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United States Department of Agriculture

Agricultural Research Service


Location: Renewable Product Technology Research

2012 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:
Annual progress was made on all four subobjectives of this project, which addresses research needs to develop commercially viable biobased products and conversion processes from vegetable oils, phospholipids and biomass. These technologies will ultimately improve sustainable agriculture and provide economic support to rural communities by providing growers and producers additional opportunities to convert local biomass into consumer and industrial products. Specific examples of significant developments in FY12 include the following: • Vegetable oil was biocatalytically modified with the antioxidants lipoic acid and dihydrolipoic acid to prepare new skin care products. An antioxidant plant phenol (ferulic acid) was biocatalytically esterified to polyunsaturated vegetable oils to confer high oxidation resistance, thereby allowing the vegetable oil to be utilized in skin care products. • Microbes were recently shown to be effective in oxygenating vegetable oil. This process will provide a convenient route to make high-value polymers from commodity vegetable oils. • A plant phenol (ferulic acid) was attached to milkweed oil and its antioxidant capacity in phospholipid vesicles was determined. This new molecule has potential in cosmeceutical applications. The interaction behavior of phospholipid vesicles with nano-size polymers was investigated. It was established that this new binary system can be used for topical delivery of cosmetic and pharmaceutical materials. • A catalytic method for producing an insect repellent from cuphea oil was developed. This process will provide a new market for cuphea oil. A catalyst was developed for the stabilization of the liquid product of biomass thermochemical conversion. This will allow the liquid fraction to be used to produce industrial chemicals.

4. Accomplishments
1. Highly stabilized plant oil for skin care. Delivering healthful plant oils to the skin is complicated by the fact that some oils are quite sensitive to destruction (oxidation), which diminishes oil quality during storage and when applied to skin. While oil destruction can be slowed by including preservatives (antioxidants) in the product formulation (e.g., lotion or cream), ARS scientists at USDA, ARS, National Center for Agricultural Utilization Research in Peoria, Illinois, found that attaching a preservative directly to the oil provides the best protection. This new approach to protecting plant oils in cosmetics allows aging skin to receive rejuvenating fatty acids uncompromised before reaching their target tissues. This work was conducted in conjunction with an industrial collaborator under a Cooperative Research and Development Agreement.

Review Publications
Compton, D.L., Jackson, M.A. 2011. Heterogeneous catalytic esterification of omega-sulfhydryl fatty acids: Avoidance of thioethers, thioesters, and disulfides. Journal of the American Oil Chemists' Society. 88:1799-1805.

Compton, D.L., Laszlo, J.A., Evans, K.O. 2011. Antioxidant properties of feruloyl glycerol derivatives. Industrial Crops and Products. 36:217-221. DOI: 10.1016/j.indcrop.2011.09.009.

Jackson, M.A., Appell, M.D., Blackburn, J.A., Rheiner, S.N., Berhow, M.A. 2011. The acrylation of glycerol: A precursor to functionalized lipids. Journal of the American Oil Chemists' Society. 89(4):713-719. DOI: 10.1007/s11746-011-1950-5.

Laszlo, J.A., Evans, K.O., Compton, D.L., Appell, M.D. 2012. Dihydrolipoyl dioleoylglycerol antioxidant capacity in phospholipid vesicles. Chemistry and Physics of Lipids. 165:160-168.

Evans, K.O. 2011. 1,2-dielaidoylphosphocholine/1,2-dimyristoylphosphoglycerol supported phospholipid bilayer formation in calcium and calcium-free buffer. Thin Solid Films. 520:3026-3030. DOI: 10.1016/j.tsf.2011.12.002.

Appell, M.D., Jackson, M.A. 2012. Sorption of Ochratoxin A from aqueous solutions using beta-cyclodextrin-polyurethane polymer. Toxins. 4:98-109. DOI: 10.3390/toxinx4020098.

Laszlo, J.A., Yu, Y., Lutz, S., Compton, D.L. 2011. Glycerol acyl-transfer kinetics of a circular permutated Candida antarctica Lipase B. Journal of Molecular Catalysis B: Enzymatic. 72:175-180. DOI: 10.1016/j.molcatb.2011.06.002.

Compton, D.L., Jackson, M.A., Mihalcik, D.J., Mullen, C.A., Boateng, A.A. 2011. Catalytic pyrolysis of oak via pyroprobe and bench scale, packed bed pyrolysis reactors. Journal of Analytical & Applied Pyrolysis. 90:174-181.

Bae, J., Hou, C.T., Kim, H. 2011. Thermostable lipoxygenase, a key enzyme in the conversion of linoleic acid into thrihydroxy-octadecenoic acid by Pseudomonas aeruginosa PR3. Journal of Biotechnology and Bioprocess Engineering. 15:1022-1030.

Suh, M., Baek, K., Kim, B., Hou, C.T., Kim, H. 2011. Production of 7,10-dihydroxy-8(E)-octadecenoic acid from olive oil by Pseudomonas aeruginosa PR3. Applied Microbiology and Biotechnology. 89:1721-1727.

Laszlo, J.A., Evans, K.O., Compton, D.L. 2012. Preservation of polyunsaturated fatty acyl glycerides via intramolecular antioxidant coupling. Chemistry and Physics of Lipids. 165:530-536.

Jackson, M.A., Cermak, S.C. 2012. Cross ketonization of Cuphea sp. oil with acetic acid over a composite oxide of Fe, Ce, and Al. Applied Catalysis A: Genera. 431-432:157-163.

Back, K., Sohn, H., Hou, C.T., Kim, H. 2012. Production of a novel 9,12-dihydroxy-10(E)-eicosenoic acid from eicosenoic acid by Pseudomonas aeruginosa PR3. Journal of Agricultural and Food Chemistry. 59:9652-9657.

Last Modified: 2/23/2016
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