IP Library › Granted Patent US 12,662,396
Granted Patent B2
US 12,662,396 · App. 18/013,853 · Granted Jun 23, 2026

Salt recovery solution and processes of use thereof

Inventors: Chaitra Prakash (Auckland, NZ); Haiming Tang (Auckland, NZ); Crystal Maddox (Auckland, NZ)
Assignee: Aquafortus Technologies Limited
C02F1/265
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,662,396
App. No.
18/013,853
Granted
Jun 23, 2026
Kind
B2
Abstract

The present invention relates to a salt recovery solution and to a process for separating a salt from an aqueous solution. The present disclosure also relates to a salt recovery solution and to its use to concentrate a salt or brine solution by recovering water therefrom. The salt recovery solution comprising at least two or more components independently selected from any combination of integers a), b), c) and d): where a) is a straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound; b) is a straight chain or branched C 3 -C 9 alkyl substituted by —OH; c) is a straight chain, branched or cyclic C 4 -C 9 ketone or C 4 -C 9 diketone; and d) is a straight chain or branched C 3 -C 9 ester containing compound.

Claims (52)

1 . A process for recovering an inorganic salt from a salt containing aqueous solution containing inorganic salts, the process comprising the steps of:

(i) adding the salt containing aqueous solution containing inorganic salts to a salt recovery solution; and

(ii) allowing the inorganic salt to precipitate on passage through the salt recovery solution,

wherein the salt recovery solution comprises at least two or more components independently selected from any combination of integers a), b), c) and d), wherein

a) is a straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound;

b) is a straight chain or branched C 3 -C 9 alkyl substituted by —OH;

c) is a straight chain, branched or cyclic C 4 -C 9 ketone; and

d) is a straight chain or branched C 3 -C 9 ester containing compound; and

wherein at least one component of the salt recovery solution is substantially immiscible with an aqueous solution of sodium chloride at a 1 molar concentration at or above 20 degrees Celsius and at 1 atmosphere.

2 . The process as claimed in claim 1 , wherein the process is

a) a zero-liquid discharge process;

b) a counter current process; or

c) is a non-membrane process.

3 . A process for concentrating a salt containing aqueous solution containing inorganic salts, the process comprising the steps of:

(i) adding the salt containing aqueous solution containing the inorganic salts to a salt recovery solution, wherein the salt recovery solution comprises at least two or more components independently selected from any combination of integers a), b), c) and d): wherein

a) is a straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound;

b) is a straight chain or branched C 3 -C 9 alkyl substituted by —OH;

c) is a straight chain, branched or cyclic C 4 -C 9 ketone or C 4 -C 9 diketone; and

d) is a straight chain or branched C 3 -C 9 ester containing compound; and

wherein at least one component of the salt recovery solution is substantially immiscible with an aqueous solution of sodium chloride at a 1 molar concentration at or above 20 degrees Celsius and at 1 atmosphere; and

(ii) allowing water from the salt containing aqueous solution containing the inorganic salts to pass into the salt recovery solution.

4 . The process as claimed in claim 3 , wherein the process is:

i) a non-membrane process;

ii) a non-osmotic process; or

iii) a non-membrane and non-osmotic process.

5 . The process as claimed in claim 3 , wherein the process concentrates the salt containing aqueous solution containing the inorganic salts by a value selected from:

a) at least 20%;

b) by at least 30%;

c) by at least 40%;

d) by at least 50%;

e) by at least 60%;

f) by at least 70%;

g) by at least 80%; and

h) by at least 90%.

6 . The process as claimed in claim 3 , wherein the process is a minimal discharge process or a zero-liquid discharge process.

7 . The process as claimed in claim 3 , wherein the salt containing aqueous solution is an industrial brine.

8 . The process as claimed in claim 3 , wherein the straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound is selected from one or more of a diether, a polyether, 2-methyltetrahydrofuran, 3-methyltetrahydrofuran, 2-ethyltetrahydrofuran, 3-ethyltetrahydrofuran, dioxane, 1-ethoxypropane, a C 4 -C 9 glycol ether, propylene glycol methyl ether, dipropylene glycol methyl ethyl acetate, dipropylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol phenyl ether, propylene glycol diacetate, and combinations thereof.

9 . The process as claimed in claim 3 , wherein the straight chain or branched C 3 -C 9 alkyl substituted by —OH is selected from one or more of: 1-butanol, 2-butanol, 1-pentanol, and combinations thereof.

10 . The process as claimed in claim 1 , wherein the straight chain, branched or cyclic C 4 -C 9 ketone or C 4 -C 9 diketone is selected from one or more of: acetonylacetone, 2-butanone, and cyclohexanone.

11 . The process as claimed in claim 3 , wherein the straight chain or branched C 3 -C 9 ester containing compound is methyl acetate or ethyl acetate.

12 . The process as claimed in claim 1 , wherein the straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound is a diether or polyether.

13 . The process as claimed in claim 1 , wherein the straight, branched or optionally substituted cyclic C 4 -C 9 ether containing compound is selected from one or more of: 2-methyltetrahydrofuran, 3-methyltetrahydrofuran, 2-ethyltetrahydrofuran, 3-ethyltetrahydrofuran, dioxane, 1-ethoxypropane, a C 4 -C 9 glycol ether, propylene glycol methyl ether, dipropylene glycol methyl ethyl acetate, dipropylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol phenyl ether, propylene glycol diacetate, and combinations thereof.

14 . The process as claimed in claim 1 , wherein the straight chain or branched C 3 -C 9 alkyl substituted by —OH is selected from one or more of: 1-butanol, 2-butanol, 1-pentanol, and combinations thereof.

15 . The process as claimed in claim 1 , wherein the straight chain, branched or cyclic C 4 -C 9 ketone is selected from one or more of: 2-butanone and cyclohexanone.

16 . The process as claimed in claim 1 , wherein the straight chain or branched C 3 -C 9 ester containing compound is methyl acetate or ethyl acetate.

17 . The process as claimed in claim 1 , wherein the salt recovery solution is a combination of:

a) 2-methyltetrahydrofuran and 1-butanol;

b) 2-methyltetrahydrofuran and 1-pentanol;

c) ethyl acetate and 2-butanone;

d) ethyl acetate and 2-methyltetrahydrofuran; or

e) ethyl acetate and 1-butanol.

18 . The process as claimed in claim 1 , wherein the salt containing aqueous solution is an industrial brine.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2023
From: PRAKASH, CHAITRA; TANG, HAIMING; MADDOX, CRYSTAL
To: AQUAFORTUS TECHNOLOGIES LIMITED
Reel/Frame 062520/0139 →
Continuity (2)
Provisional Application 63050402 · Jul 10, 2020
Related Publication 20230286833A1 · Sep 14, 2023
References Cited (130)
US 2784173A · Carmack · 1957 [cited by applicant]
US 3077500A · Heinz et al. · 1963 [cited by applicant]
US 3130156A · Neff · 1964 [cited by applicant]
US 3164539A · Smith · 1965 [cited by applicant]
US 3641181A · Robbins et al. · 1972 [cited by applicant]
US 3962074A · Schropp · 1976 [cited by applicant]
US 4275234A · Baniel et al. · 1981 [cited by applicant]
US 4430227A · Hanson et al. · 1984 [cited by applicant]
US 4624958A · Glazer · 1986 [cited by applicant]
US 4789482A · DiLeo et al. · 1988 [cited by applicant]
US 5186817A · Paspek et al. · 1993 [cited by applicant]
US 5346620A · Hendrix et al. · 1994 [cited by applicant]
US 5486314A · Wack et al. · 1996 [cited by applicant]
US 5705074A · Brient · 1998 [cited by applicant]
US 5780276A · Baniel · 1998 [cited by applicant]
US 5897750A · Berg · 1999 [cited by applicant]
US 6307087B1 · Buchwald et al. · 2001 [cited by applicant]
US 6858694B2 · Ohnishi et al. · 2005 [cited by applicant]
US 6858964B2 · Masumoto et al. · 2005 [cited by applicant]
US 7560029B2 · Mc Ginnis · 2009 [cited by applicant]
US 8143444B2 · Mariansky et al. · 2012 [cited by applicant]
US 9630861B2 · Ikeda et al. · 2017 [cited by applicant]
US 10933377B2 · Briggs et al. · 2021 [cited by applicant]
US 11020706B2 · Briggs · 2021 [cited by applicant]
US 11826704B2 · Briggs · 2023 [cited by applicant]
US 11987506B2 · Briggs et al. · 2024 [cited by applicant]
US 20020156295A1 · Buchwald et al. · 2002 [cited by applicant]
US 20030004202A1 · Elliott et al. · 2003 [cited by applicant]
US 20060086664A1 · Wills · 2006 [cited by applicant]
US 20120043274A1 · Chi et al. · 2012 [cited by applicant]
US 20120241377A1 · Ooi et al. · 2012 [cited by applicant]
US 20130012738A1 · Wu et al. · 2013 [cited by applicant]
US 20130240444A1 · Jung et al. · 2013 [cited by applicant]
US 20140076810A1 · Jessop et al. · 2014 [cited by applicant]
US 20140158621A1 · Lee et al. · 2014 [cited by applicant]
US 20140290854A1 · Parellada Llobet et al. · 2014 [cited by applicant]
US 20140319056A1 · Fuchigami et al. · 2014 [cited by applicant]
US 20150108061A1 · Chi et al. · 2015 [cited by applicant]
US 20150166363A1 · Eyal et al. · 2015 [cited by applicant]
US 20150273396A1 · Hancock et al. · 2015 [cited by applicant]
US 20150360973A1 · Eyal et al. · 2015 [cited by applicant]
US 20160023171A1 · Phillip et al. · 2016 [cited by applicant]
US 20160158705A1 · Helm et al. · 2016 [cited by applicant]
US 20160175777A1 · Ikeda et al. · 2016 [cited by applicant]
US 20170305823A1 · Fischer et al. · 2017 [cited by applicant]
US 20170354904A1 · Wilson et al. · 2017 [cited by applicant]
US 20180008933A1 · Hu et al. · 2018 [cited by applicant]
US 20180015414A1 · Hu et al. · 2018 [cited by applicant]
US 20180142117A1 · Resendes et al. · 2018 [cited by applicant]
US 20190099718A1 · Briggs et al. · 2019 [cited by applicant]
US 20200023316A1 · Briggs · 2020 [cited by applicant]
US 20200308023A1 · Briggs et al. · 2020 [cited by applicant]
US 20220185754A1 · Briggs et al. · 2022 [cited by applicant]
US 20220193608A1 · Briggs · 2022 [cited by applicant]
US 20230043356A1 · Prakash et al. · 2023 [cited by applicant]
US 20230257284A1 · Briggs et al. · 2023 [cited by applicant]
US 20230286833A1 · Prakash et al. · 2023 [cited by applicant]
US 20240262772A1 · Prakash et al. · 2024 [cited by applicant]
US 20240368001A1 · Briggs et al. · 2024 [cited by applicant]
AU 2018346086A1 · 2020 [cited by applicant]
CA 1208134A · 1986 [cited by applicant]
CN 1156418A · 1997 [cited by applicant]
CN 1717386A · 2006 [cited by applicant]
CN 104619649A · 2015 [cited by applicant]
CN 104984562A · 2015 [cited by applicant]
CN 106727143A · 2017 [cited by applicant]
CN 106942264A · 2017 [cited by applicant]
CN 108186380A · 2018 [cited by applicant]
CN 110099869A · 2019 [cited by applicant]
DE 102018119168A1 · 2019 [cited by applicant]
EP 0117870A1 · 1984 [cited by applicant]
EP 1236751A1 · 2002 [cited by applicant]
JP S5610131A · 1981 [cited by applicant]
JP H0249195A · 1990 [cited by applicant]
JP H04266845A · 1992 [cited by applicant]
JP 2007511472A · 2007 [cited by applicant]
JP 2009200349A · 2009 [cited by applicant]
JP 2013518718A · 2013 [cited by applicant]
WO 2004050601A2 · 2004 [cited by applicant]
WO 2011014850A2 · 2011 [cited by applicant]
WO 2011028629A1 · 2011 [cited by applicant]
WO 2013016491A1 · 2013 [cited by applicant]
WO 2013016499A1 · 2013 [cited by applicant]
WO 2013175380A1 · 2013 [cited by applicant]
WO 2014089142A1 · 2014 [cited by applicant]
WO 2014191504A1 · 2014 [cited by applicant]
WO 2014191522A1 · 2014 [cited by applicant]
WO 2016094835A1 · 2016 [cited by applicant]
WO 2016133464A1 · 2016 [cited by applicant]
WO 2018067019A2 · 2018 [cited by applicant]
WO 2019070134A2 · 2019 [cited by applicant]
WO 2020204733A1 · 2020 [cited by applicant]
WO 2021247354A1 · 2021 [cited by applicant]
WO 2022010366A1 · 2022 [cited by applicant]
WO 2022010367A1 · 2022 [cited by applicant]
Guo, C. et al., Structural Characteristic Integrated Computer-Aided Molecular Design for Phenols Removal Considering Synergistic Effect, Industrial & Engineering Chemistry Research, vol. 57:11374-11380 (2018). [cited by applicant]
International Preliminary Report on Patentability, PCT/NZ2021/050105, dated Jan. 10, 2023, 8 pages. [cited by applicant]
International Search Report and Written Opinion, PCT/NZ2021/050105, dated Oct. 5, 2021, 11 pages. [cited by applicant]
Li, H-B. et al., Preparative isolation and purification of salidroside from the Chinese medicinal plant Rhodiola sachalinensis by high-speed counter-current chromatography, Journal of Chromatography A,, vol. 932: 91-95 … [cited by applicant]
Walsham, J. G., “Prediction of Flash Points for Solvent Mixtures” Advances in Chemistry, vol. 124, chapter 5: 56-69 (1973). [cited by applicant]
U.S. Appl. No. 18/093,263, filed Jan. 4, 2023, Daryl Joseph Briggs, US 20230257284. [cited by applicant]
U.S. Appl. No. 16/753,263, filed Apr. 2, 2020, Daryl Joseph Briggs, US 20200308023. [cited by applicant]
U.S. Appl. No. 18/013,853, filed Dec. 29, 2022, Chaitra Prakash. [cited by applicant]
U.S. Appl. No. 18/013,852, filed Dec. 29, 2022, Chaitra Prakash. [cited by applicant]
U.S. Appl. No. 17/599,284, filed Sep. 28, 2021, Chaitra Prakash, US 20230043356. [cited by applicant]
U.S. Appl. No. 17/436,439, filed Sep. 3, 2021, Daryl Joseph Briggs, US 20220185754. [cited by applicant]
U.S. Appl. No. 17/246,440, filed Apr. 30, 2021, Daryl Joseph Briggs, US 20220193608. [cited by applicant]
U.S. Appl. No. 16/338,076, filed Mar. 29, 2019, Daryl Joseph Briggs, U.S. Pat. No. 11,020,706. [cited by applicant]
U.S. Appl. No. 16/145,968, filed Sep. 28, 2018, Daryl Joseph Briggs, U.S. Pat. No. 10,933,377. [cited by applicant]
Alonso, I. , et al., “Thermodynamics of Ketone + Amine Mixtures. Part III. Volumetric and Speed of Sound Data at (293.15, 298.15, and 303.15) K for 2-Butanone + Aniline, + N-Methylaniline, or + Pyridine Systems,” J. Che… [cited by applicant]
Bahadur Alisha, S. et al., “Ultrasonic Studies on Binary Liquid Mixtures of Triethylamine with Carbitols at 308.15 K,” Indian Journal of Advances in Chemical Science, vol. 5(3): 148-154 (2017). [cited by applicant]
CAS Registry No. 183205-66-5; STN Entry date Nov. 20, 1996; Ethanesulfonic acid, 2-hydroxy-, compd. with N,N-diethylethanamine (1:1). Retrieved on May 18, 2020. [cited by applicant]
Deshpande, M., “Polyol induced extraction (PIE) of water from organic solvents,”), Seton Hall University Dissertations and Theses (ETDs). No 1989. (2014) Retrieved from the Internet on Sep. 21, 2021 via <URL:https://sch… [cited by applicant]
Extended European Search Report, European Application No. 20768998, dated Nov. 4, 2022, 9 pages. [cited by applicant]
Extended European Search Report, European Application No. 21837257.1, dated Apr. 3, 2024, 8 pages. [cited by applicant]
González, J-A., et al. “Thermodynamics of ketone + amine mixtures. Part X. Excess molar enthalpies at 298.15 K for N, N, N-triethylamine + 2-alkanone systems. Characterization of tertiary amine + 2-alkanone, and of amin… [cited by applicant]
Govindarajan, M. et al., “Salt effect on liquid-liquid equilibrium of the methyl isobutyl ketone-acetic acid-water system at 35 °C,” Fluid Phase Equilibria, vol. 108: 269-292 (1995). [cited by applicant]
Gutierrez, E. et al., “Phase segregation in aqueous solutions of non-ionic surfactants using ammonium, magnesium and iron salts”, The Journal of Chemical Thermodynamics, vol. 70: 147-153 (2014). [cited by applicant]
Hyde, A.M., et al., “General Principles and Strategies for Salting-Out Informed by the Hofmeister Series,” Organic Process Research and Development, vol. 21:1335-1370 (2017). [cited by applicant]
International Preliminary Report on Patentability, PCT/NZ2017/050127, dated Apr. 9, 2019, 6 pages. [cited by applicant]
International Preliminary Report on Patentability, PCT/NZ2018/050135, dated Apr. 8, 2020, 8 pages. [cited by applicant]
International Preliminary Report on Patentability, PCT/NZ2020/050019, dated Aug. 25, 2021, 4 pages. [cited by applicant]
International Preliminary Report on Patentability, PCT/NZ2021/050106, dated Jan. 10, 2023, 13 pages. [cited by applicant]
International Search Report and Written Opinion, PCT/NZ2017/050127, dated Jan. 22, 2019, 8 pages. [cited by applicant]
International Search Report and Written Opinion, PCT/NZ2018/050135, dated Nov. 14, 2019, 11 pages. [cited by applicant]
International Search Report and Written Opinion, PCT/NZ2020/050019, dated Jun. 10, 2020, 7 pages. [cited by applicant]
International Search Report and Written Opinion, PCT/NZ2021/050106, dated Oct. 5, 2021, 21 pages. [cited by applicant]
Matkovich, C.E. et al., “Salting-Out of Acetone from Water—Basis of a New Solvent Extraction System,” Analytical Chemistry, vol. 45(11): 1915-1921 (1973). [cited by applicant]
Munson, C. L. et al. “Factors influencing Solvent Selection for Extraction of Ethanol from Aqueous Solutions,” Ind. Eng. Chem. Process Des. Dev., vol. 23 (1): 109-115 (1984). [cited by applicant]
Reddy, K.C. et al., “Ultrasonic Behavior of Binary Liquid Mixtures Containing Triethy lamine, Part 1,” Trans. Faraday Soc., vol. 58: 2352-2357 (1962). [cited by applicant]