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United States Department of Agriculture

Agricultural Research Service

Title: Optimization of the Sulfuric Acid Catalyzed Estolide Synthesis from Oleic Acid

Authors
item Isbell, Terry
item Frykman, Hans
item Abbott Dr, Thomas
item Lohr, Joseph - CALGENE CHEMICAL
item Drozd, Joseph - CALGENE CHEMICAL

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: December 11, 1996
Publication Date: N/A

Interpretive Summary: Inventing something new in the laboratory is the start of a process from discovery to commercial product. We work closely with industrial manufacturers to ensure our inventions can be scaled up in their factories and that the end product fits customer needs. The discovery of how to make "estolides", a new biodegradable product from vegetable oil components, is important because of their many new uses. One hurdle we had to overcome was that the process for making estolides had to be practical for industry. When we worked with one industrial partner, we learned that our process required a catlayst that might damage their equipment. This research entails work done to change the catalyst and reduce the amount used to get the mildest possible process without compromising the high productivity. Our industrial partner now feels that the process is practical and will soon begin using it to produce a new biodegradable product from oleic acid, a natural oil component.

Technical Abstract: The production of estolide from oleic acid with sulfuric acid acting as a catalyst was optimized for minimal acid concentration and temperature. Commercial oleic acid was found to have an optimum estolide formation when reacted at 55 C with 5% v/v concentrated sulfuric acid for 24 hours under vacuum. The extent of oligomerization was found to be 1.2 estolide units under these reaction conditions. Temperature plays a critical role in the rate of estolide formation as well as the overall yield with higher temperatures providing faster rates but lower yields. Ratio of sulfuric acid to oleic acid equivalents also plays a role. Higher acid concentrations gave faster rates and higher yields of estolide at constant temperature. Vacuum had a minor effect in lowering color but had no apparent effect on the rate or the yield of estolide.

Last Modified: 10/21/2014
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