Oxidative coupling of alkylphenols, alkoxyphenols and 1-naphthols catalyzed by metal complexes of amino compounds

A method of preparing a carbon-carbon coupled condensation product of an "alkylphenol", an "alkoxyphenol" or a " 1-naphthol" having one of the following formulas I-V:

• ##STR16## wherein R.sub.2 and R.sub.6 are alkyl groups, R.sub.3 and R.sub.5 are hydrogen or alkyl groups and R.sub.4 is hydrogen or methyl, provided that R.sub.3 and R.sub.5 are not simultaneously tertiary alkyl, said alkyl groups having 1-12 carbon atoms, ##STR17## wherein R.sub.2 and R.sub.4 are alkyl groups, R.sub.3 and R.sub.5 are hydrogen or alkyl groups and R.sub.6 is hydrogen, provided that at least one of R.sub.2 and R.sub.4 is a tertiary alkyl group, said alkyl groups having 1-12 carbon atoms, ##STR18## wherein each R is an alkyl group having 1-12 carbon atoms or alkoxy group having 1-6 carbon atoms and R.sub.1 is hydrogen or methyl, provided that both substituents adjacent to R.sub.1 are not simultaneously tertiary alkyl or tertiary alkoxy, ##STR19## wherein R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl groups containing from 1 to 5 carbon atoms or alkoxy groups containing 1-6 carbon atoms provided that at least one of R.sub.2 and R.sub.4 is hydrogen and R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen, alkyl groups having 1-5 carbon atoms or alkoxy groups having 1-6 carbon atoms, provided that tertiary alkyl or tertiary alkoxy groups are not attached to adjacent carbon atoms of the naphthalene molecule, or ##STR20## wherein R.sub.3 is hydrogen, an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-6 carbon atoms, R.sub.5 is a primary or secondary alkyl group having 1-5 carbon atoms and R.sub.2 and R.sub.6 are alkyl groups having 1-12 carbon atoms or alkoxy groups having 1-6 carbon atoms, by an oxidative coupling reaction said method comprising contacting an aqueous mixture of the phenol or naphthol with oxygen or oxygen containing gas in the presence of a catalyst system consisting essentially of a cupric, manganous, cobaltous, or ferric metal complex of an amine selected from the class consisting of:
• an "aliphatic hydroxy amine",
• a heterocyclic hydroxy amine, and
• an "aliphatic diamine"
• and a sufficient amount of an alkaline material selected from the group consisting of alkali metal hydroxides, alkali metal carbonates and alkali metal bicarbonates to maintain the pH in a range of about 5-10 during the oxidative coupling reaction.