CN1690694A - Reagent for lithiation reaction, preparation method and use thereof - Google Patents
Reagent for lithiation reaction, preparation method and use thereof Download PDFInfo
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- CN1690694A CN1690694A CN 200410037394 CN200410037394A CN1690694A CN 1690694 A CN1690694 A CN 1690694A CN 200410037394 CN200410037394 CN 200410037394 CN 200410037394 A CN200410037394 A CN 200410037394A CN 1690694 A CN1690694 A CN 1690694A
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Abstract
The present invention relates to reagent for lithiation reaction. On the condition of room temperature and inert atmosphere, mix lithium, organic compound contained benzene ring and ethers compound, solve and obtain solution; wherein, lithium 0.01~10M/L, organic compound contained benzene ring 0.01~5M/L, other is solvent; the general form is R<SUB>1</SUB>OR<SUB>2</SUB> or ethers compound with R<SUB>1</SUB>OR<SUB>2</SUB>OR<SUB>3</SUB>; wherein, R<SUB>1</SUB>, R<SUB>2</SUB>, R<SUB>3</SUB> are alkyl of C<SUB>1</SUB>-C<SUB>5</SUB>; organic compound contained benzene ring aforementioned comprises biphenyl or condensed-nuclei aromatics, optimization of biphenyl and its derivant, terphenyl, quaohenyl, naphthalin, anthracene, and phenanthrene. The lithiation reagent is easy for preparation, storage, cheap of cost and high activity; not only for common reaction, but also can be used to preprocess of electrode material to store lithium cell or prepare new inorganic compound contained lithium; has wide scope of usage.
Description
Technical field
The present invention relates to a kind of reagent that is used for lithiation, specifically relate to a kind of reagent that is used for lithiation that can carry out lithiumation the inorganic reaction thing, and its production and use.
Background technology
In chemical reaction, lithiation is meant lithium is incorporated into class reaction in the reactant.The reagent of widely used participation lithiation is generally the cyclohexane solution of butyl lithium, or the anhydrous acetonitrile of LiI.In this solution, the chemical state of lithium is an ionic state, this reactive activity with whether can generate stable butylation compound or can the I ionic oxide formation is not relevant.Lithiation reagent can extensively be used in the addition reaction to unsaturated link, comprises the addition reaction of the two keys of C-C, with the addition reaction of aldehyde ketone, and the preparation of reactive intermediate, with the reaction of metal halide, the catalyzer of olefinic polyreaction etc.But for the inorganic reaction thing, the lithiumation of aforementioned two kinds of lithiation reagent is limited in one's ability, and price is very expensive.
The lithium battery that can charge and discharge comprises with lithium metal as negative pole, do not contain lithium positive electrode lithium secondary battery and with graphite as negative pole, contain the lithium ion battery of the transistion metal compound of lithium as positive pole.The lithium source is a negative pole in the lithium secondary battery, and positive electrode is generally V
2O
5, Cr
3O
8Deng, its lithium storage content is greater than 250mAh/g.The energy density of this battery is higher, but owing to use lithium metal, the security of battery is lower, does not have practicability at present.Negative material is the graphite-like material with carbon element in the lithium ion battery, and positive electrode is mainly LiCoO
2, LiNiO
2, LiMn
2O
4, LiFePO
4Deng, these positive electrodes are as the lithium source in the lithium ion battery, and its lithium storage content is 110-160mAh/g.
Along with electronics, information, the energy, the develop rapidly in national defence field, more and more higher to the demand of chargeable lithium battery energy density, therefore need the lithium storage materials of research high power capacity, or improve the chemical property of present material.The aforesaid V that in lithium secondary battery, uses
2O
5, Cr
3O
8Deng positive electrode, in charge and discharge process, can form Li
2V
2O
5, Li
4Cr
3O
8Phase, if can be directly by synthetic these materials of the method for chemical lithiumation, as lithium source class positive electrode, then can provide the positive electrode that can in lithium ion battery, use of high power capacity with it.Yet, up to now, yet there are no the report of this respect.
As the negative material of lithium ion battery, that uses at present is mainly the graphite-like negative material.This material is 92～95% at the coulombic efficiency in first week, and lithium storage content is 300～360mAh/g.Discovering of recent years, hard carbon, silicon, transistion metal compound, alloy type oxide, the negative material that also can be used as lithium ion battery uses, its capacity all is higher than graphite, but first all coulombic efficiencies of these materials generally are lower than 75%, when using in lithium ion battery, first all irreversible capacitance loss will be compensated by the positive electrode as the lithium source, so the total energy density of battery can't be competed as the lithium ion battery of negative pole with use graphite.Causing the low main cause of these material first all coulombic efficiencies is on the surface or the inner reaction that irreversible and lithium take place, the decomposition of for example formation of passivating film, or oxide.Add in the material if will participate in the lithium of the loss of these reactions in advance, then can improve first all coulombic efficiencies of material greatly, these materials can be used in lithium ion battery.But at present, also do not find the efficient ways of replenishing lithium in advance.
In sum, in order to improve the performance of lithium secondary battery and lithium ion battery, need be with V in lithium secondary battery
2O
5, Cr
3O
8Deng the prior lithiumation of positive electrode, form Li
2V
2O
5, Li
4Cr
3O
8Phase; Or in advance lithium is incorporated in the negative material of lithium ion battery and reduces irreversible capacity loss.But the lithiumation of existing lithiation reagent is limited in one's ability, can't prepare as Li
2V
2O
5, Li
4Cr
3O
8Material, can not with the reaction of the negative material of lithium ion battery, and cost an arm and a leg.
Summary of the invention
The objective of the invention is to overcome existing lithiation reagent and be not suitable for inorganic reaction, lithiumation is limited in one's ability, and the very expensive defective of price, thereby provide a kind of and be applicable to all kinds of lithiations, and the reactivity height, prepare easily, be easy to preserve, the cheap reagent that is used for lithiation.
The objective of the invention is to realize by the following technical solutions:
The reagent that is used for lithiation provided by the invention, it is under the room temperature inert atmosphere, with the solution that makes behind lithium metal, the organic compound that contains phenyl ring and the ether compound mixed dissolution, wherein:
Lithium 0.01～10M/l;
Organic compound 0.01～the 5M/l that contains phenyl ring;
Surplus is a solvent, and it is R for general formula
1OR
2Or R
1OR
2OR
3Ether compound, R wherein
1, R
2, R
3Be C
1～C
5Alkyl;
The described organic compound that contains phenyl ring comprises biphenyl class or condensed-nuclei aromatics compounds, preferred biphenyl and derivant, terphenyl, quaterphenyl, naphthalene, anthracene or phenanthrene;
Described general formula is R
1OR
2Ether compound comprise dimethyl ether, diethyl ether, ethyl methyl ether, first amyl ether;
Described general formula is R
1OR
2OR
3Ether compound comprise glycol dimethyl ether, butyl cellosolve, dibutyl ethylene glycol ether, ethylene glycol diethyl ether.
The preparation process of the above-mentioned reagent that is used for lithiation is as follows: in room temperature, under the inert atmosphere glove box of argon gas (as be full of), in required ratio, the anhydrous organic compound that contains phenyl ring is dissolved in the absolute ether compounds forms clear solution, lithium metal is put into this solution in batches, lithium metal will dissolve gradually, the color of solution along with lithium dissolve in by pale yellow become blackish green, mazarine or near black (relevant with system and concentration) has so just obtained the reagent that is used for lithiation of the present invention.This lithiation reagent directly is kept in the airtight container that is full of argon shield of sealing, standby.
As the electron transfer acceptor, it can all or part ofly accept the electronics that lithium metal gives to the reagent that is used for lithiation provided by the invention with biphenyl class or condensed-nuclei aromatics compounds; Simultaneously, ether compound with shift fully or the part metastatic electron after lithium ion form complex; Like this, lithium just can constantly be dissolved in the mixed solution that the organic compound that contains phenyl ring and ether compound form.And along with the raising of lithium concentration in the solution, the chemical state of lithium is a metallicity by ionic transition.When the lithium concentration in the solution is higher, lithium is equivalent to the lithium of atomic state in solution, therefore, the reagent that is used for lithiation that obtains (i.e. this mixed system) has very high reactivity, be easy to pass through electron transfer, with other material reduction, lithium is inserted in other materials or replaces some element simultaneously.
Lithiation reagent provided by the invention prepares easily, is easy to preserve, and cheap, reactivity is very high.Both can be used as general lithiation reagent, also can be used for chargeable lithium battery electrode material pre-service or prepare the new mineral compound that contains lithium, therefore have purposes widely.
Embodiment
Embodiment 1,
In inert atmosphere (content of water is less than in 1% the glove box that is full of argon gas), the dry biphenyl of metering ratio is dissolved in the anhydrous glycol dimethyl ether, obtain the biphenyl clear solution of 0.5M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes bottle green, the concentration that obtains lithium is the solution of 1M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
In order to study the lithiation effect of this reagent that is used for lithiation, with bolarious V
2O
5Put into this reagent, V
2O
5With the mol ratio of lithium in the reagent be 1: 1.After leaving standstill 24 hours, mixed solution becomes clarification, V
2O
5All change black into.This filtration of material is separated, and spent glycol dimethyl ether flush away biphenyl, solid after the separation takes out from glove box, use conventional method then, it is made as the positive pole that lithium ion battery is used, and in the lithium ion battery of routine, test its electrochemically reactive according to a conventional method, find that it can directly show charging capacity (taking off the lithium capacity) 150mAh/g in first week, and simple V
2O
5Can only insert lithium by electrochemical method earlier, and then take off lithium.So V
2O
5Can only be used in lithium metal and can charge and discharge in the battery as positive electrode, and can not be used in the lithium ion battery as the lithium of negative pole.Above-mentioned evidence lithium in aforesaid lithiation has been embedded into V by chemical reaction really
2O
5In.That is to say, directly in solution, prepared LiV by this method
2O
5, this is that other method can't be accomplished.Therefore the lithiation reagent that adopts the present invention to propose is used for lithiation, and a kind of new method that is used for the preparation lithium compound positive electrode of lithium ion battery is provided.
Embodiment 2,
In inert atmosphere (content of water is less than 1%), the dry terphenyl of metering ratio is dissolved in the anhydrous ethylene glycol diethyl ether, obtain the terphenyl clear solution of 0.1M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 0.1M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
In order to study the lithiation effect of this reagent, with Cr
3O
8Put into this reagent, Cr
3O
8With the mol ratio of lithium in the reagent be 1: 4.After leaving standstill 48 hours, the solution clarification.This filtration of material is separated, and spent glycol diethyl ether flush away terphenyl, solid after the separation takes out from glove box, use conventional method then, it is made as the positive pole that lithium ion battery is used, and in the lithium ion battery of routine, test its electrochemically reactive according to a conventional method, find that it can directly show charging capacity (taking off the lithium capacity) 250mAh/g in first week, and simple Cr
3O
8Also can only insert lithium by electrochemical method earlier, and then take off lithium.Be similar to V
2O
5, it also can only be used in the lithium of lithium metal as negative pole and can charge and discharge in the battery, as positive electrode, and can not be used in the lithium ion battery.Above-mentioned evidence lithium in aforesaid lithiation has been embedded into V by chemical reaction really
2O
5In.That is to say, directly in solution, prepared Li by this method
4Cr
3O
8Therefore the lithiation reagent that adopts the present invention to propose is used for lithiation, and a kind of new positive electrode that is used for lithium ion battery is provided.
Embodiment 3,
In inert atmosphere (content of water is less than 1%), the dry quaterphenyl of metering ratio is dissolved in the anhydrous butyl cellosolve, obtain the quaterphenyl clear solution of 0.5M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 1M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
In order to study the lithiation effect of this reagent, with Cr
3O
8Put into this reagent, Cr
3O
8With the mol ratio of lithium in the reagent be 1: 4.After leaving standstill 48 hours, the solution clarification.This filtration of material is separated, and spent glycol butyl oxide flush away quaterphenyl, solid after the separation takes out from glove box, use conventional method then, it is made as the positive pole that lithium ion battery is used, and in the lithium ion battery of routine, test its electrochemically reactive according to a conventional method, find that it can directly show charging capacity (taking off the lithium capacity) 230mAh/g in first week.Above-mentioned evidence lithium in aforesaid lithiation has been embedded into Cr by chemical reaction really
3O
8In.That is to say, directly in solution, prepared Li by this method
4Cr
3O
8
Embodiment 4,
In inert atmosphere (content of water is less than 1%), the dry naphthalene of metering ratio is dissolved in the anhydrous dibutyl ethylene glycol ether, obtain the naphthalene clear solution of 0.01M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 0.01M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
In order to study the lithiation effect of this reagent, the hard carbon ball is put into this reagent, the mol ratio of lithium is 10: 1 in hard carbon ball and the reagent.After leaving standstill 48 hours, this filtration of material is separated, and with dibutyl ethylene glycol ether flush away naphthalene, solid after the separation takes out from glove box, use conventional method then, the hard carbon ball of handling is made as the negative pole that lithium ion battery is used, and in the lithium ion battery of routine, tests its electrochemically reactive according to a conventional method, find that its first all coulombic efficiency brings up to 85% from 63%, above-mentioned evidence lithium in aforesaid lithiation has been embedded in the hard carbon ball by chemical reaction really.That is to say that the lithiation reagent that adopts the present invention to propose is used for lithiation, has improved the chemical property of the negative material of lithium ion battery.
Embodiment 5,
In inert atmosphere (content of water is less than 1%), the dry biphenyl of metering ratio is dissolved in the dimethyl ether, obtain the biphenyl clear solution of 5M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 10M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
Embodiment 6,
In inert atmosphere (content of water is less than 1%), the dry anthracene of metering ratio is dissolved in the diethyl ether, obtain the anthracene clear solution of 0.2M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 0.5M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
Embodiment 7,
In inert atmosphere (content of water is less than 1%), the dry phenanthrene of metering ratio is dissolved in the ethyl methyl ether, obtain the anthracene clear solution of 0.5M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 1M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
Embodiment 8,
In inert atmosphere, the biphenyl of metering ratio is dissolved in the first amyl ether, obtain the biphenyl clear solution of 0.5M/l, with the metering ratio lithium metal at room temperature, put into this solution, lithium metal dissolves rapidly, and the color of solution gradually becomes blackish green, the concentration that obtains lithium is the solution of 1M/l, and this mixed liquor is the reagent that is used for lithiation of the present invention.
By electron paramagnetic resonance, nuclear magnetic resonance as can be known, this lithium state therein of reagent that is used for lithiation is kept at it in inert atmosphere near lithium metal, uses under inert atmosphere, as the reagent of lithiation.
Claims (8)
1, a kind of reagent that is used for lithiation, it is under the room temperature inert atmosphere, with the solution that makes behind lithium metal, the organic compound that contains phenyl ring and the ether compound mixed dissolution, wherein:
Lithium 0.01～10M/l;
Organic compound 0.01～the 5M/l that contains phenyl ring;
Surplus is a solvent, and it is R for general formula
1OR
2Or R
1OR
2OR
3Ether compound, R wherein
1, R
2, R
3Be C
1～C
5Alkyl;
The described organic compound that contains phenyl ring comprises biphenyl class or condensed-nuclei aromatics compounds.。
2, the reagent that is used for lithiation as claimed in claim 1 is characterized in that, described biphenyl compound is biphenyl and derivant, terphenyl or quaterphenyl.
3, the reagent that is used for lithiation as claimed in claim 1 is characterized in that, described condensed-nuclei aromatics compounds is naphthalene, anthracene or phenanthrene.
4, the reagent that is used for lithiation as claimed in claim 1 is characterized in that, described general formula is R
1OR
2Ether compound be dimethyl ether, diethyl ether, ethyl methyl ether or first amyl ether.
5, the reagent that is used for lithiation as claimed in claim 1 is characterized in that, described general formula is R
1OR
2OR
3Ether compound be glycol dimethyl ether, butyl cellosolve, dibutyl ethylene glycol ether or ethylene glycol diethyl ether.
6, the described preparation method who is used for the reagent of lithiation of a kind of claim 1, it is in room temperature, under the inert atmosphere, in required ratio, the anhydrous organic compound that contains phenyl ring is dissolved in the absolute ether compounds forms clear solution, lithium metal is put into this solution in batches, treat that lithium metal all dissolves, obtained the reagent that is used for lithiation of the present invention.
7, the described purposes that is used for the reagent of lithiation of a kind of claim 1, it is as general lithiation reagent.
8, the described purposes that is used for the reagent of lithiation of a kind of claim 1, it introduces the electrode material of chargeable lithium battery in advance with lithium, or is used to prepare the new mineral compound that contains lithium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410037394 CN1690694A (en) | 2004-04-30 | 2004-04-30 | Reagent for lithiation reaction, preparation method and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410037394 CN1690694A (en) | 2004-04-30 | 2004-04-30 | Reagent for lithiation reaction, preparation method and use thereof |
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| Publication Number | Publication Date |
|---|---|
| CN1690694A true CN1690694A (en) | 2005-11-02 |
Family
ID=35346284
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|---|---|---|---|
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| CN100460379C (en) * | 2006-09-30 | 2009-02-11 | 南开大学 | Method of synthesizing 9-phenanthrene acid |
| CN104766965A (en) * | 2014-01-03 | 2015-07-08 | 中国科学院物理研究所 | Nanometer lithium silicon alloy material, and preparation method and use thereof |
| CN104766947A (en) * | 2014-01-03 | 2015-07-08 | 中国科学院物理研究所 | Preliminary metal metallization method and its application in battery material |
| WO2016019765A1 (en) * | 2014-08-06 | 2016-02-11 | 中国科学院物理研究所 | Liquid metal cathode material and room-temperature liquid metal battery, and preparation method thereof and usage thereof |
| CN107919473A (en) * | 2016-10-09 | 2018-04-17 | 清华大学 | The preparation method of lithium ion battery electrode active material |
| CN108358175A (en) * | 2018-04-25 | 2018-08-03 | 北京卫蓝新能源科技有限公司 | A kind of preparation method of lithium sulfide |
| CN108649267A (en) * | 2018-05-11 | 2018-10-12 | 深圳市清新电源研究院 | A kind of potassium ion conductor and its preparation method and application |
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| CN112151770A (en) * | 2020-09-16 | 2020-12-29 | 天目湖先进储能技术研究院有限公司 | Preparation method of iron disulfide cathode material with pre-embedded lithium and lithium secondary battery |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100460379C (en) * | 2006-09-30 | 2009-02-11 | 南开大学 | Method of synthesizing 9-phenanthrene acid |
| CN113113571A (en) * | 2014-01-03 | 2021-07-13 | 溧阳天目先导电池材料科技有限公司 | Method for preliminary alkali metallization and application of method in battery material |
| CN104766965A (en) * | 2014-01-03 | 2015-07-08 | 中国科学院物理研究所 | Nanometer lithium silicon alloy material, and preparation method and use thereof |
| CN104766947A (en) * | 2014-01-03 | 2015-07-08 | 中国科学院物理研究所 | Preliminary metal metallization method and its application in battery material |
| CN113437282B (en) * | 2014-01-03 | 2022-05-13 | 溧阳天目先导电池材料科技有限公司 | Nanoscale lithium-silicon alloy material and preparation method and application thereof |
| CN113437282A (en) * | 2014-01-03 | 2021-09-24 | 溧阳天目先导电池材料科技有限公司 | Nano-scale lithium-silicon alloy material and preparation method and application thereof |
| WO2016019765A1 (en) * | 2014-08-06 | 2016-02-11 | 中国科学院物理研究所 | Liquid metal cathode material and room-temperature liquid metal battery, and preparation method thereof and usage thereof |
| CN107919473A (en) * | 2016-10-09 | 2018-04-17 | 清华大学 | The preparation method of lithium ion battery electrode active material |
| CN107919473B (en) * | 2016-10-09 | 2020-05-12 | 清华大学 | Preparation method of lithium ion battery electrode active material |
| CN110120496A (en) * | 2018-02-05 | 2019-08-13 | 武汉大学 | A kind of negative electrode of lithium ion battery and its prelithiation methods and applications |
| CN108358175A (en) * | 2018-04-25 | 2018-08-03 | 北京卫蓝新能源科技有限公司 | A kind of preparation method of lithium sulfide |
| CN108649267B (en) * | 2018-05-11 | 2021-09-17 | 深圳市清新电源研究院 | Potassium ion conductor and preparation method and application thereof |
| CN108649267A (en) * | 2018-05-11 | 2018-10-12 | 深圳市清新电源研究院 | A kind of potassium ion conductor and its preparation method and application |
| CN112382749A (en) * | 2020-07-03 | 2021-02-19 | 华中科技大学 | Lithium ion battery anode material and preparation method thereof |
| CN112382749B (en) * | 2020-07-03 | 2024-04-12 | 华中科技大学 | Lithium ion battery anode material and preparation method thereof |
| CN112151770A (en) * | 2020-09-16 | 2020-12-29 | 天目湖先进储能技术研究院有限公司 | Preparation method of iron disulfide cathode material with pre-embedded lithium and lithium secondary battery |
| CN112271290A (en) * | 2020-10-14 | 2021-01-26 | 华中科技大学 | Method for preparing lithium-containing titanium niobate (LTNO) material or negative electrode and application |
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