Ionic liquids and methods of using same

An ionic liquid selected from either:

• A. R1R2R3A+R8A+R5R6R7X− (III)
• wherein at least one A is or contains phosphorus or a phosphorus containing ring and the other A is or contains either phosphorus or nitrogen or a phosphorus or nitrogen containing ring;
• and wherein X is an anion selected from the group consisting of halides;
• hydroxyl;
• carbonates;
• alkyl carbonates;
• bicarbonates;
• carboxylates;
• hydroxycarboxylates;
• anionic dithiocarbonates;
• anionic trithiocarbonates;
• xanthates, thiocyanates;
• alkoxides;
• anionic urea;
• anionic alkyl substituted phosphines;
• anionic amino fatty acids;
• anionic alkoxylated fatty acids;
• anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers;
• anionic phosphated maleic copolymers;
• anionic homo or copolymers of an oxirane or methyloxirane;
• anionic metal complexes;
• sulfur or silicon containing anions;
• anionic phosphate esters;
• anionic thiophosphate esters;
• anionic phosphonate esters;
• anionic thiophosphonate esters;
• anionic thiols;
• anionic natural products;
• anionic phenols;
• anionic phenol resins;
• anionic oxirane or methyloxirane homo or copolymers;
• anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof;
• anionic alkyl substituted phosphines;
• anionic copolymers of ethylene and vinyl acetate;
• and anionic homopolymers, copolymers and terpolymers of one or more acrylates, methacrylates and acrylamides, optionally copolymerized with one or more ethylenically unsaturated monomers;
• and mixtures thereof;
• and further wherein R1, R2, R3, R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen;
• benzyl;
• alkylbenzyl, or oxyalkyl;
• a straight or branched alkyl group, an alkylbenzyl group, an arylalkyl group, a straight or branched chain alkenyl group, a hydroxyalkyl group or a hydroxyalkylbenzyl group;
• and a polyoxyalkylene group;
• and R8 is a straight or branched alkylene group, an alkylene oxyalkylene, or an alkylene polyoxyalkylene or a zwitterion;
• and further wherein R groups may be joined to form a heterocyclic nitrogen, sulfur or phosphorus containing ring;
• B. one of formulas:
• A+X− (I);
• R1R2R3R4A+X− (II);
• or
• R1R2R3A+R8A+R5R6R7X− (III)
• wherein A is or contains phosphorus or a phosphorus containing ring and X is an anion selected from the group consisting of hydroxyl;
• bicarbonates;
• alkoxides;
• anionic hydroxycarboxylates;
• silicon containing anions;
• anionic amino fatty acids;
• 4anionic alkoxylated fatty acids;
• anionic thiophosphonate esters;
• alkyl substituted phosphines;
• anionic urea;
• anionic thiourea;
• anionic natural products;
• anionic phenols;
• anionic phenol resins;
• anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof;
• anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers;
• anionic homopolymers, copolymers and terpolymers of one or more acrylates, methacrylates and acrylamides, optionally copolymerized with one or more ethylenically unsaturated monomers;
• anionic copolymers of ethylene and vinyl acetate;
• phosphated maleic copolymers;
• an anionic homo or copolymer of an oxirane or methyloxirane and mixtures thereof;
• C.
• A+X− (I);
• R1R2R3R4A+X− (II);
• or
• R1R2R3A+R8A+R5R6R7X− (III)
• wherein A is or contains nitrogen or a nitrogen heterocyclic ring and the anion X is selected from the group consisting of silicon containing anions;
• anionic thiophosphonate esters;
• anionic natural products;
• anionic phenol resins;
• alkoxides;
• anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof or a mixture thereof;
• amino fatty acids;
• anionic alkoxylated fatty acids;
• alkyl substituted phosphines;
• anionic urea;
• anionic thiourea;
• anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers;
• anionic homopolymers, copolymers and terpolymers containing acrylamide units;
• phosphated maleic copolymers;
• anionic copolymers of ethylene and vinyl acetate;
• oxirane or methyloxirane homo or copolymers;
• and mixture thereof;
• and R1, R2, R3, R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen;
• benzyl;
• alkylbenzyl, or oxyalkyl;
• a straight or branched alkyl group, an alkylbenzyl group, an arylalkyl group, a straight or branched chain alkenyl group, a hydroxyalkyl group or a hydroxyalkylbenzyl group;
• and a polyoxyalkylene group;
• and R8 is a straight or branched alkylene group, an alkylene oxyalkylene, or an alkylene polyoxyalkylene or a zwitterion;
• or
• D.
• R1R2R3R4A+X− (II);
• or
• R1R2R3A+R8A+R5R6R7X− (III)
• wherein A in formula (II) is nitrogen or a nitrogen containing ring and each A in formula (III) is nitrogen as defined herein and wherein X is an anion selected from the group consisting of anionic metallic complexes;
• sulfur or silicon containing anions;
• anionic phosphate esters;
• anionic thiophosphate esters;
• anionic phosphonate esters;
• anionic thiophosphonate esters;
• anionic thiols;
• anionic natural products;
• anionic phenols;
• anionic phenol resins;
• anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof amino fatty acids;
• anionic oxirane or methyloxirane homo or copolymers;
• anionic alkoxylated fatty acids;
• alkyl substituted phosphines;
• anionic urea;
• anionic thiourea;
• anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers;
• anionic copolymers of ethylene and vinyl acetate;
• anionic homopolymers, copolymers and terpolymers containing acrylamide units;
• phosphated maleic copolymers and mixtures thereof;
• and further wherein R1, R2, R3, R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen;
• benzyl;
• alkylbenzyl, or oxyalkyl;
• a straight or branched alkyl group, an alkylbenzyl group, an arylalkyl group, a straight or branched chain alkenyl group, a hydroxyalkyl group or a hydroxyalkylbenzyl group;
• and a polyoxyalkylene group;
• and R8 is a straight or branched alkylene group, an alkylene oxyalkylene, or an alkylene polyoxyalkylene or a zwitterion;
• and further wherein R groups may be joined to form a heterocyclic nitrogen, sulfur or phosphorus containing ring.

A method of treating a hydrocarbon containing fluid to:

• (a) inhibit or prevent the formation or precipitation of asphaltenes in the fluid;
• or
• (b) remove or reduce sulfur containing compounds in the fluid, the method comprising contacting the fluid with an ionic liquid of the formula:
• R1R2R3R4N+X− (IV);
• or
• R1R2R3N+R8N+R5R6R7X− (V)
• X is an anion selected from the group consisting of halides;
• hydroxyl;
• carbonates;
• alkyl carbonates;
• bicarbonates;
• carboxylates;
• hydroxycarboxylates;
• sulfonates;
• sulfates;
• bisulfites;
• thiocyanates;
• dithiocarbonates;
• dithiocarbonates;
• trithiocarbonates;
• carbamates;
• dithiocarbamates;
• trithiocarbamates;
• xanthates;
• sulfides;
• polysulfides;
• alkoxides;
• anionic ureas;
• anionic alkyl substituted phosphines;
• anionic amino fatty acids;
• anionic alkoxylated fatty acids;
• anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers;
• anionic phosphated maleic copolymers;
• anionic metal complexes;
• sulfur or silicon containing anions;
• anionic phosphate esters;
• anionic thiophosphate esters;
• anionic phosphonate esters;
• anionic thiophosphonate esters;
• anionic thiols;
• anionic natural products;
• anionic phenols;
• anionic phenol resins;
• anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof;
• anionic alkyl substituted phosphines;
• and anionic homopolymers, copolymers and terpolymers of one or more acrylates, methacrylates, acrylamides and acids, optionally copolymerized with one or more ethylenically unsaturated monomers;
• anionic homo and copolymers of oxirane and/or methyloxirane;
• anionic copolymers of olefins and vinyl acetate;
• and mixtures thereof;
• and further wherein R1, R2, R3, R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen;
• benzyl;
• alkylbenzyl, or oxyalkyl;
• a straight or branched alkyl group, an alkylbenzyl group, an arylalkyl group, a straight or branched chain alkenyl group, a hydroxyalkyl group or a hydroxyalkylbenzyl group;
• and a polyoxyalkylene group;
• and R8 is a straight or branched alkylene group, an alkylene oxyalkylene, or an alkylene polyoxyalkylene or a zwitterion;
• and further wherein R groups may be joined to form a heterocyclic nitrogen, sulfur or phosphorus containing ring.