Reactive extraction of water

Patent metadata

Field	Value
Publication number	US-11045745-B2
Application number	US-201816493745-A
Country	US
Kind code	B2
Filing date	Mar 13, 2018
Priority date	Mar 13, 2017
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

Described herein are methods and compounds for extracting water from an aqueous solution. For example, some embodiments include method for extracting water from an aqueous solution, comprising contacting the aqueous solution with a compound comprising one or more carbonyl moieties having an equilibrium constant for a hydration of the carbonyl moiety of at least about 0.5; separating a composition comprising the hydrated compound from the aqueous solution; and reacting the hydrated compound to obtain water.

First claim

What is claimed is:

1. A method for extracting water from an aqueous solution, comprising:
(a) contacting the aqueous solution with a compound comprising one or more carbonyl moieties and one or more electron withdrawing moieties alpha to the carbonyl, having an equilibrium constant for a hydration of the carbonyl moiety of at least about 0.5;
(b) separating a composition comprising the hydrated compound from the aqueous solution; and
(c) reacting the hydrated compound to obtain water.

2. The method of claim 1 , wherein the aqueous solution comprises a salt.

3. The method of claim 1 , wherein the aqueous solution is brine.

4. The method of claim 1 , wherein the compound comprising one or more carbonyl moieties comprises two or more electron withdrawing moieties alpha or beta to the carbonyl.

5. The method of claim 1 , wherein the electron withdrawing moiety is independently in each instance selected from the group consisting of —Z or

and wherein Z is selected from —F, —Cl, —CN, NO 2 , carbonyl, and —COO-alkyl.

6. The method of claim 1 , wherein the compound comprising one or more carbonyl moieties has a boiling point of greater than about 100° C.

7. The method of claim 1 , wherein reacting the hydrated compound to obtain water comprises heating the hydrated compound to a temperature of about 40° C. to about 100° C.

8. The method of claim 1 , wherein the compound comprising one or more carbonyl moieties has a molecular weight of about 150 g/mol to about 400 g/mol.

9. The method of claim 1 , wherein the compound comprising one or more carbonyl moieties is chemically attached to crosslinked beads or a thin film.

10. The method of claim 1 , wherein the compound comprising one or more carbonyl moieties is represented by formula (I):

wherein:
X is an electron withdrawing moiety;
Y is selected from the group consisting of an electron withdrawing moiety, H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenoxy, optionally substituted alkynoxy, optionally substituted aryloxy, optionally substituted aralkyloxy, optionally substituted heterocyclyloxy, optionally substituted heterocyclylalkoxy, optionally substituted heteroalkyl, optionally substituted heteroalkenyl, optionally substituted heteroalkynyl, and optionally substituted siloxanes; and X and Y of formula (I) together form a carbonyl or a thioketone moiety;
R 1 is selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenoxy, optionally substituted alkynoxy, optionally substituted aryloxy, optionally substituted aralkyloxy, optionally substituted heterocyclyloxy, optionally substituted heterocyclylalkoxy, optionally substituted heteroalkyl, optionally substituted heteroalkenyl, optionally substituted heteroalkynyl, and optionally substituted siloxanes;
R 2 is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenoxy, optionally substituted alkynoxy, optionally substituted aryloxy, optionally substituted aralkyloxy, optionally substituted heterocyclyloxy, optionally substituted heterocyclylalkoxy, optionally substituted heteroalkyl, optionally substituted heteroalkenyl, optionally substituted heteroalkynyl, and optionally substituted siloxanes;

with the proviso that when Y is H, then at least one of R 1 or R 2 is

and
wherein R 3 is selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenoxy, optionally substituted alkynoxy, optionally substituted aryloxy, optionally substituted aralkyloxy, optionally substituted heterocyclyloxy, optionally substituted heterocyclylalkoxy, optionally substituted heteroalkyl, optionally substituted heteroalkenyl, optionally substituted heteroalkynyl, and optionally substituted siloxanes.

11. The method of claim 10 , wherein the compound of formula (I) has a molecular weight of at least about 150 g/mol to about 400 g/mol.

12. The method of claim 10 , wherein the electron withdrawing moiety is independently in each instance selected from the group consisting of Z or

wherein Z is selected from —F, —Cl, —Br, —CF 3 , —CF 2 H, —CFH 2 , —CN, NO 2 , and —COO-alkyl.

13. The method of claim 1 , wherein the compound has a theoretical equilibrium constant for a hydration of the carbonyl moiety of at least about 1 as calculated by (1) using first principles to calculate Gibbs free energy change of a reaction (ΔG) and then (2) calculating the equilibrium constant of a reaction as K eg =e −ΔG / RT using M06-2X level of theory.

14. The method of claim 10 , wherein the one or more electron withdrawing moieties is —Z, wherein Z is selected from —F, —Cl, —Br, —CF 3 , —CF 2 H, —CFH 2 , —CN, NO 2 , and —COO-alkyl.

15. The method of claim 10 , wherein the compound has an equilibrium constant for a hydration of the carbonyl moiety of at least about 1.

16. The method of claim 10 , wherein Y is H.

17. The method of claim 10 , wherein R 1 is represented by

18. The method of claim 10 , wherein R 2 is represented by

19. The method of claim 1 , wherein the method is conducted on at least a 100 L of aqueous solution scale.

Assignees

• Univ Of Pittsburgh—Of The Commonwealth System Of Higher Education

Inventors

• Beckman Eric J
• Bourmpakis Ioannis
• Tavenor Nathan Albert

Classifications

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• B01D11/0492 Primary

  Applications, solvents used · CPC title

• B01D11/04

  of solutions which are liquid · CPC title

• C02F1/265

  Desalination · CPC title

• C01B5/00

  Water · CPC title