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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Mono and Diketo Derivatives of Jojoba Oil

Authors
item Edgcomb, Michelle
item Mund, Melissa - FORMER NCAUR EMPLOYEE
item Isbell, Terry

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 16, 2001
Publication Date: N/A

Technical Abstract: Jojoba is a desert new crop currently being grown in the American Southwest as well as Israel and Argentina. The oil is mainly an unsaturated, C42, liquid wax ester. Both the carboxylic acid and the alcohol components contain an olefin that can be functionalized in an effort to enhance the properties of the oil. The olefin groups were converted to carbonyls, thus making both mono and diketo products. Iodine in a +1 oxidation state was used to drive the reactions, which were initially run using methyl oleate as a model system. Both KI and I2 were used as oxidizing agents with aqueous NaOCl used as a re-oxidant. A series of HOI reactions was also run. In addition to changing I+ sources, series of reactions were run varying I+:NaOCl ratios, solvent present, acids present, starting material, reaction temperature, and reaction time. Complete conversion to diketojojobate (as measured by HPLC) was possible with two molar equivalents of HOI in ethyl acetate and water at reflux for 24 hours. High yields, 95% by HPLC, were also possible using KI as a reactant in the same solvent system. The reaction conditions with KI were more strenuous, however, as four equivalents of KI and two equivalents of NaOCl and a reaction time of over 48 hours were necessary. When I2 and NaOCl were used the reaction time was short, but the favored product was monoketojojobate. With 0.75 eq. each I2 and NaOCl in ethyl acetate and water at reflux, 61% monoketojojobate and 20% diketojojobate were formed in three hours.

Last Modified: 7/31/2014
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