CN109912651A - A kind of preparation method of benzyl triphenyl phosphonium chloride phosphine - Google Patents
A kind of preparation method of benzyl triphenyl phosphonium chloride phosphine Download PDFInfo
- Publication number
- CN109912651A CN109912651A CN201910285091.0A CN201910285091A CN109912651A CN 109912651 A CN109912651 A CN 109912651A CN 201910285091 A CN201910285091 A CN 201910285091A CN 109912651 A CN109912651 A CN 109912651A
- Authority
- CN
- China
- Prior art keywords
- benzyl
- triphenyl phosphonium
- phosphonium chloride
- reaction
- benzyl triphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention belongs to technical field of fine, specially a kind of preparation method of benzyl triphenyl phosphonium chloride phosphine.This method is in water and benzyl chloride mixed solution, using triphenylphosphine, benzyl chloride as raw material, exothermic heat of reaction back flow reaction is utilized under certain initial temperature, obtains benzyl triphenyl phosphonium chloride phosphine through stratification, heat preservation liquid separation, mocromembrane filtering, crystallisation by cooling, centrifuge separation, vacuum drying.Present invention process is simple, is swift in response, mild condition, purity is high, high income.Aqueous solvent and excess chlorination benzyl recycle in this method, promote reaction to carry out using exothermic heat of reaction, realize energy-saving and emission-reduction, reduce costs, it is easier to industrialized production.99% or more the benzyl triphenyl phosphonium chloride phosphine content that the present invention synthesizes, reaction yield is up to 98%.
Description
Technical field
The present invention relates to technical field of fine is belonged to, it is related to a kind of preparation process of crosslinked fluororubber promotor, has
Body is a kind of preparation method of benzyl triphenyl phosphonium chloride phosphine.
Background technique
Benzyl triphenyl phosphonium chloride phosphine is a kind of organic chemicals, is mainly used as vulcanizable fluororubber promotor, phase transfer is urged
Agent also acts as medicine, organic synthesis intermediate etc..In recent years, new application is constantly being opened up, demand also by
Year increases.
Currently, its primary synthetic methods is mainly benzyl chloride triphenylphosphine in organic solvent direct synthesis technique, this method is anti-
Acutely, and it should be easy to cause the dissipation of solvent and benzyl chloride, product separates difficulty with raw material, and need repeated recrystallize to improve purity,
Generate dangerous noxious waste pollution environment, and the defect low with energy consumption high yield.Utility model patent
A kind of reflux unit of benzyltriphenylphosphonium chloride is disclosed in CN201621275573.6, the setting of the return tank can be effective
Mitigate that steam in reaction kettle is excessive and the problem that causes reaction kettle internal pressure excessive, but does not have but to the other problems in reaction
There is solution.
Summary of the invention
The present invention against the above technical problems, provides a kind of preparation method of benzyl triphenyl phosphonium chloride phosphine.This method technique
Simply, it is swift in response, mild condition；Obtained product purity is high, high income；No three wastes generates in preparation process, and solvent
Water and recyclable, benzyl chloride also can be recycled.Reaction system in this method takes full advantage of raw material triphenylphosphine and does not dissolve in
The features such as water is soluble in benzyl chloride, and product benzyl triphenyl phosphonium chloride phosphine is highly soluble in water, and benzyl chloride is immiscible with water stratification makes to produce
Object separation；Temperature of reaction system is kept using exothermic heat of reaction, temperature of reaction system is controlled using the reflux of water, avoids temperature
The generation of the excessively high dissipation for causing benzyl chloride and side reaction reduces vent gas treatment step, easy to industrialized production.The present invention closes
At benzyl triphenyl phosphonium chloride phosphine content up to 99% or more, reaction yield is up to 98%.
In order to realize the above goal of the invention, the technical solution of the present invention is as follows:
A kind of preparation method of benzyl triphenyl phosphonium chloride phosphine comprising following steps:
(1) it is pumped by liquid relief and water (recycle-water or mother liquor) and excessive benzyl chloride is added into reaction kettle, be then turned on reaction kettle
Liquid in kettle is heated to 80~85 DEG C by the circulation fluid in collet.
(2) it is slowly added to triphenylphosphine particle through vibrating feeder (conveyer), heat, aqueous-phase reflux control are released in dissolution reaction rapidly
Temperature is lower than 110 DEG C, and benzyl chloride and triphenylphosphine generate benzyl triphenyl phosphonium chloride phosphine and dissolve in water phase, and back flow reaction again is completed in charging
1 hour.
(3) after fully reacting, keep temperature in the kettle in 80~85 DEG C of stratification, upper layer is that organic phase lower layer is water phase,
Lower water is mutually continuously put into tetrafluoro mocromembrane filter, filtered aqueous solution is put into crystallisation by cooling in reaction kettle.The step
In, the aperture of tetrafluoro mocromembrane filter is 0.1~0.5 micron, and temperature is maintained at 80~85 DEG C, and speed is kept stirring in reaction kettle
It is 80-120 revs/min.
(4) after being cooled to room temperature, by water in kettle and benzyl triphenyl phosphonium chloride phosphine mixture, continuously it is put into the centrifugation of tetrafluoro membrane type
It is separated in machine, obtains benzyl triphenyl phosphonium chloride phosphine crude product, centrifuge mother liquor, which returns, to be recycled.Film in tetrafluoro membrane type centrifuge
Aperture be 1~5 micron, enable crystal that cannot penetrate while mother liquor quick separating；The step cannot use traditional cloth-bag type
It is centrifuged pocket, avoids the fiber being mixed on centrifugation pocket in product.
(5) isolated benzyl triphenyl phosphonium chloride phosphine crude product is packed into enamel rocking-turn baking oven, opens water injection vacuum,
95~105 DEG C of Temperature Vacuums are dried to obtain finished product, are distilled to recover aqueous solution and micro benzyl chloride is recycled.It is shaken using enamel
Turning baking oven can effectively avoid product and benzyl chloride to corrosion of metal, avoid the water and chlorine of bringing impurity and pollution recycling in product into
Change benzyl；Vacuum drying purpose mainly removes water and micro benzyl chloride, and water injection vacuum suction amount is big effectively to avoid steam
Reflux can effectively remove water and micro benzyl chloride at a temperature of 95~105 DEG C, while avoid that temperature is excessively high to cause product to play group's drop
The risk of low product quality.
Reaction in this preparation method carries out in two stages, and the first stage is the electric heating liter in reacting kettle jacketing
For temperature to 80~85 DEG C, which reaches triphenylphosphine and benzyl chloride fast reaction minimum temperature；Second stage is to pass through triphenyl
Phosphine and benzyl chloride exothermic heat of reaction make water temperature rising reflux, play promotion reaction carry out and meanwhile control temperature of reaction system be lower than 110 DEG C,
It in this way can be to avoid the generation of dissipation and the side reaction of organic gas.
It is that sterling benzyl chloride and recycling benzyl chloride mix that benzyl chloride is used in the production technology of triallyl cyanurate
Object.In the present invention, under conditions of aqueous phase solvent, triphenylphosphine and benzyl chloride are reacted, liquid separation separation is stood by heat preservation
Lower layer's water phase is obtained, the weight of benzyl chloride is 2-3 times of triphenylphosphine weight, and the weight of water is 4-5 times of triphenylphosphine weight,
The ratio enables triphenylphosphine rapid dispersion to react, while the benzyl triphenyl phosphonium chloride phosphine generated can dissolve in rapidly water phase.
In order to inhibit decomposition reaction (it reduces yield), reactant is quickly sufficiently mixed, to will be equivalent to overall reaction
The addition time of the largest portion of time is maintained at minimum limit.(time of reactant is added in the total overall reaction time in benzyl chloride
With the time of subsequent reactions) it is preferably more than 3 hours, and preferably smaller than 2 hours.
In view of high reaction enthalpy, in order to realize the shorter reaction time, need strong inverse flow cooling, such as with cooling industrial
Brine-cooled.At industrial scale, special by the external cooling circuit removing heat with suitable heat exchanger and circulating pump
Effectively.
Preferably, 80~85 DEG C of stratification, upper layer are that organic phase lower layer is water phase after reaction, by lower layer's water phase
It is continuously put into 80~85 DEG C of heat preservation of tetrafluoro mocromembrane filter, product crystallization is prevented to be precipitated and water rapid evaporation, temperature preferably 85
℃；Filtered aqueous solution is put into cooling in reaction kettle and is kept stirring 80-120 revs/min of stirred crystallization, keeps away precipitation fine crystals
Exempt from package phenomenon occur, preferably stirs 100 revs/min.
In this application, about the selection of raw material: selecting recycling of the water phase instead of Organic chemical solvents, benzyl chloride
For the mixture of sterling benzyl chloride and recycling benzyl chloride, production cost is reduced, product yield is improved；Triphenylphosphine is preferably straight
Diameter is 1~5 millimeter of roundlet variole pelletized product, can quickly immersed in liquid level be reacted, and avoids generating dust pollution during charging.It is former
The change of material improves worker's production operation environment, reduces the harm to environment.
In solid-liquid reaction: excessive benzyl chloride being added in reaction kettle, excessive benzyl chloride can guarantee that triphenylphosphine has reacted
Entirely, it is slowly added to triphenylphosphine through vibrating feeder (conveyer), generates benzyl triphenyl phosphonium chloride phosphine.Benzyl chloride room temperature is liquid, triphenyl
Phosphine room temperature is solid particle, and solid-liquid directly sufficiently reacts, and excessive benzyl chloride is used as the purposes of reactant and organic solvent simultaneously,
Possibility is provided to recycle.
Liquid separation purifying process: product is dissolved in 80~85 DEG C of aqueous solutions after the reaction was completed, and benzyl chloride and aqueous solution occur
Obvious layering, and aqueous solution specific gravity is larger in lower part.Aqueous solution by kettle inside holding at 80~85 DEG C is continuously put into collet guarantor
Tetrafluoro column core type filter of the temperature at 80~85 DEG C, aqueous solution become clear by 0.1~0.5 micron of tetrafluoro filter membrane；
Crystallisation by cooling under 80-120 revs/min of stirring, is precipitated microlite in crystallization kettle, and avoiding coarse crystal package influences quality.
Centrifugal separation process: after being cooled to room temperature, by water in kettle and benzyl triphenyl phosphonium chloride phosphine mixture, four are continuously put into
Fluorine film formula centrifuge, the aperture of film is 1~5 micron herein, enables crystal that cannot penetrate while mother liquor quick separating；Without using biography
The cloth-bag type of system is centrifuged pocket, avoids the fiber being mixed on centrifugation pocket in product.
Vacuum drying process: benzyl triphenyl phosphonium chloride phosphine crude product is packed into enamel rocking-turn baking oven, water injection vacuum is opened, 95
~105 DEG C of Temperature Vacuums are dried to obtain finished product, recycle aqueous solution and micro benzyl chloride is recycled.Use enamel rocking-turn baking oven
It can effectively avoid product and benzyl chloride to corrosion of metal, avoid the water and benzyl chloride of bringing impurity and pollution recycling in product into；
Vacuum drying purpose mainly removes water and micro benzyl chloride, and water injection vacuum suction amount is big effectively to avoid opposing steam flow,
Water and micro benzyl chloride can be effectively removed at a temperature of 95~105 DEG C, at the same avoid temperature it is excessively high cause product rise group reduce produce
The risk of product quality.
Compared with prior art, the invention has the benefit that
(1) present invention has simple process, is swift in response, mild condition, purity is high, high income.
(2) present invention is using the mixed system of benzyl chloride and water as reaction solution, so that reaction product is easier to separate,
The reaction time is shortened, yield is improved, reaction system self-heat generation is made full use of to reduce energy consumption, has step simple, effect
The advantages such as rate is high, and product cost is low.
(3) the advantages that aqueous solvent and excess chlorination benzyl recycle, and promote reaction to carry out using exothermic heat of reaction, realizes
Energy-saving and emission-reduction reduce costs, easy to industrialized production.
(4) compared with the method being currently known, this method is easy to implement, and technology complexity is lower, while without the three wastes
Problem and re-crystallization step.
(5) the benzyl triphenyl phosphonium chloride phosphine content that synthesizes of the present invention is 99% or more, and reaction yield is up to 98%.
Specific embodiment
Below by embodiment, the present invention is described in further detail, but protection scope of the present invention is not limited to
This specific embodiment.The present invention expands to any new feature disclosed in the present specification or any new combination, and drapes over one's shoulders
The step of any new method or process of dew or any new combination.
Embodiment 1:
A kind of preparation method of benzyl triphenyl phosphonium chloride phosphine comprising following steps:
Have by the 1000L enamel reaction still of collet heating and sub-cooled return pipe, 400.0 kg water of initial loading (are returned
With mother liquor), the benzyl chloride of 200.0kg (excessive 314%)；Stirring is opened, solution temperature in kettle is heated to 85 DEG C by collet heating
Collet stops heating afterwards.Then it is initially added into 100.0 kg graininess triphenylphosphine in total, is slowly added to through vibrating feeder (conveyer), it is fast
Heat is released in instant solution reaction, and aqueous-phase reflux controls temperature in the kettle, generates benzyl triphenyl phosphonium chloride phosphine, and it is about 60 that the time, which is always added,
Minute.In order to convert completely, collet heating is opened, keeps continuing to be stirred to react 30 points for 80~85 DEG C of fluid temperature in reaction kettle
Clock, it is rear to stop stirring and continue to keep in kettle 80~85 DEG C of fluid temperature 30 minutes, lower water is mutually continuously put into jacket heat-preservation and is existed
In 80~85 DEG C of tetrafluoro column core type filter, aqueous solution becomes clear by 0.2 micron of tetrafluoro filter membrane；In crystallization kettle
Middle stirring crystallisation by cooling, mixing speed are 100 revs/min, and microlite is precipitated.After being cooled to room temperature, by water in kettle and benzyl triphen
Base phosphonium chloride mixture is continuously put into tetrafluoro membrane type centrifuge, and the aperture of film is 2 microns herein；Benzyl triphenyl phosphonium chloride phosphine is thick
Product are packed into enamel rocking-turn baking oven, open water injection vacuum, dry in 95~105 DEG C of Temperature Vacuums, recycle aqueous solution and micro
Benzyl chloride is recycled, and reaction obtains 145.59 kilograms of finished product, yield 98.59%, purity 99.23%.
Embodiment 2:
The preparation of benzyl triphenyl phosphonium chloride phosphine is carried out using method similarly to Example 1, difference is that water is added in original measurement
Amount be 500 kilograms (reuse mother liquor).After specified reaction process and condition are handled in embodiment 1, reaction obtains finished product
144.86 kilograms, the yield of benzyl triphenyl phosphonium chloride phosphine product is 98.08%, purity 99.61%.
Comparative example 1:
The preparation of benzyl triphenyl phosphonium chloride phosphine is carried out using the reaction process and condition specified in embodiment 1, difference is initial
The amount of metered water is 300 kilograms (reuse mother liquor).There is crystal precipitation in reaction process, portioned product is removed by organic filter membrane
Fall, obtains 134.38 kilograms of finished product, yield 91.27%, purity 99.29%.
Comparative example 2:
Specified reaction process and condition processing carry out the preparation of benzyl triphenyl phosphonium chloride phosphine in embodiment 1, and difference is chlorine
Change benzyl is 100kg, only excess 107%.Benzyl chloride is by after Aqueous dispersions, and triphenylphosphine cannot be sufficiently in contact with it, in reaction process
Triphenylphosphine is unable to rapid dispersion reaction, and organic layer has muddiness, it was demonstrated that part triphenylphosphine fails fully reacting, obtains finished product
116.65. kilogram, yield 79.54%, purity 96.38%.
Example described above is only the preferred embodiment of this patent, but the protection scope of this patent is not limited thereto.
It should be pointed out that for those skilled in the art, under the premise of not departing from this patent principle, specially according to this
The technical solution and its inventional idea of benefit, can also make several improvements and modifications, these improvements and modifications also should be regarded as this specially
The protection scope of benefit.
Claims (6)
1. a kind of preparation method of benzyl triphenyl phosphonium chloride phosphine, it is characterised in that the following steps are included:
(1) recycle-water or mother liquor are added into reaction kettle, adds benzyl chloride, the circulation fluid being then turned in reacting kettle jacketing,
Liquid in kettle is heated to 80~85 DEG C；
(2) it is slowly added to triphenylphosphine particle through vibrating feeder (conveyer), heat is released in dissolution reaction rapidly, and aqueous-phase reflux controls solution
Temperature is lower than 110 DEG C, and benzyl chloride and triphenylphosphine generate benzyl triphenyl phosphonium chloride phosphine and dissolve in water phase, and back flow reaction again is completed in charging
1 hour；
(3) after fully reacting in step (2), temperature in the kettle stratification under conditions of 80~85 DEG C is kept, upper layer is to have
Machine phase, lower layer are water phase, and lower water is mutually continuously put into the filtering of tetrafluoro mocromembrane filter, and filtered aqueous solution is put into reaction kettle
Middle cooling and stirring crystallizes, and is kept stirring 80-120 revs/min in cooling and stirring crystallization process；
(4) it after water in kettle and benzyl triphenyl phosphonium chloride phosphine mixture are cooled to room temperature, is continuously put into tetrafluoro membrane type centrifuge
Separation obtains benzyl triphenyl phosphonium chloride phosphine crude product, and centrifuge mother liquor, which returns, to be recycled；
(5) isolated benzyl triphenyl phosphonium chloride phosphine crude product is packed into enamel rocking-turn baking oven, opens water injection vacuum, 95~
105 DEG C of Temperature Vacuums are dried to obtain finished product, are distilled to recover aqueous solution and micro benzyl chloride is recycled.
2. the preparation method of benzyl triphenyl phosphonium chloride phosphine according to claim 1, it is characterised in that: the weight of benzyl chloride is three
2-3 times of Phenylphosphine weight, the weight of water are 4-5 times of triphenylphosphine weight.
3. the preparation method of benzyl triphenyl phosphonium chloride phosphine according to claim 1, it is characterised in that: in step (3), tetrafluoro is micro-
The temperature of membrane filter is kept for 80~85 DEG C, and the aperture of tetrafluoro mocromembrane filter is 0.1~0.5 micron.
4. the preparation method of benzyl triphenyl phosphonium chloride phosphine according to claim 1, it is characterised in that: in step (3), cooling is stirred
Mixing and being kept stirring speed in crystallization process is 80-120 revs/min.
5. the preparation method of benzyl triphenyl phosphonium chloride phosphine according to claim 1, it is characterised in that step (4) tetrafluoro membrane type from
The aperture of film is 1~5 micron in scheming.
6. the preparation method of benzyl triphenyl phosphonium chloride phosphine according to claim 1, it is characterised in that: entire reaction time limitation
In 3 hours, the entire reaction time includes the time that reactant is added into phosphonium chloride and the time of subsequent reactions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910285091.0A CN109912651B (en) | 2019-04-10 | 2019-04-10 | Preparation method of benzyltriphenylphosphonium chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910285091.0A CN109912651B (en) | 2019-04-10 | 2019-04-10 | Preparation method of benzyltriphenylphosphonium chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109912651A true CN109912651A (en) | 2019-06-21 |
| CN109912651B CN109912651B (en) | 2021-09-07 |
Family
ID=66969270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910285091.0A Active CN109912651B (en) | 2019-04-10 | 2019-04-10 | Preparation method of benzyltriphenylphosphonium chloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109912651B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114380670A (en) * | 2022-02-25 | 2022-04-22 | 浙江皇马科技股份有限公司 | Refining method for reducing content and smell of benzyl halide in benzyl ether |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108676029A (en) * | 2018-05-22 | 2018-10-19 | 河南大学 | The double trifluoromethanesulfonimide ionic liquids of Bian bases triphenyl phosphonium, synthetic method and its application as metal inhibitor |
-
2019
- 2019-04-10 CN CN201910285091.0A patent/CN109912651B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108676029A (en) * | 2018-05-22 | 2018-10-19 | 河南大学 | The double trifluoromethanesulfonimide ionic liquids of Bian bases triphenyl phosphonium, synthetic method and its application as metal inhibitor |
Non-Patent Citations (3)
| Title |
|---|
| BARBARA DE FILIPPIS ET AL: "Structural development studies of PPARs ligands based on tyrosine scaffold", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
| WANG, MAW LING ET AL: "Kinetic study of the reaction of benzyl chloride with triphenylphosphine to synthesize benzyltriphenylphosphonium chloride under water extraction", 《JOURNAL OF CHEMICAL ENGINEERING OF JAPAN》 * |
| WANG, MAW LING ET AL: "Kinetic study of the substitution reaction of benzyl chloride with triphenylphosphine to synthesize benzyltriphenylphosphonium chloride. Solvent effects", 《INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114380670A (en) * | 2022-02-25 | 2022-04-22 | 浙江皇马科技股份有限公司 | Refining method for reducing content and smell of benzyl halide in benzyl ether |
| CN114380670B (en) * | 2022-02-25 | 2023-08-08 | 浙江皇马科技股份有限公司 | Refining method for reducing benzyl halide content and smell in benzyl ether |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109912651B (en) | 2021-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102174040B (en) | Preparation method of electronic grade triglycidyl isocyanurate | |
| CN102775364B (en) | Preparation method of cross linking agent triallyl isocyanurate | |
| CN105271347B (en) | Method for preparing high-purity barium salt by using witherite-barytocalcite industrial waste residues | |
| CN106699831B (en) | A method of liquid crystal cholesterol is prepared using lanolin using complexometry | |
| JP2014530160A (en) | Magnesium sulfate | |
| CN102807497A (en) | Method for recovering chloroacetic acid method glycine catalyst methenamine | |
| CN109912651A (en) | A kind of preparation method of benzyl triphenyl phosphonium chloride phosphine | |
| CN107573248A (en) | The recovery method of resolving agent R phenyl ethylamines in prepared by R-DHLA | |
| CN107673979A (en) | The recoverying and utilizing method of halogenation short chain quaternary ammonium waste salt | |
| JP2931621B2 (en) | Glycine and Glauber's salt recovery from crystal effluent | |
| CN102746134A (en) | Method for decreasing content of sodium chloride impurities in recovered sodium formate | |
| CN112010792B (en) | Production method of high-purity diphenyl sulfone | |
| CN112079793B (en) | Refining process and equipment for mass production of bentazone | |
| CN111233624B (en) | Water evaporation-extraction separation extraction method for 1-bromoadamantane production | |
| CN108299538B (en) | Method for removing isoursodesoxycholic acid in duck bile | |
| CN108264457A (en) | A kind of preparation method of potassium acetate | |
| CN113480574B (en) | Recycling method of phosphorus-containing compound salt | |
| WO2023142026A1 (en) | Lithium bis(fluorosulfonyl)imide and preparation method therefor, electrolyte, and secondary battery | |
| CN107382380A (en) | A kind of method that biological potassium fertilizer is prepared using plant ash | |
| RU2196734C2 (en) | Method of production of potassium chloride | |
| CN101633596B (en) | Refining method of biphenyl functioning as addition agent of non-aqueous electrolyte | |
| AU591361B2 (en) | Process for the production of zirconium sulphate | |
| CN115141160A (en) | Preparation method of 2-thiazolidinone | |
| JP2023507342A (en) | An integrated process for producing bis(fluorosulfonyl)imides | |
| CN1037763C (en) | Method for preparation of pure cupric sulfate by using copper-contained waste liquid from preparation of guaiacol and treatment method for its waste liquid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |