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Studies on castor oil. I. Fatty acid composition of castor oil

  • B. Sreenivasan
  • N. R. Kamath
  • J. G. Kane
Article

Summary

Methyl esters of castor oil were prepared by saponifying the oil with potassium hydroxide in methanol, splitting the potassium soapsin situ with an excess of hydrochloric acid, and esterifying at room temperature. The esters had hydroxyl values comparable with those of the parent oils. The methyl esters were quantitatively resolved into hydroxy and nonhydroxy esters after reacting with succinic anhydride in toluene. The composition of castor oil was calculated from a) amount of nonhydroxy esters, b) methyl linoleate content of methyl esters determined spectro-photometrically, c) iodine value of the methyl esters determined by the Wijs method at 15–20°C., and d) iodine value of the nonhydroxy esters determined by the Woburn method. This composition was confirmed by the estimation of saturated acids in one sample and dihydroxystearic acid in all. Castor oil was readly hydrogenated with Raney nickel in alcohol at room temperature (30–33°C.) without any hydrogenolysis of the hydroxyl groups. Methyl dihydroxystearate content of the methyl esters of this hydrogenated oil was determined by reaction with 80–100% excess periodic acid at 15–20°C.

Keywords

Methyl Ester Methyl Oleate Methyl Linoleate Saturated Acid Hydroxy Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Am. Oil Chemists’ Society, Official and Tentative Methods (1946).Google Scholar
  2. 2.
    Berry, H., and Cook, A. M., J. Pharm. and Pharmacol.,2, 217 (1950).Google Scholar
  3. 3.
    Bradford, P., Pohle, W. D., Gunther, J. K., and Mehlenbacher, V. C., Oil and Soap,19, 189 (1942).CrossRefGoogle Scholar
  4. 4.
    Brown, J. B., and Green, N. D., J. Am. Chem. Soc.,62, 738 (1940).CrossRefGoogle Scholar
  5. 5.
    Burton, D., and Robertshaw, C. F., “Sulphated Oils and Allied Products,” p. 129, A. Harvey Publishers, London (1939).Google Scholar
  6. 6.
    Dupont, G., and Yvernault, F., Bull. Soc. Chim.,12, 84 (1945).Google Scholar
  7. 7.
    Eibner, A., and Munizing, E., Chem. Umschau Gebiete Fette, Öle, Wachse, u. Harze,32, 166 (1925).CrossRefGoogle Scholar
  8. 8.
    Fahrion, F., ibid.,23, 63, 71 (1916).Google Scholar
  9. 9.
    Goldsobel, A. G., Ber.27, 3121 (1894).Google Scholar
  10. 10.
    Gupta, S. S., Hilditch, T. P., and Riley, J. P., J. Sci. Food Agr.,2, 245 (1951).CrossRefGoogle Scholar
  11. 11.
    Haller, A., Compt. rend.,144, 462 (1907).Google Scholar
  12. 12.
    Haller, A., and Brochet, A.,ibid., 150, 496 (1910).Google Scholar
  13. 13.
    Heiduschka, A., and Kirsten, G., Pharm. Zentralhalle,71, 81 (1930).Google Scholar
  14. 14.
    Hilditch, T. P., Morton, R. A., and Riley, J. P., Analyst70, 68 (1945).CrossRefGoogle Scholar
  15. 15.
    Jakes, M., and Hökel, J., Chem. Listy,32, 15 (1938).Google Scholar
  16. 16.
    Jones, R. O., J. Soc. Chem. Ind.,36, 369T (1917).Google Scholar
  17. 17.
    Julliard, P., Bull. Soc. Chim.,13 (3), 238 (1895).Google Scholar
  18. 18.
    Kamath, N. R., Oils and Oil Seeds J.,5, Symp. Number, 82 (1953).Google Scholar
  19. 19.
    Kamath, N. R., Kane, J. G., Sreenivasan, B., Current Sci. (India),23, 202 (1954).Google Scholar
  20. 20.
    Kass, J. P., and Radlove, S. B., J. Am. Chem. Soc.,64, 2253 (1942).CrossRefGoogle Scholar
  21. 21.
    Kaufmann, H. P., and Bornhardt, H., Fette u. Seifen,46, 444 (1939).Google Scholar
  22. 22.
    King, G., J. Chem. Soc., 387 (1942).Google Scholar
  23. 23.
    King, G., Nature,171, 566 (1953).CrossRefGoogle Scholar
  24. 24.
    Krafft, F., Ber.,21, 2730, 2737 (1888).Google Scholar
  25. 25.
    Kurtz, F. E., and Schaffer, P. S., J. Am. Chem. Soc.,62, 1304 (1940).CrossRefGoogle Scholar
  26. 26.
    Kurz, H., Fette u. Seifen,44, 144 (1937).CrossRefGoogle Scholar
  27. 27.
    Langton, H. M., J. Soc. Chem. Ind.,50, 231T (1931).Google Scholar
  28. 28.
    LeSueur, H. R., J. Chem. Soc.,79, 1315 (1901).Google Scholar
  29. 29.
    Meyer, H., Arch. Pharm.,235, 184 (1897).CrossRefGoogle Scholar
  30. 30.
    Morrel, R. S., and Phillip, E. O., J. Soc. Chem. Ind.,57, 245T (1938).Google Scholar
  31. 31.
    Myddleton, W. W., Herchem, R. G., Barret, A. W., J. Am. Chem. Soc., 49, 2265 (1927).Google Scholar
  32. 32.
    O’Neill, L. A., Res. Assoc. Brit. Paint, Col. and Varnish Manuf., Tech. Paper, 95 (1937).Google Scholar
  33. 33.
    Panjutin, P., and Rapoport, M., Chem. Umschau Gebiete Fette, Öle, Wachse, u. Harze,37, 130 (1930).CrossRefGoogle Scholar
  34. 34.
    Pohle, W. D., and Mehlenbacher, V. C., J. Am. Oil Chemists’ Soc.,27, 54 (1950).Google Scholar
  35. 35.
    Riley, J. P., Analyst,76, 40 (1951).CrossRefGoogle Scholar
  36. 36.
    Saalmüller, L., Ann.,64, 108 (1848).Google Scholar
  37. 37.
    Saletore, S. A., and Achaya, K. T., Analyst,77, 375 (1952).CrossRefGoogle Scholar
  38. 38.
    Steger, A., Vanloon, J., and Smelt, C., J. Soc. Chem. Ind.,55, 41T (1936).Google Scholar
  39. 39.
    Toyama, Y., and Ishikawa, T., Bull. Chem. Soc. Japan,11, 735 (1936).CrossRefGoogle Scholar
  40. 40.
    Toyama, Y., and Ishikawa, T., J. Soc. Chem. Ind. (Japan), Suppl. Binding,39, 300 (1936).Google Scholar
  41. 41.
    Vogel, A. I., “Practical Organic Chemistry,” p. 370, Longmans, Green and Company, London (1948).Google Scholar
  42. 42.
    Von Mikusch, J. D., and Frazier, C., Ind. Eng. Chem., Anal. Ed.,13, 788 (1941).CrossRefGoogle Scholar
  43. 43.
    Walden, P., Ber.,27, 3471 (1894).Google Scholar
  44. 44.
    Wright, H. J., Segur, J. B., Clark, H. V., Coburn, S. K., Langdon, E. E., and Dupis, R. N., Oil and Soap,21, 145 (1944).CrossRefGoogle Scholar
  45. 45.
    Young, C. G., and Craig, B. M., J. Am. Oil Chemists’ Soc.,28, 521 (1951).Google Scholar
  46. 46.
    Zerevitinov, Th., Ber.,40, 2023 (1907).Google Scholar
  47. 47.
    Zlatrov, A., and Beliavishi, V., Annuaire univ. Sofia, Fac. phys.-math.,28 (2), 21 (1932).Google Scholar

Copyright information

© The American Oil Chemists’ Society 1956

Authors and Affiliations

  • B. Sreenivasan
    • 1
  • N. R. Kamath
    • 1
  • J. G. Kane
    • 1
  1. 1.Department of Chemical TechnologyUniversity of BombayBombay

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