# US 2013/0153464 A1 · Process for removing refractory nitrogen compounds from vacuum gas oil > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0153464 A1 - Document ID: US20130153464A1 - Status: Published application - Kind: A1 - Application number: 13/555,769 - Filed: 2012-07-23 - Published: 2013-06-20 - Earliest claimed: 2011-12-15 - Assignees: Uop LLC - Inventors: Beckay J. Mezza; Haiyan Wang; Alakananda Bhattacharyya; Christopher P. Nicholas - Web page: https://patentgrep.com/patent/US20130153464A1 ## CPC - C10G 69/04: including at least one step of catalytic cracking in the absence of hydrogen - C10G 55/06: including at least one catalytic cracking step - C10G 67/04: including solvent extraction as the refining step in the absence of hydrogen - C10G 2300/1074: Vacuum distillates - 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 A process for removing a refractory nitrogen compound from a hydroprocessed vacuum gas oil feed includes contacting the hydroprocessed vacuum gas oil feed comprising the nitrogen compound with a VGO-immiscible phosphonium ionic liquid to produce a hydroprocessed vacuum gas oil and VGO-immiscible phosphonium ionic liquid mixture, and separating the mixture to produce a hydroprocessed vacuum gas oil effluent having a reduced refractory nitrogen compound content relative to the vacuum gas oil feed. ## Claims ### Claim 1 A process for removing a refractory nitrogen compound from a vacuum gas oil comprising: (a) hydroprocessing the vacuum gas oil; (b) contacting the vacuum gas oil comprising the refractory nitrogen compound with a VGO-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil and the VGO-immiscible phosphonium ionic liquid; and (c) separating the mixture to produce a vacuum gas oil effluent and a VGO-immiscible phosphonium ionic liquid effluent, the VGO-immiscible phosphonium ionic liquid effluent comprising the refractory nitrogen compound. ### Claim 2 (depends on 1) The process of claim 1 wherein said refractory nitrogen compound comprises at least one compound selected from the group consisting of indoles and naphthenic indoles, quinolines and naphthenic quinolines, carbazoles and naphthenic carbazoles, acridines and naphthenic acridines, benzocarbazole and naphthenic benzocarbazoles, benzacridines and naphthenic benzacridines, and dibenzocarbazoles and naphthenic dibenzocarbazoles. ### Claim 3 (depends on 1) The process of claim 1 wherein the VGO-immiscible phosphonium ionic liquid comprises at least one ionic liquid selected from the group consisting 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 4 (depends on 1) The process of claim 1 wherein the VGO-immiscible phosphonium ionic liquid comprises at least one ionic liquid selected from the group consisting 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 5 (depends on 1) The process of claim 1 wherein the mixture further comprises water in an amount less than about 50% relative to the amount of VGO-immiscible phosphonium ionic liquid in the mixture on a weight basis. ### Claim 6 (depends on 1) The process of claim 1 wherein the ratio of the vacuum gas oil to the VGO-immiscible phosphonium ionic liquid in the mixture ranges from about 1:1000 to about 1000:1 on a weight basis. ### Claim 7 (depends on 1) The process of claim 1 wherein the refractory nitrogen compound is reduced by greater than 40% on a weight basis. ### Claim 8 (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 9 (depends on 8) The process of claim 8 wherein said hydrocarbon conversion process comprises catalytic cracking or hydroprocessing. ### 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 VGO-immiscible phosphonium ionic liquid effluent with a regeneration solvent and separating the VGO-immiscible phosphonium ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the refractory nitrogen compound and a regenerated VGO-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 VGO-immiscible phosphonium ionic liquid stream to the refractory nitrogen compound removal contacting step of claim 1(b). ### Claim 14 (depends on 12) The process of claim 12 wherein the regeneration solvent comprises a lighter hydrocarbon fraction relative to the vacuum gas oil and the extract stream further comprises the lighter hydrocarbon fraction, the lighter hydrocarbon fraction being immiscible with the VGO-immiscible phosphonium ionic liquid. ### Claim 15 (depends on 12) The process of claim 12 wherein the regeneration solvent comprises water. ### Claim 16 (depends on 15) The process of claim 15 wherein the vacuum gas oil effluent comprises VGO-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 VGO-immiscible phosphonium ionic liquid; wherein at least a portion of the spent water stream is at least a portion of the regeneration solvent. ### Claim 17 (depends on 1, 16) The process of claim 16 further comprising drying at least a portion of the regenerated VGO-immiscible phosphonium ionic liquid stream to produce a dried VGO-immiscible phosphonium ionic liquid stream and recycling at least a portion of the dried VGO-immiscible phosphonium ionic liquid stream to the refractory nitrogen compound removal contacting step of claim 1(b). ### Claim 18 A process for removing a refractory nitrogen compound from a vacuum gas oil comprising: (a) hydroprocessing the vacuum gas oil; (b) contacting the vacuum gas oil comprising the refractory nitrogen compound with a VGO-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil, and the VGO-immiscible phosphonium ionic liquid; (c) separating the mixture to produce a vacuum gas oil effluent with a refractory nitrogen compound level reduced in comparison to the hydroprocessed vacuum gas oil and a VGO-immiscible phosphonium ionic liquid effluent, the VGO-immiscible phosphonium ionic liquid effluent comprising the nitrogen compound; (d) 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; (e) contacting the VGO-immiscible phosphonium ionic liquid effluent with a regeneration solvent and separating the VGO-immiscible phosphonium ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the nitrogen compound and a regenerated VGO-immiscible phosphonium ionic liquid stream; and (f) drying at least a portion of at least one of the VGO-immiscible phosphonium ionic liquid effluent, the spent water stream, and the regenerated VGO-immiscible phosphonium ionic liquid stream to produce a dried VGO-immiscible phosphonium ionic liquid stream. ### Claim 19 (depends on 18) The process of claim 18 further comprising recycling at least a portion of at least one of the VGO-immiscible phosphonium ionic liquid effluent, the spent water stream, the regenerated VGO-immiscible phosphonium ionic liquid stream, and the dried VGO-immiscible phosphonium ionic liquid stream to the refractory nitrogen compound removal contacting step of claim 18(b). ### Claim 20 (depends on 18) The process of claim 18 wherein the refractory nitrogen compound level is reduced by at least 25% by weight. ### Claim 21 A process for removing a refractory nitrogen compound from a vacuum gas oil comprising: (a) contacting the vacuum gas oil comprising the refractory nitrogen compound with a VGO-immiscible phosphonium ionic liquid to produce a mixture comprising the vacuum gas oil, and the VGO-immiscible phosphonium ionic liquid; (b) separating the mixture to produce a vacuum gas oil effluent with a refractory nitrogen compound level reduced by greater than 25% by weight in comparison to the vacuum gas oil and a VGO-immiscible phosphonium ionic liquid effluent, the VGO-immiscible phosphonium ionic liquid effluent comprising the nitrogen compound; (c) contacting the VGO-immiscible phosphonium ionic liquid effluent with a regeneration solvent and separating the VGO-immiscible phosphonium ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the nitrogen compound and a regenerated VGO-immiscible phosphonium ionic liquid stream; (d) drying at least a portion of at least one of the VGO-immiscible phosphonium ionic liquid effluent, and the regenerated VGO-immiscible phosphonium ionic liquid stream to produce a dried VGO-immiscible phosphonium ionic liquid stream; and (e) passing the vacuum gas oil effluent to a hydroprocessing step wherein the desulfurization efficiency of the hydroprocessing step is greater than that obtained by hydroprocessing the untreated vacuum gas oil.