Propylene oxide
| Names | |
|---|---|
| IUPAC name
2-Methyloxirane
| |
| Other names
1,2-Epoxypropane
1,2-Propylene oxide Epoxypropane Propene oxide Methyl ethylene oxide Methyl oxirane Methylethylene oxide Propylene epoxide | |
| Properties | |
| C3H6O | |
| Molar mass | 58.080 g/mol |
| Appearance | Colorless volatile liquid |
| Odor | Benzene-like |
| Density | 0.859 g/cm3 (0 °C) 0.8304 g/cm3 (20 °C) |
| Melting point | −111.9 °C (−169.4 °F; 161.2 K) |
| Boiling point | 35 °C (95 °F; 308 K) |
| 40 g/100 ml (20 °C) 59 g/100 ml (25 °C) | |
| Solubility | Miscible with acetone, benzene, carbon tetrachloride, diethyl ether, ethanol, methanol |
| Vapor pressure | 445 mmHg (20°C) |
| Thermochemistry | |
| Std molar
entropy (S |
196.5 J·K−1·mol−1 |
| Std enthalpy of
formation (ΔfH |
−123.0 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich (racemic) |
| Flash point | −37 °C (−35 °F; 236 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
660 mg/kg (guinea pig, oral) 380 mg/kg (rat, oral) 440 mg/kg (mouse, oral) 1140 mg/kg (rat, oral) 690 mg/kg (guinea pig, oral) |
| LC50 (Median concentration)
|
1740 ppm (mouse, 4 h) 4000 ppm (rat, 4 h) |
| Related compounds | |
| Related compounds
|
Ethylene oxide |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Propylene oxide (sometimes called 1,2-propylene oxide to distinguish it from its isomer 1,3-propylene oxide, better known as oxetane) is an organic compound with the molecular formula CH3(CHCH2)O.
The molecule is a chiral, although it is commonly used as a racemic mixture.
Contents
Properties
Chemical
Like other epoxides, PO undergoes ring-opening reactions. With water, propylene glycol is produced. Grignard reagents add to propylene oxide to give secondary alcohols.
Physical
Propylene oxide is a volatile colorless clear liquid
Availability
Propylene oxide is sold by chemical suppliers.
Preparation
Propylene oxide is commonly synthesized via the conversion of propylene to propylene chlorohydrin using chlorine dissolved in water (aka hypochlorous acid), which is converted to the epoxide using a base.
The other general route to propylene oxide involves oxidation of propylene with an organic peroxide, such as hydrogen peroxide, tert-butyl hydroperoxide or DMDO.
Projects
- Make propylene glycol
Handling
Safety
It is a probable human carcinogen, and is included into the List of IARC Group 2B carcinogens.
Storage
Propylene oxide should be kept in closed bottles, away from heat or sunlight.
Disposal
Should be burned outside.
