Butyrolactone

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.
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gamma-Butyrolactone[1][2]
Identifiers
CAS number 96-48-0 YesY
PubChem 7302
ChemSpider 7029 YesY
UNII OL659KIY4X YesY
DrugBank DB04699
KEGG C01770 YesY
ChEBI CHEBI:42639 YesY
ChEMBL CHEMBL95681 YesY
RTECS number LU3500000
Jmol-3D images Image 1
Properties
Molecular formula C4H6O2
Molar mass 86.09 g mol−1
Appearance Colorless oily liquid
Density 1.1286 g/mL (15 °C), 1.1296 g/mL (20 °C)
Melting point −43.53 °C; −46.35 °F; 229.62 K
Boiling point 204 °C; 399 °F; 477 K
Solubility in water Miscible
Solubility soluble in CCl4, methanol, ethanol, acetone, benzene, ethyl ether
Acidity (pKa) 4.5
Refractive index (nD) 1.435, 1.4341 (20 °C)
Viscosity 1.7 cp (25 °C)
Hazards
R-phrases R22 R36
S-phrases S26 S36
Main hazards Harmful
Flash point 98 °C (closed cup)
LD50 17.2 mL/kg (orally, rat)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

gamma-Butyrolactone (γ-butyrolactone or GBL) is a hygroscopic colorless oily liquid with a weak characteristic odor and is soluble in water. GBL is a common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a superglue remover, as a paint stripper, and as a solvent in some wet aluminium electrolytic capacitors. In humans it acts as a prodrug for GHB, and it is used as a recreational intoxicant with effects similar to alcohol.