β-Propiolactone, often simply called propiolactone, is an organic compound with the formula CH2CH2CO2. It is a 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]
 | |
 | |
| 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 |
|
| KEGG | |
PubChem CID |
|
| RTECS number |
|
| UNII | |
| UN number | 2810 |
CompTox Dashboard (EPA) |
|
| |
| |
| 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) |
1.4131 |
| Hazards | |
| GHS labelling: | |
   | |
| 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).
| |
Production
β-Propiolactone is prepared industrially by the reaction of formaldehyde and ethenone in the presence of aluminium- or zinc chloride as catalyst:[5]
In the research laboratory, propiolactones have been produced by the carbonylation of epoxides.[6]
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.[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 example as a step in vaccine production.[8] The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.[5]
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 U.S. Occupational Safety and Health Administration, despite not having an established permissible exposure limit.[9]
See also
- 3-Oxetanone, an isomer of β-propiolactone
- Malonic anhydride (2,4-oxetanone)
- α-Propiolactone
References
Wikiwand in your browser!
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.
