IP Library Granted Patent US 10,259,788
Granted Patent B2
US 10,259,788 · App. 15/802,360 · Granted Apr 16, 2019

Ionic liquids comprising heteraromatic anions

Inventors: William F. Schneider (Granger, IN); Joan F. Brennecke (Granger, IN); Edward J. Maginn (South Bend, IN); Elaine Vazquez (Chicago, IL); Burcu Gurkan (South Bend, IN); Erica Price (Mishawaka, IN); Brett Goodrich (Mishawaka, IN)
Assignee: University of Notre Dame du Lac
C07D207/32B01D53/1456B01D53/1493C07D207/323C07D207/325C07D207/33C07D207/34C07D207/46C07D209/08C07D231/12C07D233/58C07F9/5407B01D2252/30B01D2257/302B01D2257/404B01D2257/504B01D2258/0283Y02C10/04Y02E20/326Y02P20/152
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Quick Facts
Patent No.
US 10,259,788
App. No.
15/802,360
Granted
Apr 16, 2019
Kind
B2
Abstract

Some embodiments described herein relate to ionic liquids comprising an anion of a heteraromatic compound such as optionally substituted pyrrolide, optionally substituted pyrazolide, optionally substituted indolide, optionally substituted phospholide, or optionally substituted imidazolide. Methods and devices for gas separation or gas absorption related to these ionic liquids are also described herein.

Claims (27)

1. An ionic liquid comprising an anion represented by a formula:

wherein X is N;

A is N;

E is CR 4 ; and

R 1 , R 2 , R 4 are independently H, halo, CN, CNO, NCO, or NO 2 .

2. The ionic liquid of claim 1 , wherein the reaction energy ΔH>−99 kJ/mol.

3. The ionic liquid of claim 1 , wherein the anion-CO 2 bond energy ΔE<−35 kJ/mol.

4. The ionic liquid of claim 1 , wherein R 1 and R 4 are H and R 2 is NO 2 .

5. A method of removing carbon dioxide from a mixture of gases, comprising:

providing a mixture of gases comprising carbon dioxide; and

allowing sufficient contact between the mixture of gases and a first ionic liquid comprising an anion according to the formula

wherein X is N, A is CR 3 , E is N, and R 1 , R 2 , R 3 are independently H, halo, CN, CNO, NCO, or NO 2 such that the carbon dioxide reacts with the first ionic liquid to form a second ionic liquid according to claim 1 thereby reducing the amount of carbon dioxide in the mixture of gases.

6. The method of claim 5 , wherein the mixture of gases is an exhaust from combustion of a carbon-based fuel, wherein the carbon-based fuel is coal, a petroleum product, or natural gas.

7. The method of claim 5 , wherein the mixture of gases further comprises an oxide of sulfur or nitrogen.

8. The method of claim 5 further comprising recovering the carbon dioxide from the second ionic liquid by applying at least one of heat or reduced pressure to the second ionic liquid.

9. A gas separation system comprising:

a flow component configured to provide a flow of a gas mixture, wherein the gas mixture comprises carbon dioxide; and

a separation component, in fluid communication with the flow component, configured to allow the flow of the gas mixture to pass through the separation component from the flow component, wherein a quantity of a first ionic liquid comprising an anion according to the formula

wherein X is N, A is CR 3 , E is N, and R 1 , R 2 , R 3 are independently H, halo, CN, CNO, NCO, or NO 2 , is contained within or coupled to the separation component;

wherein the system is configured to provide sufficient contact between the gas mixture and the first ionic liquid to remove at least a portion of the carbon dioxide from the gas mixture to form an ionic liquid according to claim 1 ; and

wherein the system contains the ionic liquid according to claim 1 .

10. The gas separation system of claim 9 , further comprising a regeneration component wherein the ionic liquid according to claim 1 is subjected to heat and/or reduced pressure to liberate carbon dioxide.

11. A combustion device comprising:

a combustion vessel configured to contain a combustion reaction;

an exhaust component, in fluid communication with the combustion vessel, which is configured to allow exhaust from the combustion reaction to escape from the combustion vessel, wherein the exhaust comprises carbon dioxide; and

the gas separation system of claim 9 , coupled to the exhaust component;

wherein the device is configured to provide sufficient contact between the exhaust and the separation system to remove at least a portion of the carbon dioxide from the exhaust.

Assignments (9)
CONFIRMATORY LICENSE Recorded Mar 16, 2021
From: UNIVERSITY OF NOTRE DAME
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 055607/0484 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR'S NAME FROM ELAINE MINDRUP TO ELAINE VAZQUEZ PREVIOUSLY RECORDED ON REEL 044835 FRAME 0549. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 26, 2018
From: VAZQUEZ, ELAINE
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 047635/0090 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: BRENNECKE, JOAN, DR.
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0388 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: SCHNEIDER, WILLIAM, DR.
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: GOODRICH, BRETT
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0451 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: PRICE, ERICA
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0475 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: GURKAN, BURCU
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0501 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: MAGINN, EDWARD, DR.
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0531 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2018
From: MINDRUP, ELAINE
To: UNIVERSITY OF NOTRE DAME DU LAC
Reel/Frame 044835/0549 →
Continuity (3)
Division 13505730
Provisional Application 61257795 · Nov 3, 2009
Related Publication 20180179157A1 · Jun 28, 2018