Location: Bio-oils Research Unit
2011 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 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.
Xu, Q., Nakajima, M., Liu, Z., Shiina, T. 2011. Biosurfactants for microbubble preparation and application. International Journal of Molecular Sciences. 12:462-475.
Biswas, A., Sharma, B.K., Doll, K.M., Willett, J.L., Erhan, S.Z., Vermillion, K., Cheng, H. 2009. Synthesis of an amine-oleate derivative using an ionic catalyst. Journal of Agricultural and Food Chemistry. 57(1):8136-8141.
Doll, K.M., Erhan, S.Z. 2011. Evaluation of a sugar based edible adhesive utilizing a tensile strength tester. Journal of the Association for Laboratory Automation. 16(2):153-156.
Doll, K.M., Sharma, B. 2011. Emulsification of chemically modified vegetable oils for lubricant use. Journal of Surfactants and Detergents. 14:131-138.
Doll, K.M., Sharma, B.K. 2011. Surfactant effects on bio-based emulsions used as lubrication fluids. In: Biresaw, G., Mittal, K.L., editors. Surfactants in Tribology. Vol 2. Boca Raton, FL: Taylor & Francis. p. 173-190.
Sharma, B.K., Doll, K.M., Erhan, S.Z. 2011. Chemically modified fatty acid methyl esters: their potential for use as lubrication fluids and surfactants. In: Biresaw, G., Mittal, K.L., editors. Surfactants in Tribology. Vol 2. Boca Raton, FL: Taylor & Francis. p. 387-408.
Liu, Z., Biresaw, G. 2011. Synthesis of soybean oil-based polymeric surfactants in supercritical carbon dioxide and investigation of their surface properties. Journal of Agricultural and Food Chemistry. 59:1909-1917.
Xu, Q., Nakajima, M., Liu, Z., Nakamura, N., Shiina, T. 2011. Evaluation of a novel soybean oil-based surfactant for fine emulsion preparation. Household and Personal Care Today. p. 13-15.
Liu, Z., Rempel, G.L. 2011. Removal of transition metals from dilute aqueous solution by carboxylic acid group containing absorbent polymers. Hydrology: Current Research. 2(1):1-6.