Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-12-14
2000-02-08
Carr, Deborah D
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
554161, 568876, C07D30900
Patent
active
060229829
ABSTRACT:
An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.9 to .DELTA..sup.15 unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20 to 70.degree. C. Moreover, yields of the .delta.-lactones may be increased even further by reaction in the presence of dipolar, non-participating, non-aqueous solvents. The unsaturated fatty acids may be free or esterified with glycerol or other aliphatic alcohols, and the .delta.-lactones may be produced by reacting mono-, di- or triglycerides of the unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the instant process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steam splitting. Optionally, the .delta.-lactones so formed may be further reacted to produce 5-hydroxy fatty acids. These 5-hydroxy fatty acids may be produced by reaction of the .delta.-lactones with an alkali in an aqueous solution.
REFERENCES:
Isbell, Terry A. and Plattner, Beth A., "A Highly Regioselective Synthesis of .delta.-Lactones from Meadowfoam Fatty Acids", JAOCS, vol. 74, No. 2, 1997, pp. 153-158.
Nakano, Y. and Foglia, T.A., "Methanesulfonic Acid Catalyzed Addition of Aromatic Compounds to Oleic Acid", JAOCS, vol. 61, No. 3, Mar. 1984, pp. 569-573.
Isbell, Terry A. and Kleiman, Robert, "A Highly Regioselective Synthesis of Eicosanolactone and Docosanolactone from Meadowfoam Seed Oil; Utilization of the Unique Chemical Structure of a New Crop's Fatty Acids", Abstract, 21st World Congress and Exhibition of the International Society for Fat Research (ISF), Oct. 1-5, 1996, The Hague, The Netherlands.
Showell, John S., et al., "Perchloric Acid Isomerization of Oleic Acid", J. Amer. Oil Chemists Soc., 36, 1959, p. 343.
Cermak Steven C.
Isbell Terry A.
Carr Deborah D
Deck Randall E.
Fado John D.
Silverstein M. Howard
The United States of America as represented by the Secretary of
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