SpringerLink
Log in

Fatty peroxides: Synthesis, analysis, and reactions

  • Technical
  • Lectures of the 1962 Short Course on Developments in Fat Chemistry Conducted by The American Oil Chemists’ Society at Lehigh University, Bethlehem, Pennsylvania, July 8–11
  • Published:
Journal of the American Oil Chemists' Society

An Erratum to this article was published on 01 January 1963

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Canada)

Instant access to the full article PDF.

Institutional subscriptions

References

  1. For the reader who desires access to the general literature in peroxide chemistry, the following books and reviews are recommended:Books: 1a.Rieche, A., “Alkyl Peroxyde und Ozonide,” Steinkopf, Dresden, 1931. b. Rieche, A., “Die Bedeutung, der organischen Peroxyde für die chemische Wissenschaft und Technik,” Enke, Stuttgart, 1931. c. Tobolsky, A. V., and R. B. Mesrobian, “Organic Peroxides,” Interscience Publishers, New York, 1954. d. Karnojitzki, V., Les Peroxydes Organiques, Hermann, Paris, 1958. e. Wallace, J. G., “Hydrogen Peroxide in Organic Chemistry,” E. I. du Pont de Nemours and Co., Inc. f. Hawkins, E. G., “Organic Peroxides,” D. Van Nostrand and Co., Princeton, New Jersey, 1961. g. Davies, A. G., “Organic Peroxides,” Butterworth, London, 1961. h. Schumb, W. C., C. N. Satterfield, and R. L. Wentworth, “Hydrogen Peroxide,” Reinhold Publishing Corp., New York, 1955.Reviews: i. Hawkins, E. G. E., Quart. Reviews4, 251 (1950). j. Criegee, R., Fortschr. Chem. Forsch.1, 508 (1950). k. Criegee, R., “Herstellung und Umwanglung von Peroxyden,” in Houben-Weyl, Methoden der organischen Chemie, 4th ed., Thieme, Stuttgart, Vol. VIII, 1952. l. Eggersglüss, W., “Organische Peroxyde,” Angew. Chem.62, Monographien Nr. 61, Verlag Chemie, Weinheim, 1951. m. Milas, N. A., “Peroxides and Peroxy Compounds, Organic,” in Encyclopedia of Chemical Technology, edited by R. E. Kirk and D. Othmer, Vol. X, pp. 58–88, Interscience Publishers, New York, 1953. n. Swern, D., Chem. Reviews45, 1 (1949). o. Martin, A. J., “Determination of Organic Peroxides,” in Organic Analysis, Vol. 4, pp. 1–64, Interscience Publishers, New York, 1960.

    Google Scholar 

  2. Laterjet, R. et al. (21 additional contributors), “Organic Peroxides in Radiobiology,” Pergamon Press, 1958, General Editor: M. Haissinsky.

  3. Lachapele, A. P., J. Biraben, and G. Delmon, Acta Unio Internationalis contra Cancrum16, 1228 (1960).

    CAS  Google Scholar 

  4. Steckerl, F., A. Ofidile, and R. R. Campbell, Experientia15, 423 (1959).

    Article  CAS  Google Scholar 

  5. Chem. and Eng. News, page 40, Jan. 18, 1960; Sinex, F. M., Science134, 1402 (1961).

    Google Scholar 

  6. Davies, J. W., and G. Harris, J. Chem. Soc.1961, 3193.

  7. Walling, C., and S. A. Buckler, J. Am. Chem. Soc.77, 6032 (1955).

    Article  CAS  Google Scholar 

  8. Hock, H., and H. Kropf, Chem. Ber.94, 1156 (1961).

    Article  CAS  Google Scholar 

  9. Bailey, P. S., Chem. Reviews58, 925 (1958); see references contained therein to the studies of R. Criegee and associates.

    Article  CAS  Google Scholar 

  10. Swern, D., “Primary Products of Olefinic Autoxidations,” in “Autoxidation and Antioxidants,” edited by W. O. Lundberg, Vol. 1, Chapt. 1, Interscience Publishers, New York, 1961.

    Google Scholar 

  11. M. Loury, Revue Franç, des Corps Gras8, 686 (1961).

    CAS  Google Scholar 

  12. Ref. 1 h, p. 320.

    Google Scholar 

  13. Russell, G. A., J. Chem. Ed.36, 111 (1959).

    Article  CAS  Google Scholar 

  14. Bolland, J. L., Quart. Reviews3, 1 (1949).

    Article  CAS  Google Scholar 

  15. Bateman, L., Quart. Reviews8, 147 (1954).

    Article  CAS  Google Scholar 

  16. Sanderson, R. T., J. Am. Chem. Soc.77, 4531 (1955).

    Article  CAS  Google Scholar 

  17. Hock, H., and F. Ernst, Chem. Ber.92, 2716 (1959); Hock. H., H. Kropf, and F. Ernst, Angew. Chem.71, 541 (1959).

    Article  CAS  Google Scholar 

  18. Williams, H. R., and H. S. Mosher, J. Am. Chem. Soc.76, 2984 (1954).

    Article  CAS  Google Scholar 

  19. Wawzonek, S., P. D. Klimstra, and R. E. Kallio, J. Org. Chem.25, 621 (1960).

    Article  CAS  Google Scholar 

  20. Williams, H. R., and H. S. Mosher, J. Am. Chem. Soc.76, 2987 (1954).

    Article  CAS  Google Scholar 

  21. Suter, C. M., “The Organic Chemistry of Sulfur,” John Wiley and Sons, Inc., New York, N.Y., 1944, pp. 1–94.

    Google Scholar 

  22. Calhoun, G. M., and R. L. Burwell, Jr., J. Am. Chem. Soc.77, 6441 (1955).

    Article  CAS  Google Scholar 

  23. Read, R. R., and W. G. Fredell, Drug and Cosmetic Ind.84, 178, 256 (1959).

    CAS  Google Scholar 

  24. Davies, A. G., R. V. Foster, and A. M. White,1953, 1541.

  25. Hüttel, R., and H. Ross, Chem. Ber.89, 2644 (1956).

    Article  Google Scholar 

  26. Hüttel, R., H. Schmid, and H. Ross, Chem. Ber.92, 699 (1959).

    Article  Google Scholar 

  27. Welch, F., H. R. Williams, and H. S. Mosher, J. Am. Chem. Soc.77, 551 (1955).

    Article  CAS  Google Scholar 

  28. D’Ans, J., and W. Frey, Z. anorg. Chem.84, 145 (1914).

    Article  Google Scholar 

  29. Phillips, B., P. S. Starcher, and B. D. Ash, J. Org. Chem.23, 1823 (1958).

    Article  CAS  Google Scholar 

  30. Parker, W. E., C. Ricciuti, C. L. Ogg, and D. Swern, J. Am. Chem. Soc.77, 4037 (1955); Parker, W. E., L. P. Witnauer, and D. Swern, J. Am. Chem. Soc.79, 1929 (1957).

    Article  CAS  Google Scholar 

  31. Silbert, L. S., E. Siegel, and D. Swern, J. Org. Chem.27, 1336 (1962).

    Article  CAS  Google Scholar 

  32. Vilkas, M., Bull. soc. chim. France1959, 1401.

  33. Braun, G., in “Organic Syntheses,” Second Edition, Coll. Vol. 1, p. 431, John Wiley and Sons, Inc., New York (1941).

    Google Scholar 

  34. Swern, D., T. W. Findley, and J. T. Scanlan, J. Am. Chem. Soc.66, 1925 (1944).

    Article  CAS  Google Scholar 

  35. Phillips, B., F. C. Frostick, Jr., and P. S. Starcher, J. Am. Chem. Soc.79, 5982 (1957).

    Article  CAS  Google Scholar 

  36. Starcher, P. S., B. Phillips and F. C. Frostick, Jr., J. Org. Chem.26, 3568 (1961).

    Article  CAS  Google Scholar 

  37. Silbert, L. S., and D. Swern, J. Am. Chem. Soc.81, 2364 (1959).

    Article  CAS  Google Scholar 

  38. Cooper, W., J. Chem. Soc.1951, 3106.

  39. Strain, F., W. E. Bissinger, W. R. Dial, H. Rudoff, B. J. DeWitt, H. C. Stevens, and J. H. Langston, J. Am. Chem. Soc.72, 1254 (1950).

    Article  CAS  Google Scholar 

  40. Silbert, L. S., and D. Swern, Anal. Chem.30, 385 (1958).

    Article  CAS  Google Scholar 

  41. Criegee, R., W. Schorrenberg, and J. Becke, Annalen565, 7 (1949); Altshuller, A. P., C. M. Schwab, and M. Bare, Anal. Chem.31, 1987 (1959).

    Article  CAS  Google Scholar 

  42. Silbert, L. S., L. P. Witnauer, D. Swern, and C. Ricciuti, J. Am. Chem. Soc.81, 3244 (1959).

    Article  CAS  Google Scholar 

  43. Hanst, P. L., and J. G. Calvert, J. Phys. Chem.63, 104 (1950); Thomas, J. R., J. Am. Chem. Soc.77, 246 (1955); Pritzkow, W., and K. A. Müller, Chem. Ber.89, 2321 (1956); Trachtman, M., Ph.D. Thesis, University of Pennsylvania, 1962; Smid, J., A. Rembaum, and M. Szwarc, J. Am. Chem. Soc.78, 3315 (1956); Parker, W. E., L. P. Witnauer, and D. Swern, J. Am. Chem. Soc.80, 323 (1958).

    Article  Google Scholar 

  44. Ref. 1 h, pp. 310–336; Redington, R. L., W. B. Olson, and P. C. Cross, J. Chem. Phys.36, 1311 (1962); Amako, Y., and P. A. Giguère, Can. J. Chem.40, 765 (1962).

    Google Scholar 

  45. Lobunez, W., J. R. Rittenhouse, and J. G. Miller, J. Am. Chem. Soc.80, 3305 (1958); Rittenhouse, J. R., W. Lobunez, D. Swern, and J. G. Miller, J. Am. Chem. Soc.80, 4850 (1958): Verderame, F. D., and J. G. Miller, Fourth Delaware Valley Regional Meeting, Am. chem. Soc., Philadelphia, Pa., January 25–26, 1962.

    Article  Google Scholar 

  46. Kovner, M. A., A. V. Karyakin, and A. P. Eflmov, Optics and Spectroscopy8, (No. 1), 64 (1960); Gribov, L. A., and A. V. Karyakin, ibid9, (No. 5), 350 (1960).

    Google Scholar 

  47. Minkoff, G. J., Proc. Roy. Soc.224, A 176 (1954).

    Article  CAS  Google Scholar 

  48. Swern, D., L. P. Witnauer, C. R. Eddy, and W. E. Parker, J. Am. Chem. Soc.77, 5537 (1955).

    Article  CAS  Google Scholar 

  49. Williams, H. R., and H. S. Mosher, Anal. Chem.27, 517 (1955).

    Article  CAS  Google Scholar 

  50. Porter, R. S., and G. H. Cady, J. Am. Chem. Soc.79, 5628 (1957).

    Article  CAS  Google Scholar 

  51. Shreve, O. D., M. R. Heether, H. B. Knight, and D. Swern, Anal. Chem.23, 282 (1951).

    Article  CAS  Google Scholar 

  52. Philpotts, A. R., and W. Thain, Anal. Chem.24, 638 (1952).

    Article  CAS  Google Scholar 

  53. Ory, H. A., Anal. Chem.32, 509 (1960).

    Article  CAS  Google Scholar 

  54. This laboratory, unpublished data.

  55. Leadbeater, R., Compt. rend.230, 829 (1950).

    CAS  Google Scholar 

  56. Bellamy, L. J., “The Infra-red Spectra of Complex Molecules,” Methuen and Company, Ltd., London, 1960.

    Google Scholar 

  57. Davison, W. H. T., J. Chem. Soc.1951, 2456.

  58. Bellamy, L. J., B. R. Connelly, A. R. Philpotts, and R. L. Williams, Zeit. für Elektrochemie64, 563 (1960).

    CAS  Google Scholar 

  59. Holman, R. T., C. Nickell, O. S. Privett, and P. R. Edmondson, JAOCS35, 422 (1958).

    Article  CAS  Google Scholar 

  60. Raley, J. H., F. R. Rust, and W. E. Vaughan, J. Am. Chem. Soc.70, 1336 (1948).

    Article  CAS  Google Scholar 

  61. Barlett, P. D., and R. R. Hiatt, J. Am. Chem. Soc.80, 1398 (1958).

    Article  Google Scholar 

  62. Silbert, L. S., Z. B. Jacobs, W. E. Palm, L. P. Witnauer, W. S. Port, and D. Swern, J. Polymer Sci.21, 161 (1956).

    Article  CAS  Google Scholar 

  63. Yang, N. C., and R. A. Finnegan, J. Am. Chem. Soc.80, 5845 (1958).

    Article  CAS  Google Scholar 

  64. Walling, C., “Free Radicals in Solution,” John Wiley and Sons. Inc., New York-London, 1957.

    Google Scholar 

  65. Lawesson, S-O., and N. C. Yang, J. Am. Chem. Soc.81, 4230 (1959).

    Article  CAS  Google Scholar 

  66. Hassall, C. H., in “Organic Reactions,” Vol. 9, Chapt. 3, John Wiley and Sons, Inc., New York, 1957.

    Google Scholar 

  67. Maruyama, K., Bull. Chem. Soc. Japan34, 102 (1961).

    Article  CAS  Google Scholar 

  68. Kharasch, M. S., and A. Fono, J. Am. Chem. Soc.23, 324 (1958); Kharasch, M. S., and A. Fono, J. Org. Chem.24, 606 (1959), Kharasch, M. S., G. Sosnovsky, and N. C. Yang, J. Am. Chem. Soc.81, 5819 (1959); Kochi, J., J. Am. Chem. Soc.84, 774 (1962).

    Google Scholar 

  69. Braunworth, J. B., and G. W. Crosby, J. Org. Chem.27, 2064 (1962).

    Article  Google Scholar 

  70. Parker, W. E., L. P. Witnauer, and D. Swern, J. Am. Chem. Soc.80, 323 (1958); Lefort, D., J. Sorba, and D. Rouillard, Bull. soc, Chim. France,1961, 2219.

    Article  CAS  Google Scholar 

  71. Pryde, E. H., D. E. Anders, H. M. Teeter, and J. C. Cowan, JAOCS38, 375 (1961).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Eastern Regional Research Laboratory, Philadelphia 18, Pennsylvania

    Leonard S. Silbert

Authors
  1. Leonard S. Silbert
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

A correction to this article is available at http://dx.doi.org/10.1007/BF02645791

Eastern Utilization Research and Development Division, Agricultural Research Service, U.S.D.A.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Silbert, L.S. Fatty peroxides: Synthesis, analysis, and reactions. J Am Oil Chem Soc 39, 480–487 (1962). https://doi.org/10.1007/BF02637232

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02637232

Keywords

Search

Navigation