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United States Department of Agriculture

Agricultural Research Service

Research Project: INDUSTRIAL PRODUCTS FROM NEW CROPS
2006 Annual Report


1.What major problem or issue is being resolved and how are you resolving it (summarize project aims and objectives)? How serious is the problem? Why does it matter?
This project is aligned with the National Program 306, Quality and Utilization of Agricultural Products. Commodity farming in the U.S. has been plagued by overproduction and maintained only by government subsidies. Even with heavy subsidies, farm failures are still at an all time high in most regions of the U.S. Even more costly is the loss of diversity on the farm, which has resulted in resistant pests and increased use of manufactured chemicals to maintain control. Of particular note is the emergence of corn root worm damage in first year corn. Utilization efforts for commodity raw materials has lent little relief to farmers who have seen commodity prices fall to record lows, yet input costs for production are rising. New crops in rotation with commodity crops will provide an unsubsidized crop that will provide real farm income, introduction of new raw materials and provide ecological benefits through farm diversification. The challenges to new crop development are twofold. One, the agronomics of the crop must be favorable. Two, the raw materials produced must be novel (little or no domestic source) and have superior performance to their closest competitor.

The development of new and alternative crops, enhancement of product quality during harvest storage and transport, development/improvement of methods of extraction, purification and manufacture, identification of new sources of natural products as nutriceutical and biopesticides, and development of non-food products and undervalued by-products of agriculture are relevant to program components of the National Program 306, Quality and Utilization of Agricultural Products.


2.List by year the currently approved milestones (indicators of research progress)
FY 2005 (Year 1): Complete the impact of cuphea rotation on corn root-worm in first year corn.

Develop a partial seed analysis method for determining the fatty acid profiles of lesquerella, which will direct germplasm selections.

Develop an Ultra Violet(UV) anthraquinone method and a near infrared (NIR) method for oil, protein and carbohydrate to guide sicklepod germplasm selections.

Complete oil extraction studies for pilot scale processing of cuphea seed.

Complete oil extraction and refining studies for pilot scale processing of Lesquerella.

Complete laboratory dehulling and fractionation of sicklepod seed.

Complete oil extraction study of milkweed seed.

Complete estolide number study for oleic monoestolides and the effect of capping chain length on pour points.

Provide technical assistance for the commercial production of oleic estolides.

Produce pilot scale quantities of Lesquerella estolides.

FY 2006 (Year 2): Provide oversight of 2,000 acres of cuphea production.

Support germplasm development by pulsed Nuclear Magnetic Resonance (NMR), solid state NMR and partial seed Gas Chromatography (GC) analysis for selection of improved lesquerolic acid content and natural estolides.

Transfer UV anthraquinone analysis method to breeders for sicklepod germplasm development.

Complete cuphea oil refining studies.

Crush 80,000 lbs. of Lesquerella seed for oil which will supply initial market testing.

Develop pilot scale fractionation methods to separate protein, oil and starch in sicklepod.

Complete milkweed nematocide characterization.

Study the effects of chainlength of capping group on pour points of diestolides.

Provide oversight as needed for oleic estolide commercial production.

Synthesize and explore physical properties of Lesquerella estolides.

Begin the synthesis of viscosity modifier based on vegetable oils.

FY 2007 (Year 3): Provide oversight for the full commercial production of capric cuphea.

Support germplasm development by pulsed NMR, solid state NMR and partial seed GC analysis for selection of improved lesquerolic acid content and natural estolides.

Oversee commercial Lesquerella extraction and processing.

Oversee commercial cuphea extraction and processing.

Begin the development method for the pilot scale isolation of anthraquinones from sicklepod.

Determine the effect of estolide linkage position on physical properties.

Evaluate the physical properties of lesquerolic acid estolides.

Continue the synthesis of viscosity modifiers and begin their performance evaluation.

Provide oversight as needed for oleic estolide commercial production.

FY 2008 (Year 4): Provide oversight for the full commercial production of capric cuphea.

Support germplasm development by pulsed NMR, solid state NMR and partial seed GC analysis for selection of improved lesquerolic acid content and natural estolides.

Oversee commercial Lesquerella extraction and processing.

Oversee commercial cuphea extraction and processing.

Complete the development method for the pilot scale isolation of anthraquinones from sicklepod.

Complete the synthesis of milkweed nematocidal derivatives.

Complete the synthesis of viscosity modifiers and their performance evaluation.

Provide oversight as needed for oleic estolide commercial production.

FY 2009 (Year 5): Germplasm development of lauric cuphea.

Support germplasm development by pulsed NMR, solid state NMR and partial seed GC analysis for selection of improved lesquerolic acid content and natural estolides.

Oversee commercial Lesquerella extraction and processing.

Oversee commercial cuphea extraction and processing.

Oversee commercial production of sicklepod gums.

Complete the nematocide field trials.

Produce pilot scale quantities of lesquerolic acid estolides.

Complete evaluation of viscosity modifiers.

Provide oversight as needed for oleic estolide commercial production.

Evaluate physical properties of linkage position estolides.


4a.List the single most significant research accomplishment during FY 2006.
Cuphea Commercialization: Cuphea was in the second year of commercialization in 2006. Acres have increased dramatically in the Midwest and products are being developed by an end-user. Seeds harvested from this grow-out again will serve two purposes. First, supply a high value product from cuphea oil and, secondly, to provide sufficient quantities of seed for increased production in 2007, all of which is relevant to the National Program 306 Component - New Processes, New Uses and Value-Added Foods and Biobased Products.


4b.List other significant research accomplishment(s), if any.
All accomplishments listed are relevant to the National Program 306 Component - New Processes, New Uses and Value-Added Foods and Biobased Products.

Purification of Lesquerolic Acid: Performed a distillation study for the isolation of methyl lesquerolate by molecular distillation. Obtained fractions with purities of 93-96% lesquerolic acid. This material is serving as a starting material for the synthesis of higher estolide oligomers.

Synthesis of Derivatives of New Crop Oils: These materials will be evaluated as lubricants. Scaled-up production of coco-oleic estolides in pilot plant. Completed the synthesis and physical properties of mono-capped oleic estolides. 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 Testor) at an extremely low cost. Initiated 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. Oxidative stability evaluation of oleic and coco-oleic estolides was formulated by the Cereal Products Research Unit at NCAUR.

Pennycress Development: Harvested five acres of pennycress and obtained 1,460 lbs. of seed at 10.7% moisture. The seed contained 35% oil on a dry basis with 37% erucic acid. Two hundred pounds of pennycress seeds were cold pressed, keeping the myrosinase enzyme active. The press cake was evaluated for use as soil fumigant (weed control agent). The oil will be evaluated for use as bio-diesel.

Development of Germplasm Analysis Methods: Developed an analysis method for lesquerolic acid determination in yeast samples for breeders in Arizona. Analyzed 196 accessions of Lesquerella in four replicates for the Lesquerella curator in California, and this data set will be placed in the Genetic Resources Information Network (GRIN) system. Completed the study on the Gas Chromatography (GC) separation of petroselinic acid from oleic acid. This research demonstrated that ethyl esters of coriander and an isothermal GC run will provide good quantitation of both of these isomers.

Cuphea Commercialization: Planted 28 acres of cuphea in Illinois and Ohio in FY 2006, going to evaluate swathing as a possible harvest method for lower Midwest farmers. Cuphea was successfully grown and harvested on sandy irrigated soils in Havana, IL (three acres).

Estolide Commercialization: Peaks and Prairies, LLC, has filed through the National Registry to license the estolide technology in 2006, which demonstrates the extreme value of this technology to industrial users.

Oilseed Processing: Lesquerella oil extraction study and production is still on-going. Procedure for dewinging milkweed seeds was established. Crude cuphea oil was refined following the procedure established by POS Pilot Plant Corporation (2004). Four drums of crude oil were degummed, alkali refined, bleached, and deodorized (RBD) using our new 800 gallon batch oil refiner. Two drums of RBD cuphea oil were produced, which is the largest supply of cuphea oil in the world. To date, five drums of crude oil have been accumulated from trial and data collection runs. Start up of the new 800 gallon batch oil refiner in pilot plant. Modifications of the deodorizer’s vacuum system are underway to make the refiner suitable for physical refining. About 150 lbs. of Camelina seeds were cold pressed and the oil is currently being evaluated for use in food application.

Purification of Sicklepod Gums: Lab-scale method for fractionating sicklepod seed components into anthraquinones, proteins and polysaccharides was not practicable at the kilogram (kg) scale because of interference from soluble proteins content, so a new extraction method was developed. Five-gallon buckets of anthraquinones have been extracted initially using both ethanolic HCl and ethanolic NH4OH, respectively, from 200 kg of sicklepod meal. Kilogram quantities of defatted sicklepod meal were extracted using water-acetone. Anthraquinones were co-extracted with polysaccharides in this solvent system and were recovered using a 42-liter liquid-liquid extractor. Two types of anthraquinones, the glycosylated and the free species, were partitioned into dichloromethane and diethyl ether, respectively, from the aqueous mixture. The two problems in the recovery of sicklepod polysaccharides (galactomannan) have been overcome, which were the presence of anthraquinones and proteins which tend to co-extract.

Milkweed Nematacide Characterization: Reproducible FT-IR data of specific High Pressure Liquid Chromatography (HPLC) fractions of the milkweed species suggest the active nematicide compound is a peptide.


4c.List 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, milkweed, and lesquerella crops.


4d.Progress report.
The pilot plant refiner facility was completely finished at NCAUR. 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. Drums of cuphea crude oil have been refined, bleached and deodorized (RBD) in our facility to yield about 100 gallons of refined oil. This oil was used to obtain a potential CRADA/end-user for cuphea oil in the cosmetics industry, as well as to support future milestones. Also, all Lesquerella seed on site were cleaned and are ready for pressing early this next report year 2007. The oil will be used to further develop lubricant work at NCAUR and with possible CRADA partners, as well as provide research samples for further market development in cosmetics and coatings. In addition, ~150 lbs of Camelina seeds were cold pressed and the oil is currently being evaluated for use in a food application.

Cuphea was in the second year of commercialization in 2006. NCAUR and the North Central Soil Conservation Research Lab in Morris, MN, continued to transfer all new growing conditions and procedures to Technology Crops, Inc. NCAUR directly oversaw and managed five farms of cuphea (~23 acres) in the Peoria area and (~5 acres) in Kenton, Ohio. NCAUR personnel were responsible for field cultivation, planting, scheduling spraying, row cultivation, and harvest, as well as post-harvest management - seed drying and transporting seed back to NCAUR while utilizing existing corn and soybean farm production equipment. Seeds were processed in NCAUR crushing facility and oil used for utilization work.

Synthesis and physical property data on a new class of estolides, oleic and tallow, was competed in 2006, which produced very economically feasible materials. These estolides had physical properties that exceeded other bio-based material in the marketplace, which had pour points in the -30 to -20 deg C range.

An estolide structure study was completed in 2006, where the estolide size was limited to examine the effect of chain length on pour point while (Estolide Number) EN = 1 was held constant. The physical properties were not related to the EN, but rather on the capping material.

The two problems in the recovery of sicklepod polysaccharides (galactomannan) have been overcome, which were the presence of anthraquinones and proteins which tend to co-extract in the most useful solvents. FT-IR data of specific HPLC fractions of the milkweed species suggest the active nematicide compound is a peptide. Five acres of pennycress were harvested to yield 1,460 lbs. of seed. The seed contained 35% oil on a dry basis with 37% erucic acid. Two hundred pounds of pennycress seeds were cold pressed, keeping the myrosinase enzyme active. The press cake is being evaluated for use as soil fumigant/weed control.


5.Describe the major accomplishments to date and their predicted or actual impact.
All major accomplishments listed are relevant to the National Program Component - New Processes, New Uses and Value-Added Foods and Biobased Products.

Peaks and Prairies, LLC, has filed through the National Registry to license the estolide technology in 2006. Peaks and Prairies, LLC, has formed a CRADA with the USDA. The improved saturated estolide technology has increased the functional property range of vegetable based lubricants with pour points that reach -40 deg C. Because of the decrease in the iodine values of this material, the oxidative stability has been greatly improved with RBOT times that now exceed most common synthetic oil based lubricants. The lubricity and biodegradability of the oils was maintained. The synthesis of a new class of estolides from oleic and tallow was completed in 2006, which produced a very economically feasible material. U.S. tallow could be used to substitute coconut fatty acids, which are imported into the U.S. in the estolide synthesis. These estolides had physical properties that exceeded other bio-based materials in the marketplace. Lastly, the cost of producing all types of estolides will make them very competitive against synthetic oils currently in the market. An end-user has demonstrated and published that this material lowers emissions when used as an additive to vegetable oil based lubricants.

Pennycress, a potential new crop, was identified in 2006. A five acre wild field of pennycress was harvested to yield 1,460 lbs. of wild seed at 10.7% moisture. The seed contained 35% oil on a dry basis with 37% erucic acid. Two hundred pounds of seeds were cold pressed, keeping the myrosinase enzyme active. This enzyme has shown to be an effective soil fumigant – used to control weeds. Pennycress is planted in October/November and harvested in late May or early June, thus giving Midwest farmers a two crop/year management practice.

Cuphea development has continued to proceed at a rapid pace during this project, from not being a commercial crop to having increased commercial acreages again in 2006. Many agronomic problems still exist in the crop, but initial farming practices have been established and a market for both the capric cuphea (300,000 acres required) and the lauric cuphea (two million acres required) have been identified as well as industrial partners.

Lesquerella development has continued with about ~30 acre field plots harvested in 2006. Products from Lesquerella oil have been developed and are being developed to aid in the commercialization of this new crop. Lesquerella should be having its first year of commercialization in 2007. 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 consumed, thus providing a key driving force to Lesquerella commercialization.

The NCAUR pilot plant seed processing and refining facility was completely finished in 2006. This pilot facility addressed a crucial need in U.S. new crop development by creating a location where small scale seed processing of new crop seeds and specialty oils could be refined. This will allow CRADA partners, cooperators and end-users the ability to receive oil of the same type and quality that major crushers and refiners - such as Archer Daniels Midland (ADM) and POS Pilot Plant Corporation - are able to supply on the million to billion ton scale. This will put quality new crop oil in the hands of companies to allow them to develop products and test the market as these crops are grown on large acres and agronomic problems are solved.

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.


6.What science and/or technologies have been transferred and to whom? When is the science and/or technology likely to become available to the end-user (industry, farmer, other scientists)? What are the constraints, if known, to the adoption and durability of the technology products?
New Crops and Processing Technology personnel gave presentations to farm cooperatives in Illinois and Ohio to demonstrate the potential of new crops in the Midwest, and participated in both cuphea and lesquerella development groups that included other ARS scientists, university and industrial cooperators. We have supplied industrial partners with products for industrial evaluation; 55 gallons of refined, bleached, deodorized (RBD) oil were provided to a cosmetic company, and 55 gallons of crude oil were provided to an industrial partner. Canola and coco-canola estolides have been synthesized and transferred to potential licensees. The potential cooperator seeks uses in lubricants, and full scale commercial production should begin in late FY 2006. Cuphea grow-outs are in the second year of commercialization in 2006. NCAUR and the North Central Soil Conservation Research Lab in Morris, MN, continue to transfer all growing conditions and procedures they have discovered to an industrial partner.


7.List your most important publications in the popular press and presentations to organizations and articles written about your work. (NOTE: List your peer reviewed publications below).
Popular Press: Cuphea as a third crop, Prairie Farmer, May 2006. A new biodegradable base stock, Tribology and Lubrication Technology, January 2006. Researcher: Tall grass may be Illinois’ next renewable fuel source, Pekin Daily Times, February 9, 2006. Alternative crops trying to find their niche, Peoria Journal Star, November 8, 2005. Cuphea promoted as specialty crop in 2006, Inform, December 2005. TCI gears up for cuphea entrance, Chemical Market Reporter, October 17-23, 2005. Proctor could cut costs with flower power, Cincinnati Business Courier, March 13, 2006. Growing Alternatives, Peoria Journal Star, July 18, 2006. TCI leads commercialization of new crop designed to replace imported oils, http://www.seedtoday.com, October 5, 2005. Biobased crankcase lube oils, Industrial Bioprocessing, vol 28, 2006. Scientists develop new crankcase lube from plants, http://www.ars.usda.gov/IS/pr/2006/060615.htm, June 15, 2006. Coming soon in a corn rotation, www.cornandsoybeandigest.com, January 2006. New Oilseed Crop Needs Contract Growers, Farm Journal, November 2005. Cuphea: New crop designed to replace imported oils, www.farmandranchguide.com, October 13, 2005. What’s that purple crop, The Farmer, 2006. Promising crop, www.farmindustrynews.com, March 1, 2006. Cuphea, www.agmrc.org, November 2005. ARS scientists develop new crankcase lube from plant fatty acids, www.farmassist.ca/alerts/details.asp?type= USnews&alertID=45893, June 15, 2006. Notice of Federal Invention Available for Licensing and Intent to Grant Exclusive License Federal Registry, p.3450, January 19, 2006. The New Homestead Act: Montanans for Bio-Product Development, www.matr.net/files/MontanansforBio-ProductDevelopment.pdf, 2005.

Presentations: Cuphea – New Oilseed Crop, OSU Extension Twilight Tours, July 11, 2006 Kenton, OH. Illinois Cuphea Progress, Mason Country Havana Tours, July 17, 2006, Havana, IL. Physical Properties and Uses of Estolides, Peaks and Prairies, December 7, 2005, Kalispell, MT.


Review Publications
Evangelista, R.L. 2006. Pilot-scale full press oil extraction of cuphea psr23 seeds [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 105.

Isbell, T., Lowery, B.A. 2006. Synthesis of halohydrins and haloethers from oleates [abstract]. American Oil Chemists' Society Meeting. p. 74.

Cermak, S.C., Brandon, K.B., Isbell, T.A. 2006. Synthesis and physical properties of estolides from lesquerella and castor fatty acid esters. Industrial Crops and Products. 23:54-64.

Isbell, T.A., Lowery, B.A., Dekeyser, S.S., Winchell, M.L., Cermak, S.C. 2006. Physical properties of triglyceride estolides from lesquerella and castor oils. Industrial Crops and Products. 23:256-263.

Harry-O'kuru, R.E. 2005. 4-Hydroxy-3-methoxycinnamate esters of milkweed oil: Synthesis and characterization. Lipids. 40:1179-1183.

Last Modified: 4/20/2014
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