 | |
| Names | |
|---|---|
| IUPAC name 1-Phenylethanol | |
| Other names Styrallyl alcohol | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.461 |
| EC Number |
|
| UNII | |
| UN number | 2937 |
| |
| |
| Properties | |
| C8H10O | |
| Molar mass | 122.167 g·mol−1 |
| Appearance | Colourless liquid with a floral[1] or almond-like odor[2] |
| Melting point | 20.7 °C (69.3 °F; 293.8 K) |
| Boiling point | 204 °C (399 °F; 477 K) |
| 1.95 g dm−3[3] | |
| logP | 1.4 |
| Hazards | |
| Flash point | 93 °C (199 °F; 366 K)[5] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Phenylethanol is theorganic compound with the formula C6H5CH(OH)CH3. It is one of the most commonly availablechiral alcohols. It is a colorless liquid with a mild gardenia-hyacinth scent.[4]
Phenylethanol is an aromatic alcohol, it has the role of mousemetabolite.It is a natural product and is found inCichorium endivia,Castanopsis cuspidata and other organisms.[6]
1-Phenylethanol is found in nature as aglycoside, together with itshydrolase β-primeverosidase in tea (Camellia sinensis) flowers.[7] It is also reportedly present in cranberries, grapes, chives, Scottish spearmint oil, cheeses, cognac, rum, white wine, cocoa, black tea, filbert, cloudberries, beans, mushrooms, and endives.[8]
Racemic 1-phenylethanol is produced by the reduction ofacetophenone bysodium borohydride. Alternatively,benzaldehyde can be reacted withmethylmagnesium chloride or similarorganometallic compounds to afford racemic 1-phenylethanol.
Asymmetric hydrogenation of acetophenone byNoyori catalysts proceeds quantitatively (50 atm H2, room temperature, minutes) in >99%e.e.[9]
The organic oxidising agentethylbenzene hydroperoxide yields 1-phenylethanol when reduced. Used for theepoxidation ofpropene, this coproducespropylene oxide, and is an important step in the PO/SM process for the production ofstyrene.[10]
In the final step of the PO/SM process,dehydration of 1-phenylethanol yieldsstyrene, analogous to many other dehydrations of alcohols to yieldalkenes. While secondary to the direct dehydrogenation ofethylbenzene, the PO/SM method remains industrially significant. This route accounted for approximately 15% of styrene production in the United States in 1993,[11] and has seen international development in the 21st century, especially in developing economies that have seen growth in demand for both styrene and propylene oxide.[12]
The majority of styrene is produced by dehydrogenation of ethylbenzene, with about 15 percent produced by hydroperoxidation of ethylbenzene.
