The rate of ring opening of γ- and δ-lactones derived from meadowfoam fatty acids

JAOCS, Journal of the American Oil Chemists' Society

Volumn 75, Issue 1, 1998, Pages 63-66

  Isbell, Terry A ^a   Steiner, Beth A ^b  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b ABBOTT LABORATORIES   (United States)

Author keywords

5 hydroxy eicosanamide; 5 hydroxy eicosanoate; Meadowfoam fatty acids; Rate; Ring opening; eicosanolactone; Eicosanolactone

Indexed keywords

EICOSANOLACTONE; HYDROXY EICOSANAMIDE; HYDROXY EICOSANOATE; MEADOWFAN FATTY ACIDS; RING OPENING;

ALCOHOLS; AMINATION; AMINES; ESTERIFICATION; FATTY ACIDS; REACTION KINETICS;

ESTERS;

LIMNANTHES;

EID: 0031695001     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-998-0011-1     Document Type: Article

References (16)

1. Phillips, B.E., C.R. Smith, and W.H. Tallent, Glycerides of Limnanthes douglasii Seed Oil, Lipids 6:93-99 (1971).
2. Glaser, L., I. Ahmed, and H. Parker, Meadowfoam Oil and Polyols Expand Vegetable Oil Markets, Ind. Uses Agr. Mat. 4:11-13 (1994).
3. Erhan, S.M., and R. Kleiman, Vulcanized Meadowfoam Oil, J. Am. Oil Chem. Sac. 67:670-674 (1990).
4. Erhan, S.M., and R. Kleiman, Factice from Oil Mixtures, Ibid. 70:309-311 (1993).
5. Erhan, S.M., and R. Kleiman, Meadowfoam Oil Factice and Its Performance in Natural Rubber Mixes, Rubber World 203:33-36 (1990).
6. Burg, D.A., and R. Kleiman, Meadowfoam Fatty Amides: Preparation, Purification, and Use in Enrichment of 5,13-Docosadienoic Acid and 5-Eicosenoic Acid, J. Am. Oil Chem. Soc. 65:190-192 (1991).
7. Burg, D.A., and R. Kleiman, Preparation of Meadowfoam Dimer Acids and Dimer Esters, and Their Use as Lubricants, Ibid. 68:600-603 (1991).
8. Erhan, S.M., R. Kleiman, and T.A. Isbell, Estolides from Meadowfoam Oil Fatty Acids and Other Monounsaturated Fatty Acids, Ibid. 70:461-465 (1993).
9. Isbell, T.A., and R. Kleiman, Mineral Acid Catalyzed Condensation of Meadowfoam Fatty Acids into Estolides, Ibid. 73:1097-1107 (1996).
10. Isbell, T.A., and B.A. Plattner, A Highly Regioselective Synthesis of δ-Lactones from Meadowfoam Fatty Acids, Ibid. 73:153-158 (1997).
11. Isbell, T.A., B.A. Plattner, and R. Kleiman, Method for the Development of δ-Lactones and Hydroxy Acids from Unsaturated Fatty Acids and Their Glycerides, U.S. Pat. Appl. 08/534-810 (Sept. 27, 1995).
12. Brown, H.C., J.H. Brewster, and H. Shechter, An Interpretation of the Chemical Behavior of Five-and Six-membered Ring Compounds, J. Am. Chem. Soc. 76:467-474 (1954).
13. Lagerman, R., S. Clancy, D. Tanner, N. Johnston, B. Callian, and F. Friedli, Synthesis and Performance of Ester Quaternary Biodegradable Softeners, J. Am. Oil Chem. Soc. 71:97-100 (1994).
14. Showell, J.S., D. Swern, and W. Noble, Perchloric Acid Isomerization of Oleic Acid, J. Org. Chem. 88:2691-2104 (1968).
15. Weil, J.K., F.D. Smith, and W.M. Linfield, Soap-Based Detergent Formulations: II. Oxyethylated Fatty Amides as Lime Soap Dispersing Agents, J. Am. Oil Chem. Soc. 49:383-386 (1972).
16. Feairheller, S.H., R.G. Bistline, A. Bilyk, R.L. Dudley, M.F. Kozempel, and M.J. Haas, A Novel Technique for the Preparation of Secondary Amides. III. Alkanolamides, Diamides and Aralkylamides, Ibid. 71:863-866 (1994).