Draw solutes, methods of forming draw solutes, and methods of using draw solutes to treat an aqueous liquid

a draw solute and aqueous liquid technology, applied in the field of draw solutes, methods of forming draw solutes, and methods of using draw solutes to treat an aqueous liquid, can solve the problems of exacerbated membrane fouling by inorganic and organic molecules, substantial pressure to overcome the osmotic pressure of contaminated water sources, and significant investment in equipment and substantial ongoing energy costs. , to achieve the effect of less costly, greater osmotic pressur

Inactive Publication Date: 2013-02-28
BATTELLE ENERGY ALLIANCE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0020]A phosphazene compound for use as a draw solute and a triazine compound for use as a draw solute are disclosed, as are methods of forming the phosphazene compound and the triazine compound, and methods of using at least one of the phosphazene compound and the triazine compound to treat an aqueous liquid. The phosphazene compound may include a plurality of salt-terminated pendant groups bonded to phosphorus atoms of a plurality of phosphorus-nitrogen units. The triazine compound may include a plurality of salt-terminated pendant groups bonded to carbon atoms of a triazine ring. At least one of the phosphazene compound and the triazine compound may be used as a draw solute in a draw solution to separate or remove water from an aqueous feed liquid by forward osmosis. The draw solution including at least one of the phosphazene compound and the triazine compound may have a greater osmotic pressure than the aqueous feed liquid, facilitating an osmotic pressure gradient through a semi-permeable membrane to draw the water into the draw solution while leaving at least one solute in the aqueous feed liquid. The at least one solute may a contaminant (e.g., organic or inorganic impurity) in the aqueous feed liquid. Each of the phosphazene compound and the triazine compound disclosed herein may enable a more energy efficient and less costly method and system of aqueous liquid treatment as compared to conventional forward osmosis methods and systems utilizing conventional draw solutes.

Problems solved by technology

For water desalination processes, the pressure to overcome the osmotic pressure of the contaminated water source can be substantial, such as greater than 50 atm, significant investment in equipment and substantial ongoing energy costs.
Additionally, the application of pressure in reverse osmosis processes often exacerbates membrane fouling by inorganic and organic molecules.
Unfortunately, the molecular weight and size of conventional draw solutes frequently results in back diffusion of the draw solute through the semi-permeable membrane, requiring added expense to replace the draw solute that is lost.
The molecular weight and size of conventional draw solutes also typically requires costly and energy intensive processes, such as reverse osmosis, to remove the conventional draw solutes from the water they draw.
Further, conventional draw solutes are generally non-ionic, monovalent, or divalent, meaning that the osmotic pressure they impart can be limited, as can be the flux of water through the semi-permeable membrane during forward osmosis.

Method used

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  • Draw solutes, methods of forming draw solutes, and methods of using draw solutes to treat an aqueous liquid
  • Draw solutes, methods of forming draw solutes, and methods of using draw solutes to treat an aqueous liquid
  • Draw solutes, methods of forming draw solutes, and methods of using draw solutes to treat an aqueous liquid

Examples

Experimental program
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Effect test

example 1

Synthesis and Isolation of hexa(4-ethylcarboxylatophenoxy)cyclotriphosphazene

[0065]To a three neck round bottom flask was added a mechanical stirrer, a nitrogen purge, and a condenser. The flask was charged with approximately 300 ml of anhydrous tetrahydrofuran (THF). Sodium hydride (7.5 g, 326 mmol) was added slowly, followed by 4-ethylcarboxylatophenol (57.3 g, 345 mmol) dissolved in anhydrous 1,4-dioxane (˜300 ml). The resulting mixture reacted vigorously and was stirred for one hour to ensure completion. To this solution was added a solution of hexachlorocyclotriphosphazene (10 g, 29 mmol) in anhydrous 1,4-dioxane (50 ml). The reaction was heated to reflux and THF was removed using a Dean-Stark trap until the boiling mixture reached 85° C. The reaction mixture was stirred for 43 hours under a nitrogen purge. Reaction progress was monitored by P-31 Nuclear Magnetic Resonance (NMR) spectrometry. Isolation of the compound was accomplished by filtration of the cooled reaction soluti...

example 2

Formation of hexa(4-carboxyphenoxy)cyclotriphosphazene from hexa(4-ethylcarboxylatophenoxy)cyclotriphosphazene

[0066]In an oven dried 500 ml round bottom flask was added anhydrous THF (300 ml) and potassium tert-butoxide (16 g, 143 mmol). The resulting solution was cooled to 0° C. in a water ice bath. In a separate flask, hexa(4-ethylcarboxylatophenoxy)cyclotriphosphazene (3 g, 2.1 mmol) was dissolved in anhydrous THF (20 ml). The solution was added to the base solution and the resulting mixture was allowed to come to room temperature and was stirred overnight. After stirring, the resulting mixture was poured into water (˜1 L) and the pH was adjusted to approximately 3 with concentrated hydrochloric acid where a fine white precipitate was observed to form. Centrifugation of the precipitation solution yielded 2.1 g of a fine white powder for an 80% yield.

example 3

Formation of Sodium hexa(4-carboxylatophenoxy)cyclotriphosphazene from hexa(4-carboxyphenoxy)cyclotriphosphazene

[0067]Neutralization of the acidic functionality of the product of Example 2 was performed carefully to ensure excess base was not added. A solution of sodium hydroxide was prepared and standardized against dry potassium hydrogen phthalate (KHP) to yield a concentration of 0.177 M Na. Using this solution, a sample of hexa(4-carboxyphenoxy)cyclotriphosphazene (5 g, 4 mmol) was neutralized by suspending the phosphazene in water (˜20 ml). The base was added using a buret. To assure that no excess sodium hydroxide remained, dry hexa(4-carboxyphenoxy)cyclotriphosphazene (˜100 mg) was added incrementally to a final pH of 8. Once complete, the water was removed by rotary evaporation to give sodium hexa(4-carboxylatophenoxy)cyclotriphosphazene as a white powder in quantitative yield.

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Abstract

A method of treating an aqueous liquid. The method comprises providing an aqueous feed liquid comprising water and at least one solute to a first side of a membrane. A draw solution comprising water and a draw solute comprising at least one of a phosphazene compound and a triazine compound is provided to a second side of the membrane. At least a portion of the water of the aqueous feed liquid is osmosed across the membrane and into the draw solution to form a diluted draw solution comprising water and the draw solute. The water of the diluted draw solution is separated from the draw solute of the diluted draw solution to form a purified water product. Draw solutes comprising phosphazene compounds and draw solutes comprising triazine compounds are also disclosed, as are methods of forming the draw solutes.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 527,936, filed Aug. 26, 2011, the disclosure of which is hereby incorporated herein in its entirety by this reference.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT[0002]This invention was made with government support under Contract Number DE-AC07-05ID14517 awarded by the United States Department of Energy. The government has certain rights in the invention.TECHNICAL FIELD[0003]The present disclosure, in various embodiments, relates generally to draw solutes for use in treating an aqueous liquid, to methods of forming such draw solutes, and to related methods of treating an aqueous liquid to purify or concentrate at least one of water and a solute therein. More specifically, embodiments of the present disclosure relate to phosphazene compounds and triazine compounds for use as draw solutes, to methods of forming such phosphazene compoun...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C02F1/44C07D251/54C07F9/6593C02F103/08
CPCC07F9/65815C07D251/54B01D61/007C02F2103/08C02F1/445C07D251/70B01D61/005
Inventor STEWART, FREDERICK F.BENSON, MICHAEL T.STONE, MARK L.
Owner BATTELLE ENERGY ALLIANCE LLC
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