beta-Propiolactone

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β-Propiolactone
Skeletal formula
Balla-and-stick model
Names
IUPAC names
Oxetan-2-one
3-Hydroxypropanoic acid lactone
Other names
Propiolactone
β-Propiolactone
2-Oxetanone
Identifiers
57-57-8 YesY
ChEBI CHEBI:49073 YesY
ChEMBL ChEMBL1200627 N
ChemSpider 2275 YesY
EC number 200-340-1
Jmol-3D images Image
KEGG D05630 YesY
UNII 6RC3ZT4HB0 YesY
Properties
C3H4O2
Molar mass 72.06 g·mol−1
Appearance Colorless liquid
Odor slightly sweet[1]
Density 1.1460 g/cm3
Melting point −33.4 °C (−28.1 °F; 239.8 K)
Boiling point 162 °C (324 °F; 435 K) (decomposes)
37 g/100 mL
Solubility in organic solvents Miscible
Vapor pressure 3 mmHg (25°C)[1]
1.4131
Hazards
Flash point 74 °C; 165 °F; 347 K [1]
Explosive limits 2.9%-?[1]
US health exposure limits (NIOSH):
OSHA-Regulated carcinogen[1]
Ca[1]
Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
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.[2][3] The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone.

β-Propiolactone is "reasonably anticipated to be a human carcinogen" (IARC, 1999).[2] 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.[4] 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 sterilizing and sporicidal agent, and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes.[2] 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[edit]

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

See also[edit]

References[edit]

  1. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0528". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b c "β-Propiolactone CAS No. 57-57-8" - US Department of Health and Human Services, Report on Carcinogens, National Toxicology Program, Thirteenth Edition, 2 October 2014. Accessed on 2015-01-03.
  3. ^ Merck Index, 12th Edition, entry 8005.
  4. ^ "Appendix B - Thirteen OSHA-Regulated Carcinogens" - Centers for Disease Control and Prevention. Accessed on 2013-11-06.