Glyonic liquids and uses thereof

Patent metadata

Field	Value
Publication number	US-2022064202-A1
Application number	US-202017429346-A
Country	US
Kind code	A1
Filing date	Feb 9, 2020
Priority date	Feb 10, 2019
Publication date	Mar 3, 2022
Grant date	—

Abstract

The present invention provides ionic liquids (ILs) comprising a carbohydrate anionic moiety and a cationic counter-ion moiety (Q+) and methods for producing and using the same. In one particular embodiment, the carbohydrate anionic moiety portion of ILs of the present invention is of the formula: (I) wherein G is selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide, and a derivative thereof; and L is a moiety selected from the group consisting of: (IIA) (IIB) wherein each of Ra, Rb, and Rc is independently hydrogen, C1-18 alkyl, or C2-20 mono- or di-unsaturated alkenyl; ATM is —CO2TM, —PO3HTM, or —SO3TM; and each of * marked carbon atom is independently a chiral center when said carbon atom has four different groups attached thereto.

First claim

1 . An ionic liquid comprising a carbohydrate anionic moiety and a cationic counter-ion (Q + ), wherein said carbohydrate anionic moiety is of the formula:
[G-L] −   I

wherein
G is selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide, and a derivative thereof; and
L is a moiety selected from the group consisting of:

wherein
each of R a , R b , and R c is independently hydrogen, C 1-18 alkyl, or C 2-20 mono- or di-unsaturated alkenyl;
A − is —CO 2 − , —PO 3 H − , or —SO 3 − ; and
each of * marked carbon atom is independently a chiral center when said carbon atom has four different groups attached thereto.

2 . The ionic liquid of claim 1 , wherein said cationic counter-ion is selected from the group consisting of H + , imidazolium, pyridinium, pyrrolium, ammonium, iminium, phosphonium, sulfonium, an ester derivative of amino acid, choline, an ester derivative of betaine, and acetylcholine.

3 . The ionic liquid of claim 1 , wherein G comprises glucose, galactose, rhamnose, arabinose, xylose, fucose, glucosamine, lactose, maltose, melibiose, cellobiose, rutinose, maltotriose or a combination thereof.

4 - 8 . (canceled)

9 . The ionic liquid of claim 1 , wherein L is a moiety of the formula:

wherein A − , R a , and * are as defined in claim 1 .

10 . The ionic liquid of claim 9 , wherein A − is —COO − , R a is a C 7 -, C 9 -, or C 11 alkyl, or C 9 - or C 11 -monounsaturated alkenyl, and * is an (R)-isomer.

11 . The ionic liquid of claim 1 , wherein L is a moiety of the formula:

wherein A − , R b , R c , and * are as defined in claim 1 .

12 . The ionic liquid of claim 11 , wherein A − is —COO − , and each of R b and R c is independently a C 7 -, C 9 -, or C 11 -alkyl, or C 9 - or C 11 -monounsaturated alkenyl.

13 . The ionic liquid of claim 12 , wherein each of R b and R c is independently H, or C 1 -, C 3 -, C 5 -, C 7 -, C 9 -, C 11 -, C 13 -alkyl, or C 9 - or C 11 -monounsaturated alkenyl.

14 . The ionic liquid of claim 1 , wherein the melting point temperature of said ionic liquid is at most about 50° C.

15 . The ionic liquid of claim 1 , wherein said ionic liquid is a conductive non-crystalline semi-solid or solid at room temperature with a melting point temperature of at least 20° C.

16 . A superionic proton conductive material comprising an ionic liquid of claim 1 .

17 . The ionic liquid of claim 1 , wherein said ionic liquid is solvated or hydrated.

18 . A superionic proton conductor comprising an ionic liquid of claim 17 .

19 . A fuel cell comprising an ionic liquid of claim 1 .

20 . The fuel cell of claim 19 , wherein said ionic liquid is solvated or hydrated.

21 . The fuel cell of claim 19 , wherein said fuel cell is a battery.

22 . The fuel cell of claim 19 , wherein said fuel cell is a sodium or a lithium battery.

23 . The ionic liquid of claim 1 , wherein said ionic liquid is of the formula Q x + .[G-L] − , where x ranges from 0.5 to 1.

24 . A method for separating a gas from a gaseous mixture comprising a first gas and at least one other gas that is different from said first gas, said method comprising contacting the gaseous mixture with a composition comprising an ionic liquid of claim 1 to dissolve at least a portion of said first gas in said composition, thereby separating at least a portion of said first gas from said gaseous mixture.

25 . The method of claim 24 , wherein said first gas comprises carbon dioxide, hydrogen sulfide, sulfur dioxide, methane, ethane, ethylene, propane, propylene, butane, 1-butene, oxygen, hydrogen, carbon monoxide, ammonia, water, Ar, Xe, CF 4 , BF 3 , AsH 3 , or PH 3 .

Assignees

• Univ Arizona

Inventors

• Pemberton Jeanne E
• Deodhar Bhushan

Classifications

• H01M2300/0045

  Room temperature molten salts comprising at least one organic ion · CPC title

• C07H3/04

  Disaccharides · CPC title

• C07H3/06 Primary

  Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages · CPC title

• H01M10/054

  Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium · CPC title

• C07H3/02

  Monosaccharides · CPC title