Location: Bio-oils Research Unit
2012 Annual Report
Objective 1: Develop new technologies that enable the commercial polymerization of vegetable oils into high value products.
Objective 2. Develop commercially preferred industrial/automotive lubricants based on vegetable oil.
Objective 3. Develop technologies that enable new, commercially-viable chemical processes for producing superior vegetable oil-based surfactants.
The approach to objective 2 will involve a strategic combination of chemical modification, blending, and additive packages that will produce vegetable oil-based lubrication fluids with properties superior to petroleum-based lubricants. The low stability of vegetable oil towards oxidation will be addressed by chemical modifications which remove the bis-allylic protons of the molecule while, at the same time, improve the poor low temperature flow properties of the oil. Nucleophilic addition of heteroatom-containing compounds will be performed on the activated substrates with the use of appropriate catalysts. For example, di-butyl phosphate can be added to epoxidized methyl oleate using zirconium doped titania as a ring opening catalyst, and aniline can be added to the same starting material.
The approach to objective 3 will involve the formation of a new type of structure of branched surfactants which has not been previously reported in the literature. A sugar moiety will initially be connected to the fatty material by a precedented tosylation reaction which will be updated to a modern catalytic reaction. It will have hydrophile-lipophile balances suitable for use in water in oil emulsification and as wetting agents. Functional groups will be added to the surfactant using epoxidation and ring opening addition. This will change the suitability of these surfactants leading to potential application in dispersants and coating products. This surfactant material will have significant advantages over the currently used ethylene oxide-based surfactants because traces of un-reacted ethylene oxide or dioxin byproducts will not be an issue. Also, because the soy-based monomer is large, compared to ethylene oxide, a narrow range of molecular weight surfactants will be synthesized. This project is biosafety exempt.
Arca, M., Sharma, B.K., Price, N.P.J., Perez, J.M., Doll, K.M. 2012. Evidence contrary to the accepted Diels-Alder mechanism in the thermal modification of vegetable oil. Journal of the American Oil Chemists' Society. 89:987-994.
Arca, M., Sharma, B.K., Perez, J.M., Doll, K.M. 2012. Isothermal thermogravimetric analysis of soybean oil oxidation correlated to thin film micro-oxidation test methods. Industrial and Engineering Chemistry Research. 51:3550-3555.
Selling, G.W., Hojillaevangelist, M.P., Evangelista, R.L., Isbell, T., Price, N.P., Doll, K.M. 2013. Extraction of proteins from pennycress seeds and press cake. Industrial Crops and Products. 41(1):113-119.
Doll, K.M., Sharma, B.K. 2012. Physical properties study on partially bio-based lubricant blends: Thermally modified soybean oil with popular commercial esters. International Journal of Sustainable Engineering. 5(1):33-37.
Tisserat, B., Harry O Kuru, R.E., Cermak, S.C., Evangelista, R.L., Doll, K.M. 2012. Potential uses for cuphea oil processing byproducts and processed oils. Industrial Crops and Products. 35:111-120.
Doll, K.M., Vermillion, K., Fanta, G.F., Liu, Z. 2012. Diffusion coefficients of water in biobased hydrogel polymer matrices by NMR imaging. Journal of Applied Polymer Science. 125:E580-E585.