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Abstract

The invention comprises a process for preparing a compound having the formula comprising: 1 where Z and W are the same or different, and selected from the group consisting of O, NH and NR, where R is H, alkyl, cycloalkyl or aryl, R' is alkyl, cycloalkyl, alkylene, alkyl 3-propionate, aryl or arylene. A is H if either or both of Z and W are not O, but if both Z and W are O, A is: 2 or a carbon based heterocyclic component having an amine constituent, or RR'N-, where R' is the same or different than R and is selected from the same group as R. The process comprises preparing an alkylthio-substituted benzoquinone intermediate by reacting in a first reaction mixture a thio-substituted aromatic having the formula: 3 where X is OH, NH.sub.2 or NHR when Z is O, NH or NR, respectively, and where Y is OH, NH.sub.2 or NHR when W is O, NH or NR, respectively, with an alkali metal periodate in the presence of a phase transfer catalyst, followed, if A is not H, by reacting the intermediate in a second reaction mixture containing an amine included in the group of amines comprising A, and in the presence of oxygen to obtain the compound. If A is H no second reaction mixture is employed and the intermediate comprises the compound. The invention includes a process for making the composition and the use of the composition in natural and synthetic rubber, and with monomers, gasoline and lubricating oil to inhibit polymerization.

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First Claim