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United States Department of Agriculture

Agricultural Research Service

Research Project: Novel Technology for Renewable Resource Utilization

Location: Renewable Product Technology Research Unit

2013 Annual Report

1a.Objectives (from AD-416):
The goal of this project is to create new chemical and biochemical processes for economically producing value-added products from biomass, particularly from plant lipids. Project team members will collaborate within the project, with other Agricultural Research Service (ARS) researchers, and external partners to reach the following objectives. Objective 1: Develop high-value functionalized lipids from commodity vegetable oils for cosmeceutical and industrial applications. Objective 2: Develop high-value functionalized phospholipids from soybean lecithin for cosmeceutical and nutriceutical applications. Objective 3: Develop inorganic catalytic approaches that enable the production of industrial chemicals and products from commodity vegetable oils and/or biomass (lignocellulosics).

1b.Approach (from AD-416):
The three primary objectives will each rely on a different technical approach. Commodity vegetable oils will be biocatalytically modified to introduce novel chemical functionality (Objective 1). Isolated enzymes will be used to convert plant phospholipids to ingredients for consumer products (Objective 2). Biomass will be catalytically converted under thermochemical conditions to value-added, fungible industrial chemicals and products (Objective 3).

3.Progress Report:
• Several applications for vegetable oil biocatalytically modified with the lipoic acid and dihydrolipoic acid were examined (Obj. 1a). Continuing earlier work to develop these materials for skin care applications, formulations containing these materials were prepared and tested for long-term shelf stability. This information is needed by end-users. Findings indicated that encapsulation of lipoic derivatives needs to be done using oxidation-resistant phospholipids. The lipoic-modified vegetable oils performed well in high-pressure lubrication tests. These studies were conducted as an in-house collaboration with the project “Bio-Based Lubricants From Farm-Based Raw Materials.” The production process has been patented. • The castor oil product 2-monoricinoleoylglycerol (2-MRG) was enzymatically synthesized and isolated via the improved purification method of flash chromatography (Obj. 1a). The isomeric stability of 2-MRG was determined to be kinetically stable at room temperature. Hydroxyl fatty acids and oils are used in cosmeceutical, pharmacological, industrial research, and industries. The synthesis of specifically structured lipids using 2-MRG as an intermediate is problematic because the isolation of 2-MRG by conventional methods was insufficient and resulted in unwanted side-products. A new flash chromatography method was developed, allowing for the isolation of significant quantities of pure 2-MRG. • Developed a new bioprocess, including a new microbial screening and product separation method for the production of polyol oils directly from soybean oil (Obj. 1b). Cultures were isolated from soil samples collected in Iowa and from soil and water collected around Peoria, Illinois. Samples were screened for the production of polyol oil from soybean oil. Of the 650 cultures screened, 50 cultures were positive for polyol formation. Soybean oil was converted by these positive strains to two product groups: polyol diacylglycerides and diacylglycerides with normal fatty acids. Polyol diacylglycerides can be used for the production of polyurethane, while diacylglycerides with normal fatty acids can be used as functional food ingredients. • Catalytic hydrogenation of sugars was examined as a means to produce industrially useful materials (Obj. 3). The conversion of the plant-derived sugar fructose to 2,5-dimethyltetrahydrofuran was accomplished using a platinum catalyst modified with sulfur. The product is a potential fuel, solvent, and chemical intermediate useful to industry. • Liquid and gas samples from the pyrolysis of spent agricultural plastics and swine manure or chicken litter conducted by ARS and industrial collaborators were identified and quantified (Obj. 3). Neither the pyrolysis of plastics nor livestock wastes, separately, is energetically self-sustaining. This work will help determine the feasibility of producing bio-based, value-added gases, oils, and waxes from the pyrolysis of mixtures of agricultural waste plastics and livestock wastes.

1. New uses for Cuphea plant oil. While Cuphea is being developed as an industrial crop, there remains a need for new products that provide processing opportunities to drive the adoption of this alternative crop. ARS Renewable Product Technology Research Unit scientists at the National Center for Agricultural Utilization Research, Peoria, Illinois, developed an enzymatic method that efficiently converts the oil from Cuphea seeds (Cuphea is a common perennial plant) into a high-value antioxidant. These cuphea oil-modified products have potential in nutritional and cosmetic applications.

Review Publications
Compton, D.L., Laszlo, J.A., Appell, M.D., Vermillion, K., Evans, K.O. 2012. Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols. Journal of the American Oil Chemists' Society. 89(12):2259-2267.

Laszlo, J.A., Cermak, S.C., Evans, K.O., Compton, D.L., Evangelista, R.L., Berhow, M.A. 2013. Medium-chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification. European Journal of Lipid Science and Technology. 115(3):363-371.

Sohn, H., Baek, K., Hou, C.T., Kim, H. 2012. Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against food-borne pathogenic bacteria. Biocatalysis and Agricultural Biotechnology. 2:85-87.

Lin, J.T., Chen, G.Q., Hou, C.T. 2013. Mass spectrometry of the lithium adducts of diacylglycerols containing hydroxy FA in castor oil and two normal FA. Journal of the American Oil Chemists' Society. 90:33-38.

Hou, C.T., Lin, J.T. 2012. Methods for microbial screening and production of polyol oils from soybean oil through bioprocess. Biocatalysis and Agricultural Biotechnology. 2:1-6.

Jackson, M.A. 2013. Ketonization of model pyrolysis bio-oil solutions in a plug-flow reactor over a mixed oxide of Fe, Ce, and Al. Energy and Fuels. 27:3936-3943.

Last Modified: 7/28/2014
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