Β-Propiolactone

β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst:{{Ullmann|doi=10.1002/14356007.a13_507|title=Hydroxycarboxylic Acids, Aliphatic|year=2000|last1=Miltenberger|first1=Karlheinz}}

File:Industrial synthesis of beta-propiolactone.svg

In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.{{cite journal|title=Low Pressure Carbonylation of Epoxides to β-Lactones |author=John W. Kramer |author2=Daniel S. Treitler |author3=Geoffrey W. Coates|journal=Org. Synth.|year=2009|volume=86|page=287|doi=10.15227/orgsyn.086.0287|doi-access=free}}

It reacts with many nucleophiles in a ring-opening reactions. With water hydrolysis occurs to produce 3-hydroxypropionic acid (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 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,{{cite journal|doi=10.1111/j.1749-6632.1960.tb40931.x|title=Investigations of the Use of Beta-Propiolactone in Virus Inactivation|year=1960|last1=Logrippo|first1=Gerald A.|journal=Annals of the New York Academy of Sciences|volume=83|issue=4|pages=578–594|pmid=14417982|bibcode=1960NYASA..83..578L|s2cid=6025589}} for instance the influenza virus, as a step in vaccine production.{{cite journal|journal=Science|title=Development of an inactivated vaccine candidate for SARS-CoV-2|author1=Qiang Gao |author2=Linlin Bao |author3=Haiyan Mao |author4=Lin Wang |author5=Kangwei Xu |author6=Minnan Yang |author7=Yajing Li |author8=Ling Zhu |author9=Nan Wang |author10=Zhe Lv |author11=Hong Gao |author12=Xiaoqin Ge |author13=Biao Kan |author14=Yaling Hu |author15=Jiangning Liu |author16=Fang Cai |author17=Deyu Jiang |author18=Yanhui Yin |author19=Chengfeng Qin |author20=Jing Li |author21=Xuejie Gong |author22=Xiuyu Lou |author23=Wen Shi |author24=Dongdong Wu |author25=Hengming Zhang |author26=Lang Zhu |author27=Wei Deng |author28=Yurong Li |author29=Jinxing Lu |author30=Changgui Li |author31=Xiangxi Wang |author32=Weidong Yin |author33=Yanjun Zhang |author34=Chuan Qin |date=2020-07-03|doi=10.1126/science.abc1932|volume=369|issue=6499|pages=77–81|pmid=32376603|pmc=7202686|bibcode=2020Sci...369...77G|doi-access=free}} The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.

File:AKDstructure.png (AKD), a propiolactone derivative that is used in papermaking.]]

β-Propiolactone is "reasonably anticipated to be a human carcinogen" (IARC, 1999).[http://ntp.niehs.nih.gov/ntp/roc/content/profiles/propiolactone.pdf "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 U.S. Occupational Safety and Health Administration, despite not having an established permissible exposure limit.[https://www.cdc.gov/niosh/npg/nengapdxb.html "Appendix B - Thirteen OSHA-Regulated Carcinogens"] - Centers for Disease Control and Prevention. Accessed on 2013-11-06.

• 3-Oxetanone, an isomer of β-propiolactone
• Malonic anhydride (2,4-oxetanone)
• α-Propiolactone

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Category:Beta-lactones

Category:Sweet-smelling chemicals