1596. Butyrolactone

Nomenclature

CAS number: 96-48-0
Dihydro-2(3H)-furanone; γ-butyrolactone; 1,2-butanolide; 1,4-butanolide; γ-hydroxybutyric acid lactone; 3-hydroxybutyric acid lactone; 4-hydroxybutanoic acid lactone.
C4H6O2; mol wt 86.09.
C 55.81%, H 7.02%, O 37.17%.

Description and references

Prepd from acetylene and formaldehyde: Reppe, Chem. Ing. Tech. 1950, 365; Chem. Eng. 58, no. 6, 176 (1951); also prepd from ethylene chlorohydrin, glutaric acid, ν-hydroxybutyric acid solns, tetrahydrofuran, or vinylacetic acid: F. C. Whitmore, Organic Chemistry (Van Nostrand, New York, 2nd ed., 1951). Alternate synthesis: Y. Ogata et al., J. Org. Chem. 45, 1320 (1980). Physical properties: McKinley, Copes J. Am. Chem. Soc. 72, 5331 (1950). Toxicity: H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969).

Chemical structure

Properties

Oily liquid. d00 1.1441; d015 1.1286. mp -43.53°. bp760 204°. bp12 89°. nD25 1.4348. Flash pt, open cup: 209°F (98°C). Volatile with steam. Misc with water. Sol in methanol, ethanol, acetone, ether, benzene. Hydrolyzed by hot alkaline solns. LD50 orally in rats: 17.2 ml/kg (Smyth).

Use

Intermediate in the synthesis of polyvinylpyrrolidone, dl-methionine, piperidine, phenylbutyric acid, thiobutyric acids. Solvent for polyacrylonitrile, cellulose acetate, methyl methacrylate polymers, polystyrene. Constituent of paint removers, textile aids, drilling oils.