Appearance Colorless liquid Boiling point 34 °C | Formula C3H6O Density 830 kg/m³ | |
 | ||
Propylene oxide
Propylene oxide is an organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid is produced on a large scale industrially, its major application being its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.
Contents
- Propylene oxide
- Production
- Hydrochlorination route
- Oxidation of propylene
- Uses
- Historic and niche uses
- Fumigant
- Microscopy
- Safety
- Natural occurrence
- References
This compound is sometimes called 1,2-propylene oxide to distinguish it from its isomer 1,3-propylene oxide, better known as oxetane.
Production
Industrial production of propylene oxide starts from propylene. Two general approaches are employed, one involving hydrochlorination and the other involving oxidation. In 2005, about half of the world production was through chlorohydrin technology and one half via oxidation routes. The latter approach is growing in importance.
Hydrochlorination route
The traditional route proceeds via the conversion of propylene to propylene chlorohydrin, which is produced according to the following simplified scheme:
The mixture of 1-chloro-2-propanol and 2-chloro-1-propanol, which is then dehydrochlorinated. For example:
Lime (Ca(OH)2) is often used to absorb the HCl.
Oxidation of propylene
The other general route to propylene oxide involves oxidation of propylene with an organic peroxide. The reaction follows this stoichiometry:
CH3CH=CH2 + RO2H → CH3CHCH2O + ROHThe process is practiced with three hydroperoxide]]s:
In March 2009, BASF and Dow Chemical started up their new HPPO plant in Antwerp. In the HPPO-Process, propylene is oxidized with hydrogen peroxide:
CH3CH=CH2 + H2O2 → CH3CHCH2O + H2OIn this process no side products other than water are generated.
Uses
Between 60 and 70% of all propylene oxide is converted to polyether polyols by the process called alkoxylation. These polyols are building blocks in the production of polyurethane plastics. About 20% of propylene oxide is hydrolyzed into propylene glycol, via a process which is accelerated by acid or base catalysis. Other major products are polypropylene glycol, propylene glycol ethers, and propylene carbonate.
Historic and niche uses
Propylene oxide was once used as a racing fuel, but that usage is now prohibited under the US NHRA rules for safety reasons. It has also been used in glow fuel for model aircraft and surface vehicles, typically combined in small percentages of around 2% as an additive to the typical methanol, nitromethane, and oil mix. It is also used in thermobaric weapons, and microbial fumigation.
Fumigant
The United States Food and Drug Administration has approved the use of propylene oxide to pasteurize raw almonds beginning on September 1, 2007, in response to two incidents of contamination by Salmonella in commercial orchards, one incident occurring in Canada and one in the United States. Pistachio nuts can also be subjected to propylene oxide to control Salmonella.
Microscopy
Propylene oxide is commonly used in the preparation of biological samples for electron microscopy, to remove residual ethanol previously used for dehydration. In a typical procedure, the sample is first immersed in a mixture of equal volumes of ethanol and propylene oxide for 5 minutes, and then four times in pure oxide, 10 minutes each.
Safety
Propylene oxide is a probable human carcinogen, and listed as an IARC Group 2B carcinogen.
Natural occurrence
In 2016 it was reported that propylene oxide was detected in Sagittarius B2, a cloud of gas in the Milky Way weighing three million solar masses. It is the first chiral molecule to be detected in space.