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United States Department of Agriculture

Agricultural Research Service

2008 Annual Report

1a.Objectives (from AD-416)
Establish different reaction protocols to insert branching and transesterification on triglyceride molecule of vegetable oil for use in the formulation of industrial/automotive lubricants with better lubricity, friction, wear, oxidation and low temperature properties. Such fluids include, but are not restricted to: (a) Bio-based Greases; (b) Synthetic Lubricants/Metalworking Fluids/Gear Oils/Under-carriage Oils; (c) Bio-based Specialty Additives. Investigate and develop economically feasible polymeric products from vegetable oils (with emphasis on soybean oil) and thus, expand their domestic and export markets. These biobased polymeric materials include, but are not restricted to: (a) Soybased composites reinforced with flax fibers; (b) Nanoclay reinforced soybased composites; (c) Polymeric surfactants derived from soybean oil; (d) Soybased hydrogel for controlled delivery system; (e) Energy absorbing materials.

1b.Approach (from AD-416)
Research will focus on establishing different reaction protocols to insert branching and trans-esterification, on triglycerid molecule of soybean oil that will be used in the formulation of biobased grease, synthetic lubricants, metal-working fluids, biobased specialty additives with better lubricity, friction, wear, oxidation and low temperature properties.

Research will also utilize the principles of organic chemistry and polymer science to synthesize more reactive soybean oil based monomers. New types of polymers and composites will be developed. Resulting polymers will be used in controlled delivery systems and energy absorbing materials formulations.

3.Progress Report
Significant progress was made in the project and all of the milestones were accomplished. Useful structure to property relationships for soybean oil-based lubricating greases were uncovered. The use of an epoxidized soybean oil base oil was found to improve oxidative stability in the system. Lubrication fluids were also made at a large laboratory scale and supplied to industrial partners. The fluids were also evaluated in-house for stability and friction reduction. In a collaboration with outside partners, soybean oil-based hydrogels were tested for use in drug release formulations. Work was also finished on the synthesis of a poly-soap from vegetable oil. This material has good detergent properties and has had its physical properties measured. Another project was finished where advanced composite materials were made using soybean oil and citric acid. The resins, which were developed at the National Center for Agricultural Utilization Research (NCAUR), were used by an industrial partner to fabricate panels for structural use. Natural agricultural products are not able to meet the performance requirements of industry, in many areas. The work we have performed using additives and chemical modification have increased the performance of these materials. Additionally, the knowledge which we have gained has increased our ability to provide even more enhancement of properties in the future. This research progress addresses National Program 306, Component 2 of the Action Plan.

1. Resin for use in composite panels. There is need for a readily available biobased resin which has the physical properties necessary for use in structural materials. It is of even higher interest when the composite materials are also biobased, leading to a material with a high natural content. We developed a resin technology which was used by an industrial partner to fabricate structural panels from soybean oil. The resin technology, based on soybean oil, was made at the National Center for Agricultural Utilization Research (NCAUR). The parameters of the formulations were evaluated and optimized, and samples were provided to an industrial partner. The partner fabricated the structural panels using state-of-the-art methods, then the panels were sent back to NCAUR for physical properties evaluation. The resin technology allowed the partner to use a variety of different composite materials, and could be useful in several different markets. A potential patent has been discussed with the partner. This accomplishment directly addresses NP306, Component 2, Problem Area 2a of the Action Plan.

5.Significant Activities that Support Special Target Populations

6.Technology Transfer

Number of New CRADAS1
Number of Active CRADAs1
Number of the New MTAs (providing only)1
Number of Invention Disclosures Submitted1
Number of Non-Peer Reviewed Presentations and Proceedings1
Number of Other Technology Transfer1

Review Publications
Doll, K.M., Erhan, S.Z. 2008. Synthesis of cyclic acetals (ketals) from oleochemicals using a solvent free method. Green Chemistry. 10(6):712-717.

Doll, K.M., Kenar, J.A., Erhan, S.Z. 2008. Carbonates from oleochemicals: Biobased materials to value added green chemicals. Chemistry Today/Chimica Oggi. 25(6):7-10.

Doll, K.M., Sharma, B.K., Suarez, P.A., Erhan, S.Z. 2008. Comparing biofuels obtained from pyrolysis, of soybean oil or soapstock, with traditional soybean biodiesel: density, kinematic viscosity, and surface tensions. Energy and Fuels. 22(3):2061-2066.

Sharma, B.K., Doll, K.M., Erhan, S.Z. 2008. Biobased greases: soap structure and composition effects on tribological properties. In: Biresaw, G., Mittal, K.L., editors. Surfactants in Tribology. Boca Raton, FL: CRC Press. p. 309-323.

Sharma, B.K., Perez, J.M., Erhan, S.Z. 2007. Soybean oil-based lubricants: a search for synergistic antioxidants. Energy and Fuels. 21:2408-2414.

Doll, K.M., Sharma, B.K., Erhan, S.Z. 2007. Synthesis of branched methyl hydroxy stearates including an ester from bio-based levulinic acid. Industrial and Engineering Chemistry Research. 46:3513-3519.

Kurth, T.L., Sharma, B.K., Doll, K.M., Erhan, S.Z. 2007. Adsorption behavior of epoxidized fatty esters via boundary lubrication coefficient of friction measurements. Chemical Engineering Communications. 194:1065-1077.

Kurth, T.L., Byars, J.A., Cermak, S.C., Sharma, B.K., Biresaw, G. 2007. Non-linear adsorption modeling of fatty esters and oleic estolides via boundary lubrication coefficient of friction measurements. Wear. 262(5-6):536-544.

Sharma, B.K., Doll, K.M., Erhan, S.Z. 2008. Ester hydroxy derivatives of methyl oleate: tribological, oxidation and low temperature properties. Bioresource Technology. 99(15):7333-7340.

Xu, J., Liu, Z., Erhan, S.Z. 2008. Viscoelastic properties of a biological hydrogel produced from soybean oil. Journal of the American Oil Chemists' Society. 85(3):285-290.

Carrao-Panizzi, M.C., Erhan, S.Z. 2007. Environmental and genetic variation of soybean tocopherol content under Brazilian growing conditions. Journal of the American Oil Chemists' Society. 84:921-928.

Sharma, B.K., Liu, Z., Adhvaryu, A., Erhan, S.Z. 2008. One-pot synthesis of chemically modified vegetable oils. Journal of Agricultural and Food Chemistry. 56:3049-3056.

Biswas, A., Sharma, B.K., Willett, J.L., Erhan, S.Z., Cheng, H.N. 2008. Room-temperature self-curing ene reactions involving soybean oil. Green Chemistry. 10(3):298-303.

Biresaw, G., Liu, Z., Erhan, S.Z. 2008. Investigation of the surface properties of polymeric soaps obtained by ring-opening polymerization of epoxidized soybean oil. Journal of Applied Polymer Science. 108(3):1976-1985.

Liu, Z., Erhan, S.Z., Akin, D.E., Barton Ii, F.E., Onwulata, C.I., Mckeon, T.A. 2008. Modified flax fibers reinforced soy-based composites: mechanical properties and water absorption behavior. Composite Interfaces. 15:207-220.

Liu, Z., Erhan, S.Z. 2008. "Green" composites and nanocomposites from soybean oil. Materials Science and Engineering A. 483-484(1-2c):708-711.

Doll, K.M., Moser, B.R., Sharma, B.K., Erhan, S.Z. 2007. Current uses of vegetable oil in the surfactant, fuel, and lubrication industries. Chemistry Today/Chimica Oggi. 24(6):41-44.

Last Modified: 4/18/2014
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