CN108598481A - A kind of organic electrode materials, preparation method and applications - Google Patents
A kind of organic electrode materials, preparation method and applications Download PDFInfo
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- CN108598481A CN108598481A CN201810350483.6A CN201810350483A CN108598481A CN 108598481 A CN108598481 A CN 108598481A CN 201810350483 A CN201810350483 A CN 201810350483A CN 108598481 A CN108598481 A CN 108598481A
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- electrode materials
- organic electrode
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- phenylenediamine
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- 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
- H01M4/602—Polymers
- H01M4/606—Polymers containing aromatic main chain polymers
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- 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
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- 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
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Abstract
The invention belongs to new energy fields, and in particular to a kind of organic electrode materials, preparation method and applications.The invention discloses a kind of preparation methods of organic electrode materials, include the following steps：Under the effect of the catalyst, p-phenylenediamine and crosslinking agent are dissolved in solvent and Friedel-Crafts reaction occurs, obtain organic electrode materials.Preparation method provided by the invention is simple for process, it is suitble to produce in enormous quantities, the organic electrode materials made from the preparation method are the crosslinking p-phenylenediamine with reticular structure, greatly improve cyclical stability and chemical property of the organic material when being used as lithium ion battery negative material.
Description
Technical field
The invention belongs to field of new energy technologies, and in particular to a kind of organic electrode materials, preparation method and applications.
Background technology
Because having high output voltage, excellent energy and the advantages such as power density and long-acting cyclical stability, lithium
Ion battery has been widely used for portable electronic equipment field.However, fast with accumulation power supply and electric vehicle
Exhibition and the raising of Public environmental attitude are hailed, more stringent requirements are proposed to the performance of lithium ion battery, therefore, develops high energy
The lithium ion battery material of metric density becomes one of the emphasis of Recent study.
During lithium ion battery develops, conventional lithium ion battery inorganic material is steady due to theoretical specific capacity and structure
Qualitative to be limited, energy density is difficult to further increase.In recent years, scientist has found that compared with inorganic material, organic material has
Theoretical specific capacity height, abundant raw material, it is environmental-friendly, structure designability is strong and system is safe the advantages that, be it is a kind of have it is extensive
The ergastic substances of application prospect.This makes more and more researchers begin to focus on organic electrode materials.However, in addition to
On except the satisfactory advantage that is showed, the still many technical barriers for needing to overcome of organic electrode materials, for example,
In charge and discharge process, electrode material is easily dissolved in electrolyte for it, causes the loss of great irreversible capacity, and synthesize
Complex process, since excessively cumbersome step causes production cost excessively high and the safety reduction of material production.More than being based on
These problems, organic material are temporarily difficult to apply to industrialized production and business application as the electrode material of lithium ion battery
In.Therefore, it obtains a kind of haveing excellent performance and being that current researchers compel to be essential with the organic electrode materials of good stability
Technical problems to be solved.
Invention content
In view of this, the present invention provides a kind of organic electrode materials, preparation method and applications, solves the prior art
Middle organic electrode materials capacitance loss is serious and since preparation process complexity causes cost is excessively high and production security is low to ask
Topic.The preparation method of organic electrode materials provided by the invention, it is simple for process, it is suitble to produce in enormous quantities, by the preparation method system
The organic electrode materials p-phenylenediamine obtained has two-dimensional network structure, greatly improves organic material as lithium ion battery
Cyclical stability and chemical property when negative material uses.
The present invention provides a kind of preparation methods of organic electrode materials, include the following steps：Under the effect of the catalyst,
P-phenylenediamine and crosslinking agent are dissolved in solvent and Friedel-Crafts reaction occurs, obtains organic electrode materials.
It is furthermore preferred that the solvent is dichloroethanes.
Preferably, the molar ratio of the p-phenylenediamine and the crosslinking agent is 1:1~1:8.
It is furthermore preferred that the molar ratio is 1:1、1:2、1:4、1:5 or 1:8.
Preferably, the crosslinking agent be selected from dimethoxymethane, dimethoxy-ethane, dimethoxy propane, dichloromethane,
It is one or more in dichloroethanes and dichloropropane.
It is furthermore preferred that the crosslinking agent is dimethoxymethane.
Preferably, the catalyst is in anhydrous Aluminum chloride, anhydrous ferric chloride, anhydrous stannic chloride and anhydrous zinc chloride
It is one or more.
It is furthermore preferred that the catalyst is anhydrous Aluminum chloride.
Preferably, the Friedel-Crafts reaction specifically includes following steps：
It obtains described having with catalyst and heating water bath are added in the mixed solution of the p-phenylenediamine in the crosslinking agent
Machine electrode material.
Preferably, the temperature of the heating water bath is 40~120 DEG C.It is furthermore preferred that the temperature of the heating water bath is 60
DEG C, 80 DEG C, 100 DEG C or 120 DEG C.
Preferably, the time of the heating water bath is 2~20h.
It is furthermore preferred that the time of the heating water bath is 10h.
Preferably, further comprising the steps of：
Heating water bath obtains being cleaned, filtered and being dried after the organic electrode materials.
It is furthermore preferred that the number of the cleaning is 3 times.
It is furthermore preferred that the temperature of the drying is 70 DEG C, the time of the drying is for 24 hours.
The present invention also provides a kind of organic electrode materials, are made by the preparation method of above-mentioned organic electrode materials.
A kind of application the present invention also provides organic electrode materials as lithium ion battery negative material.
A kind of organic electrode materials provided by the invention are connected p-phenylenediamine by methylene-crosslinked bridge, and being formed has greatly
The cross-linked structure of molecular weight reduces its solubility in the electrolytic solution, and the phenyl ring on p-phenylenediamine and amido function
Group can effectively store lithium ion, further reduce the loss of battery irreversible capacity, improve the stabilization of organic material
Property, and cycle characteristics can be enhanced, specific capacity is high to make the organic electrode materials have, and cycle performance is excellent and high rate performance
Good feature.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention without having to pay creative labor, may be used also for those of ordinary skill in the art
To obtain other attached drawings according to these attached drawings.
Fig. 1 is the principle of the present invention figure；
Fig. 2 is the infrared spectrogram of p-phenylenediamine and crosslinking p-phenylenediamine in the embodiment of the present invention 1；
Fig. 3 is the XPS collection of illustrative plates of crosslinking p-phenylenediamine prepared by the embodiment of the present invention 1；
Fig. 4 is the cyclic voltammetry curve of crosslinking p-phenylenediamine prepared by the embodiment of the present invention 1；
Fig. 5 is the cyclic curve figure that button cell prepared by the embodiment of the present invention 2 recycles 100 circles at 200mA g-1；
Fig. 6 is the button cell of the preparation of the embodiment of the present invention 2 in 1000mA g-1The cyclic curve figure of 1000 circle of lower cycle；
Fig. 7 is the high rate performance figure of button cell prepared by the embodiment of the present invention 2；
Fig. 8 is the impedance diagram of button cell prepared by the embodiment of the present invention 2.
Specific implementation mode
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
The every other embodiment that technical staff is obtained without making creative work belongs to the model that the present invention protects
It encloses.
In order to which the present invention is described in more detail, with reference to embodiment to a kind of organic electrode materials provided by the invention, system
Preparation Method and its application are specifically described.
Embodiment 1
It is 1 in molar ratio:5 weigh p-phenylenediamine and crosslinking agent dimethoxymethane, by two chloroethene of p-phenylenediamine and solvent
Alkane is added three-neck flask and stirs, and so that p-phenylenediamine is completely dissolved in dichloroethanes, and crosslinking agent dimethoxymethane is added
Enter into three-neck flask, the heating water bath at 80 DEG C, then by the anhydrous AlCl of catalyst3It is added portionwise in reaction solution, 80
Reactant is obtained after reacting 10h at DEG C.
Reactant is cleaned 3 times with deionized water and is filtered, finally, cleaned reactant is positioned over to 70 DEG C of vacuum
It is dry in drying box to obtain crosslinking p-phenylenediamine for 24 hours.
Fig. 1 is that the principle of the present invention figure passes through Friedel-Crafts reaction, methylene-CH as shown in Figure 12It will be right as cross-bridge
Phenylenediamine is bridged to form cross-linked structure, can inhibit the dissolubility of electrode material in the electrolytic solution well, improves
The stability of structure.
Fig. 2 is the infrared spectrogram that p-phenylenediamine is crosslinked in p-phenylenediamine and the present embodiment, in fig. 2, by with to benzene
Diamines compares, and crosslinking p-phenylenediamine is in 2923cm-1There is-CH in place2Stretching vibration peak, Fig. 3 are crosslinking manufactured in the present embodiment
The XPS collection of illustrative plates of p-phenylenediamine, there is 3 C1s peak values, respectively 287.0eV, 285.3eV and 285.0eV in Fig. 3, and 285.3 Hes
285.0eV belongs to phenyl ring and-CH2Combination energy, both of which be constitute crosslinking p-phenylenediamine skeleton constituent, it was demonstrated that
Above-described embodiment successfully prepares crosslinking p-phenylenediamine.
Fig. 4 is the cyclic voltammetry curve of crosslinking p-phenylenediamine manufactured in the present embodiment, and as shown in Figure 4, the curve is in 2.5V
There is an oxidation peak, a reduction peak occur in 1.6V, illustrates that the deintercalation reaction of lithium ion can occur for the crosslinking p-phenylenediamine,
Show that the crosslinking p-phenylenediamine prepared can carry out reversible charge and discharge process.
Embodiment 2
The crosslinking p-phenylenediamine and conductive black and polyvinylidene fluoride (PVDF) that embodiment 1 is prepared are in mass ratio
50:40:10 mixed grindings are uniform, and suitable N-Methyl pyrrolidone (NMP) is added and is tuned into slurry, above-mentioned slurry is uniformly smeared
On copper foil, after 50 DEG C are dried in vacuo 12h, roll-in obtains crosslinking p-phenylenediamine pole piece.
The crosslinking p-phenylenediamine pole piece of making is struck outDisk, withGold
It is anode to belong to lithium piece, and for Celgard2400 as diaphragm, it is 1 that electrolyte lithium hexafluoro phosphate, which is dissolved in volume ratio,:1:1 carbonic acid two
The electrolyte of 1mol/L is made, in the glove box full of argon gas in the mixed solution of methyl esters, ethylene carbonate and methyl ethyl carbonate
It is assembled into crosslinking p-phenylenediamine-lithium button cell.Using the battery test system of LAND-CT2001A in 0~3V charging/discharging voltages
The middle above-mentioned button cell of test.
Fig. 5 is the cyclic curve figure that button cell manufactured in the present embodiment recycles 100 circles at 200mA g-1, can by Fig. 5
Know, 200mA g-1Electric current under its discharge for the first time and charging capacity be respectively 1106.72mAh g-1With 542.00mAh g-1, fill
Discharging efficiency is 48.97%, and recycles the later capacity of 160 circles and still remain 679.11mAh g-1,.Fig. 6 is this implementation
Button cell prepared by example is in 1000mA g-1The cyclic curve figure of 1000 circle of lower cycle, even it will be appreciated from fig. 6 that in 1000mA
g-1High current density under 1000 circle of cycle, capacity still maintains 482.77mAh g-1,.Fig. 7 is manufactured in the present embodiment
The high rate performance figure of button cell, as shown in Figure 7, in 100mAh g-1、200mAh g-1、500mAh g-1、1000mAh g-1、
2000mAh g-1、100mAh g-1After being recycled under multiple and different current densities, capacity can be still restored to
1325.31mAh g-1, embody that the material circulation has good stability, capacity retention ratio is high and high rate performance is excellent.Fig. 8 is this reality
The impedance diagram for applying the button cell of example preparation accelerates lithium ion and exists as shown in figure 8, the resistance of the button cell is only 185 Ω
Diffusion velocity in electrode material and electrolyte significantly improves the charge-discharge performance of lithium ion battery.
Embodiment 3~7
Difference lies in the molar ratios of p-phenylenediamine and dimethoxymethane for embodiment 3~7 and embodiment 1 and embodiment 2
Difference, specific performance are as shown in table 1：
Organic electrode materials prepared by 1 embodiment 3~7 of table are in 200mA g-1Charge-discharge performance under constant current
As shown in Table 1, when the molar ratio of p-phenylenediamine and dimethoxymethane is 1:When 5, in 200mA g-1Electric current under
It discharges for the first time and charging capacity may be up to 1106.72mAh g-1With 542.00mAh g-1, efficiency for charge-discharge 48.97%, by
Cross-linking reaction can be carried out with four methylene in a p-phenylenediamine, methylene is slightly excessive can to make reaction more abundant, and
When being reacted using excessive crosslinking agent, a small amount of phenyl ring reflecting point corresponds to a large amount of crosslinking agent, easily causes only part
Crosslinking endo-methylene group is reacted with phenyl ring so that the efficiency of the yield decline and lithium ion battery that are crosslinked p-phenylenediamine is not
Height, therefore when using 1:When 5 molar ratio, kept with higher capacity with lithium ion battery prepared by the crosslinking p-phenylenediamine
The cycle performance of rate and stabilization.
Embodiment 8~12
Difference lies in organic electrode material is prepared under different hydrothermal temperatures for embodiment 8~12 and embodiment 1 and embodiment 2
Material, specific performance are as shown in table 2：
Organic electrode materials prepared by 2 embodiment 8~12 of table are in 200mA g-1Constant current charge-discharge performance
As shown in Table 2, temperature is higher, and reaction rate is faster, but temperature is excessively high, and can cause cannot be fully between reactant
It is reacted, therefore when 100 DEG C of bath temperature, in 200mA g-1Electric current under, efficiency for charge-discharge 50.05%, with this
P-phenylenediamine organic electrode materials are crosslinked as negative electrode of lithium ion battery in use, its capacity retention ratio highest, cycle performance is most
Stablize.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of organic electrode materials, which is characterized in that include the following steps：Under the effect of the catalyst, will
P-phenylenediamine is dissolved in solvent and Friedel-Crafts reaction occurs with crosslinking agent, obtains organic electrode materials.
2. the preparation method of organic electrode materials according to claim 1, which is characterized in that the p-phenylenediamine with it is described
The molar ratio of crosslinking agent is 1:1~1:8.
3. the preparation method of organic electrode materials according to claim 1, which is characterized in that the crosslinking agent is selected from diformazan
It is one or more in oxygroup methane, dimethoxy-ethane, dimethoxy propane, dichloromethane, dichloroethanes and dichloropropane.
4. a kind of preparation method of organic electrode materials according to claim 1, which is characterized in that the catalyst is selected from
It is one or more in anhydrous Aluminum chloride, anhydrous ferric chloride, anhydrous stannic chloride and anhydrous zinc chloride.
5. the preparation method of organic electrode materials according to claim 1, which is characterized in that the Friedel-Crafts reaction specifically wraps
Include following steps：
The crosslinking agent be added the catalyst in the mixed solution of the p-phenylenediamine and heating water bath obtains described has
Machine electrode material.
6. the preparation method of organic electrode materials according to claim 5, which is characterized in that the temperature of the heating water bath
It is 40~120 DEG C.
7. the preparation method of organic electrode materials according to claim 5, which is characterized in that the time of the heating water bath
For 2~20h.
8. the preparation method of organic electrode materials according to claim 5, which is characterized in that further comprising the steps of：
Heating water bath obtains being cleaned, filtered and being dried after the organic electrode materials.
9. a kind of organic electrode materials, by the preparation method system of the organic electrode materials described in claim 1~8 any one
.
10. organic electrode made from a kind of preparation method of organic electrode materials according to claim 1~8 any one
Application of a kind of organic electrode materials in preparing lithium ion battery negative material described in material or claim 9.
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| CN201810350483.6A CN108598481B (en) | 2018-04-18 | 2018-04-18 | Organic electrode material, preparation method and application thereof |
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| CN102763249A (en) * | 2009-10-27 | 2012-10-31 | 凯密特尔有限责任公司 | Nitrogen-containing hydride anodes and electrochemical elements containing nitrogen-containing hydride anodes |
| CN103910823A (en) * | 2014-03-21 | 2014-07-09 | 中南大学 | Preparation method and application of polar group-modified pendent double bond post-crosslinked polydivinylbenzene resin |
| WO2015091855A1 (en) * | 2013-12-18 | 2015-06-25 | Compagnie Generale Des Etablissements Michelin | Modified diene elastomer and rubber composition containing same |
| CN105597822A (en) * | 2015-12-29 | 2016-05-25 | 华东师范大学 | Organic multi-pore supported catalyst as well as synthesis method and application thereof |
| CN106910895A (en) * | 2017-04-06 | 2017-06-30 | 广东工业大学 | A kind of organic electrode materials and its preparation method and application |
| CN107204465A (en) * | 2017-05-23 | 2017-09-26 | 广东工业大学 | A kind of preparation method of high polymer material and a kind of lithium ion battery |
| CN107658456A (en) * | 2017-09-27 | 2018-02-02 | 杨小旭 | The method and lithium battery of lithium battery energy storage battery material are prepared using silicon chip cutting waste material |
-
2018
- 2018-04-18 CN CN201810350483.6A patent/CN108598481B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102763249A (en) * | 2009-10-27 | 2012-10-31 | 凯密特尔有限责任公司 | Nitrogen-containing hydride anodes and electrochemical elements containing nitrogen-containing hydride anodes |
| WO2015091855A1 (en) * | 2013-12-18 | 2015-06-25 | Compagnie Generale Des Etablissements Michelin | Modified diene elastomer and rubber composition containing same |
| CN103910823A (en) * | 2014-03-21 | 2014-07-09 | 中南大学 | Preparation method and application of polar group-modified pendent double bond post-crosslinked polydivinylbenzene resin |
| CN105597822A (en) * | 2015-12-29 | 2016-05-25 | 华东师范大学 | Organic multi-pore supported catalyst as well as synthesis method and application thereof |
| CN106910895A (en) * | 2017-04-06 | 2017-06-30 | 广东工业大学 | A kind of organic electrode materials and its preparation method and application |
| CN107204465A (en) * | 2017-05-23 | 2017-09-26 | 广东工业大学 | A kind of preparation method of high polymer material and a kind of lithium ion battery |
| CN107658456A (en) * | 2017-09-27 | 2018-02-02 | 杨小旭 | The method and lithium battery of lithium battery energy storage battery material are prepared using silicon chip cutting waste material |
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