Title: Butyrolactone
CAS Registry Number: 96-48-0
CAS Name: Dihydro-2(3H)-furanone
Additional Names: g-butyrolactone; 1,2-butanolide; 1,4-butanolide; g-hydroxybutyric acid lactone; 3-hydroxybutyric acid lactone; 4-hydroxybutanoic acid lactone
Molecular Formula: C4H6O2
Molecular Weight: 86.09
Percent Composition: C 55.81%, H 7.02%, O 37.17%
Literature 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, n-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).
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).
Melting point: mp -43.53°
Boiling point: bp760 204°; bp12 89°
Flash point: Flash pt, open cup: 209°F (98°C)
Index of refraction: nD25 1.4348
Density: d00 1.1441; d015 1.1286
Toxicity data: 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. |