Browse > Article
http://dx.doi.org/10.9725/kstle.2014.30.5.256

Synthesis and Lubricant Properties of Estolides based on Fatty Acid  

Son, Jeong-Mae (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Yoo, Seunghyun (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Lee, Sangjun (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Shin, Jihoon (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Chung, Kunwo (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Yang, Youngdo (EMAX Solutions Co., LTD.)
Kim, Young-Wun (Integrated Chemistry Research Division, Industrial Bio-based Materials Research Group, Korea Research Institute of Chemical Technology (KRICT))
Publication Information
Tribology and Lubricants / v.30, no.5, 2014 , pp. 256-264 More about this Journal
Abstract
Enhancing the value of fine chemicals based on biomass resources is an important objective for addressing environmental and other concerns such as demand for renewable or green products, as well as from the political perspective to reduce dependence on fossil feedstock associated with the use of petroleum-based products. Based on these considerations, we studied the synthesis of estolide using waste plant-based oil materials and their application as lubricants and pour point depressants. Five estolides were prepared by varying molar ratio of palmitic acid (PA) to oleic acid (OA) using a reaction time of 48 h. The estolides were characterized by size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR). The isolated yields were in the range of 57-78 % and purity was 93-97%, showing iodine values of 18.2-37.8, total acid numbers (TANs) of 75.6-94.2 mg KOH/g and estolide numbers (ENs) of 1.2-1.8. Increasing the ratio of OA to PA in the synthesis decreased the kinematic viscosity and clouding point of the estolides. Four ball wear test of the estolides as a base oil demonstrated that the wear scar diameter (WSD) of the estolides was significantly lower (0.320-0.495 mm) than the WSD of general base oils such as 150N and Yubase (0.735 and 0.810 mm, respectively), indicating better wear resistance of the estolides. However, the lubricant property was found to be independent of the amount of OA in the estolides. These new materials are prospective candidates for application as a lubricant base oil.
Keywords
estolides; fatty acid; lubricants; wear scar diameter;
Citations & Related Records
연도 인용수 순위
  • Reference
1 D4172, "Standard Test Method for Wear Preventive Characteristics of Lubricating Fluid (Four-Ball Method)", ASTM international, West Conshohocken, PA, 2012.
2 D6179, "Standard Test Method for Evaluating Lubricity of Diesel Fuels by the High-Frequency Reciprocating Rig (HFRR)", ASTM international, West Conshohocken, PA, 2012.
3 Smith, M. A., Zhang, H., Forseille, L., Purves, R. W., "Characterization of novel triacylglycerol estolides from the seed oil of Mallotus philippensis and Trewia nudiflora", Lipids, Vol. 48, No. 1, pp. 75-85, 2013.   DOI
4 Aguieiras, E. C. G., Veloso, C. O., Bevilaqua, J. V., Rosas, D. O., da Silva, M. A. P., Langone, M. A. P., "Estolides synthesis catalyzed by immobilized lipases", Enzyme research, Vol. 2011, pp. 1-7, 2011.
5 Garcia-Zapateiro, L. A., Franco, J. M., Valencia, C., Delgado, M. A., Gallegos, C., "Viscous, thermal and tribological characterization of oleic and ricinoleic acids-derived estolides and their blends with vegetable oils", Journal of Industrial and Engineering Chemistry, Vol. 19, No. 4, pp. 1289-1298, 2013.   DOI
6 Biresaw, G., Bantchev, G. B., Cermak, S. C. "Tribological Properties of Vegetable Oils Modified by Reaction with Butanethiol", Tribology Letters, Vol. 43, No. 1, pp. 17-32, 2011.   DOI
7 Cermak, S. C., Isbell, T. A, Evangelista, R. L., Johnson, B. L., "Synthesis and physical properties of petroselinic based estolide esters", Industrial Crops and Products, Vol. 33, No. 1, pp. 132-139, 2011.   DOI   ScienceOn
8 Cermak, S. C., Isbell, T. A., "Improved oxidative stability of estolide esters", Industrial Crops and Products, Vol. 8, No. 3, pp. 223-230, 2003.
9 Cermak, S. C., Isbell, T. A., "Synthesis and Physical Properties of Cuphea-Oleic estolides and esters", Journal of the American Oil Chemists' Society, Vol. 81, No. 3, pp. 297-303, 2004.   DOI
10 Moser, B. R., Cermak, S. C., Isbell, T. A., "Evaluation of Castor and Lesquerella Oil Derivatives as Additives in Biodiesel and Ultralow Sulfur Diesel Fuels", Energy & Fuels, Vol. 22, pp. 1349-1352, 2008.   DOI   ScienceOn
11 Hayes, D. G., Kleiman, R., "Lipase-catalyzed synthesis and properties of estolides and their esters", Journal of the American Oil Chemists' Society, Vol. 72, No. 11, pp. 1309-1316, 1995.   DOI
12 Asadauskas, S., Erhan, S. Z., "Depression of pour points of vegetable oils by blending with diluents used for biodegradable lubricants", Journal of the American Oil Chemists' Society, Vol. 76, No. 3, pp. 313-316, 1999.   DOI
13 Garcia-Zapateiro, L. A., Franco, J. M., Valencia, C., Delgado, M. A., Gallegos, C., Ruiz-Mendez, M. V., "Viscosity modification of high-oleic sunflower and castor oils with acid oils-derived estolides for lubricant applications", European Journal of Lipid Science and Technology, Vol. 115, pp. 1173-1182, 2013.
14 Cermak, S. C., Biresaw, G., Isbell, T. A., "Comparison of a New Estolide Oxidative Stability Package", Journal of the American Oil Chemists' Society, Vol. 85, No. 9, pp. 879-885, 2008.   DOI
15 Cermak, S. C., Isbell, T. A., "Pilot-plant distillation of meadowfoam fatty acids", Industrial Crops and Products, Vol. 15, No. 2, pp. 145-154, 2002.   DOI   ScienceOn
16 Isbell, T. A., Cermak, S. C., "Purification of meadowfoam monoestolide from polyestolide", Industrial Crops and Products, Vol. 19, No. 2, pp. 113-118, 2002.
17 Erhan, S. M., Kleiman, R. Isbell, T. A., "Estolides from meadowfoam oil fatty acids and other monounsaturated fatty acids", Journal of the American Oil Chemists' Society, Vol. 70, No. 5, pp. 461-465, 1993.   DOI
18 Isbell, T. A., Kleiman, R., Plattner, B. A., "Acid-catalyzed condensation of oleic acid into estolides and polyestolides", Journal of the American Oil Chemists' Society, Vol. 71, No. 2, pp. 169-174, 1994.   DOI
19 Zerkowski, J. A., "Estolides: From structure and function to structured and functionalized", Lipid Technology, Vol. 20, No. 11, pp. 253-256, 2008.   DOI
20 Cermak, S. C., Bredsguard, J. W., John, B. L., Macalvin, J. S., Thompson, T., Isbell, K. N., Feken, K. A., Isbell, T. A., "Synthesis and physical properties of new estolide esters", Industrial Crops and Products, Vol. 46, pp. 386-391, 2013.   DOI
21 Biresaw, G., Cermak, S. C., Isbell, T. A., "Film-forming properties of estolides", Tribology Letters, Vol. 27, No. 1, pp. 69-78, 2007.   DOI
22 Wang, Y., Eli, W., "Synthesis of Biodegradable High-Alkali Magnesium Oleate Detergent", Industrial & Engineering chemistry Research, Vol. 49, pp. 2589-2592, 2010.   DOI
23 Garcia-Zapateiro, L. A., Delgado, M. A., Franco, J. M., Valencia, C., Ruiz-Mendez, M. V., Garces, R., Gallegos, C. "Oleins as a source of estolides for biolubricant applications", Grasas Y Aceites, Vol. 61, No. 2, pp. 171-174, 2010.   DOI
24 Birova, A., Cvengro, J., "Lubricating Oils Based on Chemically Modified Vegetable Oils", Journal of Synthetic Lubrication , Vol. 4, No. 18, pp. 291-299, 2002.
25 Salimon, J., Salih, N., Yousif, E., "Biolubricants: Raw materials, chemical modifications and environmental benefits", European Journal of Lipid Science and Technology, Vol. 112, pp. 519-530, 2010.
26 Yao, L., Hammond, E. G., Wang, T., Bhuyan, S., Sundararajan, S., "Synthesis and Physical Properties of Potential Biolubricants based on Ricinoleic Acid", Journal of the American Oil Chemists' Society, Vol. 87, No. 8, pp. 937-945, 2010.   DOI
27 Isbell, T. A., Kleiman, R. "Mineral acid-catalyzed condensation of meadowfoam fatty acids into estolides", Journal of the American Oil Chemists' Society, Vol. 73, No. 9, pp. 1097-1107, 1996.   DOI
28 Erhan, S. M., Kleiman, R., Isbell, T. A., "Methods for increasing estolide yields in a batch reactor", Journal of the American Oil Chemists' Society, Vol. 72, No. 6, pp. 671-674, 1995.   DOI
29 Isbell, Terry A., "Chemistry and physical properties of estolides", Grasas Y Aceites, Vol. 62, No. 1, pp. 8-20, 2011.   DOI
30 Showell, J. S., Swern, D. Noble, W. R., "perchloric acid isomerization of oleic acid", The Journal of Organic Chemistry, Vol. 33, No. 7, pp. 2697-2704, 1968.   DOI
31 Isbell, T. A., Kleiman, R., "Characterization of estolides produced from the acid-catalyzed condensation of oleic acid", Journal of the American Oil Chemists' Society, Vol. 71, No. 4, pp. 379-383, 1994.   DOI
32 Cermak, S. C., Isbell, T. A., "Synthesis of estolides from oleic and saturated fatty acids", Journal of the American Oil Chemists' Society, Vol. 78, No. 6, pp. 557-565, 2001.   DOI   ScienceOn
33 D664, "Standard Test Method for Acid Number of Petroleum Products by Potentiometric Titration", ASTM international, West Conshohocken, PA, 2012.
34 D5558, "Standard Test Method for Determination of the Saponification Value of Fats and Oils", ASTM international, West Conshohocken, PA, 2012.
35 D97, "Standard Test Method for Pour Point of Petroleum Products", ASTM international, West Conshohocken, PA, 2012.
36 D2500, "Standard Test Method for Cloud Point of Petroleum Products", ASTM international, West Conshohocken, PA, 2012.