Sodium Chloride → Di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) Sebacate

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A 2-phase mixture of 85.7 g (0.666 mol) of 70% aqueous tert-butyl hydroperoxide, 200 ml of n-nonane and 10 g of sodium chloride is agitated in a separatory funnel. The organic layer is dried over anhydrous magnesium sulfate. A mixture of 40.0 g (0.0832 mol) of bis-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate and the tert-butyl hydroperoxide solution in n-nonane is heated to reflux (151° C.) under a nitrogen atmosphere. Vanadium (III) acetylacetonate (2.0 g) is added over a 15-minute interval. The reaction mixture is diluted with 50 ml of nonane. The reaction mixture is heated at reflux for 22 hours. Water is collected in a Dean-Stark trap. The mixture turns red and then darkens in color. The solvent is then removed under reduced pressure. The residue is dissolved in 150 ml of heptane and then passed through a short column of silica gel with additional heptane. The crude product is purified by chromatography (Waters Prep 500A HPLC; 29:1 heptane:ethyl acetate) to afford 2.5 g (4% yield) of the title compound.

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