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US 8,574,427 B2Granted
Process for removing refractory nitrogen compounds from vacuum gas oil
AssigneeUop LLC
InventorsBeckay J. Mezza, Haiyan Wang, Alakananda Bhattacharyya, Christopher P. Nicholas
Life of this patent
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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.
Claims18
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;
- 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;
- 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, tetraalkylphosphonium halides, 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;
- wherein the refractory nitrogen compound content of the vacuum gas oil is reduced by at least 10 wt %.
4 more elements
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.
4 more elements
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.
3 more elements
Dependencies are inferred from the claim text.