Tetrahydrofurfuryl Alcohol
Title: Tetrahydrofurfuryl Alcohol
CAS Registry Number: 97-99-4
CAS Name: Tetrahydro-2-furanmethanol
Additional Names: tetrahydro-2-furancarbinol; tetrahydro-2-furylmethanol; THFA
Molecular Formula: C5H10O2
Molecular Weight: 102.13
Percent Composition: C 58.80%, H 9.87%, O 31.33%
Literature References: Prepn by catalytic hydrogenation of furfuryl alcohol: Lukes, Nelson, J. Org. Chem. 21, 1096 (1956). Manuf by catalytic hydrogenation of furfural or furfuryl alcohol: Dunlop, Schegulla, US 2838523 (1958 to Quaker Oats). Occurs in two isomeric forms: D-isomer (levorotatory), L-isomer (dextrorotatory). Abs config: Gagnaire, Butt, Bull. Soc. Chim. Fr. 1961, 312; Hartman, Barker, J. Org. Chem. 29, 873 (1964). Review: A. P. Dunlop, F. N. Peters, The Furans (Reinhold, New York, 1953).
Properties: Liquid. Hygroscopic. d2020 1.0543; d2424 1.0511; d3131 1.0450. Melts below -80°. bp760 178°. nD20 1.4520; nD25 1.4499. Flash pt, open cup: 183°F (84°C). Flammability in air: Upper limit 9.7% by vol, lower limit 1.5% by vol. Heat capacity at 30-37°: 0.432 cal/g/°C. Heat of combustion at constant vol: 708.6 cal/g mole. Viscosity at 20°: 6.24 cP. Surface tension at 25°: 37 dyn/cm. Octane no. 82.5. Evaporation rate: 7 (n-butyl acetate = 100). Kauributanol value 71.5. Dilution ratio (lacquer ingredients): 4.5. Dielectric constant at 23°: 13.6. Miscible with water, alcohol, ether, acetone, chloroform, benzene.
Melting point: Melts below -80°
Boiling point: bp760 178°
Flash point: Flash pt, open cup: 183°F (84°C)
Index of refraction: nD20 1.4520; nD25 1.4499
Density: d2020 1.0543; d2424 1.0511; d3131 1.0450
 
Derivative Type: L-Isomer
Literature References: Prepn see Hartman, Barker, loc. cit.
Properties: [a]D24 +14.9° (c = 5.0 in nitromethane).
Optical Rotation: [a]D24 +14.9° (c = 5.0 in nitromethane)
 
CAUTION: Moderately irritating to skin, mucous membranes.
Use: Solvent for fats, waxes, resins. In organic synthesis: Undergoes the reactions of a primary alcohol, while the ring exhibits characteristics of a saturated cyclic ether.

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