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United States Department of Agriculture

Agricultural Research Service

Research Project: INDUSTRIAL PRODUCTS FROM NEW CROPS
2008 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
Our pilot facility addresses a crucial need in United States new crop development by providing small-scale oil refining of new crop oil seeds and specialty oils. Some new equipment has been added to our arsenal: a manually operated hydraulic press, a one-liter oil extractor and a one-gallon (gal) deodorizer to extract oil from small quantities of seeds. In addition, a high-speed disk stack three-phase centrifuge and a clean steam generator were added for use with the 100-gal oil refiner. Current work in the pilot plant includes: crude cuphea and lesquerella oil continues to be refined to yield drum quantities of oil. The oil expelling and extruding process is still on-going for lesquerella, pennycress 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.

Cooperative cuphea development with the North Central Soil Conservation Research Lab in Morris, Minnesota, continued in Fiscal Year (FY) 08 as all new growing conditions and procedures were transferred to Technology Crops, Inc (TCI), though many agronomic problems still exist. Directly managed two farms of cuphea (~10 acres) in the Peoria, Illinois, area. Our personnel were responsible for planting, harvesting and post-harvesting work while utilizing existing corn and soybean farm production equipment. Seeds were processed at our crushing facility and oil used for future utilization work. Drum quantities of crude cuphea were processed and sent to TCI to aid in the commercialization of cuphea in 2008.

Germplasm analysis and method development continued in FY 08 to support new crop breeding and research programs.

Peaks and Prairies (P&P), Limited Liability Company (LLC), has continued to license the estolide technology. P&P is in the process of renewing its CRADA with the United States Department of Agriculture. The CRADA will still include a formulation and testing component conducted by the Cereal Products and Food Science Research Unit in Peoria, Illinois. P&P is in the first year of commercial estolide production and is utilizing our pilot plant facilities. During FY 08, four different estolides have been produced for sampling products to interested commercial prospects. These estolides have physical properties that exceeded other bio-based materials in the marketplace.

Pennycress development has continued in 2007-2008. A 10-acre direct planting study was conducted in FY 08. Both the oil (bio-diesel 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 products have been developed and continue to be developed to aid in the commercialization of this new crop. About 900 gals of filtered crude oil has been accumulated. Another 9,000 lbs of seeds from the 2007 harvest has been cleaned and is ready for further processing. This research addresses NP 306, Component 2.


4.Accomplishments
1. CUPHEA DEVELOPMENT. Planted 10 acres of cuphea in Illinois for Fiscal Year (FY) 08, planning to re-evaluate the swathing of cuphea as a possible new harvest method for the upper Midwest farmers. Initial swathing in FY 08 showed conflicting reports compared to FY 07, but having an effective swathing method would be a great potential benefit to farmers and processors. The National Center of Agricultural Utilization Research (NCAUR), Peoria, Illinois, and the North Central Soil Conservation Research Lab in Morris, Minnesota, continue to transfer all growing conditions and procedures they have discovered to an industrial partner. The development of cuphea will lead to a United States lauric (coconut type) source of oil. The research addresses NP 306, Component 2, Problem Area 2c.

2. ESTOLIDE COMMERCIALIZATION. Peaks and Prairies (P&P), Limited Liability Company (LLC), has continued to license the estolide technology in 2008, which demonstrates the extreme value of this technology to industrial users. P&P is in the process of renewing their expired Cooperative Research and Development Agreement (CRADA) with the United States Department of Agriculture. P&P is in the first year of commercial estolide production and is utilizing our pilot plant facilities. During FY 08, four different estolides have been produced (~10 drums) for sampling products to interested commercial prospects. The estolides will be used as a bio-based lubricant in the U.S. market. The research addresses NP 306, Component 2, Problem Area 2c.

3. SYNTHESIS OF DERIVATIVES OF NEW CROP OILS. These materials will be evaluated for potential as a bio-based lubricant. We scaled-up production of a free acid estolide in our pilot plant. 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 series of blown estolides of higher viscosity were evaluated in the Rotating Bomb Oxygen Tester (RBOT) for resistance to oxidation. A series of hydroxyl compounds were synthesized from new crop oils. A new method for the lactonation of meadowfoam oil and fatty acids was explored. A study on the position of the estolide linkage was started in FY 08. The Cereal Products and Food Science Research Unit at NCAUR analyzed estolides for P&P for wear properties and formulation advice. Development of new chemical products will lead to the advancement of current and other industrial crops. The research addresses NP 306, Component 2, Problem Area 2c.

4. PENNYCRESS DEVELOPMENT. A ten acre planting study of Pennycress was conducted in FY 2008 in Peoria County, Illinois. About 800 pounds (lbs) of Pennycress seed were cleaned and density-graded, separating 550 lbs of seeds for planting and 250 lbs for oil extraction from a wild harvest. 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 bio-diesel. The development of pennycress will allow the United States farmer to produce two crops per year on one field: one for food and one for fuel. The research addresses NP 306, Component 2, Problem Area 2c.

5. OILSEED PROCESSING. The Lesquerella oil extraction study (extrusion-expelling process) and production are still on-going. Some new equipment has been added to our pilot plant: a hydraulic press, a one-liter oil extractor and a one-gallon deodorizer to extract oil from small quantities of seeds. In addition, a high-speed disk stack three-phase centrifuge and a clean steam generator were added for use with the 100-gallon oil refiner. Cuphea oil has been extracted from whole seed, either by screw pressing or by solvent extraction. The crude oil is dark green in color due to high levels of chlorophyll, about 10-15 times than that of rapeseed. Removing the green color requires 6-8% (w/w) of bleaching clay, which also absorbs oil, thus increasing refining losses. The feasibility of mechanical dehulling of cuphea seeds to reduce chlorophyll levels in the crude oil was investigated. The process included seed tempering (moisture adjustment and cooking), roller and impact milling, screening, aspirating, and density grading. With the optimum conditions established, the crude oil extracted by hexane contained 86% less chlorophyll than what was extracted from whole seeds. Although no further hull separation was performed on the fines fraction, a 70% reduction in chlorophyll content in the oil was still achieved. During FY 08, about 900 gallons of filtered crude Lesquerella oil has been accumulated. Another 9,000 lbs of seeds from the 2007 harvest has been cleaned and is ready for further processing. The ability to process small volumes of specialty seeds and oil is a must; refined oils are needed for future testing and procedure development. The research addresses NP 306, Component 2, Problem Area 2c.

6. DEVELOPMENT OF GERMPLASM ANALYSIS METHODS. Analyzed 100 Camelina accessions for free acid content and percent oil for breeders in Nebraska. Analyzed 1,000 Brassica accessions for free acid content and percent oil in a corporative study with the Plant Introduction Station in Ames, Iowa. In addition, more than 140 Jojoba accessions were analyzed for free acid content and percent oil for the National Plant Germplasm System. The continued analysis of accessions allows the breeders the information they need to make plant selections and to monitor breeding progress. The research addresses NP 306, Component 2, Problem Area 2a.

7. SICKLEPOD. A new method for the extraction and separation of novel phenolic compounds from the seed meal have been developed. Liquid Chromatography-Mass Spectrometry (LC-MS) methods have been developed to analyze the products of the extractions. Currently, the identification of these phenolic compounds and glucosidal compounds are being confirmed. Follow-up work includes identifying the importance of these compounds in the seed. In addition, the novel aqueous process that was developed in FY 07 for scaling-up the processing of the defatted sicklepod endosperm was further improved. The development of new methods for sicklepod will allow researchers to analyze products faster and more accurately. The research addresses NP 306, Component 2, Problem Area 2a.

8. SAMPLE REQUESTS/CROP DEVELOPMENT. New Crops and Processing Technology Research unit 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, which leads to the most current procedures and practices being applied to our research. The research addresses NP 306, Component 2, Problem Area 2a.


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 Active CRADAs3
Number of Non-Peer Reviewed Presentations and Proceedings2
Number of Newspaper Articles and Other Presentations for Non-Science Audiences4

Review Publications
Moser, B.R., Cermak, S.C., Isbell, T. 2008. Evaluation of castor and lesquerella oil derivatives as additives in biodiesel and ultralow sulfur diesel fuels. Energy and Fuels. 22:1349-1352.

Kuo, T., Rooney, A.P., Isbell, T. 2008. Conversion of lesquerolic acid to 14-oxo-11(Z)-eicosenoic acid by genetically variable Sphingobacterium multivorum strains. Current Microbiology. 57:55-60.

Holser, R.A., Harry O Kuru, R.E., Vaughn, S.F., Himmelsbach, D.S. 2008. Preparation and characterization of 4-methoxy cinnamoyl glycerol. Journal of the American Oil Chemists' Society. 85(4):347-351.

Cermak, S.C., Biresaw, G., Isbell, T. 2008. Comparison of a New Estolide Oxidative Stability Package. Journal of the American Oil Chemists' Society. 85(9):879-885.

Isbell, T.A., Mund, M.S., Evangelista, R.L., Dierig, D.A. 2008. Method for analysis of fatty acid distribution and oil content on a single lesquerella fendleri seed. Industrial Crops and Products. 28(2):231-236.

Last Modified: 4/18/2014
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