Phenethyl alcohol
| Names | |
|---|---|
| IUPAC name
2-Phenylethanol
| |
| Preferred IUPAC name
2-Phenylethan-1-ol | |
| Other names
2-Phenylethanol
Benzeneethanol Benzyl carbinol PEA Phenethyl alcohol Phenyl-2-ethanol β-Hydroxyethylbenzene | |
| Properties | |
| C8H10O C6H5CH2CH2OH | |
| Molar mass | 122.16 g/mol |
| Appearance | Colorless viscous liquid |
| Odor | Soft, like roses |
| Density | 1.017 g/cm3 (20 °C) |
| Melting point | −27 °C (−17 °F; 246 K) |
| Boiling point | 218.2 °C (424.8 °F; 491.3 K) |
| 2.22 g/100 ml (25 °C) | |
| Solubility | Miscible with acetone, alcohols, chloroform, glycerol, propylene glycol Slightly soluble in mineral oil |
| Vapor pressure | 0.09 mmHg (25 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 102 °C (215.6 °F; 305 K) |
| Related compounds | |
| Related compounds
|
Benzyl alcohol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Phenethyl alcohol or 2-phenylethanol, is an organic compound with the formula C8H10O.
Contents
Properties
Chemical
Oxidation of phenethyl alcohol yields phenylacetic acid.
Physical
Phenethyl alcohol is a colorless liquid, immiscible with water, but miscible with many organic solvents.
Availability
Phenethyl alcohol is sold by chemical suppliers.
It occurs widely in nature, being found in a variety of essential oils.
Preparation
Phenethyl alcohol can also be prepared by the Grignard reaction between phenylmagnesium bromide and ethylene oxide:
- C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
- C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH
Industrially 2-phenylethanol is prepared via the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of anhydrous Aluminium chloride.
- C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl
The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product.
- C6H5CH2CH2OAlCl2 + H2O → C6H5CH2CH2OH + AlCl2(OH)
It is also possible to produce phenethyl alcohol by the reduction of phenylacetic acid using sodium borohydride and iodine in THF.[1]
Projects
- Make perfumes
- Make phenylacetic acid
Handling
Safety
Phenethyl alcohol has low toxicity and it's a safe component of perfumes and aromas.
Storage
In closed bottles.
Disposal
No special disposal is required.
References
- ↑ Kanth JV, Periasamy M (1991). "Selective Reduction of Carboxylic Acids into Alcohols Using NaBH and I2". Journal of Organic Chemistry. 56: 5964–5965
