Hydrocarbon conversion processes using ionic liquids

Abstract

A method of hydrocarbon conversion is described. The hydrocarbon feed is decontaminated using an ionic liquid and introduced into a conversion zone. The conversion of the decontaminated feed is increased compared to the conversion of the contaminated feed and the yield of the desired product made from the decontaminated hydrocarbon feed is increased compared to the yield of the desired product made from the contaminated hydrocarbon feed.

What is claimed is: 
     
         1 . A method of hydrocarbon conversion comprising:
 contacting a hydrocarbon feed containing a contaminant with a hydrocarbon feed-immiscible ionic liquid to form a mixture comprising decontaminated hydrocarbon feed and hydrocarbon feed-immiscible ionic liquid containing the contaminant;   reacting the decontaminated hydrocarbon feed in a conversion zone to produce a desired product selected from gasoline, diesel, naphtha, distillate, jet, light olefins, or combinations thereof;   wherein a conversion of the decontaminated hydrocarbon feed is increased compared to a conversion of the contaminated hydrocarbon feed under comparable operating conditions, or a yield of the desired product made from the decontaminated hydrocarbon feed is increased compared to a yield of the desired product made from the contaminated hydrocarbon feed under comparable operating conditions, or both.   
     
     
         2 . The method of  claim 1  wherein the hydrocarbon feed has a density in a range of about 0.8 g/cc to about 1.1 g/cc. 
     
     
         3 . The method of  claim 1  wherein at least one of research octane number, cetane number, smoke point, nitrogen content, sulfur content, aromatic content, or density of the desired product made from the decontaminated hydrocarbon feed is improved compared to the desired product made from the contaminated hydrocarbon feed. 
     
     
         4 . The method of  claim 1  further comprising separating the mixture into a decontaminated hydrocarbon feed stream and a hydrocarbon feed-immiscible ionic liquid stream containing the contaminant and wherein introducing the decontaminated hydrocarbon feed into the conversion zone comprises introducing the decontaminated hydrocarbon feed stream into the conversion zone. 
     
     
         5 . The method of  claim 4  further comprising contacting the hydrocarbon feed-immiscible ionic liquid effluent with a regeneration solvent and separating the hydrocarbon feed-immiscible ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the contaminant and a regenerated hydrocarbon feed-immiscible ionic liquid stream. 
     
     
         6 . The method of  claim 5  wherein the regeneration solvent comprises one of the desired products from the conversion zone. 
     
     
         7 . The method of  claim 5  further comprising recycling at least a portion of the regenerated hydrocarbon feed-immiscible ionic liquid stream to the contacting step. 
     
     
         8 . The method of  claim 1  wherein the hydrocarbon feed-immiscible ionic liquid comprises at least one of an imidazolium ionic liquid, a phosphonium ionic liquid, and a pyridinium ionic liquid. 
     
     
         9 . The method of  claim 1  wherein the hydrocarbon feed-immiscible ionic liquid comprises at least one of 1-ethyl-3-methylimidazolium ethyl sulfate, 1-butyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-4-methylpyridinium chloride, N-butyl-3-methylpyridinium methylsulfate, 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 chloride, tetrabutylphosphonium bromide, triisobutyl(methyl)phosphonium tosylate, tributyl(ethyl)phosphonium diethylphosphate, tetrabutylphosphonium methanesulfonate pyridinium p-toluene sulfonate. 
     
     
         10 . The method of  claim 1  wherein the conversion of the decontaminated feed is at least 0.5 vol % higher than the conversion of the contaminated feed, or the yield of the desired product from the decontaminated feed is at least about 0.5 vol % higher than the yield of the desired product from the contaminated feed, or both. 
     
     
         11 . The method of  claim 1  wherein a selectivity of the desired product from the decontaminated feed is at least 0.1 vol % higher than a selectivity of the desired product from the contaminated feed under comparable operating conditions. 
     
     
         12 . The method of claim wherein the decontaminated hydrocarbon feed is mixed with a second hydrocarbon feed. 
     
     
         13 . The method of  claim 1  wherein the conversion zone is a catalytic cracking conversion zone. 
     
     
         14 . A method of fluid catalytic cracking comprising:
 contacting a hydrocarbon feed containing a contaminant with a hydrocarbon feed-immiscible ionic liquid to form a mixture comprising decontaminated hydrocarbon feed and feed-immiscible ionic liquid containing the contaminant, wherein the contaminated feed is selected from the group consisting of vacuum gas oil, coker gas oil, light cycle oil, vacuum residue, or combinations thereof, and wherein the hydrocarbon feed-immiscible ionic liquid comprises at least one of an imidazolium ionic liquid, a phosphonium ionic liquid, and a pyridinium ionic liquid;   separating the mixture into a decontaminated hydrocarbon feed stream and a hydrocarbon feed-immiscible ionic liquid stream containing the contaminant;   reacting the decontaminated hydrocarbon feed stream in a catalytic conversion zone in the presence of a catalyst under catalytic conversion conditions to produce desired product selected from gasoline, diesel, naphtha, distillate, jet, light olefins, or combinations thereof;   wherein a conversion of the decontaminated hydrocarbon feed is increased compared to a conversion of the contaminated hydrocarbon feed under comparable operating conditions, or a yield of the desired product made from the decontaminated hydrocarbon feed is increased compared to a yield of the desired product made from the contaminated hydrocarbon feed under comparable operating conditions, or both.   
     
     
         15 . The method of  claim 14  wherein the hydrocarbon feed has a density in a range of about 0.8 g/cc to about 1.1 g/cc. 
     
     
         16 . The method of  claim 14  wherein at least one of research octane number, cetane number, smoke point, nitrogen content, sulfur content, aromatic content, or density of the desired product made from the decontaminated hydrocarbon feed is improved compared to the desired product made from the contaminated hydrocarbon feed. 
     
     
         17 . The method of  claim 14  further comprising contacting the hydrocarbon feed-immiscible ionic liquid effluent with a regeneration solvent and separating the hydrocarbon feed-immiscible ionic liquid effluent from the regeneration solvent to produce an extract stream comprising the contaminant and a regenerated hydrocarbon feed-immiscible ionic liquid stream. 
     
     
         18 . The method of  claim 17  further comprising recycling at least a portion of the regenerated hydrocarbon feed-immiscible ionic liquid stream to the contacting step. 
     
     
         19 . The method of  claim 14  wherein the hydrocarbon feed-immiscible ionic liquid comprises at least one of 1-ethyl-3-methylimidazolium ethyl sulfate, 1-butyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, tetrabutylphosphonium methane sulfonate, pyridinium p-toluene sulfonate, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, tributyl(octyl)phosphonium chloride, and tributyl(ethyl)phosphonium diethylphosphate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-4-methylpyridinium chloride, N-butyl-3-methylpyridinium methylsulfate, 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(decyl)phosphonium bromide, tributyl(decyl)phosphonium chloride, triisobutyl(methyl)phosphonium tosylate, and tetrabutylphosphonium methanesulfonate. 
     
     
         20 . The method of  claim 14  wherein the conversion of the decontaminated feed is at least 0.5 vol % higher than the conversion of the contaminated feed, or the yield of the desired product made from the decontaminated feed is at least 0.5 vol % higher than the yield of the desired product made from the contaminated feed under comparable operating conditions, or both.