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US 8,710,265 B2Granted
Switchable solvents and methods of use thereof
AssigneesQueen's University at Kingston, Georgia Tech Research Corporation
InventorsPhilip G. Jessop, Charles A. Eckert, Charles L. Liotta, David J. Heldebrant
Life of this patent
Estimating the term…
Abstract
A solvent that reversibly converts from a nonionic liquid mixture to an ionic liquid upon contact with a selected trigger, e.g., contact with CO2, is described. In preferred embodiments, the ionic solvent is readily converted back to the nonionic liquid mixture. The nonionic liquid mixture includes an amidine or guanidine or both, and water, alcohol, or a combination thereof. Single component amine solvents that reversibly convert between ionic and non-ionic states are also described. Some embodiments require increased pressure to convert; others convert at 1 atmosphere.
Claims53
A composition comprising:
- (a) CO2 from a source other than air;
- and
- (b) a switchable solvent from by combining:
- an amount of at least one R′OH, water, or a combination thereof, wherein R′ is alkyl, alkenyl, alkynyl, aryl, silyl, or siloxyl, and may be linear, branched, or cyclic, and may be substituted or unsubstituted;
- with an amount of a compound of formula (3)
- wherein
- R1, R2, R3, R4, and R5 are independently H;
- a substituted or unsubstituted C1 to C10 alkyl group that is linear or branched;
- a substituted or unsubstituted C3 to C10 cycloalkyl group;
- a substituted or unsubstituted CnSim group where n and m are independently a number from 0 to 10 and n+m is a number from 1 to 10;
- a substituted or unsubstituted aryl group optionally containing one or more {—Si(R6)2—O—} units;
- or a substituted or unsubstituted heteroaryl group optionally containing one or more {—Si(R6)2—O—} units;
- R6 is a substituted or unsubstituted alkyl, aryl, heteroaryl, or alkoxy moiety;
- and wherein the compound of formula (3) and the corresponding ionic liquid of formula (4) may be a monocyclic or bicyclic ring structure;
- wherein the compound of formula (3) reversibly converts to an ionic liquid of formula (4)
- in the presence of the CO2, wherein R is H or R′ as defined above, and R1, R2, R3, R4, and R5 are as defined above;
- and
- wherein the amount of the compound of formula (3) is approximately equimolar to or greater than equimolar to the amount of the at least one R′OH, water, or combination thereof.
15 more elements
A composition comprising:
- (a) CO2 from a source other than air;
- and
- (b) a switchable solvent formed by combining:
- at least one R′OH, water, or a combination thereof, wherein R′ is alkyl, alkenyl, alkynyl, aryl, silyl, or siloxyl, and may be linear, branched, or cyclic, and may be substituted or unsubstituted;
- with a compound of formula (3)
- wherein
- R1, R2, R3, R4, and R5 are independently H;
- a substituted or unsubstituted C1 to C4 alkyl group that is linear or branched;
- a substituted or unsubstituted CnSim group where n and m are independently a number from 0 to 4 and n+m is a number from 1 to 4;
- a substituted or unsubstituted C3 to C4 cycloalkyl group;
- a substituted or unsubstituted heteroaryl group optionally containing one or more {—Si(R6)2—O—} units;
- R6 is a substituted or unsubstituted alkyl, aryl, heteroaryl, or alkoxy moiety;
- and wherein the compound of formula (3) and the corresponding ionic liquid of formula (4) may be a monocyclic or bicyclic ring structure;
- wherein the compound of formula (3) reversibly converts to an ionic liquid of formula (4)
- in the presence of the CO2, wherein R is H or R′ as defined above, and R1, R2, R3, R4, and R5 are as defined above.
12 more elements
A composition comprising:
- (a) CO2 from a source other than air;
- and
- (b) a switchable solvent having switchable polarity between a polar form and a nonpolar form, wherein said switchable solvent comprises:
- at least one R′OH, water, or a combination thereof, wherein R′ is alkyl, alkenyl, alkynyl, aryl, silyl, or siloxyl, and may be linear, branched, or cyclic, and may be substituted or unsubstituted;
- and a compound of formula (3)
- wherein
- R1, R2, R3, R4, and R5 are independently H;
- a substituted or unsubstituted C1 to C10 alkyl group that is linear or branched;
- a substituted or unsubstituted C3 to C10 cycloalkyl group;
- a substituted or unsubstituted CnSim group where n and m are independently a number from 0 to 10 and n+m is a number from 1 to 10;
- a substituted or unsubstituted aryl group optionally containing one or more {—Si(R6)2—O—} units;
- or a substituted or unsubstituted heteroaryl group optionally containing one or more {—Si(R6)2—O—} units;
- R6 is a substituted or unsubstituted alkyl, aryl, heteroaryl, or alkoxy moiety;
- and wherein the compound of formula (3) and the corresponding ionic liquid of formula (4) may be a monocyclic or bicyclic ring structure;
- and wherein, optionally, one of R1, R2, R3, R4, and R5 combines with R′ to connect the hydroxyl of the at least one R′OH as part of the compound for formula (3);
- wherein the compound of formula (3) reversibly converts to an ionic liquid of formula (4)
- in the presence of the CO2, wherein R is H or R′ as defined above, and R1, R2, R3, R4, and R5 are as defined above, wherein the polarity of the switchable solvent is switched by the interconversion of the compound of formula (3) and the ionic liquid of formula (4).
14 more elements
Dependencies are inferred from the claim text.