Abstract
Several fatty derivatives with bulky moieties were prepared by treatment of epoxidized isopropyl oleate with a number of alcohols in the presence of sulfuric acid catalyst to provide a series of α-hydroxy ethers in good yield. The materials were analyzed for cold flow performance through cloud point and pour point determinations. The most promising α-hydroxy ether produced in this study, with respect to both low temperature behavior and economic criteria, was isopropyl 9(10)-(2-ethylhexoxy) 10(9)-hydroxystearate, which has a cloud point of −23°C and pour point of −24°C.
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Masjuki, H.J., A.M. Zaki, and S.M. Sapuan, Methyl Ester of Palm Oil as an Alternative Diesel Fuel, in Fuels for Automotive and Industrial Diesel Engines: Proceedings of the 2nd Institute of Mechanical Engineering Seminar, Institute of Mechanical Engineering, London, 1993, pp. 129–137.
Peterson, C.L., R.A. Korus, P.G. Mora, and J.P. Madsen, Fumigation with Propane and Transesterification Effects on Injector Coking with Vegetable Oils Trans. ASAE 30:28–35 (1987).
Schwab, A.W., M.O. Bagby, and B.,Freedman, Preparation and Properties of Diesel Fuels from Vegetable Oils. Fuel 66:1372–1378 (1987).
Clark S.J., L. Wagner, M.D. Schrock, and P.G. Piennaar, Methyl and Ethyl Soybean Esters as Renewable Fuels for Diesel Engines, J. Am. Oil Chem. Soc. 61:1632–1638 (1984).
Van Gerpen, J.H., S. Soylu, and M.E. Tat, Evaluation of the Lubricity of Soybean Oil-Based Additives in Diesel Fuel, Proceedings, Annual International Meeting of the ASAE, American Society of Agricultural Engineers, St. Joseph, MI, 1996, paper no. 996134.
Sheehan, J., V. Camobreco, J. Duffield, M. Graboski, and H. Shapouri, in Final Report, Life Cycle Inventory of Biodiesel and Petroleum Diesel for Use in an Urban Bus NREL-SR-580-24089, National Renewable Energy Laboratory, Golden, CO, 1998, pp. 206–261.
Knothe, G., R.O. Dunn, and M.O. Bagby, Biodiesel: The Use of Vegetable Oils and Their Derivatives as Alternative Diesel Fuels, in Fuels and Chemicals from Biomass American Chemical Society Symposium Series No. 666, edited by B.C. Saha and J. Woodward, American Chemical Society, Washington, DC, 1997, pp. 172–208.
Krahl, J., A. Munack, M. Bahadir, L. Schumacher, and N. Elser, Survey About Biodiesel Exhaust Emissions and Their Environmental Benefits, in Proceedings, Third Liquid Fuel Conference: Liquid Fuel and Industrial Products from Renewable Resources, edited by J.S. Cundiff, E.E. Gavett, C. Hansen, C. Peterson, M.A. Sanderson, H. Shapouri, and D.L. VanDyne, American Society of Agricultural Engineers, St. Joseph, MI, 1996, pp. 136–148.
Krahl, J., J. Bunger, H.-E. Jeberien, K. Prieger, C. Schutt, A. Munack, and M. Bahadir, Analysis of Biodiesel Exhaust Emissions and Determination of Environmental and Health Effects, in Ibid., edited by J.S. Cundiff, E.E. Gavett, C. Hansen, C. Peterson, M.A. Sanderson, H. Shapouri, and D.L. VanDyne, American Society of Agricultural Engineers, St. Joseph, MI, 1996, pp. 149–165.
Scholl, K.W., and S.C. Sorenson, Combustion of Soybean Oil Methyl Ester in a Direct Injection Diesel Engine, in Society of Automotive Engineers Special Publication SP-958: New Developments in Alternative Fuels and Gasolines for SI and CI Engines (Paper No. 930936), Society of Automotive Engineers, Warrendale, PA, 1993, pp. 211–223.
Mittelbach, M., P. Tritthart, and H. Junek, Diesel Fuel Derived from Vegetable Oils, II: Emission Tests Using Rape Oil Methyl Ester, Energy Agric. 4:207–215 (1985).
Chang, D.Y.Z., J.H. Van Gerpen, I. Lee, L.A. Johnson, E.G. Hammond, and S.J. Marley, Fuel Properties and Emissions of Soybean Oil Esters as Diesel Fuel, J. Am. Oil Chem. Soc. 73:1549–1555 (1996).
Ali Y., and M.A. Hanna, Alternative Diesel Fuels from Vegetable Oils, Bioresource Technol. 50:153–163, (1994).
Dunn, R.O., Thermal Analysis of Alternative Diesel Fuels from Vegetable Oils. J. Am. Oil Chem. Soc., 76:109–115 (1999).
Dunn, R.O., and M.O. Bagby, Low-Temperature Properties of Triglyceride-Based Diesel Fuels: Transesterified Methyl Esters and Petroleum Middle Distillate/Ester Blends, J. Am. Oil Chem. Soc. 72:895–904 (1995).
Knothe, G., J. Van Gerpen, and J. Krahl (eds.), The Biodiesel Handbook, AOCS Press, Champaign, IL, 2005.
Hernqvist, L., Crystal Structures of Fats and Fatty Acids, in Crystallization and Polymorphism of Fats and Fatty Acids, edited by N. Garti and K. Sato, Marcel Dekker, Inc., New York, 1988, p. 130.
Wang, P.S., M.E. Tat, and J.H. Van Gerpen, The Production of Fatty Acid Isopropyl Esters and Their Use as a Diesel Engine Fuel, J. Am. Oil Chem. Soc. 82:845–849 (2005).
Lee, I., L.A. Johnson, and E. Hammond, Use of Branched-Chain Esters to Reduce the Crystallization Temperature of Biodiesel, J. Am. Oil Chem. Soc. 72:1155–1160 (1995).
Taylor, S.K., Reactions of Epoxides with Ester, Ketone, and Amide Enolates, Tetrahedron 56:1149–1163 (2000).
Aggarwal, V.K., I. Bae, and H.Y. Lee, Application of Sulfur Ylide Mediated Epoxidations in the Asymmetric Synthesis of β-Hydroxy-δ-lactones. Synthesis of a Mevinic Acid Analogue and (+)-Prelactone B, Tetrahedron 60:9725–9733 (2004).
Gast, L.E., C.B. Croston, W.J. Schneider and H.M. Teeter, Synthetic Lubricants from Polyhydroxystearic Acids, Ind. Eng. Chem. 46:2205–2208 (1954).
Sharma, B.K., A. Adhvaryu, Z. Liu, and S.Z. Erhan, Chemical Modification of Vegetable Oils for Lubricant Applications, J. Am. Oil Chem. Soc. 83:129–136 (2006).
Silverstein, R.M., and F.X. Webster, Spectrometric Identification of Organic Compounds, 6th Edition, John Wiley & Sons, New York, 1998, p. 92.
ATSM D 5773, Standard Test Method for Cloud Point of Petroleum Products (Constant Cooling Rate Method), in Annual Book of ASTM Standards, American Society for Testing and Materials, Philadelphia, PA, Vol. 05.03, 2003.
ASTM D 5949, Standard Test Method for Pour Point of Petroleum Products (Automatic Pressure Pulsing Method), in Annual Book of ASTM Standards, American Society for Testing and Materials, Philadelphia, PA Vol. 05.03, 2003.
Fischer, E., and A. Speier, Ber. Dtsch. Chem. Ges. 28:3252–3255 (1895).
Doll, K.M., and S.Z. Erhan, Synthesis of Carbonated Fatty Methyl Esters Using Supercritical Carbon Dioxide, J. Agric. Food Chem. 53:9608–9614 (2005).
Findley, T.W., D. Swern, and J.T. Scanlan, Epoxidation of Unsaturated Fatty Materials with Peracetic Acid in Glacial Acetic Acid Solution, J. Am. Chem. Soc. 67:412–414 (1945).
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Moser, B.R., Erhan, S.Z. πSynthesis and evaluation of a series of α-hydroxy ethers derived from isopropyl oleate. J Amer Oil Chem Soc 83, 959–963 (2006). https://doi.org/10.1007/s11746-006-5053-7
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DOI: https://doi.org/10.1007/s11746-006-5053-7