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US 11,725,340 B2Granted
Sulfonated lignin-derived compounds and uses thereof
AssigneeCMBlu Energy AG
InventorsNastaran Krawczyk, Alexander Moeller, Peter Geigle, Evgeny Larionov, Jan Hartwig
Life of this patent
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Abstract
The present invention relates to novel lignin-derived compounds and compositions comprising the same and their use as redox flow battery electrolytes. The invention further provides a method for preparing said compounds and compositions as well as a redox flow battery comprising said compounds and compositions. Additionally, an assembly for carrying out the inventive method is provided.
Claims18
A redox flow battery comprising at least one sulfonated and optionally further derivatized low molecular weight aromatic compound, wherein said compound corresponds in structure to Formula (X), (XI), (XII), (XIII), (XIV) or (XV):
- wherein each R1, R2, R3 or R4 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least three of R1-R4 are SO3H or (ii) provided that at least one of R1-R4 is SO3H and at least one of R1-R4 is hydroxy or C1-6 alcohol;
- wherein each R1, R2, R3, R4, R5 or R6 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least three of R1-R6 are SO3H or (ii) provided that at least one of R1-R6 is SO3H and at least one of R1-R6 is hydroxy or C1-6 alcohol;
- wherein each R1, R2, R3, R4, R5, R6, R7 or R8 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least three of R1-R8 are SO3H or (ii) provided that at least one of R1-R8 is SO3H and at least one of R1-R8 is hydroxy or C1-6 alcohol.
A redox flow battery comprising a composition comprising at least two sulfonated low molecular weight aromatic compounds, wherein said compounds independently correspond in structure to Formula (X), (XI), (XII), (XIII), (XIV) or (XV):
- wherein each R1, R2, R3 or R4 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least two of R1-R4 are SO3H, or provided that (ii) at least one of R1-R4 is SO3H and at least one of R1-R4 is hydroxy or C1-6 alcohol;
- wherein each R1, R2, R3, R4, R5 or R6 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least two of R1-R6 are SO3H, or provided that (ii) at least one of R1-R6 is SO3H and at least one of R1-R6 is hydroxy or C1-6 alcohol;
- wherein each R1, R2, R3, R4, R5, R6, R7 or R8 is independently selected from hydrogen, hydroxy, carboxy, linear or branched, optionally substituted, C1-6 alkyl, linear or branched, optionally substituted, C1-6 alkenyl, linear or branched, optionally substituted, C1-6 alcohol, linear or branched, optionally substituted, C1-6 aminoalkyl, linear or branched, optionally substituted, C1-6 carboxyalkyl, linear or branched, optionally substituted, C1-6 alkoxy, linear or branched, optionally substituted, C1-6 aldehyde, ester, halogen, amine, amino, amide, nitro, oxo, carbonyl, phosphoryl, phosphonyl, cyanide and sulfonyl (SO3H), provided that (i) at least two of R1-R8 are SO3H, or provided that (ii) at least one of R1-R8 is SO3H and at least one of R1-R8 is hydroxy or C1-6 alcohol;
- and wherein at least one of the sulfonated low molecular weight aromatic compounds is in an oxidized state according to Formula (X), (XII) or (XIV), and/or at least one of the sulfonated low molecular weight aromatic compounds is in a reduced state according to Formula (XI), (XIII) or (XV).
1 more element
Dependencies are inferred from the claim text.