Contaminant removal from hydrocarbon streams with lactamium based ionic liquids

Abstract

A process for removing a contaminant from a hydrocarbon stream using a lactamium based ionic liquid is described. The process includes contacting the hydrocarbon stream comprising the contaminant with a lean hydrocarbon-immiscible lactamium ionic liquid to produce a mixture comprising the hydrocarbon and a rich hydrocarbon-immiscible lactamium ionic liquid comprising at least a portion of the removed contaminant; and separating the mixture to produce a hydrocarbon effluent and a rich hydrocarbon-immiscible lactamium ionic liquid effluent comprising the rich hydrocarbon-immiscible lactamium ionic liquid.

What is claimed is: 
     
         1 . A process for removing a contaminant from a hydrocarbon stream comprising:
 contacting the hydrocarbon stream comprising the contaminant with a lean hydrocarbon-immiscible lactamium ionic liquid to produce a mixture comprising the hydrocarbon and a rich hydrocarbon-immiscible lactamium ionic liquid comprising at least a portion of the removed contaminant; and   separating the mixture to produce a hydrocarbon effluent and a rich hydrocarbon-immiscible lactamium ionic liquid effluent comprising the rich hydrocarbon-immiscible lactamium ionic liquid;   wherein the hydrocarbon-immiscible lactamium ionic liquid comprises at least one of:   a reaction product of a lactam compound having a general formula   
       
         
           
           
               
               
           
         
         wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8; 
         and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide; 
         with the proviso that when n is 3, R is not hydrogen; 
         or 
         a reaction product of a lactam compound having a general formula 
       
       
         
           
           
               
               
           
         
         wherein the ring has at least one C—C double bond, R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, 
         and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide; 
         or 
         a reaction product of a lactam compound having a general formula 
       
       
         
           
           
               
               
           
         
         wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, in is 1 to 8, and the rings can be saturated or unsaturated; 
         and at least one of a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide. 
       
     
     
         2 . The process of  claim 1  wherein the lactam reaction product is at least one of carboxylates, nitrates, phosphates, phosphinates, phosphonates, imides, cyanates, borates, sulfates, sulfonates, acetates, and halides. 
     
     
         3 . The process of  claim 1  wherein the lactam reaction product is the halometallate and wherein a metal in the halometallate is at least one of Sn, Al, Zn, Mn, Fe, Ga, Cu, Ni, and Co. 
     
     
         4 . The process of  claim 1  wherein a ratio of the Brønsted acid HX to the lactam compound is about 1:1 to about 3:1. 
     
     
         5 . The process of  claim 1  wherein the hydrocarbon stream has a boiling point in a range of about 30° C. to about 525° C. 
     
     
         6 . The process of  claim 1  wherein the contacting step is conducted at a temperature in a range of about 20° C. to about 80° C. 
     
     
         7 . The process of  claim 1  further comprising passing at least a portion of the hydrocarbon effluent to a hydrocarbon conversion process. 
     
     
         8 . The process of  claim 1  further comprising:
 regenerating the rich hydrocarbon-immiscible lactamium ionic liquid effluent; and 
 recycling the regenerated hydrocarbon-immiscible lactamium based ionic liquid to the contacting step. 
 
     
     
         9 . The process of  claim 1  wherein a ratio of the hydrocarbon to the hydrocarbon-immiscible lactamium ionic liquid is in a range of about 1:1,000 to about 1,000:1. 
     
     
         10 . The process of  claim 1  further comprising contacting the rich hydrocarbon-immiscible lactamium ionic liquid effluent with a regeneration solvent to form an extract stream comprising the contaminant and a stream of lean hydrocarbon-immiscible lactamium ionic liquid. 
     
     
         11 . The process of  claim 10  wherein the regeneration solvent comprises water, naphtha, gasoline, diesel, light cycle oil, and light coker gas oil. 
     
     
         12 . The process of  claim 10  further comprising separating the stream of lean hydrocarbon-immiscible lactamium ionic liquid from the regeneration solvent. 
     
     
         13 . The process of  claim 12  further comprising recycling the stream of lean hydrocarbon-immiscible lactamium ionic liquid to the contacting step. 
     
     
         14 . The process of  claim 13  reactivating the stream of lean hydrocarbon-immiscible lactamium ionic liquid with an acid before recycling the stream of lean hydrocarbon-immiscible lactamium ionic liquid to the contacting step. 
     
     
         15 . The process of  claim 1  wherein the ionic liquid has the general formula (III) and wherein at least one ring has at least one C—C double bond. 
     
     
         16 . A process for removing a contaminant from a hydrocarbon stream comprising:
 contacting the hydrocarbon stream comprising the contaminant with a lean hydrocarbon-immiscible lactamium ionic liquid to produce a mixture comprising the hydrocarbon and a rich hydrocarbon-immiscible lactamium ionic liquid comprising at least a portion of the removed contaminant; and   separating the mixture to produce a hydrocarbon effluent and a rich hydrocarbon-immiscible lactamium ionic liquid effluent comprising the rich hydrocarbon-immiscible lactamium ionic liquid;   regenerating the rich hydrocarbon-immiscible lactamium ionic liquid effluent to form a stream of lean hydrocarbon-immiscible lactamium ionic liquid;   recycling the stream of lean hydrocarbon-immiscible lactamium ionic liquid to the contacting step; and   passing at least a portion of the hydrocarbon effluent to a hydrocarbon conversion process;   wherein the hydrocarbon-immiscible lactamium ionic liquid comprises at least one of:   a reaction product of a lactam compound having a general formula   
       
         
           
           
               
               
           
         
         wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8; 
         and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide; 
         with the proviso that when n is 3, R is not hydrogen; 
         or 
         a reaction product of a lactam compound having a general formula 
       
       
         
           
           
               
               
           
         
         wherein the ring has at least one C—C double bond, R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, 
         and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide; 
         or 
         a reaction product of a lactam compound having a general formula 
       
       
         
           
           
               
               
           
         
         wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, in is 1 to 8, and the rings can be saturated or unsaturated; 
         and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide. 
       
     
     
         17 . The process of  claim 16  wherein regenerating the rich hydrocarbon-immiscible lactamium ionic liquid effluent comprises contacting the rich hydrocarbon-immiscible lactamium ionic liquid effluent with a regeneration solvent to form an extract stream comprising the contaminant and the stream of lean hydrocarbon-immiscible lactamium ionic liquid. 
     
     
         18 . The process of  claim 16  reactivating the stream of lean hydrocarbon-immiscible lactamium ionic liquid with an acid before recycling the stream of lean hydrocarbon-immiscible lactamium ionic liquid to the contacting step. 
     
     
         19 . The process of  claim 17  wherein the lactam reaction product is at least one of carboxylates, nitrates, phosphates, phosphinates, phosphonates, imides, cyanates, borates, sulfates, sulfonates, acetates, and halides. 
     
     
         20 . The process of  claim 17  wherein a ratio of the Brønsted acid HX to the lactam compound is about 1:1 to about 3:1.