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United States Department of Agriculture

Agricultural Research Service

2009 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; and (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
The accomplishments in this project over the term have continued toward the goal of developing technology to increase the suitability and acceptability of vegetable oil based products in non-traditional applications. All of the milestones set for this year have been accomplished. Additionally, the work has resulted in a total of four docket disclosures. These disclosures cover a variety of materials, including a new polymeric form of vegetable oil which can be used in chewing gum production and a new selection of additives which will improve the extreme pressure lubrication properties of bio-based lubricants. Two of the disclosures were accepted, and are in the docket of the patent committee awaiting patent preparation. The others both received deferments, indicating that they are suitable to be patented with some additional information. Samples of lubrication products have been sent out to several companies, which are hopeful in using these products in their formulations. In work that is complimentary to these milestones, a new method utilizing low resolution nuclear magnetic resonance (NMR) spectroscopy in order to determine the physical properties of a polymer was developed and published. Although these technologies are too new to judge completely, the amount of interest that they are drawing from industrial companies is promising. If put into practice, there is potential for the gum material to enter into a market which is both highly valued, and highly visible. The lubrication fluids are vying for a less visible market, but one that is also quite large. They bring the added benefit that in addition to being bio-based themselves, these fluids are designed to work with lubricants that are also bio-based. All of these are steps towards the new agriculturally based economy of the future.

1. New gum material. There are over 650,000 metric tons of chewing gum produced (2005 statistic) every year, which could increase to over 1 million metric tons annually in the next 5 years. That corresponds to be over 374 trillion sticks of chewing gum not including bubble gum balls/chiclets. People are sick and tired of stepping in waste chewing gum litter which is everywhere; on the sidewalks, under tables etc. Gum material currently used on the market suffers from drawbacks of poor digestibility, and/or poor biodegradability. Most of these raw materials made natural rubber or some from expensive carbohydrate materials. A new chewing gum elastomer was made from soybean oil by using a new polymerization method. This material has good flavor delivery ability, is rapidly biodegradable, and is digestible overcoming the deficiencies in current commercial products. A docket disclosure has been approved on this invention, and a patent application will be prepared. Additionally, samples of this material have been tested by commercial customers, with favorable results. Discussion of scaling up this process in a collaborative effort is underway. The potential impact of this will improve the quality of a huge retail market, and be another example for uses from the American Agricultural industry.

2. New phosphorous containing lubricant additives. Currently, many lubricant additives are based on materials which are not adequately soluble in natural oils in order to be effective. A new phosphorous containing lubricant additive was made from soybean oil using a new catalyst. A series of different catalysts were tried and the reactivity of the best one has been reported. The chemistry will work, not only on soybean oil, but on any oil which has the same chemical structure. The new compounds will enhance the friction reducing ability of oils that they are added to, and because lubricant additives are premium priced, they are of interest to manufacturers. A docket disclosure was filed for this invention, and if it is developed, it has the potential to increase the acceptance of biobased lubricants into many new markets.

6.Technology Transfer

Number of Active CRADAs1
Number of the New/Active MTAs (providing only)12
Number of Invention Disclosures Submitted4

Review Publications
Suarez, P.A., Pereira, M.S., Doll, K.M., Sharma, B.K., Erhan, S.Z. 2009. Epoxidation of Methyl Oleate using Heterogeneous Catalyst. Journal of Industrial and Engineering Chemical Research. 48:3268-3270.

Doll, K.M., Erhan, S.Z. 2009. Polyol and Amino Acid-Based Biosurfactants, Builders, and Hydrogels. In: Hayes, D.G., Kitamomo, D., Solaiman, D.K.Y., Ashby, R.D., editors. Biobased Surfactants and Detergents: Synthesis, Properties, and Applications. Urbana, IL: AOCS Press. p. 425-448.

Erhan, S.Z., Sharma, B.K., Doll, K.M. 2009. Opportunities for Industrial Uses of Agricultural Products. Chemistry Today/Chimica Oggi. 27(1):38-41.

Erhan, S.Z., Sharma, B.K., Doll, K.M. 2009. Production of Agricultural Commodities in the United States. Chemistry Today/Chimica Oggi. 27(1):34-36.

Doll, K.M. 2009. A Convenient Low-Resolution NMR Method for the Determination of the Molecular Weight of Soybean Oil-Based Polymers. Journal of the Association for Laboratory Automation. 14(4):185-189.

Doll, K.M., Sharma, B.K., Erhan, S.Z. 2008. Friction reducing properties and stability of epoxidized oleochemicals. Clean. 36(8):700-705.

Biswas, A., Sharma, B.K., Willett, J.L., Erhan, S.Z., Cheng, H. 2008. Soybean Oil as a Renewable Feedstock for Nitrogen-Containing Derivatives. Energy and Environmental Science. 1:639-644. Available:

Liu, Z., Erhan, S.Z. 2008. A new soy-based hydrogels: development, viscoelastic properties, and application for controlled drug release. In: Parris, N., Liu, L.S., Song, C. and Shastri, V.P., editors. New Delivery Systems for Controlled Drug Release from Naturally Occurring Materials. American Chemical Society Symposium Series 992, Chapter 2. Washington, DC: ACS Press. p. 17-38.

Liu, Z., Erhan, S.Z. 2009. Synthesis of Soy Polymers Using a "Green" Processing Method. In: Celina, M.C., Wiggins, J.S., Billingham, N.C., editors. Polymer Degradation and Performance. Chapter 7. Washington, DC: American Chemical Society. p. 70-87.

Last Modified: 4/20/2014
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