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United States Department of Agriculture

Agricultural Research Service

2009 Annual Report

1a.Objectives (from AD-416)
The primary goal of this project is to demonstrate the technical and commercial feasibility of using critical fluids and heterogeneous catalysts to extract and process agrimaterials into value-added products. The long-term objective of this project is to develop new chemical processes to produce high-value products from plant materials. Over the next three years, we will focus on the following objectives:

Objective 1: Develop methods for the conversion of agrimaterials to platform chemicals. There are two aspects to this objective: a) the oxidation of seed oils to platform chemicals such as diacids and hydroxyacids; and b) the design and development of better catalysts for regioselective transformations, including the selective addition of aromatics to the double bond of unsaturated fatty acids.

Objective 2: Develop commercially viable processes based on critical fluids to convert ligno-cellulosic materials to fermentable sugars as well as convert vegetable oils to high-value products. There are two sub-objectives to this objective: a) develop commercially viable processes based on critical fluids such as carbon dioxide (CO2), water and/or ethanol to pretreat ligno-cellulosic biomass prior to its conversion via enzymatic hydrolysis to fermentable sugars; and b) use CO2-based critical fluids to improve the commercial viability of processes for enzymatically converting vegetable oils to high-value products such as feruloylated monoacyl- and diacylglycerides. Critical fluid processes will be evaluated for enhancement of these conversions and integration with downstream recovery processes for these high-value products.

1b.Approach (from AD-416)
New polyoxometalate catalysts will be synthesized, characterized and used to oxidatively cleave double bonds in oleic and petroselinic acids to form platform chemicals. This research will also evaluate critical fluid processes for the conversion of vegetable oils to high-value products, and critical fluid pretreatments for converting ligno-cellulosic biomass to fermentable sugars.

3.Progress Report
Lesquerella holds promise as a new crop for the desert Southwest but, in order to be a viable new crop, new products must be manufactured using highly efficient means. We were able to improve the efficiency of the preparation of lesquerella derivatives by modifying the catalysts used in the process. The new catalysts designed last year have been characterized and improved upon for use in ether formation from the reaction of phenol with hydroxy fatty acids. These catalysts are bifunctional, consisting of a chloroethyl group and an acid group, and it is now thought that the function of the chloroethyl group is to prevent the ether from reentering the active sites of the catalyst and isomerizing. The phenoxy ether of lesquerella oil has now been prepared in large enough quantities to allow bulk properties of the product to be determined and uses proposed.

Catalysts are being developed which promote the hydrolysis of fats and oils at lower temperatures. The resulting free fatty acids are of use in the food and detergent industries. The same catalysts can be used for the reverse reaction and targeted functionalized triglycerides can be prepared.

Carbon dioxide explosion experiments of ligno-cellulosic materials have been conducted on switchgrass using carbon dioxide for varying lengths of time. These materials will be subjected to hydrolysis and fermentation to determine differences in their subsequent ethanol yields.

An enzymatic reactor was designed and constructed utilizing critical carbon dioxide to improve the conversion of soybean oil to SoyScreen™. This reactor was used to study cycling critical fluid mixtures and determine which work best for the continuous synthesis of SoyScreen™. This new synthetic method results in a more efficient conversion of vegetable oils to the product SoyScreen™.

1. PRODUCTION OF NEW PRODUCTS FROM LESQUERELLA OIL. Lesquerella is a genus native to the Southwestern United States and is currently being developed as a new oil seed crop due to its novel oil content. New catalysts have been developed which have allowed for the production of an ether of the oil in high yields. This product has potential use as a lubricant or diesel fuel additive.

2. CRITICAL FLUID MIXES FOR IMPROVING ENZYMATIC REACTIONS. Soybean oil and ethyl ferulate can be combined enzymatically to produce a product called SoyScreen™. SoyScreen™ has many potential uses, including use as a natural sunscreen and as an antioxidant in the cosmetic and food industries. Cycling carbon dioxide through an enzyme bed containing the reactants soybean oil and ethyl ferulate resulted in excellent conversion to the desired product, called SoyScreen™. The use of other gases, as well as mixtures of various gases, through the enzyme bed had a significant effect on the overall conversion to SoyScreen™. This research provides a technology which allows a more efficient conversion of low-value vegetable oil into the value-added product SoyScreen™.

6.Technology Transfer

Number of Active CRADAs1

Review Publications
Jackson, M.A., Compton, D.L., Boateng, A.A. 2009. Screening heterogenous catalysts for the pyrolysis of lignin. Journal of Analytical and Applied Pyrolysis. 85:226-230.

Eller, F.J., Taylor, S.L., Laszlo, J.A., Compton, D.L., Teel, J.A. 2009. Counter-current carbon dioxide purification of partially deacylated sunflower oil. Journal of the American Oil Chemists' Society. 86:277-282.

Last Modified: 7/30/2015
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