Lipophilic guanidinium compounds for removal of oxyanions from aqueous solutions
Methods for removing an oxyanion from an aqueous source containing said oxyanion, comprising contacting said aqueous source with an aqueous-insoluble hydrophobic solution containing an oxyanion extractant compound dissolved in an aqueous-insoluble hydrophobic solvent to result in formation of an oxyanion salt of said extractant compound and extraction of said oxyanion salt into said aqueous-insoluble hydrophobic solution, wherein said extraction results in an extraction affinity (D) of said oxyanion of at least 1, wherein D is the concentration ratio of said oxyanion in the organic phase divided by the concentration of said oxyanion in the aqueous phase; wherein said extractant compound has the following composition: wherein at least one of R 1 -R 10 is or contains a hydrocarbon (R) group containing at least 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
1. A compound having the following structure:
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from (i) hydrogen atom, (ii) hydrocarbon groups (R) containing 1-30 carbon atoms and optionally substituted with one or more fluorine atoms, (iii) —OR′ groups, and (iv) —NR′ 2 groups, wherein R′ groups are independently selected from R groups and hydrogen atoms, provided that at least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms;
R 11 and R 12 are independently selected from hydrogen atom and methyl group;
X m− is an anionic species with a magnitude of charge m, where m is an integer of at least 1; and
n is a number, provided that n×m=1.
2. The compound of claim 1 , provided that at least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
3. The compound of claim 1 , provided that:
(i) at least two of R 1 , R 2 , R 3 , R 4 , and R 5 are selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms, and
(ii) at least two of R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms.
4. The compound of claim 1 , provided that:
(i) at least two of R 1 , R 2 , R 3 , R 4 , and R 5 are selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms, and
(ii) at least two of R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
5. The compound of claim 1 , wherein X m− is halide or nitrate.
6. The compound of claim 1 , wherein X m− is sulfate or phosphate.
7. A method for removing an oxyanion from an aqueous source containing said oxyanion, the method comprising contacting said aqueous source with an aqueous-insoluble hydrophobic solution containing an oxyanion extractant compound dissolved in an aqueous-insoluble hydrophobic solvent to result in formation of an oxyanion salt of said oxyanion extractant compound and extraction of said oxyanion salt of said oxyanion extractant compound into said aqueous-insoluble hydrophobic solution, wherein said extraction results in an extraction affinity (D) of said oxyanion of at least 1, wherein D is the concentration ratio of said oxyanion in the organic phase divided by the concentration of said oxyanion in the aqueous phase;
wherein said oxyanion extractant compound has the following structure:
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from (i) hydrogen atom, (ii) hydrocarbon groups (R) containing 1-30 carbon atoms and optionally substituted with one or more fluorine atoms, (iii) —OR′ groups, and (iv) —NR′ 2 groups, wherein R′ groups are independently selected from R groups and hydrogen atoms, provided that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 is selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms;
R 11 and R 12 are independently selected from hydrogen atom and methyl group;
X m− is an anionic species with a magnitude of charge m, where m is an integer of at least 1, provided that X m− is an anionic species exchangeable with the oxyanion in said aqueous source before said oxyanion extractant compound contacts said aqueous source, and X m− is said oxyanion in the oxyanion salt of said oxyanion extractant compound; and
n is a number, provided that n×m=1.
8. The method of claim 7 , wherein said oxyanion is selected from the group consisting of sulfate, nitrate, selenate, tellurate, phosphate, arsenate, carbonate, bicarbonate, perchlorate, and metal oxyanions.
9. The method of claim 7 , wherein said oxyanion is sulfate or phosphate.
10. The method of claim 7 , wherein X m− is halide or nitrate before said oxyanion extractant compound contacts said aqueous source.
11. The method of claim 7 , provided that at least two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms.
12. The method of claim 7 , provided that at least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms.
13. The method of claim 7 , provided that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 is selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
14. The method of claim 7 , provided that at least two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
15. The method of claim 7 , provided that at least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
16. The method of claim 7 , provided that:
(i) at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms, and
(ii) at least one of R 6 , R 7 , R 8 , R 9 , and R 10 is selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms.
17. The method of claim 7 , provided that:
(i) at least two of R 1 , R 2 , R 3 , R 4 , and R 5 are selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms, and
(ii) at least two of R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 4-30 carbon atoms, or —OR groups with R containing 4-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 4-30 carbon atoms.
18. The method of claim 7 , provided that:
(i) at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms, and
(ii) at least one of R 6 , R 7 , R 8 , R 9 , and R 10 is selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.
19. The method of claim 7 , provided that:
(i) at least two of R 1 , R 2 , R 3 , R 4 , and R 5 are selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms, and
(ii) at least two of R 6 , R 7 , R 8 , R 9 , and R 10 are selected from: R groups containing 6-30 carbon atoms, or —OR groups with R containing 6-30 carbon atoms, or —NR′ 2 groups with at least one R′ group being R containing 6-30 carbon atoms.