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Complex containing monosulfonated catechol acid ligand and preparation method thereof

A technology of complexes and catechols, applied in the preparation of organic compounds, titanium organic compounds, chemical instruments and methods, etc., can solve problems such as limited solubility

Active Publication Date: 2021-11-19
LOCKHEED MARTIN ADVANCED ENERGY STORAGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, due to the limited solubility of some complexes, it may be difficult to add sufficient amounts of foreign electrolytes (e.g., non-redox active species) to the electrolyte solution to increase the conductivity to the desired level

Method used

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  • Complex containing monosulfonated catechol acid ligand and preparation method thereof
  • Complex containing monosulfonated catechol acid ligand and preparation method thereof
  • Complex containing monosulfonated catechol acid ligand and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0114] Example 1: A neat mixture containing various stoichiometric ratios of catechol and sulfuric acid was prepared and reacted at various temperatures for various lengths of time. The specific reaction conditions are summarized in Table 1 below.

[0115] Table 1

[0116]

[0117] 1 3,4-Dihydroxybenzenesulfonic acid

[0118] 2 pass 1 <5% 2,3-dihydroxybenzenesulfonic acid detected by H NMR

[0119] After cessation of heating, the reaction mixture was added to an ice / water mixture and extracted 3 times with toluene. The aqueous phase was then evaporated to dryness and then 50% aqueous NaOH was added to the resulting solid. The basic solution was then evaporated to dryness a second time. The solid was triturated with hot toluene followed by methanol, which were then removed by decantation. The solid was filtered, washed with methanol and dried. In certain instances, a second crop of product is recovered from the filtrate. In other instances, the product was recrysta...

Embodiment 2

[0122] A mixture containing 2 equivalents of catechol and 1 equivalent of 3,4-dihydroxybenzenesulfonic acid was mixed with methanol and titanium tetra(isopropoxide) was slowly added over a period of time. Distillation is performed after the addition is complete, and an alkaline solution is added to form the corresponding salt of the sulfonated catechol acid complex in aqueous solution. For example, addition of an equimolar mixture of aqueous sodium hydroxide and potassium hydroxide solutions results in a mixed sodium / potassium salt of the sulfonated catecholate complex. image 3 D showing the aromatic region of the titanium complex formed by 2 equivalents of catechol and 1 equivalent of 3,4-dihydroxybenzenesulfonic acid 2 Illustrative in O 1 H NMR spectrum.

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Abstract

Flow batteries and other electrochemical systems may contain complexes having at least one monosulfonated catechol acid ligand or salt thereof bound to a metal center as active species. The monosulfonated catechol acid ligand has the structure of formula (1). More specifically, the complex can be of formula D g Ti(L 1 )(L 2 )(L 3 ) titanium complexes, wherein D is selected from H, NH 4 + , Li + 、Na + 、K + or a counterion of any combination thereof; g is 3‑6; L 1 , L 2 and L 3 is the ligand, where L 1 , L 2 and L 3 At least one of the is a monosulfonated catechol acid ligand. A method of synthesizing such a monosulfonated catechol acid ligand may comprise providing a neat mixture of catechol and up to about 1.3 stoichiometric equivalents of sulfuric acid, and heating said neat mixture at a temperature above about 80° C. mixture to form 3,4-dihydroxybenzenesulfonic acid or its salts.

Description

[0001] Cross References to Related Applications [0002] Not applicable. [0003] Statement Regarding Federally Sponsored Research or Development [0004] Not applicable. technical field [0005] The present invention relates generally to complexes, and more particularly to flow batteries and other electrochemical systems comprising soluble complexes as active materials. Background technique [0006] Electrochemical energy storage systems such as batteries, supercapacitors, etc. have been widely used for large-scale energy storage applications. Various battery designs including flow batteries have been considered for this purpose. Compared with other types of electrochemical energy storage systems, flow batteries are advantageous, especially for large-scale applications, because of their ability to decouple power density and energy density parameters from each other. [0007] Flow batteries typically include negative and positive active materials in respective electrolyt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01M4/60H01M8/20C07F7/28
CPCH01M8/188H01M10/36Y02E60/50Y02E60/10C07C37/00H01B1/121C07F7/28H01M8/08H01M8/20
Inventor 斯科特·托马斯·汉巴格尔马修·米勒德
Owner LOCKHEED MARTIN ADVANCED ENERGY STORAGE