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 Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

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.

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 organic chemistry, ethenone is the formal name for ketene, an organic compound with formula or . It is the simplest member of the ketene class. It is an important reagent for acetylations. Properties Ethenone is a highly reactive gas (a ...

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: Industrial synthesis of beta-propiolactone

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 ...

epoxide In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...

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 In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...

. 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. AKDstructure

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 The Israel Amateur Radio Club (IA ...

, 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'' sp., '' Variovorax paradoxus'', ''

Sphingomonas paucimobilis Sphingomonas paucimobilis is a strictly aerobic Gram-negative bacterium that has a single polar flagellum with slow motility. The cell size is around 0.7 x 1.4 μm. It is usually found in soil. As with the other members of the genus, its b ...

'', ''

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.

References

{{DEFAULTSORT:Propiolactone, beta- Beta-lactones Sweet-smelling chemicals

Production

Reactions and applications

Safety

Biodegradation

See also

References