Abstract
Infrared study of the products of the addition of m-cresol to oleic acid in methanesulfonic acid, revealed the presence of both the m-creasoxy and hydroxytolyl substituted stearic acids. By employing a modified extractive procedure to recover the products of the reaction, followed by chromatography on a Florisil column, a separation of the two types of addition products was effected.
The methanesulfonic acid catalyzed addition reaction was extended to include aryl thiols. Among the sulfur analogues of the previously used phenols that were added are: benzenethiol, p-t-butyl-benzenthiol, 2-naphthalenethiol, o-, m-, and p-toluenethiol. The yields of addition products (which were unobtainable in sulfuric acid media) ranged from 37–70%. In contrast with the results obtained when phenolic nuleophiles were employed no evidence for the formation of rearranged addition products has been found. Thioethers were the only products identified.
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References
Ault, W. C., and A. Eisner, JAOCS,39, 132 (1962).
Roe, E. T., W. E. Parker, and D. Swern,Ibid., 36, 656–9 (1959).
Niederl, J. B., and S. Natelson, J. Am. Chem. Soc.,53, 272–7 (1931).
Niederl, J. B., R. A. Smith, and M. F. McGreal,Ibid., 53, 3390–6 (1931).
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Niederl, J. B., U. S. Pat. 2,082,459, June 1, 1937.
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Eastern Utilization Research and Development Division, U.S.D.A.
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Eisner, A., Perlstein, T. & Ault, W.C. Further studies on methanesulfonic acid catalyzed additions to oleic acid. J Am Oil Chem Soc 39, 290–292 (1962). https://doi.org/10.1007/BF02638119
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DOI: https://doi.org/10.1007/BF02638119