β-Propiolactone , >95.0%(GC) , 57-57-8

Synonym(s):
3-Hydroxypropionic acid lactone;Hydracrylic acid β-lactone;Oxetan-2-one

CAS NO.：57-57-8

Empirical Formula: C3H4O2

Molecular Weight: 72.06

MDL number: MFCD00005169

EINECS: 200-340-1

PRODUCT Properties

• Melting point: -33 °C (lit.)
• Boiling point: 162 °C (lit.)
• Density: 1.146 g/mL at 25 °C (lit.)
• vapor pressure: 3 at 25 °C (NIOSH, 1997)
• refractive index: n20/D 1.412(lit.)
• Flash point: 158 °F
• storage temp.: -20°C
• solubility: Miscible with acetone, alcohol, chloroform, and ether (Windholz et al., 1983)
• form: Liquid
• color: Colorless liquid with a sweet but irritating odor
• Odor: pungent odor
• Water Solubility: 37 g/100 mL
• Sensitive: Moisture Sensitive
• Merck: 14,7820
• Henry's Law Constant: 7.6 at 25 °C (approximate - calculated from water solubility and vapor pressure)
• Stability: Moisture Sensitive, Very Hygroscopic
• InChIKey: VEZXCJBBBCKRPI-UHFFFAOYSA-N

Description and Uses

Beta-propiolactone is a colorless liquid with a strong, slightly sweet odor. It may occur naturally, but no clear documentation of its occurrence in nature was found, and it must be synthesized for commercial purposes. Beta-propiolactone is unstable at room temperature but stable when stored at 5 ℃ in glass containers.
Its tendency to be unstable and react with other molecules in the vicinity is responsible for both its toxicity and its usefulness. Significant commercial production of beta-propiolactone took place during the late 1950s through the mid-1970s, when it was widely used in chemical synthesis in reactions with other molecules to produce new chemicals. All lactones are characterized by a ring structure consisting of two or more carbon atoms – as can be seen from its structure, beta-propiolactone has three in its ring – and a single oxygen, coupled with an adjacent ketone. The fewer the carbons in the ring, the more ‘strained’ is the ring structure and the more unstable and reactive its characteristics. When the ring bonds break, the betapropiolactone molecules attach to other nearby molecules.

As late as 1974, b-propiolactone was used in the United States in the preparation of acrylic acid and acrylate esters. Today, its principal significance is as a reactive intermediate in organic syntheses; a small amount is treated with ammonia to provide balanine. b-Propiolactone was also used as a disinfectant. It appeared to be an attractive replacement for formaldehyde due to its 25-fold greater disinfecting power, but it has since been abandoned because of its carcinogenic properties.

Safety

• Symbol(GHS): GHS06,GHS08
• Signal word: Danger
• Hazard statements: H315-H319-H330-H350
• Precautionary statements: P202-P260-P264-P302+P352-P304+P340+P310-P305+P351+P338
• Hazard Codes: T+
• Risk Statements: 45-26-36/38
• Safety Statements: 53-45-99
• RIDADR: UN 3382 6.1/PG 1
• WGK Germany: 3
• RTECS: RQ7350000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: I
• HS Code: 29322090
• Toxicity: LC50 (inhalation) for rats 25 ppm/6-h (quoted, RTECS, 1985).