Abstract
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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
K.-W. Lee, B. X. Mei, Q. Bo, Y.-W. Kim and Y. Han, J. Ind. & Eng. Chem., 13(4), 530 (2007).
A. Thomas, Ullmann’s Encyclopedia of Industrial Chemistry, A 10, 186 (1987).
Chinese Foodstuff Association Network (Feb. 05, 2007).
K.-W. Lee, J. X. Yu, J.H. Mei, L. Yan, Y.-W. Kim and K.-W. Chung, J. Ind. & Eng. Chem., 13(5), 799 (2007).
A. Adhvaryu, Z. Liu and S. Z. Erhan, Ind. Crops Prod., 21, 113 (2005).
S. Aydogan, S. Kusefoglu and U. Akman, Korean J. Chem. Eng., 23, 704 (2006).
K.W. Lee and Z. Y. Hong, YUST graduation paper (2007). Presented at 36th KSIEC Meeting, Nov. 2–3, 2007, Anseong, Korea.
F. P. Greenspan, J. Am. Chem. Soc., 68, 907 (1946).
D. Swern, Organic peroxides, Chapter 5 (epoxidation), Wiley-Interscience, New York, vol. 2, pp. 355–533 (1971).
B. Rangarajan, A. Havey, E. C. Grulke and P. D. Culnan, J. Am. Oil Chem. Soc., 72(10), 1161 (1995).
J. Bu, S. H. Yun and H. K. Rhee, Korean J. Chem. Eng., 17, 76 (2000).
W. F. Hölderich, L.A. Rios, P. P. Weckes and H. Schuster, J. Synthetic Lubrication, 20(4), 289 (2004).
B. K. Sharma, A. Adhvaryu and Z. Erhan, J. Agric. Food Chem., 54, 9866 (2006).
A. Biswas, A. Adhvaryu, S. H. Gordon, S. Z. Erhan and J. L. Willett, J. Agric. Food Chem., 53, 9485 (2005).
B. Freedman, W. F. Kwolek and E.H. Pryde, J. Am. Oil Chem. Soc., 63(10), 1370 (1986).
M. P. Gonzales-Maecos, J. I. Gutierrez-Ortiz, C. Gonzalez-Ortiz de Elguea, J.A. Delgado and J. R. Gonzalez-Velasco, Appl. Catal., A: General, 162, 269 (1997).
B. Drozdowski and E. Szukalska, Eur. J. Lipid Sci. Technol., 102, 642 (2000).
S. N. Khot, J. J. Lascala, E. Can, S. S. Morye, G. I. Williams, G. R. Palmese, S.H. Küsefðlu and R. P. Wool, J. Appl. Polymer Sci., 82, 703 (2001).
D. Pavia, G. M. Lampman and G. S. Kriz, Introduction to spectroscopy, Brooks/Cole (2001).
Y. Pouilloux, F. Autin, C. Guimon and J. Barault, J. Catalysis, 176, 215 (1998).
J.W.E. Coenen, J. Am. Oil Chem. Soc., 52, 382 (1976).
M.W. Balakos and E. E. Hernandez, Catal. Today, 35, 415 (1997).
G. Ligadas, J. C. Ronda, M. Galia and V. Cadiz, Biomacromolecules, 7, 2420 (2006).
T. Tsujimoto, H. Uyama and S. Kobayashi, Macromol. Rapid Commun., 24, 711 (2003).
E. Can, S. Küsefðlu and R. P. Wool, J. Appl. Polymer Sci., 83, 972 (2002).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, KW., Hailan, C., Yinhua, J. et al. Modification of soybean oil for intermediates by epoxidation, alcoholysis and amidation. Korean J. Chem. Eng. 25, 474–482 (2008). https://doi.org/10.1007/s11814-008-0081-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-008-0081-7