Abstract
Eight derivatives of 2-oxazolidone,
, have been synthesized by the Homeyer method and purified by fractional freezing or fractional distillation to obtain low-conducting liquids. Dielectric constants, viscosities, densities, and refractive indices of these 2-oxazolidones have been determined at several temperatures within the range 25 to 75°C. Values for activation energies of viscous flow also have been calculated. The isomeric 3-methyl and 5-methyl derivatives of 2-oxazolidone have high dielectric constants which differ only slightly from that of water. The 3-substituted (or N-substituted) 2-oxazolidones exhibit the most favorable combination of physical properties, stability, and ease of purification and appear to have excellent potential as new nonaqueous solvents.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. P. Seward and E. C. Vieira,j. Phys. Chem. 62, 127 (1958).
C. G. Malmberg and A. A. Maryott,J. Res. Nat. Bur. Std. 56, 1 (1956).
K. Fredenhagen and J. Dahmlos,Z. Anorg. Allgem. Chem. 178, 272 (1929).
G. E. Coates and J. E. Coates, . Chem. Soc.1944, 77.
R. J. Gillespie and R. H. Cole,Trans. Faraday Soc. 52, 1325 (1956).
G. R. Leader,J. Am. Chem. Soc. 73, 856 (1951).
G. R. Leader and J. F. Gormley,J. Am. Chem. Soc. 73, 5731 (1951).
W. S. Harris, Report UCRL-8381, USAEC, Berkeley Radiation Laboratory, Berkeley, California (1958), p. 39.
R. Kempa and W. H. Lee,J. Chem. Soc. 1958, 1936.
A.H. Saadi and W. H. Lee,J. Chem. Soc. B1966, 5.
P. G. Sears and W. C. O'Brien,J. Chem Eng. Data 13, 112 (1968).
G. R. Slayton, J. W. Simmons, and J. H. Goldstein,J. Chem. Phys. 22, 1678 (1954).
R. F. Kempa and W. H. Lee,J. Chem. Soc. 1961, 100.
L. M. Mukherjee and D. P. Boden,J. Phys. Chem. 73, 3965 (1969).
L. M. Mukherjee, D. P. Boden, and R. Lindauer,J. Phys. Chem. 74, 1942 (1970).
M. E. Dyen and D. Swern,Chem. Rev. 67, 197 (1967).
E. Fischer,J. Chem. Soc. 1952, 4525.
C. M. Lee and W. D. Kumler,J. Am. Chem. Soc. 83, 4596 (1961).
A. H. Homeyer, U. S. Patent 2,399, 118 (1946);Chem. Abstr. 40, 4084 (1946).
L. H. Horsley,Azeotropic Data, (American Chemical Society, Washington, D.C., 1952), p. 9.
L. R. Dawson, et al.,J. Phys. Chem. 67, 278 (1963).
Chem. Eng. News, July 20, 1964, p. 36.
J. I. Jones,Chem. Ind. (London) 1956, 1454.
G. Akerlöf,J. Am. Chem. Soc. 54, 4125 (1932).
J. W. Vaughn and P. G. Sears,J. Phys. Chem. 62, 183 (1958).
M. R. Cannon and M. R. Fenske,Ind. Eng. Chem. Anal. Ed. 10, 297 (1938).
J. F. Swindells, J. R. Coe, Jr., and T. B. Godfrey,J. Res. Nat. Bur. Std. 48, 1 (1952).
D. J. Denney and R. H. Cole,J. Chem. Phys. 23, 1767 (1955).
T. Hanai, N. Koizumi, and R. Gotoh,Bull. Inst. Chem. Res. Kyoto Univ. 39, 195 (1961).
T. M. Stoeckinger, Ph.D. dissertation, University of Kentucky, 1968, pp. 50, 51.
L. A. Girifalco,J. Chem. Phys. 23, 2446 (1955).
D. W. Moore, L. A. Burkardt, and W. S. McEwan,J. Chem. Phys. 25, 1235 (1956).
R. L. Blumenshine and P. G. Sears,J. Chem. Eng. Data 11, 141 (1966).
M. D. Dyke, P. G. Sears, and A. I. Popov,J. Phys. Chem. 71, 4140 (1967).
Author information
Authors and Affiliations
Additional information
Based on a portion of the Ph. D. dissertation of H. L. Huffman, Jr., University of Kentucky, 1972. Presented in major part at the 21 st Southeastern Regional Meeting of the American Chemical Society, Richmond, Virginia, 1969.
Rights and permissions
About this article
Cite this article
Huffman, H.L., Sears, P.G. Liquid 2-oxazolidones. I. Dielectric constants, viscosities, and other physical properties of several liquid 2-oxazolidones. J Solution Chem 1, 187–196 (1972). https://doi.org/10.1007/BF01028454
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01028454