Propylene oxide

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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
196.5 J·K−1·mol−1
−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):
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)
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.

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.

References

Relevant Sciencemadness threads