Title: Tetrahydrofuran
CAS Registry Number: 109-99-9
Additional Names: Diethylene oxide; tetramethylene oxide
Molecular Formula: C4H8O
Molecular Weight: 72.11
Percent Composition: C 66.62%, H 11.18%, O 22.19%
Literature References: Prepn from 1,4-butanediol: Schmoyer, Case, Nature 187, 592 (1960). Manuf by catalytic hydrogenation of maleic anhydride: Gilbert, Howk, US 2772293 (1956 to du Pont); of furan: Banford, Manes, US 2846449 (1958 to du Pont); Manly, US 3021342 (1962 to Quaker Oats). Stabilization to prevent excessive peroxide formation on storage with 0.05-1.0% p-cresol, 0.05-0.1% hydroquinone, or less than 0.01-0.1% 4,4¢-thiobis(6-tert-butyl-m-cresol): Bordner, Hinegardner, US 2489260; US 2525410; Campbell, US 3029257 (1949, 1950, 1962 all to du Pont). Review of toxicology and biological effects: D. E. Moody, Drug Chem. Toxicol. 14, 319-342 (1991).
Properties: Liquid. Ether-like odor. mp -108.5°. d420 0.8892. bp760 66°; bp176 25°. Flash pt 1°F. nD20 1.4070. Dipole moment: 1.70. uv cut-off for spectro grade: 220 nm. Miscible with water, alcohols, ketones, esters, ethers, and hydrocarbons. Caution: Distil only in presence of a reducing agent, such as ferrous sulfate; peroxide explosions have occurred: Angew. Chem. 68, 182 (1956).
Melting point: mp -108.5°
Boiling point: bp760 66°; bp176 25°
Flash point: Flash pt 1°F
Index of refraction: nD20 1.4070
Density: d420 0.8892
CAUTION: Potential symptoms of overexposure are irritation of eyes and upper respiratory system; nausea, dizziness and headache; CNS depression. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 302.
Use: Solvent for high polymers, esp polyvinyl chloride. As reaction medium for Grignard and metal hydride reactions. In the synthesis of butyrolactone, succinic acid, 1,4-butanediol diacetate. Solvent in histological techniques. May be used under Federal Food, Drug & Cosmetic Act for fabrication of articles for packaging, transporting, or storing of foods if residual amount does not exceed 1.5% of the film: Fed. Regist. 27, 3919 (Apr. 25, 1962). |