|Preferred IUPAC name|
Methyl ethylene oxide
|Molar mass||58.08 g·mol|
|Melting point||−112 °C (−170 °F; 161 K)|
|Boiling point||34 °C (93 °F; 307 K)|
|Vapor pressure||445 mmHg (20°C)|
|Main hazards||Extremely flammable|
|Safety data sheet||Oxford MSDS|
|GHS signal word||DANGER!|
|Flash point||−37 °C (−35 °F; 236 K)|
|747 °C (1,377 °F; 1,020 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)
LC (median concentration)
|1740 ppm (mouse, 4 hr)
4000 ppm (rat, 4 hr)
LC (lowest published)
|2005 ppm (dog, 4 hr)
4000 ppm (guinea pig, 4 hr)
|US health exposure limits (NIOSH):|
|TWA 100 ppm (240 mg/m)|
IDLH (Immediate danger)
|Ca [400 ppm]|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|N verify (what is ?)|
Propylene oxide is an organic compound with the molecular formula CHCHCHO. This colourless volatile liquid with and odour resembling ether, 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.
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.
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)) 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:
The process is practiced with three hydroperoxide]]s:
- tert-Butyl hydroperoxide derived from oxygenation of isobutane, which affords t-butyl alcohol. This coproduct can be dehydrated to isobutene, converted to MTBE, an additive for gasoline.
- Ethylbenzene hydroperoxide, derived from oxygenation of ethylbenzene, which affords 1-phenylethanol. This coproduct can be dehydrated to give styrene, a useful monomer.
- Cumene hydroperoxide derived from oxygenation of cumene (isopropylbenzene), which affords cumyl alcohol. Via dehydration and hydrogenation this coproduct can be recycled back to cumene. This technology was commercialized by Sumitomo Chemical.
In this process no side products other than water are generated.
Reactions of propylene oxide include:
- Reaction with aluminium oxide (AlO) at 250-260 °C leads to propionaldehyde and a little acetone.
- Reaction with AgO leads to acetic acid.
- Reaction with sodium-mercury amalgam (NaHg) and water leads to isopropyl alcohol.
- Hydrolysis with hot water leads to propylene glycol.
- Alkylation with CHMgI in diethyl ether leads to 2-pentanol.
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.
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.
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.
It is a probable human carcinogen, and listed as an IARC Group 2B carcinogen.
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.
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- ^ Nijhuis, T. Alexander; Makkee, Michiel; Moulijn, Jacob A.; Weckhuysen, Bert M. "The Production of Propene Oxide: Catalytic Processes and Recent Developments" Industrial & Engineering Chemistry Research 2006, volume 45, 3447-3459. doi:10.1021/ie0513090
- ^ "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
- ^ "New BASF and Dow HPPO Plant in Antwerp Completes Start-Up Phase". Archived from the original on 2012-07-21. Retrieved 2009-03-05.
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- ^ Heilbron (1953). Dictionary of Organic Compounds. 4. p. 249.
- ^ Norbert Adam et al. "Polyurethanes" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a21_665.pub2
- ^ "Usage of proplyene oxide, from Dow Chemical". Retrieved 2007-09-10.
- ^ See The FDA Guidance Document For More Info Archived 2011-02-09 at the Wayback Machine.
- ^ Agricultural Marketing Service, USDA (30 March 2007). "Almonds Grown in California; Outgoing Quality Control Requirements" (PDF). Federal Register. 72 (61): 15,021–15,036. Archived from the original (PDF) on 28 September 2007. Retrieved 2007-08-22.
- ^ "Safety data for propylene oxide".
- ^ Grana, R; Benowitz, N; Glantz, SA (13 May 2014). "E-cigarettes: a scientific review". Circulation. 129 (19): 1972–86. doi:10.1161/circulationaha.114.007667. PMC 4018182 . PMID 24821826.
- ^ "Scientists just detected this life-forming molecule in interstellar space for the first time". Science Alert. 2016-06-15.