2007 Annual Report 1a.Objectives (from AD-416) Support analytical methods development and analysis of developing new crop germplasm and agronomic trials. Crops that will be studied are lesquerella, cuphea and sicklepod (senna). Develop chemical and physical processes for the isolation of new crop raw materials. Oil, protein, starch, glucosinolates and other phytochemicals will be isolated and produced in pilot quantities. Products to be developed include natural pest control chemicals and hydrocolloids. Develop industrial materials through organic synthesis of novel derivatives based on new crop raw materials. Products to be developed include biodegradable lubricants, viscosity and lubricant additives. 1b.Approach (from AD-416) New crops will be developed for several growing regions within the U.S. by developing industrial products from these agricultural feed stocks. New crop development is critical to the future sustainability of U.S. agriculture by reduction of the dependance on government subsidies for a select few commodity crops. Development of cuphea, lesquerella, meadowfoam (limnanthes), milkweed (ascelipias) and sicklepod (senna) will occur through a three prong effort. First, germplasm development will be supported through analytical methods which provide procedures to rapidly analyze protein, oil and starch. GC and HPLC methods for partial seed analysis determination of oil and fatty acids will aid germplasm development. In addition non-destructive methods for oil, protein and starch will be developed using pulsed NMR and NIR technologies. Second, new chemical and physical processes for the isolation of new crop raw materials (oil, protein, starch and phytochemicals) will be established and new crop raw materials produced in pilot scale quantities. Expelling will be conducted with optimization of pre-press conditions (seed tempering with temperature and moisture, flake thickness and dehulling). Isolation of speciality chemicals from defatted meal utilizing enzymatic processes will enhance meal quality and aid in offsetting oil production costs. Lastly, development of industrial materials through organic synthesis of novel derivatives based on new crop raw materials. Products to be developed include biodegradable lubricants, viscosity and lubricant additives, natural pest control chemicals and hydrocolloids. Novel new crop chemical structures will drive the direction of isolation, synthesis, evaluation and scale-up of synthetic efforts. Cooperative efforts with academia for germplasm and agronomic development and industry for product evaluation is crucial to the successful completion of this work. 3.Progress Report The pilot plants new 800 gallon batch oil refiner deodorizer vacuum system is undergoing modifications to make the refiner suitable for physical refining. This pilot facility addressed a crucial need in U.S. new crop development by creating a location where small-scale oil refining of new crop oil seeds and specialty oils could be accomplished. Crude cuphea oil continues to be refined to yield drum quantities of oil. The oil expelling and extruding process is still ongoing for Lesquerella and cuphea. This oil was used to attract potential Cooperative Research and Development Agreement (CRADA)/end-users for cuphea and Lesquerella oil, as well as to support future milestones. All Lesquerella seed on site was cleaned and sent to Technology Crops, Inc (TCI) for the first commercialized grow-out in 2007. In addition, coriander seeds were processed in our facility for the first time; about 400 pounds (lbs) were pressed, yielding four gallons of crude oil which will be evaluated for detergent applications. Cuphea was in the third year of commercialization in 2007. Cooperative work with the research lab in Morris, Minnesota, continued to transfer all new growing conditions and procedures to TCI with many agronomic problems still existing. Directly oversaw and managed two farms of cuphea (about 15 acres) in the Peoria area. Our personnel were responsible for planting, harvest and post-harvest work while utilizing existing corn and soybean farm production equipment. Seeds were processed in our crushing facility and oil was used for future utilization work. Procedures were developed for separating four protein types from the endosperm of the legume in sicklepod. A novel aqueous process for scaling-up the process of the defatted sicklepod endosperm was developed to separate protein and anthraquinones from the bulk of the insolubles. Peaks and Prairies (P&P), Limited Liability Company (LLC), licensed the estolide technology in 2007. P&P is in the second year of its CRADA with the USDA. The CRADA was modified to include a formulation and testing component conducted by the Cereal Products and Food Science Research Unit. Four different estolides have been produced in our pilot facility for P&P this year. They are currently sampling out the products to interested commercial prospects. These estolides of interest had physical properties exceeding other biobased materials in the marketplace. Pennycress development has continued in 2006. A 10-acre direct-planting study was conducted in 2006. Both the oil (biodiesel applications) and the meal (soil fumigant – used to control weeds) are of particular interest. Pennycress is planted in the fall and harvested in late May or early June, thus giving Midwest farmers a two crop/year management practice. Lesquerella research continued at a fast rate, with more than 50 acres planted in late 2006. Products from Lesquerella oil have been developed and have aided in the commercialization of this new crop. Lesquerella oil estolides are being modified to be a viscosity modifier, which could be useful in lubricant applications, and may provide an avenue for large quantities of oil to be commercialized. 4.Accomplishments Cuphea Development: Planted 16 acres of cuphea in Illinois and Ohio in Fiscal Year (FY) 2007; re-evaluating swathing as a possible new harvest method for lower Midwest farmers. Initial swathing in FY 2006 showed great potential benefits to the farmer and processor. About 100 acres were harvested September through October in 2006 across Minnesota. Our facility and the research lab in Morris, Minnesota, continue to transfer all growing conditions and procedures they have discovered to an industrial partner. Synthesis of Derivatives of New Crop Oils: These materials will be evaluated as lubricants. Scaled-up production of coco-oleic and oleic estolides in pilot plant. Completed the synthesis of a very cost-effective tallow-oleic estolide with cold temperature properties comparable with commercially available biobased materials. These new animal-plant estolides have good oxidative stability properties (Rotating Bomb Oxygen Tester) at an extremely low cost. Continued an in-depth estolide study on Lesquerella and castor oil estolides as a potential viscosity modifier. Examined the lab synthesis and optimization of coco-canola and canola estolides from fatty methyl esters. A blown estolide of higher viscosity was developed and physical properties were comparable to materials in windmill gear boxes. Concluded the oxidative stability evaluation of oleic and coco-oleic estolides formulated by the Cereal Products and Food Science (CPF) Research Unit. The CPF Research Unit analyzed the four-ball wear properties of 12 formulated estolide samples, estolide formulation evaluation. Pennycress Development: Ten acres of pennycress were direct-seeded in Peoria County. Future press cake will be evaluated for use as a soil fumigant (weed control agent) and the oil will be evaluated for use as a biodiesel. Pennycress is a winter crop that would give the farmers a second harvestable crop with minimal inputs. Development of Germplasm Analysis Methods: Developed a half-seed analysis method for oil and fatty acid samples of Lesquerella for breeders in Arizona while returning the unused seed portion to the breeder, which remained viable. Remarkably, the breeder would then use the data and half-seed to either continue with that plant's genetics or look at other potential seeds based fatty profile and oil content. Total samples analyzed: 1,876 Brassica and 18 Viscosissima seed samples for fatty acid content and percent oil. Oilseed Processing: Lesquerella oil extraction study (extrusion-expelling process) and production is on-going. Modifications of the new 800 gallon batch oil refiner deodorizer vacuum system in the pilot plant is underway to make the refiner suitable for physical refining. About 1,800 pounds (lbs) of cuphea seeds were screw-pressed for Technology Crops Inc., a Cooperative Research and Development Agreement (CRADA) partner, to sell to a customer. About 1,400 lbs of pennycress seeds were cleaned and 200 lbs cold pressed to produce 12 gallons of crude oil. The oil will be converted to methyl esters for use as a biodiesel. Echium and Buglossoides seeds were hexane-extracted for a CRADA partner. Coriander seeds were processed in our facility for the first time. About 400 lbs of coriander seeds were cleaned, dehulled and kernels separated in preparation for screw pressing. The kernel fraction accounted for 52% (208 lbs) of the total weight and had 26% oil content, 44% higher than the starting seed. The heavy fraction was cooked and dried to around 5% moisture content before screw pressing. The four gallons of crude oil will be evaluated for detergent applications. Sicklepod: A novel aqueous process was developed for scaling-up the processing of the defatted sicklepod endosperm. This separated the water-soluble polysaccharides, water-soluble proteins and anthraquinones from the bulk of the insoluble proteins and glycoproteins which could later be reprocessed into their respective classes. Polysaccharides were recovered after coagulating the soluble proteins in the centrifugate and passing the aqueous filtrate through amberlite that adsorbed the anthraquinones. Method development for released anthraquinones enabled identification of several anthraquinones and their glycosides using electrospray ionization Liquid Chromatography-Mass Spectrometry-Mass Spectrometry (LC-MS-MS) techniques. Estolide Commercialization: Peaks and Prairies (P&P), Limited Liability Company (LLC), has licensed the estolide technology in 2007, which demonstrates the extreme value of this technology to industrial users. P&P is in the second year of the CRADA with the USDA. Four separate estolide production runs have begun in our pilot plant facility for commercial samples. Sample Requests/Crop Development: New Crops and Processing Technology personnel have supplied industrial partners and interested parties with cuphea oil, Lesquerella oil, pennycress oil, coriander oil, echium oil, buglossoides oil, and various versions of estolides for industrial evaluation. We have on-going crop development groups for cuphea (annual meeting) and Lesquerella (bi-annual meetings) with everyone involved, from growers to end-users, to make sure the best information is available to everyone. All accomplishments listed are relevant to the National Program 306, Quality and Utilization of Agricultural Products, Component 2–New Processes, New Uses and Value-Added Foods and Biobased Products, Problem Areas 2a-New Product Technology and 2c-New Improved Processes and Feedstocks. 5.Significant Activities that Support Special Target Populations New crops research offers economic opportunities to small and limited resource farmers through the development of cuphea, pennycress, coriander, milkweed, and lesquerella crops. 6.Technology Transfer Number of new CRADAs and MTAs 1 Number of active CRADAs and MTAs 3 Number of invention disclosures submitted 1 Number of patent granted 2 Number of U.S. patents granted 1 Number of new commercial licenses granted 1 Number of non-peer reviewed presentations and proceedings 51 Number of newspaper articles and other presentations for non-science audiences 26 Review Publications 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. Phippen, W.B., Isbell, T., Phippen, M.E. 2006. Total seed oil and fatty acid methyl ester contents of cuphea accessions. Industrial Crops and Products. 24(1):52-59. Hojillaevangelist, M.P., Evangelista, R.L. 2006. Effects of cooking and screw-pressing on functional properties of Cuphea PSR23 seed proteins. Journal of the American Oil Chemists' Society. 83:(8):713-718. Evangelista, R.L., Wu, Y.V., Hojilla-Evangelista, M.P. 2006. Characterization of proteins in Cuphea (PSR23) seeds. Journal of the American Oil Chemists' Society. 83(9):785-790. Biresaw, G., Cermak, S.C., Isbell, T. 2007. Film-forming properties of estolides. Tribology Letters. 27(1):69-78. Forcella, F., Spokas, K.A., Gesch, R.W., Isbell, T., Archer, D.W. 2007. Swathing and Windrowing as Harvest Aids for Cuphea. Agronomy Journal. 99: 415-418. Cermak, S.C., Skender, A.L., Deppe, A.B., Isbell, T. 2007. Synthesis and physical properties of tallow-oleic estolide 2-ethylhexyl esters. Journal of the American Oil Chemists' Society. 84(5):449-456. Finkenstadt, V.L., Liu, C., Evangelista, R.L., Liu, L.S., Cermak, S.C., Hojillaevangelist, M.P., Willett, J.L. 2007. Poly(lactic acid) green composites using oilseed coproducts as fillers. Industrial Crops and Products. 26(1):36-43. Kuo, T., Isbell, T., Rooney, A.P., Levinson, W.E., Frykman, H.B. 2007. Production of 14-oxo-cis-11-eicosenoic acid from lesquerolic acid by Sphingobacterium multivorum NRRL B-23212. Journal of the American Oil Chemists' Society. 84(7):639-643. Cermak, S.C., John, A.L., Evangelista, R.L. 2007. Enrichment of Decanoic Acid in Cuphea Fatty Acids via Distillation. Industrial Crops and Products 26(1):93-99. Dierig, D.A., Salywon, A.M., Tomasi, P., Dahlquist, G.H., Isbell, T. 2006. Variation of seed oil composition in parent and s1 generations of Lesquerella fendleri (brassicacae). Industrial Crops and Products. 24(3):274-279.