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ARS Home Midwest Area Peoria, Illinois National Center for Agricultural Utilization Research Bio-oils Research Research





- Cermak, Steven - Steve
- Evangelista, Roque
- Winfield, Demichael
- 2023
- 2022
- 2021
- 2020
- Publications
- Product Quality and New Uses (306)

Research Project: Development of New Value-Added Processes and Products from Advancing Oilseed Crops **Location:
                            Bio-oils Research** 2021 Annual Report **Objectives**
                                

Objective 1: Develop an analysis of new crop germplasm and agronomic traits of
oilseed crops such as camelina and industrial hemp.
• Sub-objective 1.1. Identify and develop off-season crops.
• Sub-objective 1.2. Identify and develop non-traditional oilseed crops.

Objective 2: Enable processes for the commercial production of oils, meal, gums,
waxes, and value-added products from advancing oilseed crops such as meadowfoam,
new pennycress varieties, camelina, lesquerella, osage orange, and industrial hemp.
• Sub-objective 2.1. Develop methods for the dry fractionation of mucilage and
enriched protein meal from brassica seeds (camelina and lesquerella).
• Sub-objective 2.2. Develop methods for the recovery of waxes and phospholipids
from meadowfoam oil.
• Sub-objective 2.3. Develop an integrated process to produce high-quality oil,
enriched protein meal, and purified protein from industrial hemp seeds.
• Sub-objective 2.4. Develop a sustainable isolation and purification protocol for
isoflavones and the other fruit components of osage orange.

Objective 3: Enable commercial processes by converting oils and gums from oilseed
crops into marketable new value-added bio-based products.
• Sub-objective 3.1. Develop new hydroxy oils and fatty acids.
• Sub-objective 3.2. Develop new biobased estolide lubricants or additives.
• Sub-objective 3.3. Develop niche products for industrial oils. **Approach**
                                

New off-season and oilseed crop development is critical to the future sustainability of the United States (U.S.) agriculture by reducing the farmer’s dependence on government subsidies for a select few commodity crops such as corn and soybeans, and by supplementing our need for energy without sacrificing food production. Several new crops (camelina, industrial hemp, meadowfoam, lesquerella, and osage orange) will be further developed for the U.S. by developing cost-effective industrial products and processes from these agricultural feedstocks. A collaborative effort in the development of camelina and industrial hemp will occur: 1) Both off-season and new crop germplasm development will be supported through developing analytical methods to rapidly analyze tetrahydrocannabinol (THC), oil, and seed quality; 2) Development of chemical and physical processes that enable the commercial production of oils, waxes, meal, gums, proteins, and isoflavones in these oilseed crops; 3) Development of novel industrial chemicals and processes through organic synthesis based on new crop raw materials derived above; and 4) Demonstrate economic viability through the production of pilot-scale quantities of new crop raw materials and products. Products to be developed include biodegradable lubricants, biobased lubricant additives, cosmetics, and common feedstocks - hydroxy acids. Overall, this research will lead to the development and expansion of off-season and new oilseed crops, which will help diversify the U.S. farm as well as expand the U.S. arsenal of industrial biofriendly chemicals and processes. **Progress Report**
                                

New off-season crop development is critical to the future sustainability of the United States agriculture by reducing farmer’s dependence on government subsidies and by supplementing our need for biobased products without decreasing food production.  

Under Objective 1, continued development of pennycress (Thlaspi arvense L.) as an off-season rotation crop. Pennycress has continued to be commercially grown (by a St. Louis, Missouri-based company) during the 2020-2021 season. Pennycress oil has properties suitable for the development of biofuels, i.e. as an aviation jet fuel drop-in replacement. Commercialization and collaborative research efforts continue as we provided consultative oversight for production, processing of the seeds for oil/meal/protein, and development of other potential industrial products from the oil. Additionally, protein isolates from wild-type pennycress and new yellow seed lines were isolated and compared. The protein isolates were sent to an independent laboratory for functional properties testing along with commercially available protein isolates.

Under Objective 1, development of industrial hemp, a new target in this research cycle, will be investigated as a potential industrial crop for the United States by developing cost-effective industrial products and processes from all parts of the crop. Currently, plant variety evaluations and seed increase for processing studies are underway.

Under Objective 2, development of another new crop, Euphorbia lagascae, continues. Euphorbia is a drought-tolerant annual plant that produces seeds with 45-50% oil rich in vernolic (12S,13R-epoxy-cis-9-octadecenoic) acid. Vernolic acid has wide applications in paints and coatings, plasticizers, adhesives, polymers, and lubricants. Due to its high oil content, prepressing followed by solvent extraction will maximize oil recovery from the seeds. The objective of the study was to evaluate the effect of starting seed moisture content and cooking/drying temperature on oil extractability and quality (free fatty acid, epoxy, and phospholipid contents and color) of pressed and solvent-extracted oils. The expelling conditions evaluated seed moisture that were subjected to different temperature levels then screw-pressed. The press cakes were Soxhlet-extracted with hexane. The oil content of the seed, press cake, and hexane-defatted meal were measured.

Under Objective 2, advancement of traditional crops such as a new variety of soybean seeds which were processed in our one-of-kind, one stop seed processing, oil processing, and oil modification pilot plant. The pilot plant gives ARS researchers the ability to process numerous types of seeds from various sources. The processed oil and protein cake from the new variety of soybean will be evaluated in some new potential food applications in conjunction with collaborators.

Under Objective 3, continued development of estolides which we previously developed and patented are a superior vegetable-based lubricant. Estolides have been commercialized as a biobased engine oil. Estolides have excellent physical properties (traits that make them excellent lubricants), such as fluidity at cold temperature and outstanding oxidative stability properties with limited additive packages and these performances exceeded other commercially available biobased oils. New synthetic feedstocks and derivatives have been developed this year to further advance this successful ARS invention.

Under Objective 3, we have developed a new renewable resource in the form of vegetable oils that have been chemically modified to polyimine triglyceride derivatives which are capable of sequestration of toxic metal species from aqueous media. Use of these agents at the generation site of the metal species will remediate the effluents containing the toxicants and thus result in a cleaner, safer environment. U.S. Patent 10,443,010 B2 was granted on October 15, 2019, on this technology. **Accomplishments**
                                

1. New insect repellent. Biting or blood sucking insects (flies, mosquitos, ticks, and bed bugs) can transmit various diseases such as Zika and yellow fever. Current control of mosquito species primarily relies on massive use of insecticides. ARS researchers at Peoria, Illinois, and Lincoln, Nebraska, developed a new series of all-natural insect repellents and formulation packages designed to meet the challenges posed by these menacing insects. ARS researchers used these new materials to test against mosquitos to show that they performed just as well as commercial standards. The estimated global mosquito repellent market was valued at $4.1 billion in 2020. This ARS advancement will help protect the general public from mosquitos using materials developed from all-natural sources. 2. A new environmentally friendly alternative to petroleum-based products. Vernolic acid (from a plant called Euphorbia lagascae) has widespread applications in paints, coatings, plasticizers, adhesives, polymers, and lubricants. However, information on processing euphorbia seeds has been very limited. ARS researchers at Peoria, Illinois, and researchers at the Ontario Ministry of Agriculture, Food and Rural Affairs, Simcoe, Ontario, Canada, developed methods to handle the high oil content of the seed and evaluated the effect of starting seed moisture content and cooking/drying temperature on oil extractability and quality of the oils. Due to development of these methods, the oil (vernolic acid) can be economically and effectively processed to aid in the development of numerous environmentally friendly products from a new crop. **Review Publications**
                            *Zhang, S., Blore, K., Xue, R., Qualls, W., Cermak, S.C., Zhu, J.J. 2021. Larvicidal activity of natural repellents against the dengue vector, aedes aegypti. Journal of the American Mosquito Control Association. 36(4):227–232. https://doi.org/10.2987/20-6916.1.*
                                *Qualls, W., Xue, R., Farooq, M., Peper, S.T., Aryaprema, V., Blore, K., Weaver, R., Autry, D., Talbalaghi, A., Kenar, J.A., Cermak, S.C., Zhu, J.J. 2020. Evaluation of lotions of botanical-based repellents against Aedes aegypti (Diptera: Culicidae). Journal of Medical Entomology. 58(2):979-982. https://doi.org/10.1093/jme/tjaa244.*
                                *Biresaw, G., Bantchev, G.B., Harry-O'kuru, R.E. 2020. Phosphonates of vegetable oils – Characterization as lubricants. Journal of the American Oil Chemists' Society. 98(1):89-102. https://doi.org/10.1002/aocs.12448.*
                                *Hwang, H-S., Winkler-Moser, J.K., Tisserat, B., Harry-O'kuru, R.E., Berhow, M.A., Liu, S.X. 2020. Antioxidant activity of Osage orange extract in soybean oil and fish oil during storage. Journal of the American Oil Chemists' Society. 98(1):73-87. https://doi.org/10.1002/aocs.12458.*
                                *Walia, M.K., Zanetti, F., Gesch, R.W., Krzyzaniak, M., Eynck, C., Puttick, D., Alexopoulou, E., Royo-Esnal, A., Stolarski, M.J., Isbell, T., Monti, A. 2021. Winter camelina seed quality to different growing environments across Northern America and Europe. Industrial Crops and Products. 169(1). Article 113639. https://doi.org/10.1016/j.indcrop.2021.113639.*


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