# US 2013/0153470 A1 · Extraction of polycyclic aromatic compounds from petroleum feedstocks using ionic liquids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0153470 A1 - Document ID: US20130153470A1 - Status: Published application - Kind: A1 - Application number: 13/447,385 - Filed: 2012-04-16 - Published: 2013-06-20 - Earliest claimed: 2011-12-15 - Assignees: Uop LLC - Inventors: Beckay J. Mezza; Alakananda Bhattacharyya; Haiyan Wang; Christopher P. Nicholas - Web page: https://patentgrep.com/patent/US20130153470A1 ## CPC - C10G 21/18: Halogen-containing compounds - C10G 21/24: Phosphorus-containing compounds - C10G 2300/1074: Vacuum distillates - C10G 2300/206: Asphaltenes - C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES ## Abstract The present invention involves a process for removing one or more polycyclic aromatic hydrocarbon compounds from a vacuum gas oil comprising contacting the vacuum gas oil with a vacuum gas oil-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil and the vacuum gas oil-immiscible phosphonium ionic liquid; and separating the mixture to produce a vacuum gas oil effluent and a vacuum gas oil-immiscible phosphonium ionic liquid effluent, the vacuum gas oil-immiscible phosphonium ionic liquid effluent comprising the polycyclic aromatic hydrocarbon compound. ## Claims ### Claim 1 A process for removing a polycyclic aromatic hydrocarbon compound from a vacuum gas oil comprising: (a) contacting the vacuum gas oil comprising the polycyclic aromatic hydrocarbon compound with a vacuum gas oil-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil and the vacuum gas oil-immiscible phosphonium ionic liquid; and (b) separating the mixture to produce a vacuum gas oil effluent and a vacuum gas oil-immiscible phosphonium ionic liquid effluent, the vacuum gas oil-immiscible phosphonium ionic liquid effluent comprising the polycyclic aromatic hydrocarbon compound. ### Claim 2 (depends on 1) The process of claim 1 wherein the vacuum gas oil-immiscible phosphonium ionic liquid comprises at least one ionic liquid from at least one of tetraalkylphosphonium dialkylphosphates, tetraalkylphosphonium dialkyl phosphinates, tetraalkylphosphonium phosphates, tetraalkylphosphonium tosylates, tetraalkylphosphonium sulfates, tetraalkylphosphonium sulfonates, tetraalkylphosphonium carbonates, tetraalkylphosphonium metalates, oxometalates, tetraalkylphosphonium mixed metalates, tetraalkylphosphonium polyoxometalates, and tetraalkylphosphonium halides. ### Claim 3 (depends on 1) The process of claim 1 wherein the vacuum gas oil-immiscible phosphonium ionic liquid comprises at least one of trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, tributyl(methyl)phosphonium bromide, tributyl(methyl)phosphonium chloride, tributyl(hexyl)phosphonium bromide, tributyl(hexyl)phosphonium chloride, tributyl(octyl)phosphonium bromide, tributyl(octyl)phosphonium chloride, tributyl(decyl)phosphonium bromide, tributyl(decyl)phosphonium chloride, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, triisobutyl(methyl)phosphonium tosylate, tributyl(methyl)phosphonium methylsulfate, tributyl(ethyl)phosphonium diethylphosphate, and tetrabutylphosphonium methanesulfonate. ### Claim 4 (depends on 1) The process of claim 1 wherein the mixture is water free. ### Claim 5 (depends on 1) The process of claim 1 wherein the mixture further comprises water in an amount less than 10% relative to the amount of vacuum gas oil-immiscible phosphonium ionic liquid in the mixture on a weight basis. ### Claim 6 (depends on 1) The process of claim 1 wherein the amount of polycyclic aromatic hydrocarbon compounds is reduced by at least 25 wt %. ### Claim 7 (depends on 1) The process of claim 1 wherein said polycyclic aromatic hydrocarbon compound has greater than or equal to two disjoint aromatic π-sextet. ### Claim 8 (depends on 7) The process of claim 7 wherein said polycyclic aromatic hydrocarbon compound with greater than or equal to 2 disjoint aromatic π-sextets is reduced by at least 40%. ### Claim 9 (depends on 1) The process of claim 1 further comprising passing at least a portion of the vacuum gas oil effluent to a hydrocarbon conversion process. ### Claim 10 (depends on 1) The process of claim 1 further comprising washing at least a portion of the vacuum gas oil effluent with water to produce a washed vacuum gas oil stream and a spent water stream. ### Claim 11 (depends on 10) The process of claim 10 further comprising passing at least a portion of the washed vacuum gas oil stream to a hydrocarbon conversion process. ### Claim 12 (depends on 1) The process of claim 1 further comprising contacting the vacuum gas oil-immiscible phosphonium ionic liquid effluent with a regeneration solvent and separating the vacuum gas oil-immiscible phosphonium ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the polycyclic aromatic hydrocarbon compound and a regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream. ### Claim 13 (depends on 1, 12) The process of claim 12 further comprising recycling at least a portion of the regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream to the polycyclic aromatic hydrocarbon removal contacting step of claim 1(a). ### Claim 14 (depends on 12) The process of claim 12 wherein the regeneration solvent comprises water and the regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream comprises water. ### Claim 15 (depends on 14) The process of claim 14 wherein the vacuum gas oil effluent comprises vacuum gas oil-immiscible phosphonium ionic liquid, further comprising washing at least a portion of the vacuum gas oil effluent with water to produce a washed vacuum gas oil and a spent water stream, the spent water stream comprising the vacuum gas oil-immiscible phosphonium ionic liquid; wherein at least a portion of the spent water stream is at least a portion of the regeneration solvent. ### Claim 16 (depends on 15) The process of claim 15 further comprising drying at least a portion of at least one of the regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream, and the spent water stream to produce a dried vacuum gas oil-immiscible phosphonium ionic liquid stream. ### Claim 17 (depends on 1, 16) The process of claim 16 further comprising recycling at least a portion of the dried vacuum gas oil-immiscible phosphonium ionic liquid stream to the polycyclic aromatic hydrocarbon compound removal contacting step of claim 1(a). ### Claim 18 A process for removing a polycyclic aromatic hydrocarbon compound from a vacuum gas oil comprising: (a) contacting the vacuum gas oil comprising the polycyclic aromatic hydrocarbon compound with a vacuum gas oil-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil, and the vacuum gas oil-immiscible phosphonium ionic liquid; (b) separating the mixture to produce a vacuum gas oil effluent and a vacuum gas oil-immiscible phosphonium ionic liquid effluent, the vacuum gas oil-immiscible phosphonium ionic liquid effluent comprising the polycyclic aromatic hydrocarbon compound; (c) washing at least a portion of the vacuum gas oil effluent with water to produce a washed vacuum gas oil stream and a spent water stream; (d) contacting the vacuum gas oil-immiscible phosphonium ionic liquid effluent with a regeneration solvent and separating the vacuum gas oil-immiscible phosphonium ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the polycyclic aromatic hydrocarbon compound and a regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream; and (e) drying at least a portion of at least one of the vacuum gas oil-immiscible phosphonium ionic liquid effluent; the spent water stream, and the regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream to produce a dried vacuum gas oil-immiscible phosphonium ionic liquid stream. ### Claim 19 (depends on 18, 19) The process of claim 18 further comprising recycling at least a portion of at least one of the vacuum gas oil-immiscible phosphonium ionic liquid effluent; the spent water stream, the regenerated vacuum gas oil-immiscible phosphonium ionic liquid stream, and the dried vacuum gas oil-immiscible phosphonium ionic liquid stream to the polycyclic aromatic hydrocarbon compound removal contacting step of claim 19(a). ### Claim 20 (depends on 18) The process of claim 18 wherein more than about 25% of the polycyclic aromatic hydrocarbon by weight with greater than or equal to one disjoint aromatic π-sextet may be extracted or removed from the vacuum gas oil feed in a single polycyclic aromatic hydrocarbon removal step.