Styrene oxide is an epoxide derived from styrene. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:[1]
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| Names | |
|---|---|
| Preferred IUPAC name
Phenyloxirane | |
| Other names
Epoxystyrene; Styryl oxide; Phenylethylene oxide
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| Identifiers | |
3D model (JSmol)
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| 108582 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.252 |
| EC Number |
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| 50213 | |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2810 3082 |
CompTox Dashboard (EPA)
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| Properties | |
| C8H8O | |
| Molar mass | 120.151 g·mol−1 |
| Appearance | Colorless to light yellow liquid |
| Density | 1.052 g/mL |
| Melting point | −37 °C (−35 °F; 236 K) |
| Boiling point | 194 °C (381 °F; 467 K) |
| Hazards | |
| GHS labelling: | |
 
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| Danger | |
| H312, H319, H350 | |
| P201, P202, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P312, P322, P337+P313, P363, P405, P501 | |
| Safety data sheet (SDS) | Oxford University MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Styrene oxide is slightly soluble in water. A trace amount of acid in water causes hydrolysis to racemic phenylethyleneglycol via a benzylic cation. If the amount of water is not sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur.[2]
Styrene oxide in the body is metabolized to mandelic acid, phenylglyoxylic acid, benzoic acid and hippuric acid.
Hydrogenation of styrene oxide affords phenethyl alcohol.[3]
Stereospecific reactions
editSince styrene oxide has a chiral center at the benzylic carbon atom, there are (R)-styrene oxide and (S)-styrene oxide. If optically pure reagent is used, only one optically pure compound will be obtained.
Toxicology
editStyrene oxide is a main metabolite of styrene in humans or animals, resulting from oxidation by cytochrome P450. It is considered possibly carcinogenic from gavaging significant amounts into mice and rats.[4] Styrene oxide is subsequently hydrolyzed in vivo to styrene glycol by epoxide hydrolase.[5]
Styrene oxide has a chiral center and thus two enantiomers. It has been reported that the two enantiomers had different toxicokinetics and toxicity[citation needed]. It was reported that the (R)-styrene oxide was preferentially formed in mice, especially in the lung, whereas the (S)-styrene oxide was preferentially generated in rats. In human volunteers, the cumulative excretion of the (S)-enantiomer of styrene glycol and mandelic acid were higher than the R form after exposure to styrene. In human liver microsomes, cytochrome P450-mediated styrene oxidation showed the production of more S enantiomer relative to the R enantiomer. It was also found that (S)-styrene oxide was preferentially hydrolyzed than the R enantiomer in human liver microsomes. Animal studies have shown that the (R)-enantiomer of styrene oxide was more toxic than the (S)-enantiomer in mice.
References
edit- ^ Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses; Collected Volumes, vol. 1, p. 494.
- ^ Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987
- ^ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.
- ^ EPA Styrene Oxide evaluation
- ^ Kenneth C. Liebman (1975). "Metabolism and toxicity of styrene" (PDF). Environmental Health Perspectives. 11: 115–119. doi:10.2307/3428333. JSTOR 3428333. PMC 1475194. PMID 809262.[permanent dead link]