β-Propiolactone

β-Propiolactone, often simply called 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 chloroform.[2][3]

"Propiolactone" redirects here. For α-propiolactone, see Methyloxiranone.
β-Propiolactone
Skeletal formula
Balla-and-stick model
Names
Preferred IUPAC name
Oxetan-2-one
Other names
Propiolactone
2-Oxetanone
3-Hydroxypropanoic acid lactone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.309
EC Number
  • 200-340-1
KEGG
RTECS number
  • RQ7350000
UNII
UN number 2810
  • InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2 checkY
    Key: VEZXCJBBBCKRPI-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O2/c4-3-1-2-5-3/h1-2H2
    Key: VEZXCJBBBCKRPI-UHFFFAOYAQ
  • O=C1OCC1
Properties
C3H4O2
Molar mass 72.063 g·mol−1
Appearance Colorless liquid
Odor slightly sweet[1]
Density 1.1460 g/cm3
Melting point −33.4 °C (−28.1 °F; 239.8 K)
Boiling point 162 °C (324 °F; 435 K) (decomposes)
37 g/100 mL
Solubility in organic solvents Miscible
Vapor pressure 3 mmHg (25°C)[1]
1.4131
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H315, H319, H330, H350
P201, P202, P260, P264, P271, P280, P281, P284, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 74 °C; 165 °F; 347 K[1]
Explosive limits 2.9%-?[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 OSHA-Regulated carcinogen[1]
REL (Recommended)
 Ca[1]
IDLH (Immediate danger)
 Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Production

β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst:[4]

Industrial synthesis of beta-propiolactone

In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.[5]

Reactions and applications

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.[4]

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.[2] It is used to inactivate a wide variety of viruses,[6] for example as a step in vaccine production.[7] The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.[4]

Structure of an alkyl ketene dimer (AKD), a propiolactone derivative that is used in papermaking.

Safety

β-Propiolactone is "reasonably anticipated to be a human carcinogen" (IARC, 1999).[2] 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.[8]

Biodegradation

Acidovorax sp., Variovorax paradoxus, Sphingomonas paucimobilis, Rhizopus delemar and thermophilic Streptomyces sp. can degrade β-propiolactone.

See also

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0528". National Institute for Occupational Safety and Health (NIOSH).
  2. "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.
  3. Merck Index, 12th Edition, entry 8005.
  4. Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507.
  5. John W. Kramer; Daniel S. Treitler; Geoffrey W. Coates (2009). "Low Pressure Carbonylation of Epoxides to β-Lactones". Org. Synth. 86: 287. doi:10.15227/orgsyn.086.0287.
  6. Logrippo, Gerald A. (1960). "Investigations of the Use of Beta-Propiolactone in Virus Inactivation". Annals of the New York Academy of Sciences. 83 (4): 578–594. Bibcode:1960NYASA..83..578L. doi:10.1111/j.1749-6632.1960.tb40931.x. PMID 14417982. S2CID 6025589.
  7. Qiang Gao; Linlin Bao; Haiyan Mao; Lin Wang; Kangwei Xu; Minnan Yang; Yajing Li; Ling Zhu; Nan Wang; Zhe Lv; Hong Gao; Xiaoqin Ge; Biao Kan; Yaling Hu; Jiangning Liu; Fang Cai; Deyu Jiang; Yanhui Yin; Chengfeng Qin; Jing Li; Xuejie Gong; Xiuyu Lou; Wen Shi; Dongdong Wu; Hengming Zhang; Lang Zhu; Wei Deng; Yurong Li; Jinxing Lu; Changgui Li; Xiangxi Wang; Weidong Yin; Yanjun Zhang; Chuan Qin (2020-07-03). "Development of an inactivated vaccine candidate for SARS-CoV-2". Science. 369 (6499): 77–81. Bibcode:2020Sci...369...77G. doi:10.1126/science.abc1932. PMC 7202686. PMID 32376603.
  8. "Appendix B - Thirteen OSHA-Regulated Carcinogens" - Centers for Disease Control and Prevention. Accessed on 2013-11-06.
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