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β-Propiolactone

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β-Propiolactone
Skeletal formula
Balla-and-stick model
Names
IUPAC name
2-oxetanone
Other names
Propiolactone
β-propiolactone
2-oxetanone
Identifiers
3D model (JSmol)
ECHA InfoCard 100.000.309 Edit this at Wikidata
  • C1(=O)CCO1
Properties
C3H4O2
Molar mass 72.06 g/mol
Appearance colorless liquid
Odor pungent, acrylic
Density 1.146 g/cm3
Melting point -33.4 °C
Boiling point 162 °C (dec.)
soluble
Solubility miscible in organic solvents
1.4131
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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β-Propiolactone is an organic compound of the lactone family, with a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ethanol, acetone, diethyl ether and chloroform.[1][2] The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone.

β-Propiolactone is "reasonably expected to be a human carcinogen" (IARC, 1999).[1] It 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. β-Propiolactone is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes.[1] The principal current use of propiolactone is an intermediate in the synthesis of other chemical compounds.

β-Propiolactone will slowly react with water and hydrolyse to produce 3-hydroxypropionic acid (hydracryclic acid).

See also

References

  1. ^ a b c "β-Propiolactone" - NIH substance profile. Accessed on 2009-07-10.
  2. ^ Merck Index, 12th Edition, entry 8005.