β-Propiolactone
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β-Propiolactone is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
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 Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
,
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
,
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
and
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 Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
and ethenone in the presence of aluminium- or
zinc chloride Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. This salt is hygroscopic and ev ...
as catalyst: In the research laboratory, propiolactones have been produced by the
carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbon ...
of epoxides.


Reactions and applications

It reacts with many nucleophiles in a ring-opening reactions. With water
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
occurs to produce
3-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 The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agenc ...
, despite not having an established
permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational S ...
."Appendix B - Thirteen OSHA-Regulated Carcinogens"
-
Centers for Disease Control and Prevention The Centers for Disease Control and Prevention (CDC) is the national public health agency of the United States. It is a United States federal agency, under the Department of Health and Human Services, and is headquartered in Atlanta, Georgi ...
. 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 Â°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