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β-Propiolactone is an organic compound of the lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ethanol, acetone, diethyl ether and
In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.
- US Department of Health and Human Services, Report on Carcinogens, National Toxicology Program, Thirteenth Edition, 2 October 2014. Accessed on 2015-01-03. 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."Appendix B - Thirteen OSHA-Regulated Carcinogens"
- Centers for Disease Control and Prevention. Accessed on 2013-11-06.
chloroform
Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
.''Merck Index'', 12th Edition, entry 8005. The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone
Methyloxiranone or α-propiolactone is a chemical compound of the lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms ...
.
Production
β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst:
In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.
Reactions and applications
It reacts with many nucleophiles in a ring-opening reactions. With water hydrolysis occurs to produce3-hydroxypropionic acid
3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.5. It is very soluble in water, soluble in ethanol and diethyl ether. Upon distillation, it dehydration reaction, dehyd ...
(hydracryclic acid). Ammonia gives the β-alanine, which is a commercial process.
Propiolactone was once widely produced as an intermediate in the production of acrylic acid
Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a ...
and its esters. That application has been largely displaced in favor of safer and less expensive alternatives. β-Propiolactone is an excellent sterilizing and sporicidal agent, but its carcinogenicity precludes that use. It is used to inactivate a wide variety of viruses, for example as a step in vaccine production. The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.
Safety
β-Propiolactone is "reasonably anticipated to be a human carcinogen" (IARC IARC may refer to:
* International Aerial Robotics Competition
* International Age Rating Coalition
* International Agency for Research on Cancer
* International Arctic Research Center
* Israel Amateur Radio Club
* iArc IARC may refer to:
* Internat ...
, 1999)."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. 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."Appendix B - Thirteen OSHA-Regulated Carcinogens"
- Centers for Disease Control and Prevention. Accessed on 2013-11-06.
Biodegradation
''Acidovorax
''Acidovorax'' is a genus of within the family Comamonadaceae. The genus contains some plant pathogens, such as ''Acidovorax avenae,'' which causes bacterial fruit blotch
Bacterial fruit blotch (BFB) affects cucurbit plants around the world and ...
'' sp., ''Variovorax paradoxus
''Variovorax paradoxus'' is a gram negative, beta proteobacterium from the genus ''Variovorax''. Strains of ''V. paradoxus'' can be categorized into two groups, hydrogen oxidizers and heterotrophic strains, both of which are aerobic. The genus na ...
'', '' Sphingomonas paucimobilis'', ''Rhizopus delemar
''Rhizopus'' is a genus of common saprophytic fungi on plants and specialized parasites on animals. They are found in a wide variety of organic substances, including "mature fruits and vegetables", jellies, syrups, leather, bread, peanuts, and t ...
'' and thermophilic ''Streptomyces
''Streptomyces'' is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of ''Streptomyces'' bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, ...
'' sp. can degrade β-propiolactone.
See also
*3-Oxetanone
3-Oxetanone, also called oxetan-3-one or 1,3-epoxy-2-propanone, is a chemical compound with formula C3H4O2. It is the
ketone of oxetane, and an isomer of β-propiolactone.
3-Oxetanone is a liquid at room temperature, that boils at 140 °C. ...
, an isomer of β-propiolactone
* Malonic anhydride (2,4-oxetanone)
* α-Propiolactone
Methyloxiranone or α-propiolactone is a chemical compound of the lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms ...
References
{{DEFAULTSORT:Propiolactone, beta- Beta-lactones Sweet-smelling chemicals