화학공학소재연구정보센터
Korean Journal of Chemical Engineering, Vol.25, No.3, 474-482, May, 2008
Modification of soybean oil for intermediates by epoxidation, alcoholysis and amidation
E-mail:
Vegetable oils are a major source of many base chemicals. Unfortunately, most vegetable oils exhibit lower thermal and oxidation stability because of double bonds and even worse low-temperature behaviors. These physical and chemical properties can be improved by various chemical modifications. The catalytic hydrogenation of soybean oil (SBO) over 25% Ni/SiO2 and 5% Pt/C is one of them, and the epoxidation of soybean oil and reduced soybean oil (RSBO) was carried out by using 30% of hydrogen peroxide and acetic acid in the presence of conc. sulfuric acid, and/or acidic Amberlyst 15 resin catalyst. Various alcohols and amines were added to the epoxidized soybean oil (ESBO) in the hope of improving lubricant properties. The reaction products were carefully analyzed by means of 1H-NMR, FT-IR spectroscopies and GC-MS spectrometry. This paper covers the epoxidation of virgin and RSBOs, alcoholysis and amidation of ESBO and SBO. Finally, the structures of cross linked products synthesized from ESBO and SBO with 1,6-hexamethylendiamine were proposed.
  1. Lee KW, Mei BX, Bo Q, Kim YW, Chung KW, Han Y, J. Ind. Eng. Chem., 13(4), 530 (2007)
  2. Thomas A, Ullmann’s Encyclopedia of Industrial Chemistry, A10, 186 (1987)
  3. Chinese Foodstuff Association Network (Feb. 05, 2007)
  4. Lee KW, Yu JX, Mei JH, Yan L, Kim YW, Chung KW, J. Ind. Eng. Chem., 13(5), 799 (2007)
  5. Adhvaryu A, Liu Z, Erhan SZ, Ind. Crop. Prod., 21, 113 (2005)
  6. Aydogan S, Kusefoglu S, Akman U, Hortacsu O, Korean J. Chem. Eng., 23(5), 704 (2006)
  7. Lee KW, Hong ZY, YUST graduation paper (2007). Presented at 36th KSIEC Meeting, Nov. 2-3, 2007, Anseong, Korea
  8. Greenspan FP, J. Am. Chem. Soc., 68, 907 (1946)
  9. Swern D, Organic peroxides, Chapter 5 (epoxidation), Wiley-Interscience, New York, vol. 2, pp. 355-533 (1971)
  10. Rangarajan B, Havey A, Grulke EC, Culnan PD, J. Am. Oil Chem. Soc., 72(10), 1161 (1995)
  11. Bu J, Yun SH, Rhee HK, Korean J. Chem. Eng., 17(1), 76 (2000)
  12. Holderich WF, Rios LA, Weckes PP, Schuster H, J. Synthetic Lubrication, 20(4), 289 (2004)
  13. Sharma BK, Adhvaryu A, Erhan Z, J. Agric. Food Chem., 54, 9866 (2006)
  14. Biswas A, Adhvaryu A, Gordon SH, Erhan SZ, Willett JL, J. Agric. Food Chem., 53, 9485 (2005)
  15. Freedman B, Kwolek WF, Pryde EH, J. Am. Oil Chem. Soc., 63(10), 1370 (1986)
  16. Gonzalezmarcos MP, Gutierrezortiz JI, Deelguea CG, Delgado JA, Gonzalezvelasco JR, Appl. Catal. A: Gen., 162(1-2), 269 (1997)
  17. Drozdowski B, Szukalska E, Eur. J. Lipid Sci. Technol., 102, 642 (2000)
  18. Khot SN, Lascala JJ, Can E, Morye SS, Williams GI, Palmese GR, Kusefoglu SH, Wool RP, J. Appl. Polym. Sci., 82(3), 703 (2001)
  19. Pavia D, Lampman GM, Kriz GS, Introduction to spectroscopy, Brooks/Cole (2001)
  20. Pouilloux Y, Autin F, Guimon C, Barault J, J. Catal., 176, 215 (1998)
  21. Coenen JWE, J. Am. Oil Chem. Soc., 52, 382 (1976)
  22. Balakos MW, Hernandez EE, Catal. Today, 35(4), 415 (1997)
  23. Lligadas G, Ronda JC, Galia M, Cadiz V, Biomacromolecules, 7(8), 2420 (2006)
  24. Tsujimoto T, Uyama H, Kobayashi S, Macromol. Rapid Commun., 24(12), 711 (2003)
  25. Can E, Kusefoglu S, Wool RP, J. Appl. Polym. Sci., 83(5), 972 (2002)