CN106478495A - Functionalized ion liquid and its synthetic method for lithium extraction - Google Patents

Functionalized ion liquid and its synthetic method for lithium extraction Download PDF

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CN106478495A
CN106478495A CN201610814036.2A CN201610814036A CN106478495A CN 106478495 A CN106478495 A CN 106478495A CN 201610814036 A CN201610814036 A CN 201610814036A CN 106478495 A CN106478495 A CN 106478495A
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synthetic method
halogen
functionalized ion
ionic liquid
ion liquid
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CN106478495B (en
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王延风
张晓梅
张平平
路文娟
周亚楠
孟李阳
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INSTITUTE OF MATERIA MEDICA SHANDONG ACADEMY OF MEDICAL SCIENCES
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
    • C22B26/10—Obtaining alkali metals
    • C22B26/12—Obtaining lithium
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
    • C22B3/36—Heterocyclic compounds
    • C22B3/362—Heterocyclic compounds of a single type
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

The invention discloses a kind of functionalized ion liquid and its synthetic method for lithium extraction, belongs to the field of chemical synthesis.The method obtains the functionalized ion liquid with amide group with halogen acyl chloride, two replacement amine, 4 N, N lutidines and Potassium Hexafluorophosphate for raw material through amidation process, salt-forming reaction and exchange reaction.Compared with prior art, the ionic liquid of the present invention and its synthetic method have simple to operate, the features such as be suitable to industrial application, with important using value.

Description

Functionalized ion liquid and its synthetic method for lithium extraction
Technical field
The present invention relates to the field of chemical synthesis, specifically a kind of functionalized ion liquid and its conjunction for lithium extraction Become method.
Background technology
Lithium is widely used in the neck such as battery, nuclear fusion generating, Aero-Space, medicine as a kind of new strategic energy Domain.In nature, mainly based on solid mineral and salt lake bittern, China's salt lake resources reserves extremely enrich lithium resource, only Qaidam The explored reserves in area just reach 20,000,000 tons (LiCl meters) more than.With the increasingly increase of the market demand, salt lake bittern Just extracting for middle lithium has important strategic importance.
In salt lake, lithium mainly in the form of an ion together with the alkali and alkaline earth metal ions association such as sodium, magnesium, potassium, particularly The content of magnesium of wherein association is very high, magnesium/lithium ratio (mass ratio) up to 40～1200 in bittern so that separation and Extraction lithium is very tired Difficult.It can be said that the key issue for being to extract lithium in salt lake bittern that efficiently separates of lithium, magnesium is located.
So far, extraction is that most promising bittern puies forward one of lithium method, and the preferable system of effect is tricresyl phosphate fourth Ester ferric trichloride-kerosene system, this system are relatively specific for the salt lake of high Mg/Li ratio and carry lithium.In this system, trichlorine Change iron first LiFeCl is formed with lithium4Complex compound, then forms ligand complex so as to be extracted to organic phase with tbp, The last back extraction for realizing lithium under strongly acidic conditions by the displacement of hydrogen ion and lithium ion.But tbp is dense in the system Degree is higher, and the corrosivity to extraction equipment is extremely strong, and solubility of the bittern in organic phase is larger, and product purity can only achieve 98.5% or so, therefore it is unable to large-scale industrial production.
Amides compound and phosphonate ester compound as mixed extractant, ferric trichloride as coextraction system, though The corrosivity to equipment can be reduced to a certain extent, but extraction efficiency also accordingly reduces.
As China salt lake has high Mg/Li ratio, therefore want effectively to carry lithium, extraction is that most effective most have work One of mode of industry application prospect.But as existing extractant is too big to equipment corrosion, find a kind of new, gentle extraction It is exactly one of problem of most critical to take system or a kind of substitute of extractant.
Ionic liquid is made up of organic cation and inorganic or organic anion, is in liquid condition below 100 DEG C Salt.Its advantage is that vapour pressure is almost nil, and non-volatility is tasteless, do not fire not quick-fried, be easy to after use product separation, can return Receive and recycle, effectively prevent conventional organic solvents and asked using caused severe environments, health, safety and equipment corrosion etc. Topic, is genuine eco-friendly green solvent.
Content of the invention
The technical assignment of the present invention be for above-mentioned the deficiencies in the prior art, provide a kind of for lithium extraction functionalization from Sub- liquid.
The further technical assignment of the present invention is the synthetic method for providing above-mentioned ionic liquid.
The technical assignment of the present invention is realized in the following manner：For the functionalized ion liquid of lithium extraction, its feature It is to be synthesized by following methods：
With halogen acyl chloride, two replacement amine, 4-N, N- lutidines and Potassium Hexafluorophosphate are raw material, through amidation process, Salt-forming reaction and exchange reaction obtain the functionalized ion liquid with amide group,
The structural formula of the functionalized ion liquid is：
Wherein, n=2 or 3, R1,R2It is C2～C8Straight chain or the alkane with side chain.
Preferably, the synthetic method of ionic liquid of the present invention is comprised the following steps：
A, with halogen acyl chloride and two replacement amine as initiation material synthesizing halogen acid amides in the presence of acid binding agent；
The reaction of b, halogen acid amide and 4-N, N- lutidines generates halogeno salt intermediate；
There is exchange reaction in c, halogeno salt intermediate and Potassium Hexafluorophosphate, obtain the functionalization ionic liquid with amide group Body.
Course of reaction is as follows：
The concrete grammar of step a is preferably：With two replacement amine as initiation material, it is dissolved in solvent, halogen acyl chloride is dripped, so Purified concentration obtains halogen acid amide afterwards.
Two replacement amine are preferably 1 with the mol ratio of acyl chlorides：(1～1.5).
The halogen acyl chloride can be chloro acyl chlorides, bromacyl chloride or iodo acyl chlorides, preferably chloro acyl chlorides.
The acid binding agent is preferably triethylamine or triethanolamine.
The solvent is DMF, dichloromethane, toluene or 1,2- dichloroethanes, preferably 1,2- dichloro Ethane.
The concrete grammar of purified concentration is：The alkali for adding appropriate hydrochloric acid solution washing excessive, after extraction, organic phase adds again Enter appropriate sodium hydroxide solution, after extracting again, organic phase is washed, and saturated common salt water washing, after anhydrous sodium sulfate drying Filter, filtrate reduced in volume obtains halogen acid amide to dry.
The concrete grammar of step b is preferably：Dropwise it is added drop-wise under halogen acid amide ice bath in 4-N, N- lutidines, stirring Microwave reaction after uniform, then purified concentration obtain halogeno salt intermediate.
Halogen acid amide is preferably 1 with the mol ratio of 4-N, N- lutidines：(1～2)；
The reaction temperature of the microwave reaction is 50～80 DEG C, preferably 60 DEG C；Power is 200～400w, preferably 300w；Reaction can single long-time react, it is also possible to intermittent reaction, preferably intermittent reaction.
The concrete grammar of purified concentration is：Suitable organic solvent is added to be washed in solution after microwave reaction, altogether Washing three times, vacuum distillation remove ethyl acetate, are dried under vacuum to constant weight at 40 DEG C, obtain halogeno salt intermediate after purification. Selected organic solvent is ethanol, ethyl acetate or dichloromethane, preferably ethyl acetate.
Exchange reaction described in step c can be completed in methyl alcohol, ethanol or water, preferably completed in water.
Halogeno salt intermediate is preferably 1 with the mol ratio of Potassium Hexafluorophosphate：(1～1.2).
After the completion of exchange reaction, reactant liquor stands split-phase, is poured off water phase, and organic phase is repeatedly washed to and deposits nothing chlorion , and cleaning solution is neutrality；Organic phase after washing is placed in vacuum drying chamber, 70 DEG C of dryings to constant weight, that is, obtain functionalization Ionic liquid sterling.
It has been found that containing, with ionic liquid obtained in synthetic method of the present invention, the amide groups for having interaction with lithium Group, occurs complexing to interact with lithium, reduces the interference of other ions, it is possible to increase the extraction selectivity of ionic liquid；And Long chain hydrocarbons are introduced in the ionic liquid, improve its hydrophobicity.Functionalized ion liquid of the present invention is applied to lithium extraction In can reach good technique effect.
The functionalized ion liquid extracted for lithium of the present invention and its synthetic method have following compared with prior art Highlightedly beneficial effect：
(1) method is simple, can be simultaneously introduced the functional groups of extraction；
(2) intermediate can adopt having a rest property microwave reaction method, prevent long-time microwave while shortening the reaction time again The potential safety hazard that the hot-spot that heating causes is brought；
(3) ionic liquid is ion composition, and extraction system need not add tbp, and it is right to significantly reduce The corrosivity of equipment；
(4), the features such as feasible process, simple to operate, easy control of reaction, popularization and application and industrialized production are conducive to.
Specific embodiment
The functionalized ion liquid lithium of the present invention extracted with specific embodiment and its synthetic method are made in detail below Explanation.
If no special instructions, the content of following each compositions used is weight percentage content.
Embodiment one：
4-N, N, the synthesis of dimethyl-N '-two (2- ethylhexyl) carbonylethyl pyridine hexafluorophosphate：
By bis- octodrine of 26.65g, 80ml1,2- dichloroethanes and 12.12g triethylamine are added in 500ml there-necked flask, The system is placed in ice salt bath is down to subzero, 35 milliliters of bis- chloroethenes of 1,2- of the chloracetyl chloride being added dropwise over containing 11.2g Alkane solution, controls rate of addition, it is ensured that reaction temperature is maintained within 10 DEG C.Reaction system is transferred to room temperature by completion of dropping, Reaction 3h.
The hydrochloric acid solution of dropping 100ml 1M is quenched the experiment, standing, split-phase, reservation organic phase；Organic phase is sequentially added 100ml 1M sodium hydroxide solution, 100ml water, 100ml saturated common salt water washing, finally use anhydrous sodium sulfate drying.After suction filtration It is spin-dried for, products therefrom is dry to constant temperature with vacuum drying chamber, obtain product 30.12g, yield 95%.
25.01g 4-N, N- lutidines is added drop-wise in the microwave reaction groove equipped with 25.05g chloroacetamide, stirring Uniformly, then it is put in microwave reactor, 60 DEG C of design temperature, power setting is 300w, reacts five minutes, shakes up, repeatedly four Secondary.To in system, add the washing of 50ml ethyl acetate not react after completion of the reaction raw material, cyclic washing three times.Revolving is removed Organic phase is gone, by products therefrom as in vacuum drying oven, 50 DEG C of dryings 48 hours, obtain intermediate 35.4g.
Weigh 9.25g KPF6Be dissolved in distilled water, 22.05g intermediate is weighed in single-necked flask, use constant pressure addition Funnel is slowly added dropwise KPF6The aqueous solution, stirs 10h under room temperature, static rear solution is divided into two-phase, water above is mutually poured out.Below The slightly yellow clear viscous liquids of organic phase unreacted raw material is removed under reduced pressure, and use distilled water cyclic washing, until using nitric acid Exist nothing Cl ion in silver-colored aqueous solution inspection cleaning solution, and cleaning solution for neutral when stop washing, obtain after purification finally produce Thing 4-N, N, dimethyl-N '-two (2- ethylhexyl) carbonylethyl pyridine hexafluorophosphate, constant weight is dried under vacuum in 70 DEG C, Obtain 25.75g,1HNMR(300MHZ,CDCl3)：8.60(d,2H),7.28(d,2H),4.05(t,2H),3.28(d,,2H),3.12 (m,4H),2.66(t,2H),1.65(m,2H),1.26(m,22H),0.91(m,12H).
Embodiment two：
4-N, N, the synthesis of dimethyl-N '-diethyl carbonyl propyIpyridine hexafluorophosphate：
By 25.42g diethylamine, 70ml1,2- dichloroethanes and 22.26g triethylamine are added in 500ml there-necked flask, should System is placed in ice salt bath is down to subzero, 48 milliliters of bis- chloroethenes of 1,2- of the 3- chlorpromazine chloride being added dropwise over containing 16.09g Alkane solution, controls rate of addition, it is ensured that reaction temperature is maintained within 10 DEG C.Reaction system is transferred to room temperature by completion of dropping, Reaction 3h.
The hydrochloric acid solution of dropping 150ml 1M is quenched the experiment, standing, split-phase, reservation organic phase；Organic phase is sequentially added 150ml 1M sodium hydroxide solution, 150ml water, 150ml saturated common salt water washing, finally use anhydrous sodium sulfate drying.After suction filtration It is spin-dried for, products therefrom is dry to constant temperature with vacuum drying chamber, obtain product 31.02g, yield 95%.
12.35g 4-N, N- lutidines is added drop-wise in the microwave reaction groove equipped with 16.38g chloroacetamide, stirring Uniformly, then it is put in microwave reactor, 60 DEG C of design temperature, power setting is 300w, reacts five minutes, shakes up, repeatedly four Secondary.To in system, add the washing of 45ml ethyl acetate not react after completion of the reaction raw material, cyclic washing three times.Revolving is removed Organic phase is gone, by products therefrom as in vacuum drying oven, 50 DEG C of dryings 48 hours, obtain intermediate 27.03g.
Weigh 12.89g KPF6Be dissolved in distilled water, 19.95g intermediate is weighed in single-necked flask, use constant pressure addition Funnel is slowly added dropwise KPF6The aqueous solution, stirs 10h under room temperature, static rear solution is divided into two-phase, water above is mutually poured out.Below Organic phase light yellow clear thick liquid unreacted raw material is removed under reduced pressure, and use distilled water cyclic washing, until using nitric acid Exist nothing Cl ion in silver-colored aqueous solution inspection cleaning solution, and cleaning solution for neutral when stop washing, obtain after purification finally produce Thing 4-N, N, dimethyl-N '-diethyl carbonyl propyIpyridine hexafluorophosphate, constant weight is dried under vacuum in 70 DEG C, obtain 24.35g.
Embodiment three：
4-N, N, the synthesis of dimethyl-N '-two (2- ethylhexyl) carbonyl propyIpyridine hexafluorophosphate：
By bis- octodrine of 26.35g, 80ml1,2- dichloroethanes and 12.35g triethylamine are added in 500ml there-necked flask, The system is placed in ice salt bath is down to subzero, 35 milliliters of 1,2- dichloros of the 3- chlorpromazine chloride being added dropwise over containing 12.73g Ethane solution, controls rate of addition, it is ensured that reaction temperature is maintained within 10 DEG C.Reaction system is transferred to room by completion of dropping Temperature, reacts 3h.
The hydrochloric acid solution of dropping 110ml 1M is quenched the experiment, standing, split-phase, reservation organic phase；Organic phase is sequentially added 110ml 1M sodium hydroxide solution, 110ml water, 110ml saturated common salt water washing, finally use anhydrous sodium sulfate drying.After suction filtration It is spin-dried for, products therefrom is dry to constant temperature with vacuum drying chamber, obtain product 31.12g, yield 94.55%.
26.55g 4-N, N- lutidines is added drop-wise in the microwave reaction groove equipped with 9.79g chloroacetamide, stirring is all Even, then it is put in microwave reactor, 60 DEG C of design temperature, power setting is 300w, reacts five minutes, shakes up, quadruplication. To in system, add the washing of 50ml ethyl acetate not react after completion of the reaction raw material, cyclic washing three times.Revolving is removed Organic phase, by products therefrom as in vacuum drying oven, 50 DEG C of dryings 48 hours, obtain intermediate 32.67g.
Weigh 11.04KPF6Be dissolved in distilled water, 27.23g intermediate is weighed in single-necked flask, leaked with constant pressure addition Bucket is slowly added dropwise KPF6The aqueous solution, stirs 10h under room temperature, static rear solution is divided into two-phase, water above is mutually poured out.Following The slightly yellow clear viscous liquids of organic phase are removed under reduced pressure unreacted raw material, and use distilled water cyclic washing, until using silver nitrate Nothing the presence of Cl ion in aqueous solution inspection cleaning solution, and cleaning solution is stopping washing during neutrality, obtains obtaining final product after purification 4-N, N, dimethyl-N '-two (2- ethylhexyl) carbonyl propyIpyridine hexafluorophosphate, constant weight is dried under vacuum in 70 DEG C, obtain 29.87g.
Embodiment four：
4-N, N, the synthesis of dimethyl-N '-diethyl carbonylethyl pyridine hexafluorophosphate：
By 26.65g diethylamine, 80ml1,2- dichloroethanes and 12.12g triethylamine are added in 500ml there-necked flask, should System is placed in ice salt bath is down to subzero, 35 milliliters of 1,2- dichloroethanes of the chloracetyl chloride being added dropwise over containing 11.2g Solution, controls rate of addition, it is ensured that reaction temperature is maintained within 10 DEG C.Reaction system is transferred to room temperature by completion of dropping, instead Answer 3h.
The hydrochloric acid solution of dropping 100ml 1M is quenched the experiment, standing, split-phase, reservation organic phase；Organic phase is sequentially added 100ml 1M sodium hydroxide solution, 100ml water, 100ml saturated common salt water washing, finally use anhydrous sodium sulfate drying.After suction filtration It is spin-dried for, products therefrom is dry to constant temperature with vacuum drying chamber, obtain product 30.12g, yield 95%.
12.23g 4-N, N- lutidines is added drop-wise in the microwave reaction groove equipped with 15.16g chloroacetamide, stirring Uniformly, then it is put in microwave reactor, 60 DEG C of design temperature, power setting is 300w, reacts five minutes, shakes up, repeatedly four Secondary.To in system, add the washing of 30ml ethyl acetate not react after completion of the reaction raw material, cyclic washing three times.Revolving is removed Organic phase is gone, by products therefrom as in vacuum drying oven, 50 DEG C of dryings 48 hours, obtain intermediate 24.61g.
Weigh 9.31KPF6Be dissolved in distilled water, 13.63g intermediate is weighed in single-necked flask, leaked with constant pressure addition Bucket is slowly added dropwise KPF6The aqueous solution, stirs 10h under room temperature, static rear solution is divided into two-phase, water above is mutually poured out.Following The slightly yellow clear viscous liquids of organic phase are removed under reduced pressure unreacted raw material, and use distilled water cyclic washing, until using silver nitrate Nothing the presence of Cl ion in aqueous solution inspection cleaning solution, and cleaning solution is stopping washing during neutrality, obtains obtaining final product after purification 4-N, N, dimethyl-N '-diethyl carbonylethyl pyridine hexafluorophosphate, constant weight is dried under vacuum in 70 DEG C, obtain 16.21g.

Claims (10)

1. the functionalized ion liquid of lithium extraction is used for, it is characterised in that synthesized by following methods：
With halogen acyl chloride, two replacement amine, 4-N, N- lutidines and Potassium Hexafluorophosphate are raw material, through amidation process, become salt Reaction and exchange reaction obtain the functionalized ion liquid with amide group,
The structural formula of the functionalized ion liquid is：
Wherein, n=2 or 3；R1,R2It is C2～C8Straight chain or the alkane with side chain.
2. the synthetic method of the functionalized ion liquid of lithium extraction is used for, it is characterised in that：With halogen acyl chloride, two replacement amine, 4- N, N- lutidines and Potassium Hexafluorophosphate are raw material, obtain with acid amides through amidation process, salt-forming reaction and exchange reaction The functionalized ion liquid of group,
The structural formula of the functionalized ion liquid is：
Wherein, n=2 or 3；R1,R2It is C2～C8Straight chain or the alkane with side chain.
3. the synthetic method of ionic liquid according to claim 2, it is characterised in that comprise the following steps：
A, with halogen acyl chloride and two replacement amine as initiation material synthesizing halogen acid amides in the presence of acid binding agent；
The reaction of b, halogen acid amide and 4-N, N- lutidines generates halogeno salt intermediate；
There is exchange reaction in c, halogeno salt intermediate and Potassium Hexafluorophosphate, obtain the functionalized ion liquid with amide group.
4. the synthetic method of ionic liquid according to claim 3, it is characterised in that the concrete grammar of step a is：With two Replacement amine is initiation material, is dissolved in solvent, drips halogen acyl chloride, and then purified concentration obtains halogen acid amide.
5. the synthetic method of ionic liquid according to claim 4, it is characterised in that：Two replacement amine and halo in step a The mol ratio of acyl chlorides is 1：(1～1.5).
6. the synthetic method of ionic liquid according to claim 4, it is characterised in that：Described in step a, halogen acyl chloride is Chloro acyl chlorides.
7. the synthetic method of ionic liquid according to claim 4, it is characterised in that：Acid binding agent described in step a is three Ethamine or triethanolamine.
8. the synthetic method of ionic liquid according to claim 3, it is characterised in that in step b, halogen acid amide and 4-N, N- lutidines reacts under microwave condition and obtains halogeno salt intermediate.
9. the synthetic method of ionic liquid according to claim 8, it is characterised in that：Halogen acid amide and 4-N in step b, The mol ratio of N- lutidines is 1：(1～2).
10. the synthetic method of ionic liquid according to claim 8, it is characterised in that：In step c halogeno salt intermediate with The mol ratio of Potassium Hexafluorophosphate is 1：(1～1.2).
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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN108379876A (en) * 2018-05-08 2018-08-10 东莞理工学院 A method of adsorbing lithium salts using adsorbent
CN112479913A (en) * 2020-11-19 2021-03-12 安徽修一制药有限公司 Preparation method of N, N-diethyl chloroacetamide
CN118006901A (en) * 2024-04-08 2024-05-10 内蒙古圣龙大地科技有限公司 Method for recycling metal materials in waste carbon-supported noble metal catalyst by utilizing ionic liquid

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CN103710549A (en) * 2013-12-13 2014-04-09 天津科技大学 Method for efficiently extracting lithium from salt lake brine

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108379876A (en) * 2018-05-08 2018-08-10 东莞理工学院 A method of adsorbing lithium salts using adsorbent
CN108379876B (en) * 2018-05-08 2020-05-19 东莞理工学院 Method for adsorbing lithium salt by using adsorbent
CN112479913A (en) * 2020-11-19 2021-03-12 安徽修一制药有限公司 Preparation method of N, N-diethyl chloroacetamide
CN118006901A (en) * 2024-04-08 2024-05-10 内蒙古圣龙大地科技有限公司 Method for recycling metal materials in waste carbon-supported noble metal catalyst by utilizing ionic liquid

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