Journal of Industrial and Engineering Chemistry

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Bond reactivity and antioxidant effect on the autoxidation of soybean oil

  • Lee, Kyu-Wan (Division of Biological and Chemical Engineering, Yanbian University of Science and Technology) ;
  • Hong, Zhenyu (Division of Biological and Chemical Engineering, Yanbian University of Science and Technology) ;
  • Piao, Fengnv (Division of Biological and Chemical Engineering, Yanbian University of Science and Technology) ;
  • Kim, Young-Wun (Surfactant & Lubricant Research Team, KRICT) ;
  • Chung, Keun-Woo (Surfactant & Lubricant Research Team, KRICT)
  • Received : 2009.06.16
  • Accepted : 2009.11.14
  • Published : 2010.05.25
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Abstract

Soybean oil (SBO) contains many unsaturated fatty acids, so that it can be easily oxidized by air/oxygen. Therefore the autoxidation of soybean oil was performed to investigate the bond reactivities of allylic, bisallylic $CH_2$, ${\alpha}-CH_2$, ${\beta}-CH_2$, chain $CH_2$ and $CH_2O$ of backbone in the presence and absence of phenolic and aniline antioxidants by means of iodometry and 500 MHz $^1H$ NMR spectroscopy. From the active oxygen concentration, the inhibiting effect and by application of proton integration of each bond of pure and oxidized soybean oil to the first order rate equation, got firstly the orders of the reactivity of each C-H bond and inhibiting effect of antioxidants. In the presence of 2,6-di-t-butyl-4-cresol, three phenol adducts from oxidation product also firstly were identified by means of GC-MS spectroscopy.

Keywords

References

  1. M.M. Kinen, A. Kamal-Eldin, A.M. Lampi, A. Hopia, J.A.O.C.S. 77 (8) (2000) 801. https://doi.org/10.1007/s11746-000-0128-z
  2. R. Yamauchi, K. Kato, Y. Ueno, J. Agric. Food Chem. 43 (1995) 1455. https://doi.org/10.1021/jf00054a008
  3. R. Yamauchi, T. Matsui, K. Kat, Y. Ueno, Agric. Biol. Chem. 54 (1990) 2703. https://doi.org/10.1271/bbb1961.54.2703
  4. K. Mukai, S. Yokoyama, K. Fukuda, Y. Uemoto, Bull. Chem. Soc. Jpn. 60 (1987) 2163. https://doi.org/10.1246/bcsj.60.2163
  5. G. Scott, Bull. Chem. Soc. Jpn. 61 (1988) 165. https://doi.org/10.1246/bcsj.61.165
  6. N.V. Khrustova, L.N. Shishkina, Kinetics Catal. 45 (6) (2004) 799. https://doi.org/10.1007/s10975-005-0038-3
  7. K. Katsuyama, T. Inoue, T. Takahashi, T. Kai, J. Jpn. Petrol. Inst. 49 (3) (2006) 121. https://doi.org/10.1627/jpi.49.121
  8. K.U. Ingold, Chem. Rev. 61 (1961) 563. https://doi.org/10.1021/cr60214a002
  9. Y. Ohkatsu, T. Haruna, T. Osa, J. Macromol. SCI.-Chem. A11 (10) (1977) 1975.
  10. K.W. Lee, X.M. Bai, B. Quan, Y.W. Kim, K.W. Chung, Y.H. Han, J. Ind. Eng. Chem. 13 (4) (2007) 530.
  11. K.W. Lee, H.L. Cheng, Y.H. Jin, Y.W. Kim, K.W. Chung, Korean J. Chem. Eng. 25 (3) (2008) 474. https://doi.org/10.1007/s11814-008-0081-7
  12. S.N. Khot, J.J. Lascala, E. Can, S.S. Morye, G.I. Williams, G.R. Palmese, S.H. Kusefoglu, R.P. Wool, J. Appl. Polym. Sci. 82 (2001) 703. https://doi.org/10.1002/app.1897
  13. N.M. Emanuel, E.T. Denisov, Z.K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum Press, New York, 1967 (Chapter VII).
  14. K.W. Lee, M.J. Choi, S.B. Kim, C.S. Choi, I. & EC. Res. 26 (1987) 1951.
  15. P.P. Klemchuk, Ullmann's Encyclopedia of Industrial Chemistry, vol. A3, 91, VCH, 1985.
  16. K.W. Lee, X.Y. Jin, Y. Li, Y.W. Kim, K.W. Chung, J. Ind. Eng. Chem. 13 (5) (2007) 799.
  17. LG-QA-20-03-A (April 15 2002. Iodometry).
  18. H. Yamashita, Y. Ohkatsu, Polymer Degrad. Stabil. 80 (2003) 421. https://doi.org/10.1016/S0141-3910(02)00373-7
  19. H. Yamashita, A. Williams Kawaguchi, Y. Ohkatsu, J. Jpn. Petrol. Inst. 49 (6) (2006) 294. https://doi.org/10.1627/jpi.49.294

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