Separation of metal ions from a sample using glycolipids

Patent metadata

Field	Value
Publication number	US-2024182513-A1
Application number	US-202318394478-A
Country	US
Kind code	A1
Filing date	Dec 22, 2023
Priority date	Jun 30, 2021
Publication date	Jun 6, 2024
Grant date	—

Abstract

Glycolipid-heavy metal ion complexes, compositions useful for forming glycolipid-heavy metal ion complexes, and methods for separating metal ion(s) from a sample using glycolipids are described herein.

First claim

What is claimed is:

1 . A glycolipid-heavy metal ion complex, comprising:
at least one glycolipid of the formula:
A-B
wherein A is selected from the group consisting of a monosaccharide, a disaccharide, and a derivative thereof; and B is a moiety of the formula:

wherein
* is a chiral center;
R 2 is C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds; and
R 1 is H, C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds, or a moiety of the formula:

wherein
R 3 is C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds, and
R 4 is H or C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds; and a heavy metal ion,
wherein the at least one glycolipid and the heavy metal ion together form the glycolipid-heavy metal ion complex.

2 . The glycolipid-heavy metal ion complex of claim 1 , wherein the heavy metal ion comprises an ion of uranium, Y, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, La, Cu, Ag, Au, Pd, Pt, Pb, Cd, Zn, Tl, Hg, or a combination thereof.

3 . The glycolipid-heavy metal ion complex of claim 1 , wherein the at least one glycolipid and heavy metal ion are present in the complex in a ratio ranging from about 1:1 to about 4:1.

4 . The glycolipid-heavy metal ion complex of claim 1 , wherein A is a monosaccharide or a thiol derivative thereof; wherein said monosaccharide is selected from the group consisting of glucose, fructose, galactose, rhamnose, arabinose, xylose, fucose and a thiol derivative thereof.

5 . The glycolipid-heavy metal ion complex of claim 4 , wherein B is attached to the hydroxyl group of the anomeric carbon or a thiol derivative thereof of said monosaccharide.

6 . The glycolipid-heavy metal ion complex of claim 1 , wherein A is a disaccharide or a thiol derivative thereof; wherein said disaccharide is selected from the group consisting of lactose, maltose, melibiose, cellobiose, rutinose, and a thiol derivative thereof.

7 . The glycolipid-heavy metal ion complex of claim 6 , wherein said disaccharide comprises a 1,4-linkage, or a 1,6-linkage, between two monosaccharides.

8 . The glycolipid-heavy metal ion complex of claim 1 , wherein R 2 is CH 3 —(CH 2 ) n — and R 3 is CH 3 —(CH 2 ) m —, and wherein each of m and n is independently an integer from 4 to 12.

9 . The glycolipid-heavy metal ion complex of claim 1 , wherein B is of the formula:

wherein *, and R 1 are those defined in claim 1 , and wherein n is an integer in a range from 0 to 19.

10 . The glycolipid-heavy metal ion complex of claim 9 , wherein R 1 is a moiety of the formula:

wherein m and n are independently an integer in a range from 0 to 19,
wherein each of m and n is independently 6, 8, or 10.

11 . The glycolipid-heavy metal ion complex of claim 1 , wherein R 1 is C 6-20 alkyl.

12 . The glycolipid-heavy metal ion complex of claim 1 further comprising at least one C1 to C6 alcohol associated with the glycolipid-heavy metal ion complex.

13 . The glycolipid-heavy metal ion complex of claim 1 , wherein the glycolipid-heavy metal ion complex is substantially insoluble at 25° C. at a pH in a range from about 3 to about 12.

14 . A method for removing a heavy metal ion from a sample, said method comprising:
contacting said sample with an aqueous solution comprising a glycolipid to form a glycolipid-heavy metal ion complex according to claim 1 ; and separating said glycolipid-heavy metal ion complex, thereby removing said heavy metal ion from said sample.

15 . The method of claim 14 , wherein said sample comprises any of soil, groundwater, industrial wastewater, acid mine drainage, mining process waters and solid residuals, produced waters, electroplating solutions, coal combustion process waters, landfill leachates, e-waste, and fly ash; wherein mining comprises coal and hard rock mining.

16 . The method of claim 14 , wherein said step of separating said glycolipid-heavy metal ion complex comprises any of ion flotation and/or precipitate flotation, precipitation, centrifugation, filtration, gravitational settling, or combinations thereof.

17 . A composition comprising:
at least one glycolipid of the formula:
A-B
wherein A is selected from the group consisting of a monosaccharide, a disaccharide, and a derivative thereof; and B is a moiety of the formula:

wherein
* is a chiral center;
R 2 is C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds; and
R 1 is H, C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds, or a moiety of the formula:

wherein
R 3 is C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds, and
R 4 is H or C 1 -C 20 hydrocarbon optionally having 1, 2, or 3 carbon-carbon double bonds;
a frothing agent, wherein the frothing agent comprises a C1-C3 alcohol; and
water.

18 . The composition of claim 17 , wherein a concentration of the glycolipid in the water is in a range of from about 50 μM to about 10 mM.

19 . The composition of claim 17 wherein a concentration of the frothing agent in the water is in a range of from about 0% to about 2% (v/v).

20 . The composition of claim 17 , wherein a ratio of frothing agent to glycolipid is in a range from about 0:1 to about 1500:1.

Assignees

• Univ Arizona

Inventors

• Hogan David
• Maier Raina M
• Pemberton Jeanne E

Classifications

• C07H23/00 Primary

  Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12 (esters with inorganic acids C07H11/00) · CPC title

• B09C1/08

  chemically · CPC title

• C02F1/001

  Processes for the treatment of water whereby the filtration technique is of importance (C02F1/44 takes precedence; construction of filters in general B01D24/00 - B01D41/00) · CPC title

• C02F1/24

  by flotation (C02F1/465 takes precedence) · CPC title

• C02F1/38

  by centrifugal separation · CPC title