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United States Department of Agriculture

Agricultural Research Service


Location: Bio-oils Research

Project Number: 5010-41000-159-00-D
Project Type: In-House Appropriated

Start Date: Oct 1, 2010
End Date: May 18, 2015

The long term objective of this project is to develop new value-added, non-food, non-fuel industrial products from vegetable oil using chemical methods. 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 1 will involve the use of a two step process. Strong acid polymerization catalyst used at relatively high temperatures will cause intermolecular polymerization of the double bonds of soybean oil. Catalyst studied will include trifluorsulfonic acid and fluorosulfuric acid, strong Lewis acids, such as aluminum trichloride, and heterogeneous catalysts such as aluminum doped titania or sulfated treated zirconia. In the second polymerization step, appropriate cross-linking agents will be used to expand the range of available materials to solid materials such as hard resins for composite panels, hydrogels and elastomeric materials for energy absorbing packaging. These polymers will be characterized by techniques such as NMR spectroscopy in order to find a large range of applications. 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. Biosafety exempt.

Last Modified: 06/25/2017
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