Abstract
Ozonization of the methyl esters of 11-eicosenoic, linoleic, erucic and linolenic acids gave a number of different homologous methyl ω-formylalkanoates. Complete ozonization of the monounsaturated esters formed C11 and C13 compounds with 90% conversion; partial ozonization of the polyunsaturated esters gave C12 and C15 products with maximum conversions at ca. 75% consumption of fatty ester. Thus, methyl linoleate gave 52 and 23% conversions to the 9- and 12-carbon products, and methyl linolenate gave 29, 27 and 19% conversions to the 9-, 12- and 15-carbon products. Yields of aldehyde or acetal esters in distilled products were 70–90% in preparative-scale experiments. Kinetic analysis showed that ozone attack was essentially random. Methanol was used as a participating solvent.
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Beal, R. E., and O. L. Brekke, JAOCS36, 397–400 (1959).
Beal, R. E., V. E. Sohns, R. A. Eisenhauer and E. L. Griffiin, Jr., Ibid. 524–527 (1961).
Frost, A. A., and R. G. Pearson, “Kinetics and Mechanism,” 2nd ed., John Wiley & Sons, Inc., New York, 1961.
Hagemann, J. W., K. L. Mikolajczak and I. A. Wolff, JAOCS39, 196–197 (1962).
Mikolajczak, K. L., T. K. Miwa, F. R. Earle, I. A. Wolff and Quentin Jones, Ibid. 678–681 (1961).
Mikolajczak, K. L., C. R. Smith, Jr. and I. A. Wolff, Ibid. 294–295 (1963).
Noller, C. R., and R. Adams, J. Am. Chem. Soc.48, 1074–1080 (1926).
Otsuki, H., and H. Funahashi, U.S. 2,862,940 (1958).
Pryde, E. H., D. E. Anders, H. M. Teeter and J. C. Cowan, J. Org. Chem.25, 618–621 (1960).
Pryde, E. H., D. E. Anders, H. M. Teeter and J. C. Cowan, Ibid. 3055–3059 (1962).
Pryde, E. H., R. A. Awl, H. M. Teeter and J. C. Cowan, Ibid. 2260 (1960).
Pryde, E. H., R. A. Awl, H. M. Teeter and J. C. Cowan, J. Polymer Sci.59, 1–11 (1962).
Pryde, E. H., and J. C. Cowan, JAOCS39, 496–500 (1962).
Pryde, E. H., D. J. Moore, H. M. Teeter and J. C. Cowan, Abstracts of Papers, Paper No. 202, Div. of Organic Chemistry, 140th Meeting, ACS, Chicago, Ill., September 1961.
Pryde, E. H., D. J. Moore, H. M. Teeter and J. C. Cowan, J. Polymer Sci.58, 611–620 (1962).
Schmidt, U., and P. Grafen, Ann.656, 7–108 (1962).
Siggia, S., “Quantitative Organic Analysisvia Functional Groups,” 3rd ed., John Wiley & Sons, Inc., New York, 1963, p. 74.
Smith, D. M., and J. Mitchell, Jr., Anal. Chem.22, 750–755 (1950).
Tomecko, C. G., and R. Adams, J. Am. Chem. Soc.49, 522–530 (1927).
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A laboratory of the No. Util. Res. & Dev. Div., ARS, USDA.
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Anders, D.E., Pryde, E.H. & Cowan, J.C. Omega-formylalkanoates by ozonization of unsaturated fatty esters. J Am Oil Chem Soc 42, 236–243 (1965). https://doi.org/10.1007/BF02541138
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DOI: https://doi.org/10.1007/BF02541138