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US 12,428,381 B2Granted
Gas treating solutions containing imidazole-amine compounds and methods of making the same
AssigneeThe Board of Trustees of The University of Alabama
InventorsJason E. Bara, Kathryn E. O'Harra
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Abstract
Systems comprising a composition where an imidazole is tethered to an amine and a solvent are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and a liquid stream.
Claims24
A method of reducing one or more volatile compounds from a stream, comprising:
- contacting a stream with a solution consisting of an imidazole having formula (I) or a salt thereof, and a solvent,
- wherein
- R is selected from null, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy;
- wherein R is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- and
- R1 and R2 are, independent of one another, hydrogen, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- wherein each R1 or R2 independent of each other is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- R3 is selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, C6-C14 aryl, C1-C13 heteroaryl, C6 C14 aryloxy, wherein R3 is optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- R4 and R5 are each independent of the other, selected from hydrogen, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- wherein each R1 or R2 independent of each other is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- or wherein
- R4 and R5 together form a 6 membered aromatic ring containing 6 carbon atoms, wherein the solvent consists essentially of water.
9 more elements
A method for sweetening a natural gas feed stream, comprising:
- a) contacting the natural gas feed stream with a solution consisting of an imidazole of formula (I) or a salt thereof, and a solvent,
- wherein
- R is selected from null, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy;
- wherein R is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- and
- R1 and R2 are, independent of one another, hydrogen, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- wherein each R1 or R2 independent of each other is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- R3 is selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, wherein R3 is optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- R4 and R5 are each independent of the other, selected from hydrogen, C1-20 alkyl, C2-20 alkenyl, C1-C20 alkoxy, C2-20 alkynyl, C1-20 heteroalkyl, C2-20 heteroalkenyl, C2-20 heteroalkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- wherein each R1 or R2 independent of each other is optionally substituted with C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, amino, carbonyl, ester, ether, halide, carboxyl, hydroxy, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
- or wherein
- R4 and R5 together form a 6 membered aromatic ring containing 6 carbon atoms,
- wherein the solvent consists essentially of water;
- b) forming a purified gas feed stream and a gas-rich solution;
- and
- c) separating the purified gas feed stream and the gas-rich solution.
13 more elements
Dependencies are inferred from the claim text.