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.

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.

Methods and apparatuses are provided for deoxygenating pyrolysis oil. A method includes contacting a pyrolysis oil with a deoxygenation catalyst in a first reactor at deoxygenation conditions to produce a first reactor effluent. The first reactor effluent has a first oxygen concentration and a first hydrogen concentration, based on hydrocarbons in the first reactor effluent, and the first reactor effluent includes an aromatic compound. The first reactor effluent is contacted with a dehydrogenation catalyst in a second reactor at conditions that deoxygenate the first reactor effluent while preserving the aromatic compound to produce a second reactor effluent. The second reactor effluent has a second oxygen concentration lower than the first oxygen concentration and a second hydrogen concentration that is equal to or lower than the first hydrogen concentration, where the second oxygen concentration and the second hydrogen concentration are based on the hydrocarbons in the second reactor effluent.

Methods and apparatuses are provided for deoxygenating pyrolysis oil. A method includes contacting a pyrolysis oil with a deoxygenation catalyst in a first reactor at deoxygenation conditions to produce a first reactor effluent. The first reactor effluent has a first oxygen concentration and a first hydrogen concentration, based on hydrocarbons in the first reactor effluent, and the first reactor effluent includes an aromatic compound. The first reactor effluent is contacted with a dehydrogenation catalyst in a second reactor at conditions that deoxygenate the first reactor effluent while preserving the aromatic compound to produce a second reactor effluent. The second reactor effluent has a second oxygen concentration lower than the first oxygen concentration and a second hydrogen concentration that is equal to or lower than the first hydrogen concentration, where the second oxygen concentration and the second hydrogen concentration are based on the hydrocarbons in the second reactor effluent.

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.

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.

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.

The present invention provides an indene composition having a content of indene of 80 to 99.5% by mass, in which a content ratio of a hydrocarbon compound having a condensed ring structure of a 5-membered ring and a 6-membered ring, and having 9 or 10 carbon atoms, in a component contained in addition to indene, is 90% by mass or more, and a content of benzonitrile is 0.5% by mass or less, and a content of sulfur is 5 ppm by mass or less.

The present invention provides an indene composition having a content of indene of 80 to 99.5% by mass, in which a content ratio of a hydrocarbon compound having a condensed ring structure of a 5-membered ring and a 6-membered ring, and having 9 or 10 carbon atoms, in a component contained in addition to indene, is 90% by mass or more, and a content of benzonitrile is 0.5% by mass or less, and a content of sulfur is 5 ppm by mass or less.

In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula: ##STR00001##
wherein each of m and n is independently 1, 2, or 3, is contacted with hydrogen in the presence of a hydrogenation catalyst to produce a hydrogenation reaction product comprising at least one methyl-substituted bicyclohexane compound, and the methyl-substituted bicyclohexane compound is then contacted with a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound.