Ionic liquids comprising heteraromatic anions

Patent metadata

Field	Value
Publication number	US-10889544-B2
Application number	US-201816121239-A
Country	US
Kind code	B2
Filing date	Sep 4, 2018
Priority date	Nov 3, 2009
Publication date	Jan 12, 2021
Grant date	Jan 12, 2021

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.

First claim

What is claimed is:

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

wherein X is N;
A is N or CR 3 ;
E is N or CR 4 ;
R 1 , R 2 , R 3 , and R 4 are each independently H, halo, CN, CNO, NCO, NO 2 , R 11 , OR 11 , SR 11 , NR 12 R 13 , —YC(O)ZR 11 , SO 2 R 11 , SO 3 R 11 , or SO 2 NR 12 R 13 ;
Y is a single bond, optionally substituted C 1-6 hydrocarbyl, —N(R 12 )—, O, or S;
Z is a single bond, —N(R 12 )—, O, or S;
each R 11 is H or optionally substituted C 1-12 hydrocarbyl; and
each R 12 and each R 13 is independently H or optionally substituted C 1-6 hydrocarbyl.

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

3. 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 N or CR 3 ;
E is N or CR 4 ; and
R 1 , R 2 , R 3 , and R 4 are each independently H, halo, CN, CNO, NCO, NO 2 , R 11 , OR 11 , SR 11 , NR 12 R 13 , —YC(O)ZR 11 , SO 2 R 11 , SO 3 R 11 , or SO 2 NR 12 R 13 ;
Y is a single bond, optionally substituted C 1-6 hydrocarbyl, —N(R 12 )—, O, or S;
Z is a single bond, —N(R 12 )—, O, or S;
each R 11 is H or optionally substituted C 1-12 hydrocarbyl; and
each R 12 and each R 13 is independently H or optionally substituted C 1-6 hydrocarbyl;
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.

4. The method of claim 3 , 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.

5. The method of claim 3 , wherein the mixture of gases further comprises an oxide of sulfur or nitrogen.

6. The method of claim 3 , 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.

7. 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 is contained within or coupled to the separation component, wherein the first ionic liquid comprises a first anion according to the formula

wherein:
X is N;
A is N or CR 3 ;
E is N or CR 4 ;
R 1 , R 2 , R 3 , and R 4 are each independently H, halo, CN, CNO, NCO, NO 2 , R 11 , OR 11 ,
SR 11 , NR 12 R 13 , —YC(O)ZR 11 , SO 2 R 11 , SO 3 R 11 , or SO 2 NR 12 R 13 ;
Y is a single bond, optionally substituted C 1-6 hydrocarbyl, —N(R 12 )—, O, or S;
Z is a single bond, —N(R 12 )—, O, or S;
each R 11 is H or optionally substituted C 1-12 hydrocarbyl; and
each R 12 and each R 13 is independently H or optionally substituted C 1-6 hydrocarbyl;
and
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 and thereby form a second ionic liquid comprising a second anion represented by a formula

wherein X is N;
A is N or CR 3 ;
E is N or CR 4 ;
R 1 , R 2 , R 3 , and R 4 are each independently H, halo, CN, CNO, NCO, NO 2 , R 11 , OR 11 , SR 11 , NR 12 R 13 , —YC(O)ZR 11 , SO 2 R 11 , SO 3 R 11 , or SO 2 NR 12 R 13 ;
Y is a single bond, optionally substituted C 1-6 hydrocarbyl, —N(R 12 )—, O, or S;
Z is a single bond, —N(R 12 )—, O, or S;
each R 11 is H or optionally substituted C 1-12 hydrocarbyl; and
each R 12 and each R 13 is independently H or optionally substituted C 1-6 hydrocarbyl; and
wherein the system contains the second ionic liquid.

8. The gas separation system of claim 7 , further comprising
a regeneration component wherein the second ionic liquid is subjected to heat and/or reduced pressure to liberate carbon dioxide.

9. 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 7 , 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.

Assignees

• Univ Notre Dame Du Lac

Inventors

• Schneider William F
• Brennecke Joan F
• Maginn Edward J
• Vazquez Elaine
• Gurkan Burcu
• Price Erica
• Goodrich Brett

Classifications

• B01D2257/404

  Nitrogen oxides other than dinitrogen oxide · CPC title

• B01D2258/0283

  Flue gases · CPC title

• C07D207/46

  with hetero atoms directly attached to the ring nitrogen atom · CPC title

• C07D207/323

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms · CPC title

• C07D207/33

  with substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title