Beta-Propiolactone
- Propiolactone
- 1.3 -propiolactone
- 2- Oxetanone
- Propanolid
- Oxetane -2-one (IUPAC)
Colorless liquid with a faint sweet odor
Liquid
1.15 g · cm -3 ( 20 ° C)
-33 ° C
155 ° C ( decomposition)
3 hPa (20 ° C)
Soluble in water
1.4105 (20 ° C)
Risk
Not assigned because carcinogenic
-329.9 KJ / mol
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Propiolactone ( IUPAC oxetane - 2-one) is an organic chemical compound and belongs to the group of substances β - lactones, intramolecular, cyclic esters.
Representation
Propiolactone can be prepared from ketene and formaldehyde in the presence of zinc chloride as catalyst:
Recently, the synthesis of propiolactone by reacting ethylene oxide with carbon monoxide in the presence of a complex-stabilized Carbonylcobaltats in a high-boiling dipolar aprotic solvent, has been described in the conversion and selectivity of up to 99 %.
Properties
Physical Properties
Propiolactone is readily soluble in water and also dissolves in ethanol. At room temperature propiolactone is a flammable, colorless liquid with a slightly sweet odor before. The substance irritates the eyes and skin and is considered carcinogenic. Propiolactone has a disinfecting effect.
Chemical Properties
The highly reactive compound is dissolved in water for a few hours stable; only at high dilution or standing for several hours the lactone hydrolyzed to β -hydroxy- propionic acid:
The compound can react with analogous amines, thiols and other nucleophiles, with ring opening, in which case the created corresponding β -amino- β - or thio compound of the propionic acid.
Propiolactone reacted at 140-180 ° C and 25-250 bar, with orthophosphoric acid and copper powder as a catalyst, acrylic acid and quantitatively in the presence of an alcohol into the corresponding acrylic esters.
Use
Propiolactone is used among other things for virus inactivation and sterilization of vaccines. In this case, 0.2 to 0.4 % by weight aqueous solutions over a wide pH range virucidal effect. As the substance in the aqueous medium decays within a few hours, no residue of toxic lactone remains.