Conclusions
It has been shown that the effectiveness of certain divalent metal salts as esterification catalysts can be quantitatively compared and that for the Group II B series their effectiveness is inversely proportional to their ionic volume. The rates of esterification using these metal salts are not as great as for strong acids, but it is probable that the mechanism is similar and that the metal salts act as acids in the general sense.
The rates of esterification differ appreciably for different primary polyols. It is also probable that these differences are related to the comparative acidity or basicity of the alcohols.
It would be particularly desirable to investigate the activity of the catalysts in different alcohols. It is possible that infrared studies might show formation of a complex between the catalyst and either the alcohol or the acid or both. A number of possibilities may be formulated; at present we lack critical evidence to distinguish between them and this area provides a fruitful field for further research.
Similar content being viewed by others
References
Flory, P. J., J. Am. Chem. Soc.,59, 466 (1937).
Ibid.,,62, 2255 (1940).
Othmer, D. F., and Rao, S. A., Ind. Eng. Chem.,42, 1912 (1950).
Rubin, W., J. Oil and Colour Chemists' Assoc.,35, 418 (1952).
Feuge, R. O., Kraemer, E. A., and Bailey, A. E., Oil and Soap,22, 202 (1945).
Blagonravova, A. A., and Lazarev, A. M., J., Appl. Chem. U.S.S.R.,13, 879 (1940).
Sudborough, J. J., and Gittins, J. M., J. Chem. Soc.,95, 315 (1909).
Goldsmith, H. A., Chem. Revs.22, 257 (1943).
Newman, M. S., “Steric Effects in Organic Chemistry,”, p. 209, John Wiley and Sons, New York, 1956.
Tommila, E., Ann. Acad. Sci. Fennicae, Ser.A, 59, No. 3, 3 (1942).
Langenbeck, W., and Mahrwald, R., Ann.,605, 111 (1957).
Smith, H. A., J. Am. Chem. Soc.,61, 254 (1939).
Tang, A.-C., and Yao, K.-S., J. Polymer Sci.35, 219 (1959).
Flory, P. J., J. Am. Chem. Soc.,62, 2255 (1940).
Roberts, I., and Urey, H. C., J. Am. Chem. Soc.,61, 2584 (1939).
Bender, M. L., J. Am. Chem. Soc.,73, 1626 (1951).
Syrkin, Ya. K., and Moiseev, I. I., Uspekhi Khim.,27, 717 (1958).
Kapoor, R. N., and Nehrotra, R. C., J. Chem. Soc.,1959, 422.
Berner, E., and Raberg, E., Suomen, Kemistilehti,31B, 53 (1958).
Moeller, T., “Inorganic Chemistry,” p. 865, John Wiley and Sons Inc., New York, 1952.
Myers, R. R., Lehigh University, Bethlehem, Pa., private communication.
Smith, T. L., and Elliott, J. H., J. Am. Oil Chemists' Soc.,35, 692 (1958).
Author information
Authors and Affiliations
About this article
Cite this article
Dunlap, L.H., Heckles, J.S. Catalyzed esterification of oleic acid. J Am Oil Chem Soc 37, 281–285 (1960). https://doi.org/10.1007/BF02631766
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02631766