CN109160883B - Anthraquinone salt positive electrode material and synthetic method thereof - Google Patents

Anthraquinone salt positive electrode material and synthetic method thereof Download PDF

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CN109160883B
CN109160883B CN201711241281.XA CN201711241281A CN109160883B CN 109160883 B CN109160883 B CN 109160883B CN 201711241281 A CN201711241281 A CN 201711241281A CN 109160883 B CN109160883 B CN 109160883B
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dinitroanthraquinone
methyl
bis
mixture
dimethylethylenediamino
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CN109160883A (en
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王德安
詹世英
马美品
吴敏聪
尚永亮
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Yinlong New Energy Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • H01M4/628—Inhibitors, e.g. gassing inhibitors, corrosion inhibitors
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Abstract

The invention discloses an anthraquinone salt cathode material and a synthesis method thereof, wherein the method comprises the following steps: stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone; under ice bath, 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt is obtained; therefore, the parent structure of the anthraquinone salt cathode material is a large conjugated ring, the organic compound molecules with the conjugated structure can stably exist no matter the molecules, the intermediates or the products, and the large conjugated ring system can reduce the solubility in the electrolyte and improve the conductivity on the other hand; the two side chains change the organic phase from organic phase to water-soluble phase, thereby effectively inhibiting the dissolution of the organic anode material in the electrolyte from the source.

Description

Anthraquinone salt positive electrode material and synthetic method thereof
Technical Field
The invention belongs to the technical field of lithium ion batteries, and particularly relates to an anthraquinone salt cathode material and a synthesis method thereof.
Background
The lithium ion battery core mainly comprises a positive plate, a negative plate, a diaphragm and electrolyte. The anode material used in the lithium ion battery at present comprises inorganic materials such as lithium cobaltate anode material, lithium nickel cobaltate anode material, lithium iron phosphate anode material, lithium manganate anode material and the like.
Compared with inorganic anode materials, the organic anode materials have the advantages of high theoretical specific capacity, rich raw materials, environmental friendliness, strong structure designability, safe system and the like, are energy storage substances with wide application prospects, and although the organic anode materials have many advantages, the organic anode materials have a fatal characteristic, and can be dissolved in electrolyte, so that the cycle life of the battery is influenced.
In order to effectively inhibit the dissolution of the anode material in the electrolyte, researchers take measures such as lithium salinization and polymerization; however, the lithiation measures, although inhibiting the dissolution, additionally introduce a plurality of electrochemically inactive Li+-O-Functional group, resulting in a decrease in specific capacity, and functional group Li+-O-The electron donating effect of (2) reduces the oxidation-reduction potential of the corresponding small molecule conjugated carbonyl compound, which is not beneficial to the performance of the anode material; although the polymerization process can effectively inhibit the dissolution of organic materials, chemically inactive components are introduced to reduce the specific capacity, the low conductivity of the polymer and the large charge repulsion among monomers easily cause a slower ion/electron transmission rate, and the swelling property of the polymer and the condensed state structure of the polymer in the charging and discharging processes also have an influence on the diffusion migration rate of lithium ions.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide an anthraquinone salt cathode material and a synthesis method thereof.
The embodiment of the invention provides an anthraquinone salt cathode material which is characterized in that the structural formula is shown in the specification
Figure BDA0001489871760000021
The embodiment of the invention also provides a synthesis method of the anthraquinone salt cathode material in the scheme, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
and 2, adding dichloroethane and hydrochloric acid into the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone under ice bath, stirring, and performing rotary evaporation to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt.
In the above scheme, the step 1 specifically includes the following steps:
step 1.1, adding a solvent and N, N-dimethylethylenediamine into 1, 5-dialdehyde-4, 8-dinitroanthraquinone under the protection of argon, and heating and stirring to obtain a first mixture;
step 1.2, adding a reducing agent into the first mixture, and continuously stirring for reaction to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method until the reaction of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone and the N, N-dimethyl ethylenediamine in the second mixture is terminated, extracting and collecting an organic phase of the second mixture to obtain a 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
and step 1.4, separating and purifying by adopting a column chromatography to obtain the 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone.
In the scheme, the molar mass ratio of the 1, 5-dicarboxyl-4, 8-dinitroanthraquinone to the N, N-dimethylethylenediamine in the step 1.1 is 1: 1-5.
In the above scheme, the solvent in step 1.1 is any one of tetrahydrofuran, 1, 2-dichloroethane and 1, 4-dioxane.
In the scheme, the stirring temperature in the step 1.1 is 30-80 ℃, and the stirring time is 0.2-5 hours; the reaction time of the step 1.2 is 5-12 h.
In the above scheme, the reducing agent in step 1.2 is any one of potassium borohydride, lithium aluminum hydride, and sodium triacetoxyborohydride.
In the above scheme, the step 1.4 specifically includes: and (3) spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading a sample, using 300-mesh 400-mesh silica gel powder as a packed column, passing through the column by using an eluent, collecting a target compound, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
In the scheme, the eluent and the proportion thereof are that ethyl acetate, isopropanol and 25% ammonia water are used, and the proportion is 1-8: 1-6: 0.1-1.5.
In the scheme, the molar ratio of the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone to the hydrochloric acid is 2-5: 1.
In the scheme, the stirring time in the step 2 is 1-3 h.
Compared with the prior art, the invention provides an anthraquinone salt cathode material and a synthesis method thereof, and the method comprises the following steps: stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone; under ice bath, adding dichloroethane and hydrochloric acid into the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone, stirring, and performing rotary evaporation to obtain 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt; therefore, the parent structure of the anthraquinone salt positive electrode material 1, 5-di (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone salt is a large conjugated ring, and organic compound molecules with conjugated structures can stably exist no matter the molecules or intermediates or products, so that the large conjugated system can reduce the solubility in electrolyte and improve the conductivity; the purpose of the two side chains is to change the organic phase from organic phase to water-soluble phase, thereby effectively inhibiting the dissolution of the organic anode material in the electrolyte from the source; and two nitro groups participate in electrochemical reaction, so that the cathode material has the advantages of stable structure, high theoretical specific capacity and safe system.
Drawings
Fig. 1 is a structural diagram of 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt in an anthraquinone salt cathode material and a synthesis method thereof provided by an embodiment of the present invention;
fig. 2 is a synthesis route diagram of an anthraquinone salt cathode material and a synthesis method thereof provided by an embodiment of the present invention;
fig. 3 is an electrochemical reaction diagram of 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt participating in the anthraquinone salt cathode material and the synthesis method thereof provided by the embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides an anthraquinone salt cathode material, and the structure diagram of the anthraquinone salt cathode material is shown in figure 1.
The embodiment of the invention also provides a synthesis method of the anthraquinone salt cathode material, wherein a synthesis route diagram of the anthraquinone salt cathode material is shown in fig. 2, and the synthesis method comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, adding a solvent and N, N-dimethylethylenediamine into 1, 5-dialdehyde-4, 8-dinitroanthraquinone under the protection of argon, and stirring for 0.2-5 h at the temperature of 30-80 ℃ to obtain a first mixture;
wherein the molar mass ratio of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone to the N, N-dimethylethylenediamine is 1: 1-5.
Wherein the solvent is any one of tetrahydrofuran, 1, 2-dichloroethane and 1, 4-dioxane
Step 1.2, adding a reducing agent into the first mixture, and continuously reacting for 5-12 hours to obtain a second mixture;
wherein the reducing agent is any one of potassium borohydride, lithium aluminum hydride and sodium triacetoxyborohydride.
Step 1.3, monitoring the second mixture by adopting a TLC method until the reaction of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone and the N, N-dimethyl ethylenediamine in the second mixture is terminated, extracting and collecting an organic phase of the second mixture to obtain a 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
the TLC method is a thin layer chromatography, and particularly relates to a method for identifying a medicine, checking impurities or measuring the content by coating a proper stationary phase on a glass plate, plastic or aluminum substrate to form a uniform thin layer, and comparing a specific shift value (Rf) with a chromatogram obtained by a proper reference substance according to the same method after spotting and developing; thin layer chromatography is an important experimental technique for rapid separation and qualitative analysis of small amounts of substances, and is also used to follow the progress of the reaction.
The method specifically comprises the following steps: monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate is 5:1, eluent is ethyl acetate, isopropanol and 25% ammonia water are 1-8: 1-6: 0.1-1.5, the reaction is monitored until the reaction of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone and the N, N-dimethyl ethylenediamine is terminated, and 100mL of dichloromethane and 40mL of saturated 40mL of NaHCO are respectively added into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
and step 1.4, separating and purifying by adopting a column chromatography to obtain the 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone.
The method specifically comprises the following steps: and (3) spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading a sample, using 300-mesh 400-mesh silica gel powder as a packed column, passing through the column by using an eluent, collecting a target compound, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
Wherein the eluent and the proportion thereof are 1-8: 1-6: 0.1-1.5 of ethyl acetate, isopropanol and 25% ammonia water, and the eluent proportion is changed according to the monitoring of TLC.
And 2, adding dichloroethane and hydrochloric acid into the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone under ice bath, stirring, and performing rotary evaporation to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt.
Wherein the molar ratio of the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone to the hydrochloric acid is 2-5: 1.
Wherein the stirring time in the step 2 is 1-3 h.
In the anthraquinone salt cathode material and the synthesis method thereof provided by the embodiment of the invention, an electrochemical reaction diagram of 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone salt participates is shown in fig. 3, as can be seen from the diagram, the parent structure of 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone salt is a large conjugated ring, and organic compound molecules with conjugated structures can stably exist no matter the molecules or the intermediates or the products, besides, the large conjugated system can reduce the solubility in electrolyte on one hand and improve the conductivity on the other hand; the purpose of the two side chains is to change the organic phase from organic phase to water-soluble phase, thereby effectively inhibiting the dissolution of the organic anode material in the electrolyte from the source; and two nitro groups participate in the electrochemical reaction.
The process for preparing the lithium ion battery by adopting the anthraquinone salt cathode material provided by the invention comprises the following steps: the positive electrode material 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt is mixed with an appropriate amount of active material and solvent and acetylene black to prepare a positive electrode material, a carbon felt is used to prevent direct reaction between the positive electrode active material and lithium metal, propylene carbonate is used as a main solvent as an electrolyte, a porous polypropylene sheet is used as a separator, and lithium is used as a negative electrode.
Compared with inorganic anode materials, the organic anode materials have the advantages of high theoretical specific capacity, rich raw materials, environmental friendliness, strong structure designability, safe system and the like, are energy storage substances with wide application prospects, and although the organic anode materials have many advantages, the organic anode materials have a fatal characteristic, and can be dissolved in electrolyte, so that the cycle life of the battery is influenced.
Example 1
The embodiment 1 of the invention provides a method for synthesizing an anthraquinone salt cathode material, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of tetrahydrofuran and 2.04mmol of N, N-dimethylethylenediamine, and stirring at 50 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding potassium borohydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia 6:3:0.7, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 6:3:0.7, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 6mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 2
The embodiment 2 of the invention provides a synthetic method of an anthraquinone salt cathode material, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of tetrahydrofuran and 4.04mmol of N, N-dimethylethylenediamine, and stirring at 50 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding potassium borohydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia 6:3:0.7, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 6:3:0.7, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 4mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL of hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 3
The embodiment 3 of the invention provides a method for synthesizing an anthraquinone salt cathode material, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of tetrahydrofuran and 6.04mmol of N, N-dimethylethylenediamine, and stirring at 50 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding potassium borohydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, applying TLC method to the secondMonitoring the mixture, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia 6:3:0.7, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 6:3:0.7, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 8mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 2h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 4
The embodiment 4 of the invention provides a method for synthesizing an anthraquinone salt cathode material, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of tetrahydrofuran and 8.04mmol of N, N-dimethylethylenediamine, and stirring at 50 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding potassium borohydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia 6:3:0.7, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 6:3:0.7, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 10mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 5
Embodiment 5 of the present invention provides a method for synthesizing an anthraquinone salt positive electrode material, which comprises:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of tetrahydrofuran and 10.04mmol of N, N-dimethylethylenediamine, and stirring at 50 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding potassium borohydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia 6:3:0.7, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 6:3:0.7, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 10mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 3h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 6
Embodiment 6 of the present invention provides a method for synthesizing an anthraquinone salt positive electrode material, which comprises:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of 1, 2-dichloroethane and 4.04mmol of N, N-dimethylethylenediamine, and stirring at 40 ℃ for 2.5 hours to obtain a first mixture;
step 1.2, adding lithium aluminum hydride into the first mixture, and continuing to react for 5 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia water 5:4:0.1, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol and 25% ammonia water, namely 5:4:0.1, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 6mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 7
Embodiment 7 of the present invention provides a method for synthesizing an anthraquinone salt positive electrode material, which comprises:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of 1, 2-dichloroethane and 4.04mmol of N, N-dimethylethylenediamine, and stirring at 30 ℃ for 5 hours to obtain a first mixture;
step 1.2, adding lithium aluminum hydride into the first mixture, and continuing to react for 8 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia water 5:4:0.1, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting the organic phase, and adding water to the aqueous phaseAdding 2mL of ammonia water, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol and 25% ammonia water, namely 5:4:0.1, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 6mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 8
The embodiment 8 of the invention provides a synthetic method of an anthraquinone salt cathode material, which comprises the following steps:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of 1, 4-dioxane and 4.04mmol of N, N-dimethylethylenediamine, and stirring at 80 ℃ for 0.2h to obtain a first mixture;
step 1.2, adding sodium triacetoxyborohydride into the first mixture, and continuing to react for 10 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by TLC, using unfoldingDeveloping with a developing agent, and eluting with an eluent, wherein the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia water 9:2:0.4, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 9:2:0.4, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 6mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
Example 9
Embodiment 9 of the present invention provides a method for synthesizing an anthraquinone salt positive electrode material, which comprises:
step 1, stirring 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethylethylenediamine for reaction to obtain 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone;
the step 1 specifically comprises the following steps:
step 1.1, under the protection of argon, adding 2.0mmol of 1, 5-dialdehyde-4, 8-dinitroanthraquinone into a 25mL round-bottom flask, fixing the flask on an iron support, sequentially adding 10mL of 1, 4-dioxane and 4.04mmol of N, N-dimethylethylenediamine, and stirring at 60 ℃ for 0.5h to obtain a first mixture;
step 1.2, adding sodium triacetoxyborohydride into the first mixture, and continuing to react for 12 hours to obtain a second mixture;
step 1.3, monitoring the second mixture by adopting a TLC method, developing by adopting a developing agent, and eluting by adopting an eluent, wherein the ratio of the developing agent is petroleum ether: ethyl acetate 5:1, eluent ethyl acetate isopropanol 25% ammonia water 9:2:0.4, monitoring reaction termination, namely, after raw materials 1, 5-dialdehyde-4, 8-dinitroanthraquinone and N, N-dimethyl ethylenediamine are completely terminated, respectively adding 100mL of dichloromethane and 40mL of saturated NaHCO into the reaction system3Extracting the aqueous solution, collecting an organic phase, adding 2mL of ammonia water into the aqueous phase, extracting for 3 times by using dichloromethane, and collecting to obtain a 1, 5-di (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 1.4, spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator to obtain a white crude compound, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading the sample, using 300-mesh 400-mesh silica gel powder as a packed column, using ethyl acetate, isopropanol, 25% ammonia water, 9:2:0.4, as an eluent to pass through the column, changing the eluent ratio according to TLC monitoring, collecting a target compound according to TLC monitoring, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
And 2, adding 6mmol of 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone into a 10mL round-bottom flask, fixing the flask on an iron support, adding dichloroethane and 2mL hydrochloric acid under ice bath, stirring for 1h, and spin-drying the solvent by using a rotary evaporator to obtain the 1, 5-bis (N, N-dimethyl ethylenediamine) methyl-4, 8-dinitroanthraquinone salt.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention.

Claims (6)

1. The anthraquinone salt positive electrode material is characterized in that the structural formula is shown in the specification
Figure FDA0003143693930000011
2. A method for synthesizing an anthraquinone salt positive electrode material as claimed in claim 1, characterized in that: which comprises the following steps:
step 1, adding a solvent and N, N-dimethylethylenediamine into 1, 5-dialdehyde-4, 8-dinitroanthraquinone under the protection of argon, and heating and stirring to obtain a first mixture; wherein the molar mass ratio of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone to the N, N-dimethylethylenediamine is 1: 1-5;
step 2, adding a reducing agent into the first mixture, and continuously stirring for reaction to obtain a second mixture; wherein the reducing agent is any one of potassium borohydride, lithium aluminum hydride and sodium triacetoxyborohydride;
step 3, monitoring the second mixture by adopting a TLC method until the reaction of the 1, 5-dialdehyde-4, 8-dinitroanthraquinone and the N, N-dimethylethylenediamine in the second mixture is terminated, extracting and collecting an organic phase of the second mixture to obtain a 1, 5-bis (N, N-dimethylethylenediamine) methyl-4, 8-dinitroanthraquinone organic phase;
step 4, separating and purifying by adopting a column chromatography to obtain 1, 5-di (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone;
and 5, adding dichloroethane and hydrochloric acid into the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone under ice bath, stirring, and performing rotary evaporation to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone salt.
3. The method for synthesizing the anthraquinone salt cathode material as claimed in claim 2, wherein the solvent in the step 1 is any one of tetrahydrofuran, 1, 2-dichloroethane and 1, 4-dioxane.
4. The method for synthesizing the anthraquinone salt cathode material as claimed in claim 3, wherein the step 4 specifically comprises: and (3) spin-drying the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone organic phase by using a rotary evaporator, adding dichloroethane and 200-mesh silica gel powder to mix, spin-drying, loading a sample, using 300-mesh 400-mesh silica gel powder as a packed column, passing through the column by using an eluent, collecting a target compound, spin-drying, and finally pumping by using a diaphragm pump to obtain the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone.
5. The method for synthesizing the anthraquinone salt cathode material as claimed in claim 4, wherein the ratio of the eluent to the ethyl acetate to the isopropanol to the 25% ammonia water is 1-8: 1-6: 0.1-1.5.
6. A synthesis method of an anthraquinone salt cathode material according to any one of claims 2 to 5, wherein the molar ratio of the 1, 5-bis (N, N-dimethylethylenediamino) methyl-4, 8-dinitroanthraquinone to hydrochloric acid is 2-5: 1.
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