β-Propiolactone
| Names | |
|---|---|
| Preferred IUPAC name
Oxetan-2-one | |
| Other names
Propiolactone
2-Oxetanone 3-Hydroxypropanoic acid lactone | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2810 |
CompTox Dashboard (EPA)
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| 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] |
Refractive index (nD)
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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)
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OSHA-Regulated carcinogen[1] |
REL (Recommended)
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Ca[1] |
IDLH (Immediate danger)
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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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β-Propiolactone, often simply called propiolactone, is an organic compound with the formula CH2CH2CO2. It is a member of the lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents.[2][3] The carcinogenicity of this compound has limited its commercial applications.[4]
Production
[edit | edit source]β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst:[5]
Industrial synthesis of beta-propiolactone
In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.[6]
Reactions and applications
[edit | edit source]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.[5]
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,[7] for instance the influenza virus, as a step in vaccine production.[8] The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.[5]
Safety
[edit | edit source]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 U.S. Occupational Safety and Health Administration, despite not having an established permissible exposure limit.[9]
See also
[edit | edit source]- 3-Oxetanone, an isomer of β-propiolactone
- Malonic anhydride (2,4-oxetanone)
- α-Propiolactone
References
[edit | edit source]- ^ a b c d e f g Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c "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.
- ^ Merck Index, 12th Edition, entry 8005.
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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- ^ "Appendix B - Thirteen OSHA-Regulated Carcinogens" - Centers for Disease Control and Prevention. Accessed on 2013-11-06.