The subject invention provides synthetic compounds, and compound complexes having catalytic activities towards oxidation or oxygenation, and/or dehydrogenation of various substrates comprising C—H bonds. The catalysts of the subject invention comprise a dinuclear Cu(I)/Cu(II) center that can convert between a resting state and a reactive species. The subject invention also provides methods of using such catalysts for the oxidation of substrates comprising C—H bonds, e.g., hydrocarbons, to synthesize chemicals for use as pharmaceuticals and industrial feedstock.

A process for aromatizing hydrocarbons comprises: converting at least a portion of highly branched hydrocarbons in a feed stream into selectively convertible components, and aromatizing the selectively convertible components to produce an aromatization reactor effluent. The aromatization reactor effluent comprises an aromatic product. Converting at least the portion of the highly branched hydrocarbons into the selectively convertible components may include contacting the feed stream with an isomerization catalyst in an isomerization reaction system under isomerization reaction conditions; and isomerizing the portion of the highly branched hydrocarbons in the feed stream into the selectively convertible components.

A process for aromatizing hydrocarbons comprises: converting at least a portion of highly branched hydrocarbons in a feed stream into selectively convertible components, and aromatizing the selectively convertible components to produce an aromatization reactor effluent. The aromatization reactor effluent comprises an aromatic product. Converting at least the portion of the highly branched hydrocarbons into the selectively convertible components may include contacting the feed stream with an isomerization catalyst in an isomerization reaction system under isomerization reaction conditions; and isomerizing the portion of the highly branched hydrocarbons in the feed stream into the selectively convertible components.

This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.0 angstroms or more present at 60 wt % or more, (based upon weight of final catalyst composition); (b) dehydrogenating the hydroalkylation reaction product using a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds; (c) contacting at the dehydrogenation reaction product with an oxidizing gas to convert the methyl-substituted biphenyl compounds to biphenyl carboxylic acids; and (d) reacting the biphenyl carboxylic acids with one or more C.sub.1 to C.sub.14 alcohols to produce biphenyl esters.

This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.0 angstroms or more present at 60 wt % or more, (based upon weight of final catalyst composition); (b) dehydrogenating the hydroalkylation reaction product using a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds; (c) contacting at the dehydrogenation reaction product with an oxidizing gas to convert the methyl-substituted biphenyl compounds to biphenyl carboxylic acids; and (d) reacting the biphenyl carboxylic acids with one or more C.sub.1 to C.sub.14 alcohols to produce biphenyl esters.

This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.0 angstroms or more present at 60 wt % or more, (based upon weight of final catalyst composition); (b) dehydrogenating the hydroalkylation reaction product using a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds; (c) contacting at the dehydrogenation reaction product with an oxidizing gas to convert the methyl-substituted biphenyl compounds to biphenyl carboxylic acids; and (d) reacting the biphenyl carboxylic acids with one or more C.sub.1 to C.sub.14 alcohols to produce biphenyl esters.

Processes are described for separating 3,4′- and 4,4′-dimethylbiphenyl from a mixture comprising at least 3,3′-, 3,4′- and 4,4′-dimethylbiphenyl. In the processes, the mixture is cooled to produce a crystallization product comprising at least of the 4,4′-dimethylbiphenyl from the feed mixture and a first mother liquor product. The first mother liquor product is distilled to produce a bottoms stream enriched in 4,4′-dimethylbiphenyl as compared with the first mother liquor product and an overhead stream deficient in 4,4′-dimethylbiphenyl as compared with the first mother liquor product. The overhead stream is then cooled to produce a second crystallization product comprising at least part of the 3,4′-dimethylbiphenyl from the overhead stream and a second mother liquor product.

Processes are described for separating 3,4′- and 4,4′-dimethylbiphenyl from a mixture comprising at least 3,3′-, 3,4′- and 4,4′-dimethylbiphenyl. In the processes, the mixture is cooled to produce a crystallization product comprising at least of the 4,4′-dimethylbiphenyl from the feed mixture and a first mother liquor product. The first mother liquor product is distilled to produce a bottoms stream enriched in 4,4′-dimethylbiphenyl as compared with the first mother liquor product and an overhead stream deficient in 4,4′-dimethylbiphenyl as compared with the first mother liquor product. The overhead stream is then cooled to produce a second crystallization product comprising at least part of the 3,4′-dimethylbiphenyl from the overhead stream and a second mother liquor product.

Processes are described for separating 3,4′- and 4,4′-dimethylbiphenyl from a mixture comprising at least 3,3′-, 3,4′- and 4,4′-dimethylbiphenyl. In the processes, the mixture is cooled to produce a crystallization product comprising at least of the 4,4′-dimethylbiphenyl from the feed mixture and a first mother liquor product. The first mother liquor product is distilled to produce a bottoms stream enriched in 4,4′-dimethylbiphenyl as compared with the first mother liquor product and an overhead stream deficient in 4,4′-dimethylbiphenyl as compared with the first mother liquor product. The overhead stream is then cooled to produce a second crystallization product comprising at least part of the 3,4′-dimethylbiphenyl from the overhead stream and a second mother liquor product.

In a process for dehydrogenating cyclohexylbenzene and/or alkyl-substituted cyclohexylbenzene compounds, a dehydrogenation catalyst comprising at least one Group 10 metal compound on a support is heated in the presence of hydrogen from a first temperature from 0° C. to 200° C. to a second, higher temperature from 60° C. to 500° C. at a ramp rate no more than 100° C./hour. The dehydrogenation catalyst is contacted with hydrogen at the second temperature for a time from 3 to 300 hours to produce an activated dehydrogenation catalyst. A feed comprising cyclohexylbenzene and/or an alkyl-substituted cyclohexylbenzene compound is then contacted with hydrogen in the presence of the activated dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising biphenyl and/or an alkyl-substituted biphenyl compound.