Journal of the American Oil Chemists' Society

, Volume 77, Issue 3, pp 243–248 | Cite as

Synthesis of δ-stearolactone from oleic acid

  • Steven C. CermakEmail author
  • Terry A. Isbell


δ-Stearolactone was prepared from oleic acid using concentrated sulfuric acid under various conditions in the presence of polar, nonparticipating solvents. δ-Stearolactone was formed in as high as 15∶1 ratios over the thermodynamic product, ψ-lactone, in the presence of methylene chloride, 100% wt/vol, at room temperature with two equivalents of sulfuric acid for 24 h. This procedure is applicable to other olefinic fatty acids such as estolides and fatty acid methyl esters. Temperature plays a role in the regioselectivity of the cyclization for δ-lactone, as lower temperatures (20°C) gave higher σ/ψ ratios. At higher temperatures (50°C) in the presence of sulfuric acid and methylene chloride the yield of lactone was 75% but with a σ/ψ ratio of only 0.3∶1. Cyclization of oleic acid to lactone also occurred with other acids. Oleic acid underwent reaction with perchloric acid, one equivalent, in the absence of solvent at 50°C, which yielded σ-lactone in a modest yield with a 3.1 σ/ψ ratio. The same temperature effect was observed with perchloric acid that was observed in the case of sulfiric acid. Because σ-stearolactone is much more reactive than the corresponding fatty acid, fatty acid ester, or ψ-lactone, we believe that it will be a useful synthon for many new industrial products including new biodegradable detergents.

Key Words

Acid catalyzed lactone oleic acid perchloric acid regioselective σ-stearolactone sulfuric acid 


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Copyright information

© AOCS Press 2000

Authors and Affiliations

  1. 1.New Crops ResearchNCAUR, ARS, USDAPeoria

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