(US20190152902) Sulfonated Aromatic Compounds 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(US20190152902) Sulfonated Aromatic Compounds
公开号/公开日
US20190152902 / 2019-05-23
申请号/申请日
US16/091,436 / 2017-04-07
发明人
KRAWCZYK NASTARANMOELLER ALEXANDERGEIGLE PETERLARIONOV EVGENYHARTWIG JAN;
申请人
CMBLU PROJEKT;
主分类号
IPC分类号
C07C-303/06 C07C-309/43 C07C-309/46 H01M-008/18
摘要
(US20190152902) 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.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2016WO-EP00575 2017WO-EP00198 2017WO-EP00461
主权利要求
(US20190152902) 1. A sulfonated low molecular weight aromatic compound, wherein said compound is characterized by 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 at least one of R1-R4 is SO3H;  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 at least one of R1-R6 is SO3H;  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 at least one of R1-R8 is SO3H,   preferably selected from a sulfonated compound according to Table 1, 2 or 3. 2. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound is characterized by Formula (X) or (XI) and wherein R1 and R4 are independently selected from H or SO3H, R2 is selected from H, OH, and C1-C6 alkoxy, preferably methoxy, or SO3H, R3 is selected from H, OH and C1-C6 alkoxy, preferably methoxy. 3. The sulfonated low molecular weight aromatic compound according to claim 1 or 2, wherein the compound is characterized by one of the following:   a) R4 is SO3H;   b) R4 is SO3H, R3 is methoxy;   c) R4 is SO3H, R2 and R3 are methoxy;   d) R1 and R4 are SO3H;   e) R1 and R4 are SO3H, R3 is methoxy;   f) R1 and R4 are SO3H, R2 and R3 are methoxy; or   g) R2 and R4 are SO3H, and R3 is methoxy,   wherein each of the other of R1-R4 is OH or H, preferably H. 4. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound is characterized by Formula (XII) or (XIII), wherein R1 and R2 are independently selected from H, OH and C1-C6 alkoxy, preferably methoxy, and R3-R6 are independently selected from H and SO3H. 5. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound is characterized by Formula (XIV) or (XV) and wherein R1, R2 and R4 are independently selected from H, OH and C1-C6 alkoxy, preferably methoxy, and R3, R5-R8 are independently selected from H and SO3H. 6. The sulfonated low molecular weight aromatic compound according to claim 1 or 5, wherein the compound is characterized by one of the following:   a) R1 is SO3H;   b) R2 is SO3H; R1, R3 and R4 are preferably OH;   c) R6 is SO3H; R1 and R4 or R1, R2 and R4 are preferably OH;   d) R2 and R6 are SO3H; R1 and R4 or R1, R3 and R4 are preferably OH;   e) R3 and R6 are SO3H; R1, R2 and R4 are preferably OH;   f) R2 and R7 are SO3H; or   g) R1 and R4 are SO3H;   wherein each of the other of R1-R8 is/are C1-C6 alkoxy or H, preferably H. 7. A composition comprising at least two sulfonated low molecular weight aromatic compounds according to any one of claims 1 to 6, preferably at least two distinct low molecular weight aromatic compounds with at least one compound being in the oxidized state according to Formula (X), (XII) or (XIV), and/or at least corresponding compound being in the reduced state according to Formula (XI), (XIII) or (XV). 8. The composition according to claim 7, wherein said at least two sulfonated low molecular weight aromatic compounds are characterized by the following:   (a) at least one compound according to Formula (X) and (XI), preferably as defined in claim 2 or 3, preferably at least one compound of Formula (X) (oxidized state) and at least one corresponding compound of Formula (XI) (reduced state);   (b) at least one compound according to Formula (XII) and (XIII), preferably as defined in claim 4, preferably at least one compound of Formula (XII) (oxidized state) and at least one corresponding compound of Formula (XIII) (reduced state); and/or   (c) at least one compound according to Formula (XIV) and (XV), optionally as defined in claim 5 or 6, preferably at least one compound of Formula (XIV) (oxidized state) and at least one corresponding compound of Formula (XV) (reduced state). 9. The composition according to claim 8, said composition comprising   (a) at least two compounds according to Formula (X) and (XI), wherein said at least two compounds are distinctly sulfonated and/or substituted, preferably at least two distinct compounds being in the oxidized state according to Formula (X) and at least two corresponding distinct compounds according to Formula (XI) in the respective reduced state;   (b) at least two compounds according to Formula (XII) or (XIII), wherein said at least two compounds are distinctly sulfonated and/or substituted, preferably at least two distinct compounds being in the oxidized state according to Formula (XII) and at least two corresponding distinct compounds according to Formula (XIII) in the respective reduced state; and/or   (c) at least two compounds according to Formula (XIV) or (XV), wherein said at least two compounds are distinctly sulfonated and/or substituted, preferably at least two distinct compounds being in the oxidized state according to Formula (XIV) and at least two corresponding distinct compounds according to Formula (XV) in the respective reduced state. 10. The composition according to claim 9, wherein each of said at least two compounds comprises at least two SO3H groups, preferably two SO3H groups. 11. A method for preparing a sulfonated low molecular weight aromatic compound or a composition comprising or (essentially) consisting of the same, preferably according to any one of claims 1 to 10, comprising the steps of   (1) providing a starting material;   (2) optionally subjecting said starting material to a process suitable to obtain at least one low molecular weight precursor compound;   (3) isolating and optionally modifying at least one low molecular weight precursor compound; thereby obtaining at least one low molecular weight aromatic precursor compound;   (4) subjecting said at least one low molecular weight precursor compound to a sulfonation reaction, wherein one or more SO3H groups are introduced into said at least one precursor compound; thereby obtaining at least one sulfonated low molecular weight aromatic compound or a composition comprising the same or (essentially) consisting thereof;   wherein said starting material is preferably selected from lignocellulosic material, crude oil, coal or pure organic substances. 12. The method according to claim 11, wherein said starting material is lignocellulosic material and said method comprises the followings steps:   (1) subjecting lignocellulosic material to a pulping process; thereby obtaining modified lignin-derived components;   (2) isolating said modified lignin-derived components;   (3) subjecting said modified lignin-derived components to a chemical decomposition step; thereby obtaining at least one low molecular weight precursor compound;   (4) isolating and optionally modifying at least one low molecular weight precursor compound; thereby obtaining at least one low molecular weight aromatic precursor compound;   (5) subjecting said at least one low molecular weight aromatic precursor compound to a sulfonation reaction, wherein one or more —SO3H groups are introduced into said at least one precursor compound; thereby obtaining at least one sulfonated low molecular weight aromatic compound or a composition comprising the same or (essentially) consisting thereof. 13. The method according to claim 12, wherein step (1) comprises the sub-steps of:   (1.1) providing a lignocellulosic material;   (1.2) subjecting said lignocellulosic material to (a) a Kraft process or (b) a sulfite process;   (1.3) optionally separated the pulp from the process stream obtainable from the pulping process in sub-step (1.2). 14. The method according to claim 12 or 13, wherein step (3) comprises:   (a) oxidative cracking (cracking and oxidizing) of the modified lignin-derived components in the presence of a heterogeneous or homogeneous catalyst comprising a metal ion or a metalloid component; or   (b) reductive cracking (cracking and reducing) of the modified lignin-derived components in the presence of a heterogeneous or homogeneous catalyst comprising a metal ion or metalloid component; or   (c) subjecting the modified lignin-derived components to electro-oxidation in alkaline or acidic solution. 15. The method according to of any one of claims 12 to 14, wherein the at least one precursor compound comprises one or two aromatic ring(s), preferably two non-annulated aromatic rings. 16. The method of according to claim 15, wherein the at least one precursor compound comprises two aromatic rings, wherein said two aromatic rings are linked by a linker moiety, preferably an aliphatic linker, or by a bond. 17. The method according to any one of claim 15 or 16, wherein the at least one precursor compound comprises two aromatic rings which form a biphenylic moiety. 18. The method according to any one of claims 15 to 17, wherein the one or two aromatic ring(s) is/are carbocyclic. 19. The method according to any one of claims 15 to 18, wherein the aromatic ring(s) is/are substituted in at least one, preferably two positions by a functional group, wherein at least one of these functional groups is preferably alkoxy or hydroxyl. 20. The method according to any one of claims 15 to 19, wherein the at least one precursor compound is characterized by Formula (Ia):  wherein    each of R1-R5 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, oxo or carbonyl, wherein at least one of R1, R3 or R5 is hydroxy or linear or branched, optionally substituted, C1-6 alkoxy; and    R6 is selected from the group consisting of hydrogen, hydroxy, linear or branched, optionally substituted, C1-6 carboxyl, linear or branched C1-6 aldehyde, and linear or branched, optionally substituted, C1-6 alcohol;    or by Formula (Ib):  wherein    each of R1-R9 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, C6 aldehyde, ester, oxo or carbonyl, wherein R5 is preferably hydroxy or linear or branched, optionally substituted, C1 6 alkoxy; and    R10 is selected from the group consisting of hydrogen, hydroxy, linear or branched, optionally substituted, C1-6carboxyl, linear or branched, optionally substituted, C1-6 aldehyde, and linear or branched C1-6 alcohol. 21. The method according to claim 20, wherein the at least one precursor compound is selected from the group consisting of phenolic derivatives of biphenyl, benzylalcohol, benzaldehydes and benzoic acid, preferably derivatives of p-hydroxy benzylalcohol, p-hydroxy benzaldehydes and p-hydroxy benzoic acid, or more preferably vanillin, guaiacol, eugenol, syringol, phenol, syringaldehyde, and/or a derivative of any of the above, and/or a combination of the above. 22. The method according to any one of claims 12 to 21, wherein step (4) comprises the sub-steps of   (4.1) isolating said precursor compound; and optionally   (4.2) subjecting said precursor compound to an annulation reaction; and/or   (4.3) subjecting said precursor compound to an oxidation reaction. 23. The method according to claim 22, wherein the at least one precursor compound comprises one aromatic ring and is further processed in a sub-step (4.2), wherein said precursor compound comprising one aromatic ring is subjected to an annulation reaction, preferably a Diels-Alder reaction or a Friedel Crafts acylation, wherein the annulation reaction product is a low molecular weight aromatic bi- or tricyclic annulated aromatic compound, wherein said compound is characterized by Formula (II), (III) or (IV)  wherein    each of R2, R3, R5-R8 of Formula (II) 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, oxo or carbonyl,    wherein preferably at least one of R2, R3, R5-R8 is hydroxy or C1-3 alkoxy, and    R1 and R4 of Formula (II) is/are selected from the group consisting of hydrogen, hydroxy, linear or branched, optionally substituted, C1-6 carboxyl, linear or branched, optionally substituted, C1-6 aldehyde, and linear or branched, optionally substituted, C1-6 alcohol,    each of R1-R10 of Formula (III) 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, oxo or carbonyl,    wherein preferably at least one of R2, R5, R6 and R8 is hydroxy or C1-3 alkoxy,    wherein preferably R1, R4, R9 and R10 of Formula (III) is/are selected from the group consisting of hydrogen, hydroxy, linear or branched, optionally substituted, C1-6 carboxyl, linear or branched, optionally substituted, C1-6 aldehyde, and linear or branched, optionally substituted, C1-6 alcohol,    each of R2, R3 and R1-R10 of Formula (IV) 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, oxo or carbonyl,    wherein preferably at least one of R2, R3 and R1-R10 is hydroxy or C1-3 alkoxy, and    R1, R4, R5 and R6 of Formula (IV) is selected from the group consisting of hydrogen, hydroxy, linear or branched, optionally substituted C1-6 carboxyl, linear or branched, optionally substituted, C1-6 aldehyde, and linear or branched, optionally substituted, C1-6 alcohol. 24. The method according to any one of claim 22 or 23, wherein the at least one monocyclic or (optionally annulated) bi- or tricyclic precursor compound obtained from any one of sub-steps (4.1) or (4.2) is further modified in a sub-step (4.3) by oxidizing said at least precursor compound in the presence of (i) an oxidizing agent selected from the group consisting of H2O2, O2 and air, and (ii) a homogeneous or heterogeneous catalyst, preferably comprising a metal ion or a metalloid component. 25. The method according to claim 24, wherein the at least one oxidized monocyclic precursor compound obtained from any one of sub-steps (4.1) or (4.3) comprises at least one hydroquinone compound, characterized by Formula (Va):  wherein each of R1-R5 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, oxo or carbonyl, and wherein preferably one of R1, R3 and R5 is hydroxy;   or by formula (Vb),  wherein each of R1-R9 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, oxo or carbonyl, and wherein R5 is preferably hydroxy; and/or at least one quinone compound characterized by any of Formulae (VIa) to (VIb):  wherein each of R1-R2 and R4-R5 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, oxo or carbonyl; or  wherein each of R2-R5 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, oxo or carbonyl; or  wherein each of R1-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, oxo or carbonyl; or  wherein each of R1-R4 and R6-R9 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, oxo or carbonyl. 26. The method according to claim 24 or 25, wherein the at least one oxidized (optionally annulated) bi- or tricyclic precursor compound obtained from any one of sub-steps (4.1)-(4.3) comprises at least one quinone and/or hydroquinone compound characterized by any of Formula (VII), (VIII) and/or (IX):  wherein each of R1-R8 with regard to Formula (VII) and/or each of R1-R10 with regard to Formula (VIII) and (IX) 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, oxo or carbonyl;   wherein at least one of R8 and R5 or R1 and R4 of Formula (VII) are hydroxy or oxo, or at least one of R9 and R6, R10 and R5, or R1 and R4 of Formula (VIII) are hydroxy or oxo, or at least one of R10 and R7 or R1 and R4 of Formula (IX) are hydroxy or oxo. 27. The method according to any one of claims 12 to 26, wherein step (4) further comprises a purification sub-step (4.4) to separate the at least one precursor compound, preferably a quinone or hydroquinone compound, from residual compounds by an extraction method, preferably by solid phase extraction or fluid-fluid phase extraction. 28. The method according to any one claims 12 to 27, wherein the at least one precursor compound, preferably a quinone or hydroquinone compound, is further subjected to a derivatization step (4.5), wherein one or more 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 or cyanide groups are introduced into a compound according to any of Formulae (I) to (IX) at a position of the aryl structure other than those characterized by an oxo or hydroxyl group, wherein said group(s) is/are directly bound to the aryl structure or bound via an alkyl linker to the aryl structure, preferably via a methyl linker. 29. The method according to any one of claims 12 to 28, wherein step (5) comprises introducing one or more SO3H-groups into a compound according to any of Formulae (I) to (IX) at a position of the aryl structure other than those characterized by an oxo or hydroxyl group, wherein said group(s) is/are directly bound to the aryl structure or bound via an alkyl linker to the aryl structure, preferably via a methyl linker. 30. The method according to any one of claims 12 to 29, wherein the at least one sulfonated low molecular weight aromatic compound, preferably a quinone or hydroquinone compound, is further subjected to a derivatization step (6), wherein one or more groups 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 or cyanide groups are introduced into said compound, preferably at a position of the aryl structure other than those characterized by an oxo or hydroxyl or sulfonyl group, wherein said group(s) is/are directly bound to the aryl structure or bound via an alkyl linker to the aryl structure, preferably via a methyl linker. 31. The method according to any one of claims 12 to 30, further comprising a step (7) of isolating said at least one sulfonated (and optionally further derivatized) low molecular weight aromatic compound or a composition comprising or (essentially) consisting of the same. 32. The method according to any one claims 12 to 31, further comprising after step (5), (6) or (7) a step (8) of providing said one sulfonated (optionally further derivatized) low molecular weight aromatic compound or a composition comprising the same or (essentially) consisting thereof as a redox flow battery electrolyte. 33. A sulfonated (and optionally further derivatized) low molecular weight aromatic compound or a composition comprising or (essentially) consisting of the same, obtainable by a method according to any one of claims 11 to 32. 34. The sulfonated (and optionally further derivatized) low molecular weight aromatic compound or composition according to claim 33, wherein said compound is characterized by any one of Formulae (X)-(XV) as defined in any one of claims 1 to 6, and/or said composition comprises or (essentially) consists of compounds characterized by any one of Formulae (X)-(XV) as defined in any one of claims 1 to 6. 35. A redox flow battery electrolyte solution comprising the sulfonated (and optionally further derivatized) low molecular weight aromatic compound or composition according to any one of claims 1 to 10 or 33 or 34 dissolved or suspended in a suitable solvent, said solvent preferably being selected from water. 36. Use of a sulfonated (and optionally further derivatized) low molecular weight aromatic compound or a composition according to any one of claims 1 to 10 or 33 or 34 as a redox flow battery electrolyte. 37. A redox flow battery comprising the sulfonated and optionally further derivatized low molecular weight aromatic compound or the composition according to any one of claims 1 to 10 or 33 or 34 or the electrolyte solution according to claim 35. 38. The redox flow battery according to claim 37, wherein said redox flow battery comprises a first (optionally aqueous) electrolyte solution comprising a first (redox active) electrolyte; a first electrode in contact with said first (optionally aqueous) electrolyte solution; a second (optionally aqueous) electrolyte solution comprising a second (redox active) electrolyte; a second electrode in contact with said second (optionally aqueous) electrolyte solution; wherein one or both of the first and second (redox active) electrolytes comprise at least one sulfonated (and optionally further derivatized) low molecular weight aromatic compound as defined in any one of the preceding claims (preferably at least one sulfonated (and optionally further derivatized) (hydro-)quinone) or a composition comprising or (essentially) consisting of the same as defined in any one of the preceding claims.
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