Oxidation and halogenation of jojoba wax

The oxidation with hydrogen peroxide and permanganate and the allylic bromination, chlorination and chloro-etherification of the olefinic bonds of the liquid wax extracted from beans of jojoba (Simmondsia chinensis) were studied. Hydrolytic splitting of the wax into its carboxylic and alcoholic components competed with most reactions carried out in aqueous systems. The use of a suitable phase-transfer catalyst enabled the oxidation of the double bonds to carboxyls using permanganate in aqueous systems. Reaction of the wax with hydrogen peroxide in formic acid yielded formates, which were then hydrolyzed to vicinal glycols. The diglycols obtained by hydrogen peroxide oxidation were benzoylated. Allylic chlorination of jojoba wax with t-butyl hypochlorite in organic solvents was carried out. Conditions were found for the allylic bromination of the wax, yielding mono-, di-, tetra-, or octabromo derivatives.