Propiolactone

From Wikipedia, the free encyclopedia

Propiolactone
IUPAC name 2-oxatanone
Other names Propiolactone
β-propiolactone
Identifiers
CAS number [57-57-8]
SMILES C1(=O)CCO1
Properties
Molecular formula C3H4O2
Molar mass 72.06 g/mol
Density 1.146 g/cm3
Melting point

-33.4 °C
Boiling point

162 °C (dec.)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Propiolactone, or β-propiolactone, is an organic compound classified as a lactone containing a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, although given that propiolactone is "reasonably expected to be a human carcinogen" (IARC 1999) smelling propiolactone is not advisable. It is well soluble in water and miscible with ethanol, acetone, diethyl ether and chloroform. It will slowly react with water to hydrolize to produce 3-hydroxypropanoic acid (hydracryclic acid).

Propiolactone was once widely used in the manufacture of acrylic acid and its esters, but its use has been mostly phased out in favor of safer and less expensive alternatives. Propiolactone is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes. The principle current use of propiolactone is an intermediate in the synthesis of other chemical compounds.

[edit] References

 The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.