Beta-Propiolactone

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β-Propiolactone
IUPAC name

Oxetan-2-one
3-Hydroxypropanoic acid lactone

Other names

Propiolactone
β-Propiolactone
2-Oxetanone

Identifiers
CAS number 57-57-8 YesY
ChemSpider 2275 YesY
UNII 6RC3ZT4HB0 YesY
KEGG D05630 YesY
ChEBI CHEBI:49073 YesY
ChEMBL CHEMBL1200627 N
Jmol-3D images Image 1
Properties
Molecular formula C3H4O2
Molar mass 72.06 g mol−1
Appearance Colorless liquid
Odor Pungent, acrylic
Density 1.146 g/cm3
Melting point −33.4 °C; −28.1 °F; 239.8 K
Boiling point 162 °C; 324 °F; 435 K (dec.)
Solubility in water Soluble
Solubility in organic solvents Miscible
Refractive index (nD) 1.4131
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 is one of 13 "OSHA-regulated carcinogens," chemicals regarded occupational carcinogens by the Occupational Safety and Health Administration, despite not having an established permissible exposure limit.[3] 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 hydrolyze to produce 3-hydroxypropionic acid (hydracryclic acid).

Biodegradation

Acidovorax sp., Variovorax paradoxus, Sphingomonas paucimobilis, Rhizopus delemar and thermophilic Streptomyces sp. can degrade β-propiolactone.

See also

References

  1. ↑ 1.0 1.1 1.2 "β-Propiolactone" - NIH substance profile. Accessed on 2009-07-10.
  2. ↑ Merck Index, 12th Edition, entry 8005.
  3. ↑ "Appendix B - Thirteen OSHA-Regulated Carcinogens" - Centers for Disease Control and Prevention. Accessed on 2013-11-06.
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