CN105858626B - A preparing method of lithium bis(fluorosulfonyl)imide - Google Patents
A preparing method of lithium bis(fluorosulfonyl)imide Download PDFInfo
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- C01B21/00—Nitrogen; Compounds thereof
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- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
- C01B21/096—Amidosulfonic acid; Salts thereof
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Abstract
A synthetic method of novel lithium bis(fluorosulfonyl)imide is provided. Compared with the prior art, the method is characterized in that the lithium bis(fluorosulfonyl)imide is prepared through reacting an aromatic methylamine that is adopted as an initial compound with organoboron, reacting with halogen sulfonyl to obtain a sulfonyl-containing aromatic methylamine, performing a hydrogenation reduction reaction to obtain bis(fluorosulfonyl)imide, and performing ion exchange with resin lithium. In a final strong base reaction for preparing the lithium bis(fluorosulfonyl)imide, the method adopts a resin lithium ion exchange technique, thus breaking away from convention, and the method researches the possibility that the reaction is performed without a solvent for the first time at home and abroad and synthesizes the lithium bis(fluorosulfonyl)imide in an ion exchange manner. The method has advantages of a simple process, convenience, simple after-treatment, no complex operation, and cyclic use of the resin lithium, and the like.
Description
Technical field
The invention belongs to lithium ion battery electrolyte technical field, more particularly, to a kind of preparation of imidodisulfuryl fluoride lithium salt
Method.
Background technology
Since phase early 1990s proposes the concept of lithium ion battery and realizes its commercial applications, lithium-ion electric
The basic research in pond and application rapidly become one of focus of International Electrochemical research.Electrolyte is the weight constituting lithium ion battery
Want key element, by the optimization to electrolyte system, electrode interface SEI film (solid electrolyte can be improved
Interphase, solid electrolyte interface) composition and battery performance, increase the reversible capacity of electrode, extend cycle life,
Improve the charge-discharge performance of electrode.Therefore, the electrolyte of exploitation superior performance is to the market competitiveness tool improving lithium ion battery
There is larger realistic meaning.
Double fluorine sulfimide lithium LiN (SO2F)2, (abbreviation LiFSI) is an electrolyte thing with wide application prospect
Matter, because the conductance of LiFSI is suitable, and heat endurance, electrochemical stability are high；Occur side reaction probability little, will not produce
The corrosive gas such as HF, are applied in the electrolyte of chargeable lithium cell, can effectively reduce and be formed on electrode plate surface
SEI layer high/low temperature resistance at low temperature, reduce capacitance loss in placement process for the lithium battery, thus providing high power capacity electricity
Pond, improves the chemical property of battery.
At present, the synthetic method of double fluorine sulphonyl ammonia lithium salts mainly with ammoniacal liquor, ammonium salt, or other organic ammonia classes for ammonia
Source, adds thereafter chlorosulfuric acid, fluorosulfuric acid, sulfuric chlorohydrin etc. intermediate to synthesize double fluorine sulphonyl ammonia lithiums, then carries out lithiumation anti-
Answer the double fluorine sulphonyl ammonia lithium salts of gained.Similar the method has some shortcoming following：1) ammonia of the overwhelming majority is with liquid or gas
Based on, during industrial mass production, the correct amount of ammonia is to be difficult to the excessively very few of sizing to promote to generate unnecessary by-product
Thing, be more also a large amount of using ammonia when be easy at different temperatures and pressures set off an explosion so that safety problem always
For hidden danger.2) the superpower alkalescence lithium salt solution carrying out being used during lithiation in double fluorine sulphonyl ammonia is inflammable and explosive superfine danger
Dangerous chemical reagent, improper use can produce serious consequence.
Content of the invention
Goal of the invention：There are a lot of hazards in the synthetic method due to of the prior art pair of fluorine sulphonyl ammonia lithium salts, this
Invention, with the synthetic method of double fluorine sulphonyl ammonia lithium salts of autonomous original creation type, makes input cost, risk factor substantially reduces so that adapting to
Domestic a large amount of industrialized production.
Technical scheme：The invention provides a kind of synthetic method of new imidodisulfuryl fluoride lithium salt, with prior art not
It is with part, is reacted with organic boron for starting material with fragrant methyl amine, then reacted with halogen family sulphonyl, obtain containing sulphonyl
Fragrant methyl amine；Hydro-reduction reaction obtains double fluorine sulfimides；Carry out ion exchange with resin lithium, obtain double fluorine sulphonyl sub-
Amine lithium salts.
Synthetic line is as follows：
The specific preparation process of the present invention is：
A, with fragrant methyl amine as starting material, adds organic boron system, and reaction obtains intermediate；
B, under conditions of organic solvent and alkaline reagent exist, intermediate obtained above and halogen family sulphonyl is carried out instead
Should, obtain the fragrant methyl amine containing sulphonyl；
C, by the fragrant methyl amine containing sulphonyl obtained above, after inorganic alkali process, is deposited with metallic catalyst in hydrogen
Condition obtain double fluorine sulfimides carrying out hydro-reduction reaction,
D, by obtained above pair of fluorine sulfimide, under conditions of organic solvent exists, carries out ion friendship with resin lithium
Change, obtain imidodisulfuryl fluoride lithium salt.
More specifically, in described step a, fragrant methyl amine can be the class material as structural formula as shown in Formula II, virtue
The tertiary amine of fragrant methyl amine is easy to carry out hydrogen reduction reaction obtain secondary amine, but aniline is that hydrogen reduction reaction will not occur, because
Its stability is more stable than benzene methanamine, and accordingly, as the starting material of the present invention, fragrant methyl amine is preferably benzene methanamine, 4- methylbenzene
The double methyl benzene methanamine of methylamine, 3,5-.More preferably benzene methanamine.
Organic boron in described step a is boron alkoxide class, and formula is B (R2)3, wherein R2For hydrogen or alkoxyl, preferably first
Epoxide or ethyoxyl.Described organic boron system can be, borine-oxolane, trimethoxy-boron, three epoxide boron etc..Pin
Feature to the present invention, preferably borine-Tetrahydrofuran System.The consumption of described organic boron with the mol ratio of fragrant methyl amine is
1～1.5：1, preferably 1～1.1：1, more preferably 1.1～1.2：1.
Organic solvent in described step b be dichloromethane, chloroform, oxolane, toluene, 1,2- dimethylether, oneself
One or more of alkane mixture.Polar form and non-polar form mixed solvent increase lithium ion in a solvent under condition of ultralow temperature
Stability is so as to fully react raising reaction efficiency and product yield with amine.Especially 1,2- dimethylether and hexane
Mixture, the mass ratio of preferably two components is 1：1.The consumption of described organic solvent is 3～5 with the mol ratio of fragrant methyl amine：
1, preferably 3～4：1, more preferably 4～5：1.
In described step b alkaline reagent be butyl lithium, isobutyl group lithium, tert-butyl lithium, lithium amide, lithium hydride, two different
Propyl group ammonia lithium or lithium metal.The consumption of described alkaline reagent is 2.0～2.5 with the mol ratio of fragrant methyl amine：1, preferably 2.2～
2.5：1, more preferably 2.4～2.5：1.
In described step b, halogen family acyl chlorides is fluoro sulphonyl, chloro fluorine sulphonyl or fluorosulfuric acid.The consumption of described halogen family acyl chlorides with
The mol ratio of fragrant methyl amine is 2.0～2.5：1, preferably 2.2～2.5：1, more preferably 2.4～2.5：1.
Metallic catalyst in described step c is palladium, nickel, platinum, iron, zinc.For contrasting this reaction, in platinum, nickel is catalyzed bar
Have under part yield high the features such as, but noble metal catalyst expensive be not easy very much reclaim, because of activity problems in removal process
It is easy to blast and other accidents, catalyst iron, though zinc is cheap, the relatively low post-reaction treatment of reactivity ratio is very
Loaded down with trivial details, though palladium catalyst/carbon is precious metal the inside and to alleviate the activity of palladium and substantially increases security containing 90% carbon,
Practicality and price comparison are cheap, easily reclaim yield effect high.
Organic solvent in described step d is oxolane, ether, dimethoxy ether, preferably oxolane.Consumption is every
Gram 40-50ml (based on imidodisulfuryl fluoride lithium salt).
The resin lithium of described step d is the product of resin and organolithium；Described resin is high molecular functional group
One or more of polymer that benzene methanamine or benzene and its side chain are linked；Described organolithium is butyl lithium or tertiary fourth
Base lithium.For examplePreferably
Cholestyramine lithium exchanger resin.
Above-mentioned resin lithium is with cholestyramine as starting material, is subsequently added butyl lithium, isobutyl group lithium, tert-butyl lithium, amino
The lithium base highly basic with side chain such as lithium, lithium hydride, diisopropyl ammonia lithium or lithium metal carries out lithium exchange reactions in solution and is drawn
Final product resin amine lithium salts.
Beneficial effect：Compared with prior art, feature is with fragrant methyl amine as starting material the present invention；With resin lithium it is
Lithiumation agent.
This preparation method carries out series reaction, arene using the amine of organic arene for the main material source of ammonia
Amine produced with by-product form in petrochemical industry refinement, price is dirt cheap and is easy to get, and nitrogen in existing conventional method
Source be limited to based on common Ammonia, such as ammonia, liquefied ammonia, ammonium salt etc..Particularly ammonia and liquefied ammonia are in Different climate
With under the conditions of be difficult to be reacted, such as concentration, internal pressure, the factor such as density, the amine of arene is not subject to any weather bar
Part can carry out volume production reaction at any time.Common Ammonia and halogen family acyl chloride reaction produce a large amount of hydrogen chloride gas under conditions of not having alkali
Body, thus leading to reaction controlling difficult, generation accessory substance increases and reaction condition is unkind.The amine of arene is during the course of the reaction
Add amine Louis's highly basic (such as butyl lithium, isobutyl group lithium, tert-butyl lithium etc.) come reaction speed and temperature and
The generation of accessory substance, generates lithium salts after also reaction terminates, does not produce corrosiveness to reaction kit.
The final step of the present invention is with resin lithium as lithiumation agent, and in existing conventional method, final step uses highly basic anti-
Ying Zhong, is substantially stirring gained in polar solvent, then carries out post-processing such as being filtered to remove and reacts generation salt in institute
Material and the excessive highly basic elimination process adding etc., all times reacting used are long, and follow-up work is more multiple
Miscellaneous.Present invention resin lithium ion exchanged technology used in the final step highly basic reaction of double fluorine sulphonyl ammonia lithium salts is broken in the past
Conventional method, and be also at home and abroad to research and develop such reaction in a solvent, with the synthesis of ion exchange form method at first
Go out double fluorine sulphonyl ammonia lithium salts, the method course of reaction is simple, convenient, and post processing is simple, and without complex work, last resin lithium can
The advantages of to recycle.
Specific embodiment：
Embodiment 1
Step a, weighs 10.7g benzene methanamine, is added in the there-necked flask with constant pressure funnel and thermometer and is dissolved in four
Among hydrogen furans 100ml, temperature is down to 0 DEG C and is slowly added dropwise 1M BH afterwards3- THF10.2ml, time for adding is 20min, entirely
Drip reacting temperature is maintained at 0 DEG C～5 DEG C, and the direct vacuum distillation of completion of dropping obtains 12 grams of intermediates.
Step b, is added in the there-necked flask with constant pressure funnel and thermometer and is dissolved among oxolane 500ml,
Temperature is down to -78 DEG C and is slowly added dropwise tert-butyl lithium 141ml afterwards, and time for adding is 1h, and whole drip reacting temperature is maintained at -75
DEG C～-78 DEG C, after completion of dropping, -75 DEG C～-78 DEG C are continued reaction 1h, and band after completion of the reaction, is slowly added dropwise fluorine chlorosulfuric acid
17.4ml, time for adding is 20min, completion of dropping, and temperature is slowly increased to -78 DEG C-room temperature and continues reaction 4h, and band reaction finishes
Afterwards, add saturated solution of sodium carbonate 300ml stirring 2h, add dichloromethane 800ml to be extracted, the organic solvent obtaining adds
MgSO4It is dried, filters, washed with 50ml dichloromethane three times, collect mother liquor vacuum distillation and obtain the double fluorine sulphur of 22.2g benzyl
Acid imide, yield 82%, in terms of benzyl amine.
Step c, weighs the double fluorine sulfimide of 22.2g benzyl and is added among hydrogen reactor and be dissolved in oxolane/ethanol
(1：1) 8000ml, adds noble metal catalyst 10% palladium/carbon 0.79g, carries ready slow importing hydrogen, general pressure control
In 20psi, it is 8h that temperature is slowly adjusted to 40 DEG C of reaction time from 25 DEG C every 1h to system, and band reaction finishes after temperature is down to room temperature
Directly filter and washed three times with 50ml oxolane, collect mother liquor vacuum distillation and obtain the double fluorine sulfimide of 11.3g, yield
76%, in terms of the double fluorine sulfimide of benzyl.
Step d, under nitrogen protective condition, weighs 0.8gCholestyramine lithium exchanger resin and is dissolved in oxolane 20ml
It is added in the there-necked flask with constant pressure funnel and thermometer, the double fluorine sulfimide of 11.3g is dissolved in oxolane 500ml and adds
Enter in constant pressure funnel, temperature is down to -78 DEG C and is slowly added dropwise afterwards, time for adding is 1h, whole drip reacting temperature is protected
Hold at -75 DEG C～-78 DEG C, after completion of dropping, -75 DEG C～-78 DEG C are continued reaction 2h, band after completion of the reaction, take over filter and use by fast direct
50ml oxolane washs three times, after collecting mother liquor vacuum distillation, after adding ether 500ml that 1h is stirred at room temperature directly
Filter and washed three times with 50ml ether, collect mother liquor vacuum distillation and obtain 8.3g benzyl imidodisulfuryl fluoride lithium salt, yield
71%, in terms of double fluorine sulfimides.
Embodiment 2～3
Reactions steps are identical with embodiment 1 condition, and difference is, by the starting material in step a, to replace with 4- respectively
The double methyl benzene methanamine of methyl benzene methanamine, 3,5-, the double fluorine sulfimide yield of the fragrant methyl finally giving is respectively 78% He
74%.
Embodiment 4～5
Reactions steps are substantially the same manner as Example 1, and difference is the BH in step a3- THF, replaces with three respectively
Methoxyl group boron, three epoxide boron, the fragrant methyl-boric acid yield finally giving is respectively 88% and 83%.
Embodiment 6～9
Reactions steps are substantially the same manner as Example 1, and difference is, by the oxolane in step b, to replace with respectively
Dichloromethane, toluene, chloroform, 1,2- dimethylether and the mixture (mass ratio 1 of hexane:1).
Embodiment 10～12
Reactions steps are substantially the same manner as Example 1, and difference is, by tert-butyl lithium in step b, to replace with fourth respectively
Base lithium, isobutyl group lithium, lithium amide, lithium hydride, diisopropyl ammonia lithium or lithium metal.
Embodiment 13～15
Reactions steps are substantially the same manner as Example 1, and difference is, by the sodium carbonate in step b, to replace with carbon respectively
Sour potassium, NaOH or potassium hydroxide, the double fluorine sulfimide yield of the fragrant methyl finally giving is respectively 76%, 81% He
77%.
Embodiment 16～17
Reactions steps are substantially the same manner as Example 1, and difference is, by the fluorine chlorosulfuric acid in step b, to replace with respectively
Fluorosulfuric acid, fluoro sulphonyl.
Embodiment 18～19
Reactions steps are substantially the same manner as Example 1, and difference is, by the palladium/carbon catalyst in step c, to replace with platinum
Catalyst, Raney nickel, iron catalyst, zinc catalyst.
Embodiment 20～21
Reactions steps are substantially the same manner as Example 1, and difference is oxolane in step d, replace with ether, two
Methyl ethyl ether.
Embodiment 22～23
Reactions steps are substantially the same manner as Example 1, and difference is for Cholestyramine lithium in step d to exchange tree
Fat, replaces with epoxy lithium exchanger resin, Cholestyrphenolamine lithium exchanger resin.
Embodiment 24
Weigh 10gCholestyramine resin, 10g smellyization ammonia, 40g ethylenediamine is added among sealed glass tube,
Under microwave irradiation temperature rise to 80 DEG C reaction 1h, band after completion of the reaction, temperature add methylene chloride after being down to room temperature 800ml with
100ml 1M HCl solution is extracted, and isolates organic solvent and is adding 100ml 1M NaOH solution to be extracted, isolates
Organic solvent is through MgSO4It is dried, filter, collect mother liquor vacuum distillation and obtain 5.3g resin amine.
Weigh 5.3g resin amine and be added in there-necked flask and be dissolved in oxolane 250ml, temperature is down to -78 DEG C and is slowly dripped afterwards
Plus tert-butyl lithium 5.3ml, time for adding is 30min, and whole drip reacting temperature is maintained at -75 DEG C～-78 DEG C, completion of dropping
- 75 DEG C afterwards～-78 DEG C are continued reaction 1h, and band after completion of the reaction, take over filter and washed three times with 50ml oxolane by fast direct, collects
To after mother liquor vacuum distillation, directly filter after adding ether 200ml that 1h is stirred at room temperature and washed three times with 50ml ether, receive
Collection obtains 4.2g resin lithium.
Claims (8)
1. a kind of preparation method of imidodisulfuryl fluoride lithium salt is it is characterised in that comprise the following steps：
A, with fragrant methyl amine as starting material, adds organic boron system, and reaction obtains intermediate；
B, under conditions of organic solvent and strong basic reagent exist, intermediate obtained above is reacted with halogen family sulphonyl,
Obtain the fragrant methyl amine containing sulphonyl；
C, by the fragrant methyl amine containing sulphonyl obtained above, after inorganic alkali process, is existed with noble metal catalyst in hydrogen
Condition obtain double fluorine sulfimides carrying out hydro-reduction reaction,
D, by obtained above pair of fluorine sulfimide, under conditions of organic solvent exists, carries out ion exchange with resin lithium, obtains
To imidodisulfuryl fluoride lithium salt；
Organic boron in described step a, formula is B (R2)3, wherein R2For hydrogen or alkoxyl；
Alkaline reagent in described step b is butyl lithium, isobutyl group lithium, tert-butyl lithium, lithium amide, lithium hydride, diisopropyl ammonia
Lithium or lithium metal；
The resin lithium of described step d is the product of resin and organolithium.
2. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that fragrance in described step a
The formula of methyl amine is as formulaShown, wherein R1For methyl, ethyl or phenyl.
3. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that organic in described step b
Solvent is one or more of dichloromethane, chloroform, oxolane, toluene, 1,2- dimethylether, hexane mixture.
4. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that halogen family sulphur in described step b
Acyl is fluoro sulphonyl, chloro fluorine sulphonyl or fluorosulfuric acid.
5. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that metal in described step c
Catalyst is palladium, nickel, platinum, iron or zinc.
6. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that organic in described step d
Solvent is oxolane, ether or dimethoxy ether.
7. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 1 is it is characterised in that the resin lithium of described step d
Product for resin and organolithium；Described resin is the polymer of high molecular functional group benzene methanamine and benzene；Described
Organolithium is butyl lithium or tert-butyl lithium.
8. the preparation method of imidodisulfuryl fluoride lithium salt as claimed in claim 7 is it is characterised in that the resin lithium of described step d
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| US11267707B2 (en) | 2019-04-16 | 2022-03-08 | Honeywell International Inc | Purification of bis(fluorosulfonyl) imide |
| CN111128567B (en) * | 2019-12-23 | 2022-03-22 | 中国电子科技集团公司第十八研究所 | Preparation method of organic prelithiation material |
| WO2021082447A1 (en) * | 2020-06-05 | 2021-05-06 | 广州理文科技有限公司 | Method for preparing lithium fluorosulfate using organic metal lithium reagent |
| CN116462165A (en) * | 2023-04-28 | 2023-07-21 | 湖北兴发化工集团股份有限公司 | Preparation method of lithium bis (fluorosulfonyl) imide |
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