Provided here are systems and methods that integrate a hydrodearylation process and a hydrodealkylation process into an aromatic recovery complex. Various other embodiments may be disclosed and claimed.

Systems and methods for hydrodearylation of a hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons, the method including supplying a hydrogen feed to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; mixing the hydrogen feed with the hydrocarbon feed stream to saturate the hydrocarbon feed stream with hydrogen gas to create a hydrogen-enriched liquid hydrocarbon stream; passing the hydrogen-enriched liquid hydrocarbon stream to a hydrodearylation reactor without a separate gaseous phase of hydrogen; allowing the hydrogen-enriched liquid hydrocarbon stream to react in presence of a catalyst under specific reaction conditions to produce a product stream comprising a reduced concentration of di-aromatic compounds and an increased concentration of mono-aromatic compounds compared to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; and recovering, from the hydrodearylation reactor, a product stream for a downstream process, wherein the non-condensed alkyl-bridged multi-aromatic hydrocarbons include at least two benzene rings connected by an alkyl bridge group having at least two carbons, wherein the benzene rings are connected to different carbons of the alkyl bridge group.

Systems and methods for hydrodearylation of a hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons, the method including supplying a hydrogen feed to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; mixing the hydrogen feed with the hydrocarbon feed stream to saturate the hydrocarbon feed stream with hydrogen gas to create a hydrogen-enriched liquid hydrocarbon stream; passing the hydrogen-enriched liquid hydrocarbon stream to a hydrodearylation reactor without a separate gaseous phase of hydrogen; allowing the hydrogen-enriched liquid hydrocarbon stream to react in presence of a catalyst under specific reaction conditions to produce a product stream comprising a reduced concentration of di-aromatic compounds and an increased concentration of mono-aromatic compounds compared to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; and recovering, from the hydrodearylation reactor, a product stream for a downstream process, wherein the non-condensed alkyl-bridged multi-aromatic hydrocarbons include at least two benzene rings connected by an alkyl bridge group having at least two carbons, wherein the benzene rings are connected to different carbons of the alkyl bridge group.

A method of making a multifunctional catalyst for upgrading pyrolysis oil includes contacting a hierarchical mesoporous zeolite support with a solution including at least a first metal catalyst precursor and a second metal catalyst precursor, each or both of which may include a heteropolyacid. The hierarchical mesoporous zeolite support may have an average pore size of from 2 nm to 40 nm. Contacting the hierarchical mesoporous zeolite support with the solution deposits or adsorbs the first metal catalyst precursor and the second catalyst precursor onto outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support to produce a multifunctional catalyst precursor. The method further includes removing excess solution and calcining the multifunctional catalyst precursor to produce the multifunctional catalyst comprising at least a first metal catalyst and a second metal catalyst deposited on the outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support.

Systems and methods for hydrodearylation of a hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons, the method including supplying a hydrogen feed to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; mixing the hydrogen feed with the hydrocarbon feed stream to saturate the hydrocarbon feed stream with hydrogen gas to create a hydrogen-enriched liquid hydrocarbon stream; passing the hydrogen-enriched liquid hydrocarbon stream to a hydrodearylation reactor without a separate gaseous phase of hydrogen; allowing the hydrogen-enriched liquid hydrocarbon stream to react in presence of a catalyst under specific reaction conditions to produce a product stream comprising a reduced concentration of di-aromatic compounds and an increased concentration of mono-aromatic compounds compared to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; and recovering, from the hydrodearylation reactor, a product stream for a downstream process, wherein the non-condensed alkyl-bridged multi-aromatic hydrocarbons include at least two benzene rings connected by an alkyl bridge group having at least two carbons, wherein the benzene rings are connected to different carbons of the alkyl bridge group.

Systems and methods for hydrodearylation of a hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons, the method including supplying a hydrogen feed to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; mixing the hydrogen feed with the hydrocarbon feed stream to saturate the hydrocarbon feed stream with hydrogen gas to create a hydrogen-enriched liquid hydrocarbon stream; passing the hydrogen-enriched liquid hydrocarbon stream to a hydrodearylation reactor without a separate gaseous phase of hydrogen; allowing the hydrogen-enriched liquid hydrocarbon stream to react in presence of a catalyst under specific reaction conditions to produce a product stream comprising a reduced concentration of di-aromatic compounds and an increased concentration of mono-aromatic compounds compared to the hydrocarbon feed stream comprising non-condensed alkyl-bridged multi-aromatic hydrocarbons; and recovering, from the hydrodearylation reactor, a product stream for a downstream process, wherein the non-condensed alkyl-bridged multi-aromatic hydrocarbons include at least two benzene rings connected by an alkyl bridge group having at least two carbons, wherein the benzene rings are connected to different carbons of the alkyl bridge group.

A method of making a multifunctional catalyst for upgrading pyrolysis oil includes contacting a hierarchical mesoporous zeolite support with a solution including at least a first metal catalyst precursor and a second metal catalyst precursor, each or both of which may include a heteropolyacid. The hierarchical mesoporous zeolite support may have an average pore size of from 2 nm to 40 nm. Contacting the hierarchical mesoporous zeolite support with the solution deposits or adsorbs the first metal catalyst precursor and the second catalyst precursor onto outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support to produce a multifunctional catalyst precursor. The method further includes removing excess solution and calcining the multifunctional catalyst precursor to produce the multifunctional catalyst comprising at least a first metal catalyst and a second metal catalyst deposited on the outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support.

A method of making a multifunctional catalyst for upgrading pyrolysis oil includes contacting a hierarchical mesoporous zeolite support with a solution including at least a first metal catalyst precursor and a second metal catalyst precursor, each or both of which may include a heteropolyacid. The hierarchical mesoporous zeolite support may have an average pore size of from 2 nm to 40 nm. Contacting the hierarchical mesoporous zeolite support with the solution deposits or adsorbs the first metal catalyst precursor and the second catalyst precursor onto outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support to produce a multifunctional catalyst precursor. The method further includes removing excess solution and calcining the multifunctional catalyst precursor to produce the multifunctional catalyst comprising at least a first metal catalyst and a second metal catalyst deposited on the outer surfaces and pore surfaces of the hierarchical mesoporous zeolite support.

A method of making a multifunctional catalyst for upgrading pyrolysis oil includes contacting a zeolite support with a solution including at least a first metal catalyst precursor and a second metal catalyst precursor, the first metal catalyst precursor, the second metal catalyst precursor, or both, including a heteropolyacid. Contacting the zeolite support with the solution deposits or adsorbs the first metal catalyst precursor and the second catalyst precursor onto outer surfaces and pore surfaces of the zeolite support to produce a multifunctional catalyst precursor. The method further includes removing excess solution from the multifunctional catalyst precursor and calcining the multifunctional catalyst precursor to produce the multifunctional catalyst comprising at least a first metal catalyst and a second metal catalyst deposited on the outer surfaces and pore surfaces of the zeolite support.

A method of making a multifunctional catalyst for upgrading pyrolysis oil includes contacting a zeolite support with a solution including at least a first metal catalyst precursor and a second metal catalyst precursor, the first metal catalyst precursor, the second metal catalyst precursor, or both, including a heteropolyacid. Contacting the zeolite support with the solution deposits or adsorbs the first metal catalyst precursor and the second catalyst precursor onto outer surfaces and pore surfaces of the zeolite support to produce a multifunctional catalyst precursor. The method further includes removing excess solution from the multifunctional catalyst precursor and calcining the multifunctional catalyst precursor to produce the multifunctional catalyst comprising at least a first metal catalyst and a second metal catalyst deposited on the outer surfaces and pore surfaces of the zeolite support.