Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines

Claim 1

A process for the preparation of an N-hydrocarbyloxy compound of the formula ##STR8## wherein the nitrogen atom is flanked by two quaternary carbon atoms where E 1 and E 3 are independently alkyl of 1 to 5 carbon atoms or phenyl, E 2 and E 4 are independently alkyl of 1 to 5 carbon atoms, or E 1 and E 2 together or E 3 and E 4 together or both E 1 and E 2 together and E 3 and E 4 together are tetramethylene or pentamethylene, R is a hydrocarbyl radical, and T is a divalent group required to form a cyclic 5- or 6-membered ring, T being inert to chemical change in the presence of hydroperoxide, which comprises dissolving a highly colored N-oxyl compound of the formula ##STR9## where E 1 , E 2 , E 3 , E 4 and T have the meanings given above, in a hydrocarbon organic solvent, said hydrocarbon having at least one labile hydrogen atom and no ethylenic unsaturation, in the presence of a hydroperoxide and 0.001 to 0.1 mole percent, based on the hydroperoxide, of a catalyst selected from the group consisting of the metal carbonyls, the metal oxides, the metal acetylacetonates and the metal alkoxides where the metal is selected from groups IVb, Vb, VIb, VIIb and VIII of the periodic table, with the mole ratio of hydroperoxide to N-oxyl compound being 50:1 to 2:1, and heating the reaction mixture at a temperature of 50° to 200° C. for a period of time sufficient to discharge the color associated with the presence of N-oxyl compound and to form concomitantly the desired N-hydrocarbyloxy product.