Oxidative coupling of phenols and naphthols

Claim 1

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 ##STR14## wherein R 2 and R 6 are alkyl groups containing from 1 to about 12 carbon atoms, provided that only one of said alkyl groups may be a tertiary alkyl, and R 3 and R 5 are hydrogen or alkyl groups containing from 1 to about 12 carbon atoms provided that if both R 3 and R 5 are alkyl only one of said alkyl groups may be a tertiary alkyl; ##STR15## wherein R 2 and R 4 L are alkyl groups containing from 1 to about 12 carbon atoms, provided that at least one of said alkyl groups is a tertiary alkyl, and R 3 and R 5 are hydrogen or alkyl; ##STR16## wherein OR' is an alkoxy group containing from 1 to about 6 carbon atoms; ##STR17## wherein R is an alkyl group containing from 1 to about 12 carbon atoms and OR' is an alkoxy group containing from 1 to about 6 carbon atoms; ##STR18## wherein R 3 and R 5 are hydrogen, alkyl groups containing from 1 to about 5 carbon atoms, or alkoxy groups containing from 1 to about 6 carbon atoms provided that if both R 3 and R 5 are alkyl or alkoxy groups only one of said groups may be a tertiary alkyl or alkoxy; and R 2 and R 6 are alkyl groups containing from 1 to about 12 carbon atoms or alkoxy groups containing from 1 to about 6 carbon atoms provided that only one of said substituents may be a tertiary alkyl or alkoxy; and ##STR19## wherein R 2 , R 3 and R 4 are hydrogen, alkyl containing from 1 to 5 carbon atoms, or alkoxy containing from 1 to 6 carbon atoms, provided that either R 2 or R 4 is hydrogen and R 5 , R 6 , R 7 and R 8 are hydrogen, alkyl containing from 1 to 5 carbon atoms or alkoxy containing from 1 to 6 carbon atoms provided that tertiary alkyl or alkoxy groups are not attached to adjacent carbon atoms of the naphthalene molecule, said method comprising contacting an aqueous mixture of the phenol or naphthol with oxygen in the presence of a catalyst consisting essentially of: a. a copper compound selected from the group consisting of cupric halides, basic cupric halohydroxides, cupric carboxylates, cupric nitrate, cupric sulfate, cupric alkylsulfates, cupric aryl sulfonates, cupric carbonate, basic cupric carbonate, cupric hydroxide, cupric chlorate, cuprous halides, and cuprous red oxide, b. an anionic surfactant in which the hydrophilic moiety is selected from the group consisting of carboxylate, phosphate, sulfate and sulfonate, and c. an alkaline material selected from the group consisting of alkali metal hydroxides, alkali metal carbonates and alkali metal bicarbonates.

Claim 2

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 ##STR14## wherein R 2 and R 6 are alkyl groups containing from 1 to about 12 carbon atoms, provided that only one of said alkyl groups may be a tertiary alkyl, and R 3 and R 5 are hydrogen or alkyl groups containing from 1 to about 12 carbon atoms provided that if both R 3 and R 5 are alkyl only one of said alkyl groups may be a tertiary alkyl; ##STR15## wherein R 2 and R 4 L are alkyl groups containing from 1 to about 12 carbon atoms, provided that at least one of said alkyl groups is a tertiary alkyl, and R 3 and R 5 are hydrogen or alkyl; ##STR16## wherein OR' is an alkoxy group containing from 1 to about 6 carbon atoms; ##STR17## wherein R is an alkyl group containing from 1 to about 12 carbon atoms and OR' is an alkoxy group containing from 1 to about 6 carbon atoms; ##STR18## wherein R 3 and R 5 are hydrogen, alkyl groups containing from 1 to about 5 carbon atoms, or alkoxy groups containing from 1 to about 6 carbon atoms provided that if both R 3 and R 5 are alkyl or alkoxy groups only one of said groups may be a tertiary alkyl or alkoxy; and R 2 and R 6 are alkyl groups containing from 1 to about 12 carbon atoms or alkoxy groups containing from 1 to about 6 carbon atoms provided that only one of said substituents may be a tertiary alkyl or alkoxy; and ##STR19## wherein R 2 , R 3 and R 4 are hydrogen, alkyl containing from 1 to 5 carbon atoms, or alkoxy containing from 1 to 6 carbon atoms, provided that either R 2 or R 4 is hydrogen and R 5 , R 6 , R 7 and R 8 are hydrogen, alkyl containing from 1 to 5 carbon atoms or alkoxy containing from 1 to 6 carbon atoms provided that tertiary alkyl or alkoxy groups are not attached to adjacent carbon atoms of the naphthalene molecule, said method comprising contacting an aqueous mixture of the phenol or naphthol with oxygen in the presence of a catalyst consisting essentially of: a. a copper compound selected from the group consisting of cupric halides, basic cupric halohydroxides, cupric carboxylates, cupric nitrate, cupric sulfate, cupric alkylsulfates, cupric aryl sulfonates, cupric carbonate, basic cupric carbonate, cupric hydroxide, cupric chlorate, cuprous halides, and cuprous red oxide, b. an anionic surfactant in which the hydrophilic moiety is selected from the group consisting of carboxylate, phosphate, sulfate and sulfonate, and c. an alkaline material selected from the group consisting of alkali metal hydroxides, alkali metal carbonates and alkali metal bicarbonates.