(US20200283380) Process For The Production Of Lignin Derived Low Molecular Products 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(US20200283380) Process For The Production Of Lignin Derived Low Molecular Products
公开号/公开日
US20200283380 / 2020-09-10
申请号/申请日
US16/484,301 / 2018-02-13
发明人
KRAWCZYK NastaranMÖLLER AlexanderGEIGLE PeterLARIONOV EvgenyHARTWIG Jan;
申请人
CMBLU PROJEKT;
主分类号
IPC分类号
C07C-303/02 C07C-309/42 C07C-309/44 H01M-008/18
摘要
(US20200283380) 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
2017WO-EP00198 2017WO-EP00463
主权利要求
(US20200283380) 1. A sulfonated 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; carboxylic acids; esters; halogen; optionally substituted 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; carboxylic acids; esters; halogen; optionally substituted 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; carboxylic acids; esters; halogen; optionally substituted amine; amino; amide; nitro; oxo; carbonyl; phosphoryl; phosphonyl; cyanide and sulfonyl (—SO3H),   provided that at least one of R1-R8 is SO3H. 2. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound corresponds in structure to Formula (X) or (XI) and wherein R1 and R4 are independently selected from H and SO3H, R2 is selected from H, OH, and C1-C6 alkoxy, or SO3H, R3 is selected from H, OH and C1-C6 alkoxy. 3. The sulfonated low molecular weight aromatic compound according to claim 1, wherein the compound corresponds in structure to Formula (X) or (XI) and wherein:   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. 4. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound corresponds in structure to Formula (XII) or (XIII), wherein R1 and R2 are independently selected from H, OH and C1-C6 alkoxy, 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 corresponds in structure to Formula (XIV) or (XV) and wherein R1, R2 and R4 are independently selected from H, OH and C1-6 alkoxy, and R3, R5-R8 are independently selected from H and SO3H. 6. The sulfonated low molecular weight aromatic compound according to claim 1, wherein the compound corresponds in structure to Formula (XIV) or (XV), wherein:   a) R1 is SO3H;   b) R2 is SO3H;   c) R6 is SO3H;   d) R2 and R6 are SO3H;   e) R3 and R6 are SO3H;   f) R2 and R7 are SO3H; or   g) R1 and R4 are SO3H;   wherein each of the other of R1-R8 is/are C1-6 alkoxy or H. 7. The sulfonated low molecular weight aromatic compound according to claim 1, said compound corresponding in structure to Formula (XIV) or (XV), wherein R1 and R2 are, each independently or both, not selected from hydrogen; hydroxy or sulfonyl. 8. The sulfonated low molecular weight aromatic compound according to claim 1, said compound corresponding in structure to Formula (X) or (XI), wherein R1 and R2 are, each independently or both, not selected from sulfonyl. 9. The sulfonated low molecular weight aromatic compound according to claim 1, said compound corresponding in structure to Formula (XIV) or (XV), wherein R1, R3, R4 are, each independently or all of them, not selected from C1-6 alkyl. 10. The sulfonated low molecular weight aromatic compound according to claim 9, wherein R1, R3, R4 are, each independently or all of them, not selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl and cyclohexyl. 11. A composition comprising at least two sulfonated low molecular weight aromatic compounds according to claim 1. 12. The composition according to claim 11, wherein said at least two sulfonated low molecular weight aromatic compounds are the following:   (a) at least one compound according to Formula (X) and (XI);   (b) at least one compound according to Formula (XII) and (XIII); and/or   (c) at least one compound according to Formula (XIV) and (XV). 13. The composition according to claim 11, 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;   (b) at least two compounds according to Formula (XII) or (XIII), wherein said at least two compounds are distinctly sulfonated and/or substituted; 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. 14. The composition according to claim 13, wherein each of said at least two compounds comprises at least two SO3H groups. 15. A method for preparing a sulfonated low molecular weight aromatic compound or a composition comprising the same, the method 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. 16. The method according to claim 15, 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. 17. The method according to claim 15, 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). 18. The method according to claim 15, 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. 19. The method according to of any one claim 15, wherein the at least one precursor compound comprises one or two aromatic ring(s). 20. The method of according to claim 19, wherein the at least one precursor compound comprises two aromatic rings, wherein said two aromatic rings are linked by a linker moiety or by a bond. 21. The method according to claim 19, wherein the at least one precursor compound comprises two aromatic rings which form a biphenylic moiety. 22. The method according to claim 19, wherein the one or two aromatic ring(s) is/are carbocyclic. 23. The method according to claim 19, wherein the aromatic ring(s) is/are substituted in at least one position by a functional group. 24. The method according to claim 19, wherein the at least one precursor compound corresponds in structure to 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; carboxylic acids; esters; oxo and carbonyl,   wherein at least one of R1, R3 or R5 is hydroxy or linear or branched, optionally substituted, C1-6 alkoxy; and wherein 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 corresponds in structure to 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, C1-6 aldehyde; carboxylic acids; esters; oxo and carbonyl; and    R10 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 C1-6 alcohol. 25. The method according to claim 24, wherein the at least one precursor compound is selected from the group consisting of a phenolic derivatives of biphenyl, benzylalcohol, a benzaldehydes and benzoic acid, a derivative of any thereof, and a combination of any thereof. 26. The method according to claim 15, 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. 27. The method according to claim 26, 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, wherein the annulation reaction product is a low molecular weight aromatic bi- or tricyclic annulated aromatic compound, wherein said compound corresponds in structure to 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; carboxylic acids; esters; oxo and carbonyl;    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; carboxylic acids; esters; oxo and carbonyl. 28. The method according to claim 26, 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. 29. The method according to claim 28, 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 corresponding in structure to 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; carboxylic acids; esters; oxo and carbonyl,   or corresponding in structure to 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; carboxylic acids; esters; oxo and carbonyl,   and/or   at least one quinone compound corresponding in structure to 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; carboxylic acids; esters, oxo and 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; carboxylic acids; esters; oxo and 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; carboxylic acids; esters; oxo and 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; carboxylic acids; esters, oxo and carbonyl. 30. The method according to claim 28, 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 corresponding in structure to 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; carboxylic acids; esters, oxo and 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. 31. The method according to claim 15, wherein step (4) further comprises a purification sub-step (4.4) to separate the at least one precursor compound from residual compounds by an extraction method. 32. The method according to claim 15, wherein the at least one precursor 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; carboxylic acid; 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. 33. The method according to claim 15, 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. 34. The method according to claim 15, wherein the at least one sulfonated low molecular weight aromatic 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; carboxylic acid; ester; halogen; amine; amino; amide; nitro; oxo; carbonyl; phosphoryl; phosphonyl and a cyanide group are introduced into said compound, wherein said group(s) is/are directly bound to the aryl structure or bound via an alkyl linker to the aryl structure. 35. The method according to claim 15, 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 the same. 36. The method according to claim 15, 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 as a redox flow battery electrolyte. 37. A sulfonated (and optionally further derivatized) low molecular weight aromatic compound or a composition comprising the same, obtainable by a method according to claim 15. 38. (canceled) 39. A redox flow battery electrolyte solution comprising the sulfonated (and optionally further derivatized) low molecular weight aromatic compound or composition according to claim 1 dissolved or suspended in a suitable solvent. 40. (canceled) 41. A redox flow battery comprising the sulfonated and optionally further derivatized low molecular weight aromatic compound or the composition according to claim 1 or an electrolyte solution comprising the sulfonated and optionally further derivatized low molecular weight aromatic compound. 42. (canceled) 43. The sulfonated low molecular weight aromatic compound according to claim 1, wherein said compound is selected from a sulfonated compound listed in Tables 1, 2 and 3. 44. The method according to claim 15, wherein said starting material is selected from the group consisting of lignocellulosic material, crude oil, coal and a pure organic substance. 45. The method according to claim 19, wherein the at least one precursor compound comprises two non-annulated aromatic rings. 46. The method according to claim 31, wherein the at least one precursor compound is a quinone or hydroquinone compound and the extraction method is a solid phase extraction or fluid-fluid phase extraction.
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专利类型码
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