2011 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).
Objective 1a: A modified lipase was studied and found to have improved catalytic capabilities in comparison to the original enzyme. This enzyme will permit more efficient manufacture of high-value lipids. Novel triglycerides containing potent antioxidant capabilities were synthesized and characterized in phospholipid vesicles. Functionalized lipids were synthesized containing acrylic acid. These new compounds will be used to produce high-value lipids for industry.
Objective 1b: We successfully developed new analytical methods for screening operations using high-performance liquid chromatography (HPLC), gas chromatography (GC) and thin layer chromatography (TLC). With our new HPLC method, we are able to detect both substrate soybean oil and product soy polyols. With our new TLC method, we are able to identify different kinds of soy polyols. We also developed a suitable screening medium for the operation.
Objective 2: Soybean lecithin (phospholipids) is a by-product of processing soybean oil that has an increased commercial application when functionalized for consumer use. Procedures for enzymatically functionalizing soybean phospholipids were planned after thorough review of literature. HPLC methods were established for analysis of reaction products.
Objective 3: Several inorganic catalysts were examined to determine which were most useful for thermochemically converting vegetable oil into useful industrial chemicals. Acidic inorganic catalysts were the best catalysts for thermochemically converting vegetable oils to aromatic commodity chemicals such as benzene, toluene, and xylene. Acidic inorganic catalysts were also found to selectively catalyze the esterification of bifunctional fatty acids to esters without catalyzing unwanted side reactions at the secondary functional group.
Conversion of vegetable oils and biomass to useful industrial chemicals. USDA, ARS scientists in the Renewable Product Technology Research Unit at the National Center for Agricultural Utilization Research, Peoria, IL, have focused research on converting biomass into commodity chemicals. Seven basic building block chemicals used in the synthesis of many polymers and consumer products, from carpets to plastic bottles, are derived from petroleum. We developed inorganic catalysts that convert vegetable oils and biomass at high temperatures to some of these basic building block, commodity chemicals. This research has led to a pending Cooperative Research and Development Agreement (CRADA) with industry collaborators to develop catalysts for converting alternative oils and biomass to commodity chemicals.
Sustainable insect repellent made from row crop. Cuphea is an oil seed crop being grown in limited quantities in the upper Midwest. USDA, ARS scientists in the Renewable Product Technology Research Unit at the National Center for Agricultural Utilization Research, Peoria, IL, developed a method to produce 2-undecanone, a compound known to repel biting insects, from the oil extracted from the seeds of Cuphea. Because this conversion is relatively simple and the value of the resulting compound is high, growing Cuphea for this specific use may make this a profitable alternative crop. A patent has been applied for covering the synthesis of 2-undecanone from Cuphea oil. 2-Undecanone is both a fragrance and an insect repellent, and this approach affords a cost-effective natural, sustainable product. The technology has yet to be transferred, but users could include manufacturers of sustainable fragrances and insect repellents. The latter use is an especially valuable alternative to the most common insect repellent, DEET. This natural and less toxic alternative for DEET is expected to create a large-volume use for Cuphea oil. Commercialization of this process will provide economic incentives for farmers to grow Cuphea.
Laszlo, J.A., Jackson, M.A., Blanco, R.M. 2011. Active-site titration analysis of surface influence on immobilized Candida antarctica Lipase B activity. Journal of Molecular Catalysis B: Enzymatic. 69:60-65.