D-Optimal Design Optimization for the Separation of Oleic Acid from Malaysian High Free Fatty Acid Crude Palm Oil Fatty Acids Mixture Using Urea Complex Fractionation
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Published:
Mar 19, 2021
Keywords:
Oleic acid isolation Crude palm oil, Urea complex fractionation Response surface methodology
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Abstract
Oleic acid (OA) rich vegetable oils is important for the daily essential dietary oils intake but restrict to particular oil such as olive oil. However OA enrichment to other vegetable oil such as palm oil is always possible. OA can be obtained from cheap resources such as high free fatty acid crude palm oil (HFFA-CPO). OA concentrate from HFFA-CPO fatty acids mixture requires efficient and low cost technique. Urea complex crystallization fractionation is a classic method for fractionating saturated and monounsaturated fatty acids from polyunsaturated fatty acids of many vegetable oils. In this work, the separation and purification of oleic acid (OA) from unsaturated fatty acids mixture fraction (USFA) of HFFA-CPO fatty acids mixture by urea complex fractionation (UCF) was studied. The crystallization reaction conditions of urea inclusion for the non-urea complex fraction (NUCF) were optimized using the response surface methodology (RSM) and the optimal model was developed. The results showed high content of OA (88%) in urea complex fraction (UCF) with 86% yield at optimal conditions of urea-to-USFAs ratio of 4.62 : 1 (w/w), crystallization temperature at –10°C and crystallization time of 24 h. The results have demonstrated that urea complex crystallization fractionation method is a very effective with low cost, stable, obtainable, and comparatively ease to recover of OA from polyunsaturated fatty acids (PUFA) of an oil fatty acids mixture. Pure OA is plausible to be used back for the OA enrichment modification into palm oil for new dietary oil.
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Bahadi, M., Salih, N., & Salimon, J. (2021). D-Optimal Design Optimization for the Separation of Oleic Acid from Malaysian High Free Fatty Acid Crude Palm Oil Fatty Acids Mixture Using Urea Complex Fractionation. Applied Science and Engineering Progress, 14(2), 175–186. https://doi.org/10.14416/j.asep.2021.03.004
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References
[1] A. Trichopoulou, A. Kouris-Blazos, M. L. Wahlqvist, C. Gnardellis, P. Lagiou, E. Polychronopoulos, T. Vassilakou, L. Lipworth, and D. Trichopoulos, “Diet and overall survival in elderly people,” The British Medical Journal, vol. 311, pp. 1457–1460, Dec. 1995.
[2] P. Yaqoob, “Monounsaturated fatty acids and immune function,” European Journal of Clinical Nutrition, vol. 56, pp. 9–13, Aug. 2002.
[3] D. B. Panagiotakos, K. Dimakopoulou, K. Katsouyanni, T. Bellander, M. Grau, W. Koenig, T. Lanki, R. Pistelli, A. Schneider, and A. Peters, “Mediterranean diet and inflammatory response in myocardial infarction survivors,” International Journal of Epidemiology, vol. 38, pp. 856–866, Jun. 2009.
[4] S. Teres, G. Barcelo-Coblijn, M. Benet, R. Alvarez, R. Bressani, J. E. Halver, and P. V. Escriba, “Oleic acid content is responsible for the reduction in blood pressure induced by olive oil,” Proceeding of the National Academy of Sciences of the United States of America, vol. 105, pp. 13811–13816, Sep. 2008.
[5] A. Bersamin, B. R. Luick, I. B. King, J. S. Stern, and S. Zidenberg-Cherr, “Westernizing diets influence fat intake, red blood cell fatty acid composition, and health in remote Alaskan Native communities in the center for Alaska Native health study,” Journal of American Dietetic Association, vol. 108, pp. 266–273, Feb. 2008.
[6] R. W. Owen, W. Mier, A. Giacosa, W. E. Hull, B. Spiegelhalder, and H. Bartsch, “Phenolic compounds and squalene in olive oils: The concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignansand squalene,” Food and Chemical Toxicology, vol. 38, pp. 647–659, Aug. 2000.
[7] H. T. Besler and R. F. Grimble, “Comparison of the modulatory influence of maize and olive oils and butter on metabolic responses to endotoxin in rats,” Clinical Science (London), vol. 88, pp. 59– 66, Jan. 1995.
[8] P. Yaqoob, “Monounsaturated fats and immune function,” Brazilian Journal of Medicinal and Biological Research, vol. 31, pp. 453–465, Apr. 1998.
[9] P. Sanderson, P. Yaqoob, and P. C. Calder, “Effects of dietary lipid manipulation upon graft vs host and host vs graft responses in the rat,” Cellular Immunology, vol. 164, pp. 240–247, Sep. 1995.
[10] L. A. Ferrara, A. S. Raimondi, L. d'Episcopo, L. Guida, D. A. Russo, and T. Marotta, “Olive oil and reduced need for antihypertensive medications,” Archives of Internal Medicine, vol. 160, pp. 837– 842, Mar. 2000.
[11] A. Linos, E. Kaklamanis, A. Kontomerkos, Y. Koumantaki, S. Gazi, G. Vaiopoulos, G. C. Tsokos, and P. Kaklamanis, “The effect of olive oil and fish consumption on rheumatoid arthritis-A case control study,” Scandi Journal of Rheumatology, vol. 20, pp. 419–426, Jul. 1991.
[12] J. M. Kremer, D. A. Lawrence, W. Jubiz, R. Digiacomo, R. Rynes, L. E. Bartholomew, and M. Sherman, “Dietary fish oil and olive oil supplementation in patients with rheumatoid arthritis: Clinical and immunologic effects,” Arthritis & Rheumatology, vol. 33, pp. 810–820, Jun. 1990.
[13] L. Lipworth, M. E. Martinez, J. Angell, C. C. Hsieh, and D. Trichopoulos, “Olive oil and human cancer: An assessment of the evidence,” Preventive Medicine, vol. 26, pp. 181–190, Mar. 1997.
[14] G. Assmann, G. de Backer, S. Bagnara, J. Betteridge, G. Crepaldi, A. Fernandez-Cruz, J. Godtfredsen, B. Jacotot, R. Paoletti, S. Renaud, G. Ricci, E. Rocha, E. Trautwein, G. C. Urbinati, G. Varela, and C. Williams, “International consensus statement on olive oil and the Mediterranean diet: Implications for health in Europe. The olive oil and the Mediterranean diet panel,” European Journal of Cancer Prevention, vol. 6, pp. 418–421, Oct. 1997.
[15] J. M. Martin-Moreno, W. C. Willett, L. Gorgojo, J. R. Banegas, F. Rodriguez-Artalejo, J. C. Fernandez-Rodriguez, P. Maisonneuve, and P. Boyle, “Dietary fat, olive oil intake and breast cancer risk,” International Journal of Cancer, vol. 58, pp. 774–780, Sep. 1994.
[16] N. R. Simonsen, J. N. Fernandez-crehuet, J. M. Martin-moreno, J. J. Strain, J. K. Huttunen, B. C. Martin, M. Thamm, A. F. Kardinaal, P. van't Veer, F. J. Kok, and L. Kohlmeier, “Tissue stores of individual monounsaturated fatty acids and breast cancer: The euramic study. European community multicenter study on antioxidants, myocardial infarction, and breast cancer,” The American Journal of Clinical Nutrition, vol. 68, pp. 134–141, Jul. 1998.
[17] M. Solanas, A. Hurtado, I. Costa, R. Moral, J. A. Menendez, R. Colomer, and E. Escrich, “Effects of a high olive oil diet on the clinical behavior and histopathological features of rat DMBA-induced mammary tumors compared with a high corn oil diet,” International Journal of Oncology, vol. 21, pp. 745–753, Oct. 2002.
[18] G. Lligadas, J. C. Ronda, M. Galià, and V. Cádiz, “Oleic and undecylenic acids as renewable feedstocks in the synthesis of polyols and polyurethanes,” Polymers, vol. 2, pp. 440–453, Oct. 2010.
[19] S. Sumathi, S. P. Chai, and A. R. Mohamed, “Utilization of oil palm as a source of renewable energy in Malaysia,” Renewable and Sustainable Energy Reviews, vol. 12, pp. 2404–2421, Dec. 2008.
[20] K. Poku, “Small-scale palm oil processing in Africa,” FAO Agricultural Services Bulletin, vol. 148, pp. 1010–1365, Jun. 2002.
[21] S. F. Cheng and C. H. Chuah, “Microwave pretreatment: A clean and dry method for palm oil production,” Industrial Crops and Products, vol. 34, pp. 967–971, Jul. 2011.
[22] A. A. Japir, J. Salimon, D. Derawi, B. H. Yahaya, M. Bahadi, S. Al-Shuja’a, and M. R. Yusop, “A highly efficient separation and physicochemical characteristics of saturated fatty acids from crude palm oil fatty acids mixture using methanol crystallisation method,” Oilseeds & Fats Crops and Lipids, vol. 25, no. 2, pp. 1–8, 2018.
[23] M. A. Bahadi, A. W. Japir, N. Salih, and J. Salimon, “Free fatty acids separation from Malaysian high free fatty acid crude palm oil using molecular distillation,” Malaysian Journal of Analytical Sciences, vol. 20, pp. 1042–1051, May 2016.
[24] M. Wu, H. Ding, S. Wang, and S. Xu, “Optimizing conditions for the purification of linoleic acid from sunflower oil by urea complex fractionation,” Journal of the American Oil Chemists' Society, vol. 85, pp. 677–684, Jul. 2008.
[25] H. Mu, J. Jin, D. Xie, X. Zou, X. Wang, X. Wang, and Q. Jin, “Combined urea complexation and argentated silica gel column chromatography for concentration and separation of PUFAs from tuna oil: Based on improved DPA level,” Journal of the American Oil Chemists' Society, vol. 93, pp. 1157–1167, May 2016.
[26] N. Aldaw, M. Haroun, M. Nasser, and Y. Mousa, “Isolation and ultra-purification of oleic acid extracted from olive oil using urea crystallization,” Research Journal of Pharmacy and Technology, vol. 11, pp. 624–627, Feb. 2018.
[27] J. T. Dillon, J. C. Aponte, Y.-J. Tsai, and Y. Huang, “Thin layer chromatography in the separation of unsaturated organic compounds using silverthiolate chromatographic material,” Journal of Chromatography A, vol. 1251, pp. 240–243, Aug. 2012.
[28] F.-H. Wang, X.-J. Xiong, X.-F. Guo, H. Wang, and H.-S. Zhang, “Determination of fatty acids in biosamples based on the pre-column fluorescence derivatization with 1,3,5,7-tetramethyl-8- butyrethylenediaminedifluoroboradiaza-sindacene by high performance liquid chromatography,” Journal of Chromatography A, vol. 1291, pp. 84–91, May 2013.
[29] J. L. Bernal, M. T. Martin, and L. Toribio, “Supercritical fluid chromatography in food analysis,” Journal of Chromatography A, vol. 1313, pp. 24–36, Oct. 2013.
[30] F. D. Gunstone, J. McLaughlan, C. M. Scrimgeour, and A. P. Watson, “Improved procedures for the isolation of pure oleic, linoleic, and linolenic acids or their methyl esters from natural sources,” Journal of the Science of Food and Agriculture, vol. 27, pp. 675–680, Jul. 1976.
[31] J. Salimon, B. M. Abdullah, and N. Salih, “D-optimal design optimization of Jatropha curcas L. seed oil hydrolysis via alkali-catalyzed reactions,” Sains Malaysiana, vol. 41, pp. 731–738, Jun. 2012.
[32] U. N. Wanasundara, P. K. Wanasundara, and F. Shahidi, “Novel separation techniques for isolation and purification of fatty acids and oil by‐products,” Bailey's Industrial Oil and Fat Products, 2005, doi: 10.1002/047167849X. bio065.
[33] J. Salimon, M. Said, S. Ramli, and M. Lazim, Oil and Fat Analysis. Bangi, Malaysia: UKM Publishing, 2006.
[34] K. I. Ichihara and Y.Fukubayashi, “Preparation of fatty acid methyl esters for gas-liquid chromatography,” Journal of Lipid Research, vol. 51, pp. 635–640, Mar. 2010.
[35] J. Salimon, B. M. Abdullah, and N. Salih, “Selectively increasing of polyunsaturated (18:2) and monounsaturated (18:1) fatty acids in Jatropha curcas seed oil by crystallization using D-optimal design,” Chemistry Central Journal, vol. 6, no. 1, pp. 65, Jul. 2012.
[36] K.Yang and B. El-Haik, Design for Six Sigma: Roadmap to Product Development. 2nd ed., New York: McGraw-Hill Companies, Inc., 2008.
[37] D. Swern and W. E. Parker, “Application of urea complexes in the purification of fatty acids, esters, and alcohols. II. Oleic acid and methyl oleate from olive oil,” Journal of the American Oil Chemists' Society, vol. 29, pp. 614–615, 1952.
[38] L. J. Rubin and W. Paisley, “Pure oleic acid from olive oil,” Journal of the American Oil Chemists Society, vol. 37, pp. 300–302, Jun. 1960.
[2] P. Yaqoob, “Monounsaturated fatty acids and immune function,” European Journal of Clinical Nutrition, vol. 56, pp. 9–13, Aug. 2002.
[3] D. B. Panagiotakos, K. Dimakopoulou, K. Katsouyanni, T. Bellander, M. Grau, W. Koenig, T. Lanki, R. Pistelli, A. Schneider, and A. Peters, “Mediterranean diet and inflammatory response in myocardial infarction survivors,” International Journal of Epidemiology, vol. 38, pp. 856–866, Jun. 2009.
[4] S. Teres, G. Barcelo-Coblijn, M. Benet, R. Alvarez, R. Bressani, J. E. Halver, and P. V. Escriba, “Oleic acid content is responsible for the reduction in blood pressure induced by olive oil,” Proceeding of the National Academy of Sciences of the United States of America, vol. 105, pp. 13811–13816, Sep. 2008.
[5] A. Bersamin, B. R. Luick, I. B. King, J. S. Stern, and S. Zidenberg-Cherr, “Westernizing diets influence fat intake, red blood cell fatty acid composition, and health in remote Alaskan Native communities in the center for Alaska Native health study,” Journal of American Dietetic Association, vol. 108, pp. 266–273, Feb. 2008.
[6] R. W. Owen, W. Mier, A. Giacosa, W. E. Hull, B. Spiegelhalder, and H. Bartsch, “Phenolic compounds and squalene in olive oils: The concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignansand squalene,” Food and Chemical Toxicology, vol. 38, pp. 647–659, Aug. 2000.
[7] H. T. Besler and R. F. Grimble, “Comparison of the modulatory influence of maize and olive oils and butter on metabolic responses to endotoxin in rats,” Clinical Science (London), vol. 88, pp. 59– 66, Jan. 1995.
[8] P. Yaqoob, “Monounsaturated fats and immune function,” Brazilian Journal of Medicinal and Biological Research, vol. 31, pp. 453–465, Apr. 1998.
[9] P. Sanderson, P. Yaqoob, and P. C. Calder, “Effects of dietary lipid manipulation upon graft vs host and host vs graft responses in the rat,” Cellular Immunology, vol. 164, pp. 240–247, Sep. 1995.
[10] L. A. Ferrara, A. S. Raimondi, L. d'Episcopo, L. Guida, D. A. Russo, and T. Marotta, “Olive oil and reduced need for antihypertensive medications,” Archives of Internal Medicine, vol. 160, pp. 837– 842, Mar. 2000.
[11] A. Linos, E. Kaklamanis, A. Kontomerkos, Y. Koumantaki, S. Gazi, G. Vaiopoulos, G. C. Tsokos, and P. Kaklamanis, “The effect of olive oil and fish consumption on rheumatoid arthritis-A case control study,” Scandi Journal of Rheumatology, vol. 20, pp. 419–426, Jul. 1991.
[12] J. M. Kremer, D. A. Lawrence, W. Jubiz, R. Digiacomo, R. Rynes, L. E. Bartholomew, and M. Sherman, “Dietary fish oil and olive oil supplementation in patients with rheumatoid arthritis: Clinical and immunologic effects,” Arthritis & Rheumatology, vol. 33, pp. 810–820, Jun. 1990.
[13] L. Lipworth, M. E. Martinez, J. Angell, C. C. Hsieh, and D. Trichopoulos, “Olive oil and human cancer: An assessment of the evidence,” Preventive Medicine, vol. 26, pp. 181–190, Mar. 1997.
[14] G. Assmann, G. de Backer, S. Bagnara, J. Betteridge, G. Crepaldi, A. Fernandez-Cruz, J. Godtfredsen, B. Jacotot, R. Paoletti, S. Renaud, G. Ricci, E. Rocha, E. Trautwein, G. C. Urbinati, G. Varela, and C. Williams, “International consensus statement on olive oil and the Mediterranean diet: Implications for health in Europe. The olive oil and the Mediterranean diet panel,” European Journal of Cancer Prevention, vol. 6, pp. 418–421, Oct. 1997.
[15] J. M. Martin-Moreno, W. C. Willett, L. Gorgojo, J. R. Banegas, F. Rodriguez-Artalejo, J. C. Fernandez-Rodriguez, P. Maisonneuve, and P. Boyle, “Dietary fat, olive oil intake and breast cancer risk,” International Journal of Cancer, vol. 58, pp. 774–780, Sep. 1994.
[16] N. R. Simonsen, J. N. Fernandez-crehuet, J. M. Martin-moreno, J. J. Strain, J. K. Huttunen, B. C. Martin, M. Thamm, A. F. Kardinaal, P. van't Veer, F. J. Kok, and L. Kohlmeier, “Tissue stores of individual monounsaturated fatty acids and breast cancer: The euramic study. European community multicenter study on antioxidants, myocardial infarction, and breast cancer,” The American Journal of Clinical Nutrition, vol. 68, pp. 134–141, Jul. 1998.
[17] M. Solanas, A. Hurtado, I. Costa, R. Moral, J. A. Menendez, R. Colomer, and E. Escrich, “Effects of a high olive oil diet on the clinical behavior and histopathological features of rat DMBA-induced mammary tumors compared with a high corn oil diet,” International Journal of Oncology, vol. 21, pp. 745–753, Oct. 2002.
[18] G. Lligadas, J. C. Ronda, M. Galià, and V. Cádiz, “Oleic and undecylenic acids as renewable feedstocks in the synthesis of polyols and polyurethanes,” Polymers, vol. 2, pp. 440–453, Oct. 2010.
[19] S. Sumathi, S. P. Chai, and A. R. Mohamed, “Utilization of oil palm as a source of renewable energy in Malaysia,” Renewable and Sustainable Energy Reviews, vol. 12, pp. 2404–2421, Dec. 2008.
[20] K. Poku, “Small-scale palm oil processing in Africa,” FAO Agricultural Services Bulletin, vol. 148, pp. 1010–1365, Jun. 2002.
[21] S. F. Cheng and C. H. Chuah, “Microwave pretreatment: A clean and dry method for palm oil production,” Industrial Crops and Products, vol. 34, pp. 967–971, Jul. 2011.
[22] A. A. Japir, J. Salimon, D. Derawi, B. H. Yahaya, M. Bahadi, S. Al-Shuja’a, and M. R. Yusop, “A highly efficient separation and physicochemical characteristics of saturated fatty acids from crude palm oil fatty acids mixture using methanol crystallisation method,” Oilseeds & Fats Crops and Lipids, vol. 25, no. 2, pp. 1–8, 2018.
[23] M. A. Bahadi, A. W. Japir, N. Salih, and J. Salimon, “Free fatty acids separation from Malaysian high free fatty acid crude palm oil using molecular distillation,” Malaysian Journal of Analytical Sciences, vol. 20, pp. 1042–1051, May 2016.
[24] M. Wu, H. Ding, S. Wang, and S. Xu, “Optimizing conditions for the purification of linoleic acid from sunflower oil by urea complex fractionation,” Journal of the American Oil Chemists' Society, vol. 85, pp. 677–684, Jul. 2008.
[25] H. Mu, J. Jin, D. Xie, X. Zou, X. Wang, X. Wang, and Q. Jin, “Combined urea complexation and argentated silica gel column chromatography for concentration and separation of PUFAs from tuna oil: Based on improved DPA level,” Journal of the American Oil Chemists' Society, vol. 93, pp. 1157–1167, May 2016.
[26] N. Aldaw, M. Haroun, M. Nasser, and Y. Mousa, “Isolation and ultra-purification of oleic acid extracted from olive oil using urea crystallization,” Research Journal of Pharmacy and Technology, vol. 11, pp. 624–627, Feb. 2018.
[27] J. T. Dillon, J. C. Aponte, Y.-J. Tsai, and Y. Huang, “Thin layer chromatography in the separation of unsaturated organic compounds using silverthiolate chromatographic material,” Journal of Chromatography A, vol. 1251, pp. 240–243, Aug. 2012.
[28] F.-H. Wang, X.-J. Xiong, X.-F. Guo, H. Wang, and H.-S. Zhang, “Determination of fatty acids in biosamples based on the pre-column fluorescence derivatization with 1,3,5,7-tetramethyl-8- butyrethylenediaminedifluoroboradiaza-sindacene by high performance liquid chromatography,” Journal of Chromatography A, vol. 1291, pp. 84–91, May 2013.
[29] J. L. Bernal, M. T. Martin, and L. Toribio, “Supercritical fluid chromatography in food analysis,” Journal of Chromatography A, vol. 1313, pp. 24–36, Oct. 2013.
[30] F. D. Gunstone, J. McLaughlan, C. M. Scrimgeour, and A. P. Watson, “Improved procedures for the isolation of pure oleic, linoleic, and linolenic acids or their methyl esters from natural sources,” Journal of the Science of Food and Agriculture, vol. 27, pp. 675–680, Jul. 1976.
[31] J. Salimon, B. M. Abdullah, and N. Salih, “D-optimal design optimization of Jatropha curcas L. seed oil hydrolysis via alkali-catalyzed reactions,” Sains Malaysiana, vol. 41, pp. 731–738, Jun. 2012.
[32] U. N. Wanasundara, P. K. Wanasundara, and F. Shahidi, “Novel separation techniques for isolation and purification of fatty acids and oil by‐products,” Bailey's Industrial Oil and Fat Products, 2005, doi: 10.1002/047167849X. bio065.
[33] J. Salimon, M. Said, S. Ramli, and M. Lazim, Oil and Fat Analysis. Bangi, Malaysia: UKM Publishing, 2006.
[34] K. I. Ichihara and Y.Fukubayashi, “Preparation of fatty acid methyl esters for gas-liquid chromatography,” Journal of Lipid Research, vol. 51, pp. 635–640, Mar. 2010.
[35] J. Salimon, B. M. Abdullah, and N. Salih, “Selectively increasing of polyunsaturated (18:2) and monounsaturated (18:1) fatty acids in Jatropha curcas seed oil by crystallization using D-optimal design,” Chemistry Central Journal, vol. 6, no. 1, pp. 65, Jul. 2012.
[36] K.Yang and B. El-Haik, Design for Six Sigma: Roadmap to Product Development. 2nd ed., New York: McGraw-Hill Companies, Inc., 2008.
[37] D. Swern and W. E. Parker, “Application of urea complexes in the purification of fatty acids, esters, and alcohols. II. Oleic acid and methyl oleate from olive oil,” Journal of the American Oil Chemists' Society, vol. 29, pp. 614–615, 1952.
[38] L. J. Rubin and W. Paisley, “Pure oleic acid from olive oil,” Journal of the American Oil Chemists Society, vol. 37, pp. 300–302, Jun. 1960.