Patent ID: 11939336
Assignee: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION
Field: Chemical engineering (Chemistry)
Classification: CPC C  B | IPC B  C

Claim 31:
32. A method of removing an anion from aqueous solution containing the anion, comprising:
(a) contacting the aqueous solution with an immiscible organic solution comprising an aryl-triazole bicyclic macrocycle selected from the group consisting of Formulas (I), (III), (IV), (V), (VI) and (VII):, wherein for (I), R1, R2, and R3 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR4, —N(R5R6), —CO2R7, —C(O)—N(R8R9), wherein R4, R5, R6, R7, R8, and R9 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,
wherein for (III), X is independently selected from the group consisting of CH, CF and N, and R1, R2, and R3 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR4, —N(R5R6), —CO2R7, —C(O)—N(R8R9), wherein R4, R5, R6, R7, R8, and R9 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,
wherein for (IV), n=1 to 10, and R1 and R2 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR3, —N(R4R5), —CO2R6, —C(O) N(R7R8), wherein R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,
wherein for (V), X and Y are independently selected from the group consisting of CH, CF and N, and R1, R2, R4, R5, R6 and R7 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR8, —N(R9R10), —CO2R11, —C(O)—N(R12R13), wherein R1, R9, R10, R11, R12 and R13 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,
wherein for (VI), R1, R2, and R3 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR4, —N(R5R6), —CO2R′, —C(O)—N(R8R9), wherein R4, R5, R6, R7, R8, and R9 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,
wherein for (VII), n=1 to 4, and R1 and R2 are independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR3, —N(R4R5), —CO2R6, —C(O) N(R7R8), wherein R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen;
(b) forming a complex, said complex comprising the anion, a cation and the aryl-triazole bicyclic macrocycle in the organic layer; and
(c) separating the organic layer from aqueous layer.