Methods of using ionic liquids as demulsifiers
A method of demulsifying an emulsion with an ionic liquid having a nitrogen or phosphorus cation.
1. A method of demulsifying an emulsion comprising contacting the emulsion with an ionic liquid of the formula:
R 1 R 2 R 3 N + R 8 N + R 5 R 6 R 7 X − (I)
wherein:
R 1 , R 2 , R 3 , R 5 , R 6 and R 7 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 R 8 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 containing ring; and
X is an anionic ethylene oxide/propylene oxide copolymer.
2. The method of claim 1 , wherein R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen; benzyl; oxyalkyl; a straight or branched C 1-30 alkyl group; a C 7-30 alkylbenzyl group; a C 7-30 arylalkyl group; a straight or branched C 3-30 alkenyl group; a C 1-30 hydroxyalkyl group; a C 7-30 hydroxyalkylbenzyl group; and a polyoxyalkylene group and further wherein R groups may be joined to form a heterocyclic nitrogen containing ring; and R 8 is a straight or branched C 1-30 alkylene, an alkylene oxyalkylene, or an alkylene polyoxyalkylene.
3. The method of claim 1 , wherein R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are independently selected from —H, a C 1-20 alkyl, —CH 2 CH 2 OH, —CH 2 CH(CH 3 )OH, and an oxirane or methyloxirane homo or copolymer containing (CH 2 CH 2 O) x CH 2 CH(CH 3 )O) y where x and y are independently selected from 1 to 1500 and mixtures thereof.
4. The method of claim 1 , wherein X is the anion of a polymer of the structure:
wherein x is independently selected from integer of 1 to 1500 and R is a C 1 -C 10 alkylene group.
5. The method of claim 1 , wherein the ionic liquid is a component of a demulsifying composition which further contains a second demulsifier which is not an ionic liquid.
6. The method of claim 5 , wherein the second demulsifier is an ethylene oxide/propylene oxide copolymer.
7. The method of claim 5 , wherein the ionic liquid enhances the performance of the second demulsifier.
8. The method of claim 5 , wherein the ionic liquid and second demulsifier form a reaction product.
9. The method of claim 5 , wherein the ionic liquid and second demulsifier are a synergistic blend.
10. The method of claim 5 , wherein the amount of ionic liquid demulsifier in the demulsifying composition is from about 3 to about 99 weight percent.
11. The method of claim 5 , wherein the amount of second demulsifier in the demulsifying composition is from about 3 to about 99 weight percent.
12. The method of claim 5 , wherein the demulsifying composition is contacted with the emulsion in a conduit or vessel wherein a hydrocarbon stream is in contact with the conduit or vessel.
13. The method of claim 5 , wherein the demulsifying composition is contacted with the emulsion during storage and/or transportation of a petroleum hydrocarbon fluid.
14. The method of claim 5 , wherein the emulsion is demulsified with the demulsifying composition during production or refining of crude oil or during removal of metals, amines and/or phosphorus from a petroleum hydrocarbon or an industrial stream.
15. The method of claim 1 , wherein the emulsion is a water-in-oil emulsion.
16. The method of claim 15 , wherein the water-in-oil emulsion is a crude oil emulsion.
17. The method of claim 16 , wherein the crude oil emulsion is a refinery desalting emulsion or a crude oil production emulsion.
18. The method of claim 1 , wherein the melting point of the ionic liquid is −100° C. to 200° C.
19. The method of claim 1 , wherein the ionic liquid is contacted with the emulsion in a conduit or vessel wherein a hydrocarbon stream is in contact with the conduit or vessel.
20. The method of claim 1 , wherein the ionic liquid is contacted with the emulsion during storage and/or transportation of a petroleum hydrocarbon fluid.
21. The method of claim 1 , wherein the ionic liquid is contacted with a hydrocarbon-containing stream at a temperature from about −50° C. to about 250° C. and/or a pressure of about 14.7 psia to about 40,000 psia.
22. The method of claim 1 , wherein the emulsion is demulsified with the ionic liquid during production or refining of crude oil.
23. The method of claim 1 , wherein the emulsion is demulsified with the ionic liquid during removal of metals, amines and/or phosphorus from a petroleum hydrocarbon or an industrial stream.
24. The method of claim 1 , wherein the emulsion is a water-in-oil emulsion and further wherein the ionic liquid separates, breaks or resolves oil from the water-in-oil emulsion.
25. The method of claim 1 , wherein the emulsion is an oil-in-water emulsion and further wherein the ionic liquid separates, breaks or removes oil from the oil-in-water emulsion.