Progress 11/22/01 to 07/28/04
Outputs
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? What does it matter? Commodity farming in the U.S. has been plagued by overproduction and maintained only by subsidy. 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, introduce a new raw material 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 byproducts of agriculture are relevant to program components of NP-306. 2. List the milestones (indicators of progress) from your Project Plan. This is the final Report of Progress (AD-421) for this project, which has been replaced with project 3620-41000-115-00D. The new project plan was certified by the Office of Scientific Quality Review as having completed NP 306, Quality and Utilization of
Agricultural Products Panel Review on 7/15/04. Milestones for terminating CRIS Project 3620-41000-092-00D FY 2002 (Year 1): Establish field plots of cuphea and lesquerella through Specific Cooperative Research Agreement (SCRA) with farmers. Support germplasm research for high lauric and lesquerolic acid contents. Support meadowfoam breeding efforts for high and low glucosinolate varieties. Establish preliminary agronomic traits for the production of penycress seed. Establish allyl isothiocyanate fumigant properties in the laboratory. Characterize milkweed nematicide. Characterize carbohydrates in North Carolina sicklepod. Establish a pilot facility capable of expelling new crop seed. Develop generation one lubricant from lesquerella oil and fatty acids. Determine role of oligomer on lubricant properties. Initiate work on vegetable based viscosity modifier. Synthesize first generation detergent from new crop oil. Isolate and characterize aglycones from new crop seed meals. FY
2003 (Year 2): Complete study of cuphea crop rotation on corn root worm control in first year corn. Continue agronomic trait evaluation on wild pennycress population screen germplasm for desired traits. Research plot evaluation of allyl isothiocyanate as soil fumigant completed. Laboratory evaluation of milkweed nematicide. Rheological evaluation of sicklepod gums. Crush 40,000 lbs. of lesquerella seed for oil protein and gums. Develop pilot process for aglycone isolation form glucosinolate seed meals. Synthesize improved lubricant from lesquerella oil and fatty acids. Examine anti-oxidant properties of aglycone derivatives. Determine detergent properties of new crop oil derivative. Determine viscometric properties of vegetable based modifier. Determine detergent properties of candidates. FY 2004 (Year 3): Transfer agronomic information and field contract work to cooperators to increase new crop acreage into several hundred to a thousand acres. Establish field plots of
pennycress and its impact on rotation. Conduct research plots of nematode control in potatoes of milkweed nematicide. Support germplasm development of desired carbohydrate profile in sicklepod. Continued crushing of lesquerella as necessary to supply trial markets of oil protein and starch. Develop expelling method for cuphea and pennycress. Pilot scale preparation of top lubricant candidates, viscosity modifiers detergents and anti- oxidants. Begin next generation derivatives from new crop sources. Milestones for new CRIS Project 3620-41000-115-00D 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 a rapid anthraquinone method by Ulta Violet(UV) to guide sicklepod germplasm selections. Complete oil extraction studies for pilot scale processing of cuphea seed. 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 stae 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. Synthesis and explore physical properties of lesquerella estolids Begin the synthesis of viscosity modifer based on vegetable oils. FY 2007 (Years 3 and 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 and cuphea extraction and processing. Develop method for the pilot scale isolation of anthraquinones from sicklepod. Synthesis of milkweed nematocidal derivatives to improve efficacy. Determine the effect of estolide linkage position on physical properties. Evaluate the physical properties of lesquerolic acid estolides. Complete the synthesis of viscosity modifiers and begin their performance evaluation. 3. Milestones: A. List the milestones
(from the list in Question #2) that were scheduled to be addressed in FY 2004. How many milestones did you fully or substantially meet in FY 2004 and indicate which ones were not fully or substantially met, briefly explain why not, and your plan to do so: Transfer agronomic information and field contract work to cooperators to increase new crop acreage into several hundred to a thousand acres. Substantially met this milestone with 100 acres of cuphea in the field in 2004 growing season. Establish field plots of pennycress and its impact on rotation. Partially met with approximately 2 acres of pennycress in a green manure rotation. However, the enzyme system in pennycress was found to be weaker than other brassica species for the production of volatile isothiocyantes (released fumigant) and work on pennycress will be suspended. Conduct research plots of nematode control in potatoes of milkweed nematicide. Not met since milkweed nematocide has yet to be fully characterized. Support
germplasm development of desired carbohydrate profile in sicklepod. Fully met. Developed a NIR method for carbohydrate analysis and screened current years breeding effort. Continued crushing of lesquerella as necessary to supply trial markets of oil protein and starch. Fully met. Crushed 40,000 lbs. of lesquerella seed for oil which was fully refined and drum quantities supplied to cooperators. Develop expelling method for cuphea and pennycress. Fully met. Both pennycress and cuphea were crushed for oil. Pilot scale preparation of top lubricant candidates, viscosity modifiers detergents and anti-oxidants. Substantially met. Pilot scale synthesis of oleic and lesquerella oil estolides and methyl esters of ricinoleic and lesquerolic acids were completed and materials supplied to industry for evaluation. Begin next generation derivatives from new crop sources. Fully met. A synthesis of simple alkyl ethers was initiated with the first intermediate products isolated and
characterized. A method to complete the synthesis is currently under investigation. B. List the milestone (from the list in Question #2) that you expect to address over the next 3 years (FY 2005. 2006, 2007). What do you expect to accomplish, year by year, over the next 3 years under each milestone: Milestones for new CRIS Project 3620-41000-115-00D 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 a rapid anthraquinone method by Ulta Violet(UV) to guide sicklepod germplasm selections. Complete oil extraction studies for pilot scale processing of cuphea seed. 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 stae 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. Synthesis and explore physical properties of lesquerella estolids Begin the synthesis of
viscosity modifer based on vegetable oils. FY 2007 (Years 3 and 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 and cuphea extraction and processing. Develop method for the pilot scale isolation of anthraquinones from sicklepod. Synthesis of milkweed nematocidal derivatives to improve efficacy. Determine the effect of estolide linkage position on physical properties. Evaluate the physical properties of lesquerolic acid estolides. Complete the synthesis of viscosity modifiers and begin their performance evaluation. We plan to address each research component in the months described in the table. 4. What were the most significant accomplishments this past year? A. Single most significant accomplishment during FY 2004: Cuphea grow-outs were scaled to 100 acres in field
plots of 5 to 10 acres. This size of acreage is a pre-commercialization study to determine the feasibility of scaling high-capric cuphea to full scale farm production in an attempt to meet the market demand for capryl alcohol. Seed harvested from this grow-out will serve two purposes. First, to supply seed for much needed oil production which will allow post harvest utilization research to proceed. Second, to provide sufficient quantities of seed for increased production in 2005. B. Other significant accomplishment(s), if any: Completed the synthesis of cuphea estolides which had excellent pour points in the -40 C range. These new estolides had outstanding oxidative stabilities with Rotating Bomb Oxygen Tester (RBOT) times around 400 min with very little oxidative stability package added. This material will be a useful co-product while this crop is being commercialized. Completed the synthesis of alpha-hydroxy phosphonates from Lesquerella/Castor. The alpha-hydroxy
phosphonates utilized the natural stereochemistry in the molecule to induce the stereochemistry of the alpha-hydroxy. These materials were sent to Knox College for further derivatization assay testing. Started the study on the synthesis of a cost effective lard-oleic estolide with cold temperature properties comparable with oleic estolides. These new animal-plant estolides should have superior oxidative stability properties. Worked on the derivatization of lesquerella/castor fatty acids to improve cold temperature properties. New estolides that are capped with 2-ethylhexanoic acid have pour points in the -60 C range. Scaled-up of coco-oleic estolides in pilot plant. Defatted lesquerella meal was further fractionated into salt, water, ethanol and alkali soluble fractions and protein contents determined. Fine grinding and sieving of sicklepod seed enriched gum in the fraction with largest particle size and enrich protein in the fraction with smallest particle size. Sicklepod meal 138
Kg was extracted to remove anthraquinones and the meal component supplied to North Carolina State University for poultry feeding trials. Oil extraction studies for determining the conditions for pressing of milkweed seed into oil were conducted. De-winged milkweed seed was shown to reduce mass input to the press and gave resulting higher pressing throughput even though seed oil extraction was not significantly improved. A study to optimize the separation of octadecanoic acid isomers Delta-6 (petroselenic) from Delta-9 (oleic) by gas chromatography was completed. The study indicated that branched esters gave superior isomer separation over straight esters with iso-amyl alcohol esters giving the greatest extent of ester formation and isomer separation. This methodology then was used to quantitate over 300 corriander samples from the Plant Introduction Station in Ames, IA. A study on the gravity table separation of cuphea seeds into high oil and germination rates was conducted with
over 1,000 lbs of cuphea seeds fractionated. This process provided high germinating seed for 2004 grow- outs and high oil, low germination seed for oil production. C. Significant activities that support special target populations: New crops research offers economic opportunities to small and limited resource farmers throught the development of cuphea and lesquerella. D. Progress Report: This is the final Report of Progress (AD-421) for this project, which has been replaced with project 3620-41000-115-00D. The new project plan was certified by the Office of Scientific Quality Review as having completed NP 306, Quality and Utilization of Agricultural Products Panel Review on 7/15/04. A pilot plant scale seed oil crushing facility was constructed at NCAUR. This pilot facility addressed a crucial need in U.S. new crop development by creating a location where small scale crushing of new crops seed could be accomplished. Seven drums of crude lesquerella oil has been produced to date
from pressing of 20,000 lbs. of lesquerella seed. The oil was used to further lubricant work at NCAUR and at Terresolve Technologies Ltd., as well as provide research samples for further market development in cosmetics and coatings. In addition, two gallons of cuphea oil has also been produced thus far and will allow much needed utilization research to begin on this oil. Over three hundred coriander seed analysis for oil and fatty acid profile were conducted and provided a definition of the petroselenic acid composition in coriander germplasm. This work was performed in cooperation with the plant introduction station in Ames who conducted the grow out. A method for making lesquerella and castor methyl esters was developed. This method was then used to produce 5 gallon batches of each ester with the samples supplied to DOE for testing. Lesquerella fatty acids were converted to lesquerella-oleic estolide 2-ethylhexyl esters that had pour points of -50 C. These pour points exceed
other derivatives and will be suitable to meet the pour point requirements of some of the most demanding environmental applications. Lesquerella triglyceride estolides were synthesized using an optimized tin 2- ethylhexanoate catalyst (0.1 wt%) which reduced reaction temperatures from 200 C to 130 C. This temperature reduction in the synthesis of estolides will allow scale-up of these materials in our pilot plant. Camellia seed analysis for fatty acid, protein and amino acid was completed with fatty acid and protein profiles similar to soybean. Salicornia meal was further fractionated into salt, water and ethanol soluble fractions and protein contents determined. Pennycress was harvested from a 4 acre field which provided seed for additional soil fumigant research. Natural estolides were found by solid state NMR in whole lesquerella auriculata seed. Natural estolide may provide a lower cost route to highly functionalized lubricants from vegetable oils. A milkweed nematicidic
fraction was identified from meal fractions. This isolate possessed higher activity than the original meal and characterization of this fraction is in progress. Milkweed oil has been converted to a ferulate derivative via epoxidation and esterification. These ferulate derivatives will be useful as part of a broader sun-screen technology developed within the management unit. Sicklepod meal was extracted to remove anthraquinone and the resulting detoxified meal is being examined in chicken feeding trials. Cuphea was grown on a five acre field plot for seed production and this plot was used to demonstrate the feasibility of cuphea production utilizing existing corn and soybean farm production equipment. Seed was pressed for oil. 5. Describe the major accomplishments over the life of the project, including their predicted or actual impact. The development of saturated capped estolides have increased the functional property range of vegetable based lubricants with pour points that now
reach -36 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 mineral oil based lubricants. The lubricity and biodegradability of the oils was maintained. Lastly, the cost of producing these materials will make them very competitive against synthetic oils currently in the market. An end-user has demonstrated that this material lowers emissions when used as an additive to vegetable oil based lubricants. Cuphea development has proceeded at a rapid pace during this project from no acres being grown at the start to 100 acres cultivated in 2004. 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 (2 million acres required) have been identified. Lesquerella has grown from no production at the project start to 40 acre field plots harvested in 2004.
Products from lesquerella oil were developed to aid in the commercialization of this new crop. Lesquerella oil estolides were synthesized from the oil and physical properties were determined. Lesquerella estolides 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. A database of oil amount and structure for over 15,000 seeds went on the Internet and has been used worldwide over 2,500 times. Many new products have been made from meadowfoam oil and patented. Some patents have been licensed. New products include delta lactones, hydroxy fatty acids, fatty ethers and estolides. These products can be used as is or as building blocks for new lubricants, personal care ingredients, biodegradable detergents and a number of uses. Oil from meadowfoam is the most oxidatively stable vegetable oil known in the presence of heat and air. We identified a new antioxidant
in meadowfoam oil which improves stability of refined oils. Meadowfoam antioxidants were compared to commercially available antioxidants and found to have equal or greater antioxidant efficacy on several common vegetable oils. Demonstrated use of meal components could improve the economics of meadowfoam oil production by development of co-product streams. New crop oils were chemically converted with household bleach and acetic acid (the main ingredient in vinegar) to novel derivatives with potential in cosmetic applications. Further exploration of this basic chemistry has led to cooperation with an industrial partner and we supplied pound quantities of the new derivative for their formulation studies. A process was developed to isolate pounds of a new hunger satiation component from jojoba. It is being tested for safety in animals. Research in the medical school and several universities on this new material would not be possible without our process and our cooperation in supplying
the quantities needed. The patent for the process to isolate pure simmondsin from the seed meal was issued in December, 1999. A lab-scale process for converting kenaf lignin (a waste product from paper making) to non-polluting, valuable co-products was developed. We have discovered that several new crop seed meals are effective against agricultural pests. One example is that milkweed seeds (after their oil is recovered for another product) and ground pods kill a pest (nematodes) that causes a great deal of damage on potatoes in the Northwestern U.S. We have formed crop development groups with everyone involved from growers to end-users to make sure the best information is available to everyone. An economic and research plan to commercialize lesquerella was initiated in 2000. 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 to demonstrate the potential of New Crops in the Midwest, participated in a cuphea development group that includes other ARS scientists, university and industrial cooperators. Transferred meadowfoam estolide technology and advised an industrial cooperator who commercially produced meadowfoam estolide for hair conditioner. Full scale commercial production began in FY03. 7. List your most important publications in the popular press and presentations to organizations and articles written about your work. The Next Bio-Based Functional Fluid, Inform 2004. Cuphea Those Sticky American Plants, Ag Innovation News 2003. Ag lab develops cuphea's potential, Peoria Journal Star January 7, 2003. Meadowfoam seed oil gears up in hydraulic oils market, Chemical Marketing Reporter, November 4, 2002. Cuphea those sticky
American plants, Auri Ag Innovation News, July 2003.
Impacts
(N/A)
Publications
- CERMAK, S.C., ISBELL, T. 2003. IMPROVED OXIDATIVE STABILITY OF ESTOLIDE ESTERS. INDUSTRIAL CROPS AND PRODUCTS. 18:223-230.
- Cermak, S.C., Isbell, T. 2004. Synthesis and physical properties of cuphea- oleic estolides and esters. Journal of the American Oil Chemists' Society. 81:297-303.
- Isbell, T., Cermak, S.C. 2004. Purification of meadowfoam monoestolide from polyestolide. Industrial Crops and Products. 19:119-118.
- WU, Y., PAYNE WAHL, K.L., VAUGHN, S.F. 2003. ANALYSIS OF HEADSPACE VOLATILES OF CORN GLUTEN MEAL. CEREAL CHEMISTRY. Vol 80(5)567-569.
- WU, Y., SESSA, D.J. 2004. PROTEIN FRACTIONATION AND PROPERTIES OF SALICORNIA MEAL. JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY. 38:1083- 1085.
- Isbell, T., Behle, R.W. 2004. Progress in the development of cuphea as a crop for midwest growers. Inform. 14(8)513-515.
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Progress 10/01/02 to 09/30/03
Outputs
1. What major problem or issue is being resolved and how are you resolving it? The farm economy in the U.S. relies on a few commodity crops whose returns have fallen and whose low biodiversity is susceptible to pests and disease. In order to develop new markets for agricultural materials, unique new products from alternative crops are needed to economically pull these crops into production. 2. How serious is the problem? Why does it matter? It has been estimated that the U.S. is losing hundreds of farmers a year due to poor economics. Alternative crops such as jojoba, crambe, milkweed, meadowfoam and kenaf had little or no impact 10-15 years ago but produced over 46 million dollars in raw agricultural commodities in 1999, which has saved a number of farms. Most of the products from these new crops are for industrial uses which do not displace markets for traditional commodity crops. 3. How does it relate to the National Program(s) and National Program Component(s)
to which it has been assigned? National Program 306, Quality, Utilization of Agricultural Products (100%). This project develops new industrial uses of new crop components. This program also relates directly to National Program 301, Plant, Microbial Insect Genetic Resources, Genomics and Genetic Improvement in that product value from new crops often impacts breeding targets. This project's personnel work closely with new crop breeders to commercialize new industrial crops. 4. What were the most significant accomplishments this past year? A. Single most significant accomplishment during FY 2003: This project is a bridging project replacing 3620-41000-071-00D in January of 2002. A pilot plant scale seed oil crushing facility was constructed at USDA-ARS-National Center for Agricultural Utilization Research (NCAUR), Peoria, IL. This pilot facility addressed a crucial need in U.S. new crop development by creating a location where small scale crushing of new crops seed could be
accomplished. Seven drums of crude lesquerella oil has been produced to date from pressing of 20,000 lbs. of lesquerella seed. The oil was used to further lubricant work at NCAUR and at Terresolve Technologies Ltd., as well as provide research samples for further market development in cosmetics and coatings. In addition, two gallons of cuphea oil has also been produced thus far and will allow much needed utilization research to begin on this oil. B. Other significant accomplishments(s), if any: Over three hundred coriander seed analysis for oil and fatty acid profile were conducted and provided a definition of the petroselenic acid composition in coriander germplasm. This work was performed in cooperation with the USDA-ARS North Central Region Plant Introduction Station, Ames, IL, whose scientists conducted the grow out. A method for making lesquerella and castor methyl esters was developed. This method was then used to produce 5 gallon batches of each with the samples supplied
to U.S. Department of Energy (DOE) for testing. Lesquerella fatty acids were converted to lesquerella-oleic estolide 2-ethylhexyl esters that had pour points of -50oC. These pour points exceed other derivatives and will be suitable to meet the pour point requirements of some of the most demanding environmental applications. Lesquerella triglyceride estolides were synthesized using an optimized tin 2- ethylhexanoate catalyst (0.1 wt%) which reduced reaction temperatures from 200oC to 130oC. This temperature reduction in the synthesis of estolides will allow scale-up of these materials in our pilot plant. Camellia seed analysis for fatty acid, protein and amino acid was completed with fatty acid and protein profiles similar to soybean. Salicornia meal was further fractionated into salt, water and ethanol soluble fractions and protein contents determined. Pennycress was harvested from a 4 acre field which provided seed for additional soil fumigant research. Natural estolides were
found by solid state Nuclear Magnetic Resonance (NMR) in whole lesquerella auriculata seed. Natural estolide may provide a lower cost route to highly functionalized lubricants from vegetable oils. A milkweed nematicidic fraction was identified from meal fractions. This isolate possessed higher activity than the original meal and characterization of this fraction is in progress. Milkweed oil has been converted to a ferulate derivative via epoxidation and esterification. These ferulate derivatives will be useful as part of a broader sun-screen technology developed within the management unit. Sicklepod meal was extracted to remove anthraquinone and the resulting detoxified meal is being examined in chicken feeding trials. Cuphea was grown on a five acre field plot for seed production and this plot was used to demonstrate the feasibility of cuphea production utilizing existing corn and soybean farm production equipment. Seed was pressed for oil. C. Significant activities that
support special target populations: New crops research offers economic opportunities to small and limited resource farmers through the development of cuphea and lesquerella. 5. Describe the major accomplishments over the life of the project, including their predicted or actual impact. In terms of impact, the new crops that we have contributed our effort to had essentially no value 10 to 15 years ago and are producing over 46 million dollars of seed oil, meal and fiber in 1999 and that figure is increasing every year. In addition, the agricultural ecosystem adds biodiversity and the farmers growing these crops have a more diverse source of income and crop alternatives. A database of oil amount and structure for over 15,000 seeds went on the Internet and has been used worldwide over 2,500 times. We are adding new information at the rate of 50 new analyses per year and discovering which wild plants have the most potential to become a new crop of the future. Many new products have
been made from meadowfoam oil and patented. Some patents have been licensed. New products include delta lactones, hydroxy fatty acids, fatty ethers and estolides. These products can be used as is or are building blocks for new lubricants, personal care ingredients, biodegradable detergents and a number of uses. A biodegradable hydraulic fluid was sold commercially for the first time in 1997 by an industrial partner based on the new chemical called estolide which can be made from several vegetable oils. An end-user has demonstrated that this material lowers emissions when used as an additive to vegetable oil based lubricants. New crop oils were chemically converted with household bleach and acetic acid (the main ingredient in vinegar) to novel derivatives with potential in cosmetic applications. Further exploration of this basic chemistry has led to cooperation with an industrial partner and our supplying pound quantities of the new derivative for their formulation studies. A
process was developed to isolate pounds of a new hunger satiation component from jojoba. It is being tested for safety in animals. Research in the medical school and several universities on this new material would not be possible without our process and our cooperation in supplying the quantities needed. The patent for the process to isolate pure simmondsin from the seed meal was issued in December, 1999. A lab-scale process for converting kenaf lignin (a waste product from paper making) to non-polluting, valuable co-products was developed. Oil from meadowfoam is the most stable vegetable oil known in the presence of heat and air. We identified and synthesized a new antioxidant in meadowfoam oil which improves stability of refined oils. We have discovered that several new crop seed meals are effective against agricultural pests. One example is that milkweed seeds (after their oil is recovered for another product) and ground pods kill a pest (nematodes) that causes a great deal
of damage on potatoes in the Northwestern U.S. For new crops which are not yet commercial, we have developed processes for extracting the oil and supplied oil and meal to potential users. Demonstrated new uses for milkweed meal as a nematicide, jojoba meal as a pet food ingredient and lesquerella gum as a thickener are accomplishments in the development of oilseed co-products. We have formed crop development groups with everyone involved from growers to end- users to make sure the best information is available to everyone. An economic and research plan to commercialize lesquerella was initiated in 2000. Cuphea has been successfully bred to an acceptable crop by Oregon State University and grown in Central Illinois by our group. A working pilot plant production facility at NCAUR for vegetable oil derivatives and an oil expelling facility at an industrial cooperator's plant have been successfully developed. Mixed estolides of cuphea and oleic acid were made in the laboratory and
shown to have a superior pour point and oxidative stability than estolides made solely from oleic acid. These mixed estolides will provide enhanced performance that was previously unattainable from vegetable based products and allow these materials into lubricants suitable for general industrial use. Research was performed to increase the use of meadowfoam meal and improve vegetable oil oxidative stability by developing the unique antioxidant in meadowfoam oil into a commercial products. Meadowfoam antioxidants were compared to commercially available antioxidants and found to have equal or greater antioxidant efficacy on several common vegetable oils. Demonstrated use of meal components could improve the economics of meadowfoam oil production by development of co-product streams. Products from lesquerella oil were developed to aid in the commercialization of this new crop. Lesquerella oil estolides were synthesized from the oil and physical properties were determined.
Lesquerella estolides 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. Nematodes are a significant problem in potato production often requiring a very toxic chemical such as methyl bromide for their control. Milkweed meals were shown to be effective at controlling nematodes in potato and extracts of meal fractions have shown increased activity. Once nematicidic components are identified, demand for milkweed meal will increase milkweed acreage and eliminate methyl bromide treatments for nematode control in potato production. 6. What do you expect to accomplish, year by year, over the next 3 years? Each year we plan to perform basic research and develop new organic synthesis methods for unique oil and plant derived chemicals. We will develop new seed oil derivatives in cooperation with our industrial partners to meet their product requirements for new
commercial products from lesquerella, cuphea, meadowfoam, milkweed and lesquerella oil. Every year we plan to use our pilot scale vegetable oil chemicals production line and make 25 to 50 gallons of several new products for our industrial partners to formulate into products. In FY04 we will press 50, 000 lbs of lesquerella seed for oil which will be used to develop lubricants. The lesquerella oil will be converted into one drum of lesquerella estolide and supplied to industrial cooperators for market sampling. One to five drums of oleic, oleic-cuphea and oleic-coco estolides will be produced in our pilot plant and supplied to industrial cooperators for market sampling. We will press 1000 lbs of cuphea seed for oil and begin derivative research in our laboratory as well as supply samples for commercial testing. Lesquerella and sicklepod gums will be isolated and their physical properties determined. Enriched protein fractions from lesquerella and sicklepod will be isolated and
properties determined. Lesquerella and pennycress isothiocyanates will be isolated and their anti-oxidant properties evaluated in vegetable oils. We will develop a new Gas Chromatography method for germplasm support of lesquerella by partial seed analysis and continue a coriander fatty acid germplasm survey. In FY05 and FY06 we will continue to press lesquerella and cuphea seed to supply starting oil markets. Transfer of all estolide technology to industrial partners for full commercial production with products utilized in industrial markets. Derivatives of lesquerella and sicklepod gums directed to specific performance properties and initial pilot scale production of gums for commercial testing will be made. 7. 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? A cuphea rotation study with scientists from another Management Unit at NCAUR was continued at the University of Illinois Farm to study potential elimination of corn root worm carry-over in Eastern Illinois fields. New Crops and Processing Technology Research personnel gave presentations to farm cooperatives in Illinois to demonstrate the potential of new crops in the Midwest, participated in a cuphea development group that includes other ARS scientists, university and industrial cooperators. Transferred meadowfoam estolide technology and advised an industrial cooperator who commercially produced meadowfoam estolide for hair conditioner. Full scale commercial production began in FY03. 8. List your most important publications in the popular press and presentations to organizations and articles written about your work. (NOTE: This does not replace your peer-reviewed publications listed below). Ag Lab Develops Cuphea's Potential. Peoria Journal Star. January 7,
2003. Meadowfoam Seed Oil Gears Up in Hydraulic Oils Market. Chemical Marketing Reporter. November 4, 2002. Cuphea Those Sticky American Plants. Auri Ag Innovation News. July 2003. Progress In the Development of Cuphea As a Crop for Midwest Growers. INFORM. 2003.
Impacts
(N/A)
Publications
- WU, Y.V., ABBOTT, T.P. PROTEIN ENRICHMENT OF DEFATTED SALICORNIA MEAL BY AIR CLASSIFICATION. JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY. 2003. V. 80(2). P. 167-169
- CERMAK, S.C., ISBELL, T.A. SYNTHESIS AND PHYSICAL PROPERTIES OF ESTOLIDE- BASED FUNCTIONAL FLUIDS. 2003. JOURNAL OF INDUSTRIAL CROPS AND PRODUCTS. V. 18. P. 183-196.
- ISBELL, T.A., CERMAK, STEVEN. SYNTHESIS OF TRIGLYCERIDE ESTOLIDES FROM LESQUERELLA AND CASTOR OILS. JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY. 2003. V. 79(12). P. 1227-1233.
- HOLSER, R.A., ISBELL, T.A. EFFECT OF PROCESSING CONDITIONS ON THE OXIDATIVE STABILITY OF MEADOWFOAM PRESS OIL. 2002. V. 79(10). P 1051-1052
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Progress 10/01/01 to 09/30/02
Outputs
1. What major problem or issue is being resolved and how are you resolving it? The farm economy in the U.S. relies on a few commodity crops whose returns have fallen and whose low biodiversity is susceptible to pests and disease. In order to develop new markets for agricultural materials, unique new products from alternative crops are needed to economically pull these crops into production. 2. How serious is the problem? Why does it matter? It has been estimated that the U.S. is losing hundreds of farmers a year due to poor economics. Alternative crops such as jojoba, crambe, milkweed, meadowfoam and kenaf had little or no impact 10-15 years ago but produced over 46 million dollars in raw agricultural commodities in 1999, which has saved a number of farms. Most of the products from these new crops are for industrial uses which do not displace markets for traditional commodity crops. 3. How does it relate to the national Program(s) and National Program Component(s)
to which it has been assigned? National Program 306, Quality and Utilization of Agricultural Products (100%). This project develops new industrial uses of new crop components. This program also relates directly to National Program 301, Plant, Microbial & Insect Genetic Conservation, & Development in that product value from new crops often impacts breeding targets. This project's personnel work closely with new crop breeders to commercialize new industrial crops. 4. What was your most significant accomplishment this past year? A. Single Most Significant Accomplishment During FY2002: This project was bridged from 3620-41000-071-00D entitled New Crops for Industrial Products. Performed to increase the utilization of New Crop raw materials, our research promoted a more diversified cropping environment for farmers. Mixed estolides of cuphea and oleic acid were made in the laboratory and shown to have a superior pour point and oxidative stability then estolides made solely from oleic
acid. These mixed estolides will provide enhanced performance that was previously unattainable from vegetable based products and allow these materials into lubricants suitable for general industrial use. B. Other Significant Accomplishment (s), if any: To increase vegetable oil oxidative stability, research was performed to compare the unique antioxidant in meadowfoam oil to commercially available antioxidants. Meadowfoam antioxidants were compared to commercially available antioxidants and found to have equal or greater antioxidant efficacy on several common vegetable oils. Demonstrated use of meal components could improve the economics of meadowfoam oil production by development of co-product streams. Products from lesquerella oil were developed to aid in the commercialization of this new crop. Lesquerella oil estolides were synthesized from the oil and physical properties were determined. Lesquerella estolides 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. Nematodes are a significant problem in potato production often requiring very toxic chemicals such as methyl bromide for their control. Milkweed meals were shown to be effective at controlling nematodes in potato and extracts of meal fractions have shown increased activity over the meal. Once nematocidic components are identified demand for milkweed meal will increase milkweed acreage and eliminate methyl bromide treatments for nematode control in potato production. C. Significant Activities that Support Special Target Populations: New crops research offers economic opportunities to small and limited resource farmers through the development of cuphea and lesquerella. 5. Describe your major accomplishments over the life of the project, including their predicted or actual impact? This is a bridging project for 3620-41000-071-00D of the same title. In terms of
impact, the new crops that we have contributed our effort to had essentially no value 10 to 15 years ago and are producing over 46 million dollars of seed oil, meal and fiber in 1999 and that figure is increasing every year. In addition, the agricultural ecosystem adds biodiversity and the farmers growing these crops have a more diverse source of income and crop alternatives. A database of oil amount and structure for over 15,000 seeds went on the Internet and has been used worldwide over 2,500 times. We are adding new information at the rate of 50 new analyses per year and discovering which wild plants have the most potential to become a new crop of the future. Many new products have been made from meadowfoam oil and patented. Some patents have been licensed. New products include delta lactones, hydroxy fatty acids, fatty ethers and estolides. These products can be used as is or are building blocks for new lubricants, personal care ingredients, biodegradable detergents and a
number of uses. A biodegradable hydraulic fluid was sold commercially for the first time in 1997 by an industrial partner based on the new chemical called estolide which can be made from several vegetable oils. An end-user has demonstrated that this material lowers emissions when used as an additive to vegetable oil based lubricants. New crop oils were chemically converted with household bleach and acetic acid (the main ingredient in vinegar) to novel derivatives with potential in cosmetic applications. Further exploration of this basic chemistry has led to cooperation with an industrial partner and our supplying pound quantities of the new derivative for their formulation studies. A process was developed to isolate pounds of a new hunger satiation component from jojoba. It is being tested for safety in animals. Research in the medical school and several universities on this new material would not be possible without our process and our cooperation in supplying the quantities
needed. The patent for the process to isolate pure simmondsin from the seed meal was issued in December, 1999. A lab-scale process for converting kenaf lignin (a waste product from paper making) to non- polluting, valuable co-products was developed. Oil from meadowfoam is the most stable vegetable oil known in the presence of heat and air. We identified and synthesized a new antioxidant in meadowfoam oil which improves stability of refined oils. We have discovered that several new crop seed meals are effective against agricultural pests. One example is that milkweed seeds (after their oil is recovered for another product) and ground pods kill a pest (nematodes) that causes a great deal of damage on potatoes in the Northwestern U.S. For new crops which are not yet commercial, we have developed processes for extracting the oil and supplied oil and meal to potential users. Demonstrated new uses for milkweed meal as a nematicide, jojoba meal as a pet food ingredient and
lesquerella gum as a thickener are accomplishments in the development of oilseed co-products. We have formed crop development groups with everyone involved from growers to end-users to make sure the best information is available to everyone. An economic and research plan to commercialize lesquerella was initiated in 2000. Cuphea has been successfully bred to an acceptable crop by Oregon State University and grown in Central Illinois by our group. A working pilot plant production facility at NCAUR for vegetable oil derivatives and an oil expelling facility. Because of continued development, lesquerella has been grown on tens of acreas in 2002 and 4,000 lbs of seed crushed thus far for oil and derivatives. 6. What do you expect to accomplish, year by year, over the next 3 years? Each year we plan to perform basic research and develop new organic synthesis methods for unique oil and plant derived chemicals. We will develop new seed oil derivatives in cooperation with our industrial
partners to meet their product requirements for new commercial products from lesquerella, cuphea, meadowfoam, milkweed and lesquerella oil. Every year we plan to use our pilot scale vegetable oil chemicals production line and make 25 to 50 gallons of several new products for our industrial partners to formulate into products. In FY03, FY04 and FY05 we plan to explore the applications of the new antioxidant from meadowfoam and lesquerella. In FY03 we will continue to do research to identify the active nematicide in milkweed and the sticky component in cuphea. Also in FY03, we will process lesquerella and cuphea seed to oil and meal and optimize both the processing and products. In FY03 pilot scale production of lesquerella oil lubricants will be made. In FY04 unique antioxidants from lesquerella will enter pilot scale. Finally in FY03 we will perform pilot scale batches of mixed estolides for lubricant cooperators to start the process for the complete commercialization of this
patented ARS technology. 7. What technologies have been transferred and to whom? When is the technology likely to become available to the end user (industry, farmer other scientist)? What are the constraints, if known, to the adoption durability of the technology? A cuphea rotation study with scientists from another Research Unit at NCAUR was continued at the University of Illinois Farm to study potential elimination of corn root worm carry-over in Eastern Illinois fields. New Crops and Processing Technology Research Unit personnel gave presentations to farm cooperatives in Illinois to demonstrate the potential of new crops in the Midwest, participated in a cuphea development group that includes other ARS scientists, university and industrial cooperators. Developed a method that an industrial cooperator used to manufacture 400 lbs of meadowfoam estolide for hair conditioner. Refined 500 lbs of lesquerella oil that was supplied to a lubricant manufacturer for testing. Entered into
a Cooperative Research and Development Agreement (CRADA) to develop sicklepod as a rotation crop in North Carolina. 8. List your most important publications and presentations, and articles written about your work (NOTE: this does not replace your review publications which are listed below) Jojoba Market to Level Out on Lowered Inventories, Chemical Market Reporter, February 11, 2002.
Impacts
(N/A)
Publications
- Cermak, S.C., Isbell, T.A. Pilot-plant distillation of meadowfoam fatty acids. Industrial Crops and Products. 2002. v. 15. p. 145-154.
- Cermak, S.C., Isbell, T.A. Synthesis of estolides from oleic and saturated fatty acids. Journal of the American Oil Chemists' Society. 2001. v. 78(6). p. 557-565
- Corl, B.A., Baumgard, L.H., Dwyer, D.A., Griinari, J.M., Phillips, B.S., Bauman, D.E. The role of Delta 9-desaturase in the production of cis-9, trans-11 CLA. Journal of Nutritional Biochemistry. 2002. v. 12. p. 622-630.
- Harry-O'kuru, R.E., Holser, R.A., Abbott, T.P. Weisleder, D. Synthesis and characteristics of polyhydroxy triglycerides from milkweed oil. Industrial Crops and Products. 2002. v. 15. p. 51-58.
- Isbell, T.A. Current Progress in the Development of Cuphea. Lipid Technology. 2002. v. 14. p. 77-80.
- Abbott, T.P., Wohlman, A., Isbell, T.A., Momany, F.A., Cantrell, C.L., Garlotta, D.V., Weisleder, D. 1,3-di (3-Methoxybenzyl) thiourea and related lipid antioxidants. Industrial Crops and Products. 2002. v. 16(1). p. 43-57.
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