.com/watch?v=l6LdMYOx1ag
- ↑ Styrene from Styrofoam
- ↑ T. W. Abbott, John R. Johnson, Org. Synth. 1928, 8, 84, 10.15227/orgsyn.008.0084
