beta-Propiolactone

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β-Propiolactone
Skeletal formula
Balla-and-stick model
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) (decomposes)
Solubility in water Soluble
Solubility in organic solvents Miscible
Refractive index (nD) 1.4131
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/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.[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[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 "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.