Β-Butyrolactone
chemical compound
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.
For this purpose, ethenone can also be produced in-situ by dehydrobromination of acetyl bromide with the Hünig base diisopropylethylamine. In the presence of a chiral aluminium complex, the ethenone reacts enantioselectively to (S)-β-butyrolactone in 92% yield with an enantiomeric excess ee of over 98%.
Hydrogenation of diketene at a palladium contact catalyst provides β-butyrolactone in 93% yield.
The asymmetric hydrogenation of diketene with a ruthenium BINAP catalyst to optically active (R)-β-butyrolactone with 97% selectivity and 92% enantiomeric excess is also described.
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