Propiolactone

Structural formula
General
Surname	Propiolactone
other names	Oxetan-2-one ( IUPAC ) Propiolactone 1,3-propiolactone 2-oxetanone Propanolide
Molecular formula	C 3 H 4 O 2
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 57-57-8 EC number 200-340-1 ECHA InfoCard 100,000,309 PubChem 2365 ChemSpider 2275 DrugBank DB09348 Wikidata Q420715
properties
Molar mass	72.06 g mol −1
Physical state	liquid
density	1.15 g cm −3 (20 ° C)
Melting point	−33 ° C
boiling point	155 ° C (decomposition)
Vapor pressure	3 h Pa (20 ° C) 5 hPa (30 ° C) 12 hPa (50 ° C)
solubility	soluble in water, ethanol, acetone and chloroform
Refractive index	1.4105 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 330-315-319-350 P: 280-302 + 352-304 + 340 + 310-305 + 351 + 338-362
MAK	not assigned as it is carcinogenic Switzerland: 0.5 ml m −3 or 1.5 mg m −3
Thermodynamic properties
ΔH f 0	−329.9 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Propiolactone (according to IUPAC oxetan-2-one ) is an organic chemical compound and belongs to the group of β- lactones , intramolecular , cyclic esters .

Extraction and presentation

Propiolactone is produced industrially by reacting formaldehyde with ketene in the presence of aluminum chloride , zinc chloride or boron trifluoride as a catalyst .

The selectivity to propiolactone is 90%. The reaction can be carried out in a solvent or in the gas phase .

In 2010, the synthesis of propiolactone by reacting ethylene oxide with carbon monoxide in the presence of a complex-stabilized carbonyl cobaltate in a higher-boiling dipolar aprotic solvent with conversion and selectivity of up to 99% was described.

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. The substance irritates eyes and skin and is considered to be carcinogenic. Propiolactone has a disinfecting effect.

Chemical properties

The highly reactive compound is stable for a few hours when dissolved in water; Only when strongly diluted or left to stand for several hours does the lactone hydrolyze to β-hydroxypropionic acid :

${\displaystyle \mathrm {C_{3}H_{4}O_{2}\ +H_{2}O\ \longrightarrow \ HO-CH_{2}-CH_{2}-COOH} }$

Propiolactone hydrolyzes to β-hydroxypropionic acid

The compound can react analogously with amines , thiols and other nucleophiles with ring opening, in which case the corresponding amides, thiol carboxylic acids or other carboxylic acid derivatives of 3-hydroxypropionic acid are formed.

Propiolactone reacts quantitatively at 140–180 ° C and 25–250 bar with orthophosphoric acid and copper powder as a catalyst to form acrylic acid and, in the presence of an alcohol, the corresponding acrylic acid esters .

use

Propiolactone is among other things to virus inactivation and sterilization of vaccines used. 0.2 to 0.4% aqueous solutions are virucidal over a wide pH range . Since the substance disintegrates in an aqueous medium within a few hours, no residue of the toxic lactone remains.

literature

• W. Stephan: Inactivation of hepatitis viruses and HIV in plasma and plasma derivatives by treatment with beta-propiolactone / UV irradiation. In: Current studies in hematology and blood transfusion. Number 56, 1989, pp. 122-127, PMID 2642784 (review).

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on propiolactone in the GESTIS substance database of the IFA , accessed on July 2, 2016(JavaScript required) .
2. ↑ Hans-Dieter Jakubke, Ruth Karcher (coordinators): Lexicon of Chemistry in three volumes, Spektrum Verlag, Heidelberg, Volume 3, 1999, ISBN 3-8274-0381-2 , p. 105.
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-408.
4. ↑ Entry on Propiolactone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Schweizerische Unfallversicherungsanstalt (Suva): Limits - Current MAK and BAT values (search for 57-57-8 or propiolactone ), accessed on November 2, 2015.
6. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.
7. ↑ ^{a b c} Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , p. 322 .
8. ↑ Patent application WO 2010/118128: Process for beta-lactone production. Scott D. Allen et al., Novomer Inc., published 14 October 2010.
9. ↑ ^{a b} F. v. Rheinbaben, MH Wolff: Manual of virus-effective disinfection. Springer, 2002, ISBN 978-3-540-67532-7 .
10. ↑ HP Latscha, U. Kazmaier, HA Klein: Organische Chemie: Chemie-Basiswissen II , 6th Edition, Springer, 2008, ISBN 978-3-540-77106-7 , p. 281.