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United States Department of Agriculture

Agricultural Research Service

Title: Preparation and Characterization of Methyl 11-Amino-(N-P-Toluenesulfonyl) 9-E-Octadecenoate and Methyl 8-Amino-(N-P-Toluenesulfonyl)-9-E Octadecenoate

item Herron, Barry - EX-EMPLOYEE, USDA/ARS
item Bagby, Marvin - RETIRED, USDA/ARS
item Isbell, Terry
item Byrdwell, William
item Plattner, Ronald
item Weisleder, David

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 17, 1996
Publication Date: N/A

Interpretive Summary: Soybeans provide the lions share of food oil consumed around the world, and the meal remaining after the oil is removed from the bean is a major source of protein in animal feeds in developed countries. A much smaller, but very important, portion of soybean oil is used in commerce in nonfood applications. This smaller industrial market for the oil plays an important role in the economics of soybean production and marketing. Farmers have greater production and marketing flexibility when more nonfood uses for soybean oil are found, the focus of this research. Novel materials were made from a major fatty acid of soybean that could be used in formulating inks and coatings. These are fruitful application areas for expanded use of soybean oil.

Technical Abstract: Allylic amination of methyl oleate with bis (N-p- toluenesulfonyl) sulfodiimide results in a mixture of methyl 11-amino-(N-p-toluenesulfonyl)-9-E-octadecenoate and methyl 8-amino-(N-p-toluenesulfonyl)-9-E-octadecenoate in 58% yield. These novel products were isolated and characterized by nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, mass spectrometry (MS) and melting point. The reaction was analyzed by high performance liquid chromatography (HPLC) and thin-layer chromatography (TLC).

Last Modified: 4/19/2015
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