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β-butyrolactone
Sign in to saveβ-Butyrolactone is the intramolecular carboxylic acid ester (lactone) of the optically active 3-hydroxybutanoic acid. It is produced during chemical synthesis as a racemate. β-Butyrolactone is suitable as a monomer for the production of the biodegradable polyhydroxyalkanoate poly(3-hydroxybutyrate) (PHB). Polymerisation of racemic (RS)-β-butyrolactone provides (RS)-polyhydroxybutyric acid, which, however, is inferior in essential properties (e.g. strength or degradation behaviour) to the (R)-poly-3-hydroxybutyrate originating from natural sources.
Chemical data
- Formula
- C4H6O2
- Molecular weight
- 86.09 g/mol
- IUPAC name
- 4-methyloxetan-2-one
- SMILES
- CC1CC(=O)O1
- InChIKey
- GSCLMSFRWBPUSK-UHFFFAOYSA-N
- XLogP
- 0.3
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- hydrogen
- Mass
- 86.037
Show 4 more facts
- Commons category
- Beta-Butyrolactone
- chemical formula
- C₄H₆O₂
- canonical SMILES
- CC1CC(=O)O1
- subject has role
- carcinogen
via Wikidata · CC0
~7 min read
Encyclopedic overview
5 sectionsContents
- Production
- Properties
- Use
- Homo- and copolymers from β-butyrolactone
- References
β-Butyrolactone is the intramolecular carboxylic acid ester (lactone) of the optically active 3-hydroxybutanoic acid. It is produced during chemical synthesis as a racemate. β-Butyrolactone is suitable as a monomer for the production of the biodegradable polyhydroxyalkanoate poly(3-hydroxybutyrate) (PHB). Polymerisation of racemic (RS)-β-butyrolactone provides (RS)-polyhydroxybutyric acid, which, however, is inferior in essential properties (e.g. strength or degradation behaviour) to the (R)-poly-3-hydroxybutyrate originating from natural sources.
== Production == β-Butyrolactone is obtained in 63% yield by the addition of ethanal to ethenone (ketene) in the presence of the clay mineral montmorillonite.
Excerpted from Wikipedia’s “β-butyrolactone” article, available under the CC BY-SA 4.0 licence.