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US 2026/0175168 A1Published application
Compositions, articles, and methods related to redox-active sorbents for electrochemical carbon dioxide separation
AssigneeMassachusetts Institute of Technology
InventorsBetar Gallant, Fang-Yu Kuo, Glen Junor, Akachukwu Obi
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Abstract
Compositions, articles, systems, and methods related to redox-active sorbents for electrochemical carbon dioxide separation are generally described.
Claims29
An electrochemical cell, comprising:
- a first electrode;
- a second electrode;
- and
- a carbon dioxide (CO2) adduct comprising a reaction product between CO2 and a N-heterocyclic imine (NHI) compound of Formula (I) and/or a metal ion-stabilized derivative thereof:
- wherein:
- each R is the same or different and:
- (i) is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, OR3, and N(R3)2, each of which is optionally substituted;
- and/or (ii) at least one R combines together with at least one R1 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- and/or (iii) at least one R combines together with R2 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- or (iv) each R combines together with the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted,
- each R1 is the same or different and:
- (i) is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, OR3, and N(R3)2;
- and/or (ii) at least one R1 combines together with R2 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- or (iii) each R1 combines together with the carbon atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted,
- R2 is selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, OR3, N(R3)2, and a NHI moiety, each of which is optionally substituted, and wherein one or more optional substituents comprise a NHI substituent, and
- each R3 is the same or different and is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, each of which is optionally substituted.
13 more elements
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5-9. (canceled)
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A method, comprising:
- exposing a composition to a fluid stream suspected of comprising CO2, wherein the composition comprises a NHI compound of Formula (I) and/or a metal ion-stabilized derivative thereof:
- wherein:
- each R is the same or different and:
- (i) is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, OR3, and N(R3)2, each of which is optionally substituted;
- and/or (ii) at least one R combines together with at least one R1 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- and/or (iii) at least one R combines together with R2 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- or (iv) each R combines together with the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted,
- each R1 is the same or different and:
- (i) is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C6-C40 heteroaryl, OR3 and N(R3)2;
- and/or (ii) at least one R1 combines together with R2 and the atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted;
- or (iii) each R1 combines together with the carbon atoms to which they are attached to form a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C6-C40 aryl group, or a C5-C40 heteroaryl group, each of which is optionally substituted,
- R2 is selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, OR3, N(R3)2, and a NHI moiety, each of which is optionally substituted, and wherein one or more optional substituents comprise an NHC substituent, and
- each R3 is the same or different and is individually selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C3-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C40 aryl, C5-C40 heteroaryl, each of which is optionally substituted;
- absorbing the CO2, if present, from the fluid stream, wherein absorbing the CO2 from the fluid stream comprises reacting the NHI compound of Formula (I) and/or the metal ion-stabilized derivative thereof and the CO2 to form a CO2 adduct;
- and
- applying a stimulus to release the CO2 from the CO2 adduct and regenerate the NHI compound of Formula (I) and/or the metal ion-stabilized derivative thereof.
13 more elements
27-36. (canceled)
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40-43. (canceled)
A CO2 sequestering agent, comprising:
- a redox-active moiety comprising at least two functional groups capable of binding and releasing CO2,
- wherein the at least two functional groups, when the moiety is arranged in a set system, are configured to:
- (i) bind CO2 without application of a redox-inducing electrical potential;
- and (ii) release bound CO2 upon application of a stimulus, and
- wherein the moiety is configured to bind and release greater than or equal to 1.4 mol of CO2 per mol of the CO2 sequestering agent.
2 more elements
45-47. (canceled)
Dependencies are inferred from the claim text.