CN109369609A - A kind of preparation method of sulfuric acid vinyl ester - Google Patents
A kind of preparation method of sulfuric acid vinyl ester Download PDFInfo
- Publication number
- CN109369609A CN109369609A CN201811300700.7A CN201811300700A CN109369609A CN 109369609 A CN109369609 A CN 109369609A CN 201811300700 A CN201811300700 A CN 201811300700A CN 109369609 A CN109369609 A CN 109369609A
- Authority
- CN
- China
- Prior art keywords
- solution
- reaction
- preparation
- added
- sulfuric acid
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation methods of sulfuric acid vinyl ester, the following steps are included: ethylene glycol is added into the reaction kettle A for fill halogenated hydrocarbon solvent and stirs evenly, thionyl chloride is gradually added dropwise and carries out substitution reaction, de-chlorine hydride is removed by vacuum distillation, reaction solution is washed to neutrality with saturated sodium bicarbonate solution again, it stands, liquid separation obtains ethylene sulfite halohydrocarbon solution；Above-mentioned solution is put into reaction kettle B, potassium dihydrogen phosphate or sodium tungstate is added as catalyst, pH is adjusted by sodium bicarbonate aqueous solution, aqueous sodium hypochlorite solution is added and carries out oxidation reaction.Liquid separation obtains sulfuric acid vinyl ester halogenated alkane solution after completion of the reaction, and n-hexane is added after concentration and is recrystallized, the sulfuric acid vinyl ester of high-purity is obtained by filtration.Above-mentioned preparation method raw material is easy to get, and catalyst is cheap, and product purification is easy, and products obtained therefrom acidity is low, and moisture is low, and purity is high is suitble to large-scale production.
Description
[technical field]
A kind of preparation method of sulfuric acid vinyl ester, belongs to lithium-ion battery electrolytes additive technology field.
[background technique]
With the exacerbation of exhaustion and the environmental pollution of petroleum resources, the new energy electric motor vehicle of lithium-ion-power cell driving at
It for the direction of future automobile development, while being also the commanding elevation that competitively competes of various countries.Wherein ternary NCM and NCA battery have height
Energy density, low cost the features such as, become power lithium-ion battery research hot spot, but its cycle life and high/low temperature circulation and
There is also some defects for storage performance.Sulfuric acid vinyl ester can effectively inhibit lithium as a kind of lithium-ion battery electrolytes additive
The decline of ion battery initial capacity, increases initial discharge capacity, improves the charge-discharge performance of battery, extends battery cycle life,
High temperature performance is compatible, is a kind of excellent lithium-ion battery electrolytes additive.It is reported largely in document and patent at present
Sulfuric acid vinyl ester synthetic method, such as: CN102241662A is disclosed using ruthenium trichloride as catalyst, sodium hypochlorite conduct
Oxidizing ethylene sulfite prepares sulfuric acid vinyl ester, but ruthenium trichloride, as catalyst, catalyst is expensive, accounts for
50% or more product cost, causes product cost to increase considerably.CN106831701A is disclosed using sulfur trioxide and epoxy second
Alkane carries out catalytic addition and prepares sulfuric acid vinyl ester, although the method atom utilization is high, ethylene oxide belongs to high-risk chemistry
Product, sulfur trioxide are highly corrosive.
[summary of the invention]
In view of this, the technical problem to be solved in the present invention is that improvement the deficiencies in the prior art, it is easy to provide a kind of raw material
, catalyst price economy, the reaction time is short, and easy to operate, by-product is less, the high sulfuric acid vinyl ester preparation side of product purity
Method.
In order to achieve the above object, the present invention adopts the following technical scheme:
(1) cyclization: addition halogenated alkane solvents and ethylene glycol into reaction kettle A, 10~20 DEG C of control system temperature,
Thionyl chloride, reaction 2h is added dropwise；After completion of the reaction, it is evaporated under reduced pressure, removes de-chlorine hydride, adding alkaline washing to pH value of solution is 7
~8；Liquid separation, extraction obtain the halogenated alkane solution containing ethylene sulfite, and the halogenated alkane containing ethylene sulfite is molten
Liquid puts into spare in reaction kettle B.
(2) oxidation reaction: catalyst is added into reaction kettle B, and adjusts pH with sodium bicarbonate aqueous solution, controls solution temperature
Aqueous sodium hypochlorite solution is added dropwise in 0~10 DEG C of degree, the reaction was continued 2~5h after being added dropwise.After completion of the reaction, after liquid separation, extraction
Into the halogenated alkane solution containing sulfuric acid vinyl ester, low-temperature reduced-pressure is concentrated into solution saturation, and poor solvent is added and is tied again
Crystalline substance obtains sulfuric acid vinyl ester product after filtering.
Preferably, in the above preparation method, the mass ratio of ethylene glycol and halogenated alkane solvents is 1 in step (1):
0.3~1:2, preferably 1:0.5；The molar ratio of ethylene glycol and thionyl chloride is 1:0.8~1:1.5, preferably 1:1.2.
Preferably, in the above preparation method, the halogenated alkane solvents in the step (1) are methylene chloride, 1,
One of 2- dichloroethanes, chloroform, carbon tetrachloride or multiple combinations.
Preferably, in the above preparation method, reaction temperature is 10~20 DEG C in the step (1), preferably 12
℃。
Preferably, in the above preparation method, the alkaline aqueous solution in the step (1) be sodium bicarbonate solution,
One of sodium carbonate liquor, solution of potassium carbonate or multiple combinations.
Preferably, in the above preparation method, the catalyst in the step (2) is potassium dihydrogen phosphate, sodium tungstate
One or both of combination.
Preferably, in the above preparation method, mole of catalyst and ethylene sulfite in the step (2)
Than for 1:0.001~1:0.08, preferably 1:0.0024.
Preferably, in the above preparation method, pH is adjusted using sodium bicarbonate in the step (2), pH value is 7~
10, preferably 9.
Preferably, in the above preparation method, reaction temperature is 0~10 DEG C, preferably 8 DEG C in the step (2).
Preferably, in the above preparation method, sodium hypochlorite used and sulfurous acid ethylene in the step (2)
The molar ratio of ester is 1:1~1:2.5, preferably 1:2.
Preferably, in the above preparation method, the insulation reaction in the step (2) is that temperature is 0~10 DEG C, excellent
8 DEG C are selected as, the reaction time is 2~5h, preferably 3h.
Preferably, in the above preparation method, low-temperature reduced-pressure vapo(u)rizing temperature is 5~15 DEG C in the step (2), excellent
It is selected as 10~12 DEG C.
Preferably, in the above preparation method, the poor solvent in the step (2) is n-hexane, hexamethylene, stone
Oily ether, ether, preferably one of hexamethylene or multiple combinations.
Preferably, in the above preparation method, vacuum distillation gained solvent can be recycled and carry out rectifying separation, repeat
It utilizes.
Advantages of the present invention are as follows: the preparation method of sulfuric acid vinyl ester of the present invention is easy to get with reaction raw materials, preparation
At low cost, products obtained therefrom purity is high, the advantages such as acid value is low, moisture is low, moderate purity is up to 99.9% or more, acid value≤30ppm, water
Point≤40ppm.Potassium dihydrogen phosphate, sodium tungstate are cheap, and the production cost of DTD can be greatly lowered.
[specific embodiment]
It is as follows that the present invention enumerates embodiment, and illustrated embodiment is used only for helping to understand the present invention, is not intended to limit this
The range of invention.
Embodiment 1:
(1) cyclization: ethylene glycol 100g, methylene chloride 50g are added into reaction kettle A, and temperature of reaction kettle is adjusted
To 12 DEG C, it is added dropwise 230g thionyl chloride, time for adding 30min, after being added dropwise, the reaction was continued 2h.End of reaction is depressurized
Distillation removes the HCl and complete SOCl of unreacted2, add saturated sodium bicarbonate aqueous solution and washed, until solution ph
>=7, liquid separation is carried out, the dichloromethane solution 200g of ethylene sulfite, 160g containing product, yield 92% are obtained.By sulfurous acid
Vinyl acetate dichloromethane solution is transferred to spare in reaction kettle B.
(2) oxidation reaction: methylene chloride 150g being added into reaction kettle B, and 10% potassium dihydrogen phosphate 7.3g is added, and
PH=9 is adjusted using 15% sodium bicarbonate solution, temperature of reaction kettle is down to 8 DEG C, 30% aqueous sodium hypochlorite solution is added dropwise
734.4g, time for adding 1h after sodium hypochlorite is added dropwise, continues insulation reaction 3h and obtain the methylene chloride of sulfuric acid vinyl ester
Solution.Reaction solution is stood, liquid separation, obtain dichloromethane solution, then water phase is extracted with dichloromethane twice, merges methylene chloride
Solution.
(3) it is concentrated under reduced pressure at 10 DEG C and white solid occurs, 300g n-hexane is added and is recrystallized, sulphur is obtained by filtration
Vinyl acetate 115.7g, yield 63%, purity 99.91%, moisture 29ppm, acid value 22ppm.
Embodiment 2:
(1) cyclization: ethylene glycol 100g, methylene chloride 100g are added into reaction kettle A, and temperature of reaction kettle is adjusted
To 12 DEG C, it is added dropwise 250g thionyl chloride, time for adding 30min, after being added dropwise, the reaction was continued 2h.End of reaction is depressurized
Distillation, the SOCl for removing HCl and not reacting completely2, add saturated sodium bicarbonate aqueous solution and washed, until solution ph
>=7, liquid separation is carried out, the dichloromethane solution 210g of ethylene sulfite, 152g containing product, yield 87.3% are obtained.By sulfurous
Vinyl acetate dichloromethane solution is transferred to spare in reaction kettle B.
(2) oxidation reaction: methylene chloride 100g being added into reaction kettle B, and 10% potassium dihydrogen phosphate 0.69g is added,
And pH=9 is adjusted using 15% sodium bicarbonate solution, temperature of reaction kettle is down to 8 DEG C, 30% aqueous sodium hypochlorite solution is added dropwise
697.7g, time for adding 1h, after sodium hypochlorite is added dropwise, the methylene chloride of the reaction was continued 3h obtains sulfuric acid vinyl ester is molten
Liquid.Reaction solution is stood, liquid separation, obtain dichloromethane solution, then water phase is extracted with dichloromethane twice, it is molten to merge methylene chloride
Liquid.
(3) it is concentrated under reduced pressure at 10 DEG C and white solid occurs, 300g n-hexane is added and is recrystallized, sulphur is obtained by filtration
Vinyl acetate 108.1g, yield 61.9%, purity 99.93%, moisture 34ppm, acid value 27ppm.
Embodiment 3:
(1) cyclization: ethylene glycol 100g, methylene chloride 50g are added into reaction kettle A, and temperature of reaction kettle is adjusted
To 12 DEG C, it is added dropwise 230g thionyl chloride, time for adding 30min, after being added dropwise, the reaction was continued 2h.End of reaction is depressurized
Distillation, the SOCl for removing HCl and not reacting completely2, add saturated sodium bicarbonate aqueous solution and washed, until solution ph
>=7, liquid separation is carried out, the dichloromethane solution 203g of ethylene sulfite, 161g containing product, yield 92.4% are obtained.By sulfurous
Vinyl acetate dichloromethane solution is transferred to spare in reaction kettle B.
(2) oxidation reaction: methylene chloride 150g being added into reaction kettle B, and 10% wolframic acid sodium water solution 11.61g is added, and
PH=9 is adjusted using 15% sodium bicarbonate solution, temperature of reaction kettle is down to 8 DEG C, 30% aqueous sodium hypochlorite solution is added dropwise
739.2g, time for adding 1h, after sodium hypochlorite is added dropwise, the methylene chloride of the reaction was continued 3h obtains sulfuric acid vinyl ester is molten
Liquid.Reaction solution is stood, liquid separation, obtain dichloromethane solution, then water phase is extracted with dichloromethane twice, it is molten to merge methylene chloride
Liquid.
(3) it is concentrated under reduced pressure at 10 DEG C and white solid occurs, 300g n-hexane is added and is recrystallized, sulphur is obtained by filtration
Vinyl acetate 106.1g, yield 57.4%, purity 99.90%, moisture 37ppm, acid value 23ppm.
Embodiment 4:
(1) cyclization: ethylene glycol 100g, methylene chloride 50g are added into reaction kettle one, and temperature of reaction kettle is adjusted
To 14 DEG C, it is added dropwise 230g thionyl chloride, time for adding 30min, after being added dropwise, the reaction was continued 2h.End of reaction is depressurized
Distillation, the SOCl for removing HCl and not reacting completely2, add saturated sodium bicarbonate aqueous solution and washed, until solution ph
>=7, liquid separation is carried out, the dichloromethane solution 187g of ethylene sulfite, 143g containing product, yield 82.1% are obtained.By sulfurous
It is spare that vinyl acetate dichloromethane solution is transferred to reaction kettle B.
(2) oxidation reaction: methylene chloride 150g being added into reaction kettle B, 10% wolframic acid sodium water solution 13g is added, and adopt
PH=9 is adjusted with 15% sodium bicarbonate solution, temperature of reaction kettle is down to 8 DEG C, 30% aqueous sodium hypochlorite solution 656.4g is added dropwise,
Time for adding is 1h, and after sodium hypochlorite is added dropwise, the reaction was continued, and 3h obtains the dichloromethane solution of sulfuric acid vinyl ester.It will reaction
Liquid is stood, and liquid separation obtains dichloromethane solution, then water phase is extracted with dichloromethane twice, merges dichloromethane solution.
It is concentrated under reduced pressure at 10 DEG C and white solid occurs, 300g n-hexane is added and is recrystallized, sulfuric acid is obtained by filtration
Vinyl acetate 90.4g, yield 55.1%, purity 99.94%, moisture 34ppm, acid value 25ppm.
The above description is only an embodiment of the present invention, not limits the technical scheme described by the invention, all according to this
The modification or equivalence replacement that description of the invention content is made, should all be included within the scope of protection of the present invention.
Claims (13)
1. a kind of preparation method of sulfuric acid vinyl ester, which comprises the following steps:
(1) cyclization: halogenated alkane solvents and ethylene glycol are added into reaction kettle A, 10~20 DEG C of control system temperature, is added dropwise
Thionyl chloride reacts 2h；After completion of the reaction, it is evaporated under reduced pressure, removes de-chlorine hydride, adding alkaline washing to pH value of solution is 7~8；
Liquid separation, extraction obtain the halogenated alkane solution containing ethylene sulfite, and the halogenated alkane solution containing ethylene sulfite are thrown
Enter spare in reaction kettle B；
(2) oxidation reaction: catalyst is added into reaction kettle B, and adjusts pH with sodium bicarbonate aqueous solution, controls solution temperature 0
~10 DEG C, aqueous sodium hypochlorite solution is added dropwise, the reaction was continued 2~5h after being added dropwise, after completion of the reaction, liquid separation is obtained by extraction and contains
Having in the halogenated alkane solution of sulfuric acid vinyl ester, low-temperature reduced-pressure is concentrated into solution saturation, and poor solvent is added and is recrystallized, row
Sulfuric acid vinyl ester product is obtained after filtering.
2. preparation method according to claim 1, which is characterized in that ethylene glycol and halogenated alkane solvents in step (1)
Mass ratio is 1:0.3~1:2；The molar ratio of ethylene glycol and thionyl chloride is 1:0.8~1:1.5.
3. preparation method according to claim 1, which is characterized in that the halogenated alkane solvents in the step (1) are two
One of chloromethanes, 1,2- dichloroethanes, chloroform or carbon tetrachloride or multiple combinations.
4. preparation method according to claim 1, which is characterized in that reaction temperature is 10~20 DEG C in the step (1).
5. preparation method according to claim 1, which is characterized in that the alkaline aqueous solution in the step (1) is carbonic acid
One or more combinations of hydrogen sodium solution, sodium carbonate liquor, solution of potassium carbonate.
6. preparation method according to claim 1, which is characterized in that the catalyst in the step (2) is biphosphate
Potassium, the combination of sodium tungstate one or two.
7. preparation method according to claim 1, which is characterized in that catalyst and sulfurous acid second in the step (2)
The molar ratio of enester is 1:0.001~1:0.1.
8. preparation method according to claim 1, which is characterized in that pH is adjusted using sodium bicarbonate in the step (2),
PH value is 7~10.
9. preparation method according to claim 1, which is characterized in that reaction temperature is 0~10 DEG C in the step (2).
10. preparation method according to claim 1, which is characterized in that sodium hypochlorite used in the step (2) with
The molar ratio of ethylene sulfite is 1:1~1:2.5.
11. preparation method according to claim 1, which is characterized in that the reaction in the step (2) be temperature be 0~
10 DEG C, the reaction time is 2~5h.
12. preparation method according to claim 1, which is characterized in that in the step (2) vacuum distillation temperature be 5~
15℃。
13. preparation method according to claim 1, which is characterized in that the poor solvent in the step (2) is positive oneself
One of alkane, hexamethylene, petroleum ether, ether or multiple combinations.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811300700.7A CN109369609A (en) | 2018-11-02 | 2018-11-02 | A kind of preparation method of sulfuric acid vinyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811300700.7A CN109369609A (en) | 2018-11-02 | 2018-11-02 | A kind of preparation method of sulfuric acid vinyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109369609A true CN109369609A (en) | 2019-02-22 |
Family
ID=65396908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811300700.7A Pending CN109369609A (en) | 2018-11-02 | 2018-11-02 | A kind of preparation method of sulfuric acid vinyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109369609A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109988145A (en) * | 2019-05-13 | 2019-07-09 | 福建博鸿新能源科技有限公司 | A kind of preparation method of sulfuric acid vinyl ester |
| CN110117297A (en) * | 2019-04-10 | 2019-08-13 | 珠海市赛纬电子材料股份有限公司 | A kind of preparation method of 2- phosphate base sulfuric acid acrylic ester |
| CN111925352A (en) * | 2020-07-09 | 2020-11-13 | 常州孚新睿科新材料有限公司 | Method for synthesizing vinyl sulfate |
| CN115141175A (en) * | 2022-07-04 | 2022-10-04 | 多氟多新材料股份有限公司 | Method for preparing cyclic sulfate |
| CN115536630A (en) * | 2022-11-02 | 2022-12-30 | 新乡市宏蒙新材料有限公司 | Preparation method of ethylene sulfate based on lithium ion battery electrolyte additive |
| CN115677652A (en) * | 2022-11-14 | 2023-02-03 | 陕西煤业化工技术研究院有限责任公司 | Method for continuously preparing vinyl sulfate |
| CN115806540A (en) * | 2022-11-18 | 2023-03-17 | 山东兴文工业技术研究院有限公司 | Preparation method of ethylene sulfite |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101068782A (en) * | 2004-10-13 | 2007-11-07 | 神经研究瑞典公司 | Process for the synthesis of 4-(3-sulfonylphenyl)-piperidines |
| CN102241662A (en) * | 2011-05-06 | 2011-11-16 | 凯莱英医药化学（天津）有限公司 | Synthetic method of thiophene-3-ethanol |
| CN106187989A (en) * | 2016-07-26 | 2016-12-07 | 张家港瀚康化工有限公司 | The preparation method of sulfuric acid vinyl ester |
-
2018
- 2018-11-02 CN CN201811300700.7A patent/CN109369609A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101068782A (en) * | 2004-10-13 | 2007-11-07 | 神经研究瑞典公司 | Process for the synthesis of 4-(3-sulfonylphenyl)-piperidines |
| CN102241662A (en) * | 2011-05-06 | 2011-11-16 | 凯莱英医药化学（天津）有限公司 | Synthetic method of thiophene-3-ethanol |
| CN106187989A (en) * | 2016-07-26 | 2016-12-07 | 张家港瀚康化工有限公司 | The preparation method of sulfuric acid vinyl ester |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110117297A (en) * | 2019-04-10 | 2019-08-13 | 珠海市赛纬电子材料股份有限公司 | A kind of preparation method of 2- phosphate base sulfuric acid acrylic ester |
| CN109988145A (en) * | 2019-05-13 | 2019-07-09 | 福建博鸿新能源科技有限公司 | A kind of preparation method of sulfuric acid vinyl ester |
| CN109988145B (en) * | 2019-05-13 | 2021-05-28 | 福建博鸿新能源科技有限公司 | Preparation method of vinyl sulfate |
| CN111925352A (en) * | 2020-07-09 | 2020-11-13 | 常州孚新睿科新材料有限公司 | Method for synthesizing vinyl sulfate |
| CN115141175A (en) * | 2022-07-04 | 2022-10-04 | 多氟多新材料股份有限公司 | Method for preparing cyclic sulfate |
| CN115141175B (en) * | 2022-07-04 | 2024-02-02 | 多氟多新材料股份有限公司 | Method for preparing cyclic sulfate |
| CN115536630A (en) * | 2022-11-02 | 2022-12-30 | 新乡市宏蒙新材料有限公司 | Preparation method of ethylene sulfate based on lithium ion battery electrolyte additive |
| CN115677652A (en) * | 2022-11-14 | 2023-02-03 | 陕西煤业化工技术研究院有限责任公司 | Method for continuously preparing vinyl sulfate |
| CN115806540A (en) * | 2022-11-18 | 2023-03-17 | 山东兴文工业技术研究院有限公司 | Preparation method of ethylene sulfite |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109369609A (en) | A kind of preparation method of sulfuric acid vinyl ester | |
| CN104447564B (en) | High-purity 4,5-dicyano-2-trifluoromethyl imidazoles and the preparation method of salt thereof | |
| CN109485633A (en) | A kind of preparation method of sulfuric acid vinyl ester | |
| CN109776487A (en) | A kind of preparation method of sulfuric acid vinyl ester | |
| CN106187989A (en) | The preparation method of sulfuric acid vinyl ester | |
| CN109516971A (en) | A kind of synthetic method of LITHIUM BATTERY sulfuric acid vinyl ester | |
| CN111825652A (en) | Method for preparing vinyl sulfate | |
| CN101717348B (en) | Synthesis method of diisopropyl azodiformate | |
| CN111224164B (en) | Preparation method of lithium difluorophosphate | |
| CN114133375B (en) | Synthetic method and application of vinyl sulfate | |
| CN113800485B (en) | Preparation method of lithium bis (fluorosulfonyl) imide | |
| CN112320772A (en) | Preparation method of lithium bis (fluorosulfonyl) imide | |
| CN102515133A (en) | Preparation method of lithium hexafluorophosphate of lithium ion battery electrolyte | |
| WO2017031871A1 (en) | Method for preparing 1,3,6-hexanetricarbonitrile | |
| CN115141175B (en) | Method for preparing cyclic sulfate | |
| CN113912581B (en) | Preparation method of high-purity chloroethylene carbonate | |
| CN217149037U (en) | Vinylene carbonate production system | |
| CN111116429A (en) | Method for synthesizing alkali metal trifluoromethanesulfonate | |
| CN101570337A (en) | Production method of battery- grade lithium fluoride | |
| CN106039964A (en) | Method for desulfurization cogenerating of hydrogen and sulfuric acid | |
| CN113444066A (en) | Preparation method of vinyl sulfate | |
| CN115849410B (en) | Preparation method of alkali metal hexafluorophosphate | |
| CN219156514U (en) | Production system of lithium bis (fluorosulfonyl) imide | |
| CN115448268B (en) | Production method and production system of lithium bis (fluorosulfonyl) imide | |
| CN217756905U (en) | Preparation process system of lithium bis (fluorosulfonyl) imide |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190222 |