CN114105938A - Preparation method of vinyl sulfate for lithium battery - Google Patents
Preparation method of vinyl sulfate for lithium battery Download PDFInfo
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- CN114105938A CN114105938A CN202111304960.3A CN202111304960A CN114105938A CN 114105938 A CN114105938 A CN 114105938A CN 202111304960 A CN202111304960 A CN 202111304960A CN 114105938 A CN114105938 A CN 114105938A
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- C07—ORGANIC CHEMISTRY
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- 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
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- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
- B01J27/19—Molybdenum
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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Abstract
The invention discloses a preparation method of vinyl sulfate for a lithium battery, relating to the technical field of lithium ion batteries. Therefore, the vinyl sulfate containing heteropoly blue lithium salt prepared by the invention can be directly used as an electrolyte additive.
Description
Technical Field
The invention belongs to the technical field of lithium ion batteries, and particularly relates to a preparation method of vinyl sulfate for a lithium battery.
Background
Lithium ion batteries are common secondary batteries in the market and mainly compriseThe application range is on power batteries, energy storage batteries and 3C products. Lithium ion batteries operate primarily by movement of lithium ions between a positive electrode and a negative electrode. During charging and discharging, Li+Do and do go between two electrodes, Li during charging+The lithium ion battery is extracted from the positive electrode and is inserted into the negative electrode through the electrolyte, and the negative electrode is in a lithium-rich state; the opposite is true during discharge.
The electrolyte of the lithium ion battery is one of main materials of the lithium ion battery, determines the electrical property of lithium ions as other main materials of the lithium ion battery, and is an indispensable important part in the material link of the lithium ion battery. The electrolyte of the lithium battery is a carrier for ion transmission in the battery, generally consists of lithium salt and an organic solvent, plays a role in conducting ions between the positive electrode and the negative electrode of the lithium battery, and is a guarantee for the lithium battery to obtain the advantages of high voltage, high specific energy and the like.
The lithium ion battery electrolyte is a core material of the lithium ion battery, wherein the vinyl sulfate is an important additive of the lithium ion battery electrolyte. In the prior art, the preparation method of the vinyl sulfate basically aims at preparing general vinyl sulfate, and there is no method specially for preparing the vinyl sulfate suitable for the lithium ion electrolyte additive, and the vinyl sulfate prepared by the existing preparation method of the vinyl sulfate contains a certain amount of impurities, and further impurity removal is needed when the vinyl sulfate is applied to the lithium battery electrolyte, and then necessary lithium salt and the like need to be added again according to the preparation requirement of the lithium battery so as to meet the use requirement.
Disclosure of Invention
The invention aims to provide a preparation method of vinyl sulfate for a lithium battery aiming at the defects of the prior art, wherein heteropoly blue lithium salt subjected to deprotonation treatment and vinyl sulfite are used as preparation raw materials, and a vinyl sulfite additive containing heteropoly blue lithium salt and suitable for lithium ion battery electrolyte is directly prepared.
The invention provides a preparation method of vinyl sulfate for a lithium battery, which comprises the following steps:
deprotonation of the polyacid, the anion of the polyacid containing more protons for lithium ionFor the sub-electrolyte, protons will combine with fluoride ions in the electrolyte to form hydrofluoric acid, causing a chain reaction that is detrimental to the performance of the lithium ion battery, and thus the polyacid needs to be deprotonated to have H3XY12O40Or H4XY12O40Reacting the polyacid with a lithium hydroxide solution, and drying the solid obtained by the reaction at the temperature of 40-60 ℃ to obtain heteropoly blue lithium salt Li3XY12O40Or Li4XY12O40Wherein, X is Si or P, Y is W or Mo;
a step of synthesizing ethylene sulfite, namely adding dichloromethane into a stainless steel reaction kettle at a reaction temperature of 0-3 ℃, adding ethylene glycol into the dichloromethane, and then dropwise adding thionyl chloride; then keeping the reaction kettle at room temperature for reacting for 4 hours, adding triethylamine into the reaction kettle, continuing to react for 3 hours, carrying out suction filtration on the reaction kettle after the reaction is finished, carrying out reduced pressure distillation on the filtrate obtained by the suction filtration to recover dichloromethane in the solvent, wherein the rest part of the solvent is the ethylene sulfite;
a step of synthesizing vinyl sulfate, namely, deprotonating the polyacid lithium salt obtained in the step of deprotonating the polyacid and synthesizing the vinyl sulfite obtained in the step of synthesizing the vinyl sulfite according to the mass ratio of 1: 2, adding the mixture into dichloromethane recovered in the step of synthesizing the vinyl sulfite, reacting at room temperature for 8 hours, removing the dichloromethane by reduced pressure distillation after the reaction is finished to obtain residual solid, and recrystallizing the residual solid to obtain the vinyl sulfite containing the heteropolyblue lithium salt.
Preferably, in the step of synthesizing the vinyl sulfite, the ethylene glycol is added to the methylene chloride in a ratio of 20 g per 100 ml of the methylene chloride.
Furthermore, in the step of synthesizing the ethylene sulfite, the thionyl chloride is added dropwise at a ratio of 50 g per 100 ml of dichloromethane.
More preferably, in the step of synthesizing the ethylene sulfite, the thionyl chloride is added dropwise into the reaction kettle at a speed of not more than 1 g per thionyl chloride drop.
More specifically, in the step of synthesizing the ethylene sulfite, the triethylamine is added into the reaction kettle in a proportion of 40 g of triethylamine per 100 ml of dichloromethane.
Compared with the prior art, the method adopted by the invention is that a strong oxidant polyacid lithium salt is used as a material for oxidizing the ethylene sulfite, the polyacid lithium salt is reduced into the heteropolyblue lithium salt by the ethylene sulfite while being used as the oxidant for oxidizing the ethylene sulfite, the heteropolyblue lithium salt is used as an accessory product and coexists with the ethylene sulfate, but the heteropolyblue lithium salt can be used as electrolyte salt and the ethylene sulfate to be simultaneously used in the electrolyte without removing impurities. Therefore, the vinyl sulfate containing heteropoly blue lithium salt prepared by the invention can be directly used as an electrolyte additive.
Detailed Description
The technical solutions for achieving the objects of the present invention are further illustrated by the following specific examples, and it should be noted that the technical solutions claimed in the present invention include, but are not limited to, the following examples.
Example 1
Embodiment 1 discloses a method for preparing vinyl sulfate for a lithium battery, which includes the following steps:
deprotonation of the polyacid H3PMo12O40And lithium hydroxide solution according to the mass ratio of 1: 3, fusing and reacting, and drying the obtained solid at the temperature of 40-60 ℃ to obtain heteropoly blue lithium salt Li3 PMo12O40。
And a step of synthesizing the ethylene sulfite, namely adding 400 ml of dichloromethane into a stainless steel reaction kettle at the reaction temperature of 0-3 ℃, adding 80 g of ethylene glycol into the dichloromethane, slowly dropwise adding 200 g of thionyl chloride, keeping the reaction kettle at room temperature for reacting for 4 hours, adding 160 g of triethylamine into the reaction kettle, continuing to react for 3 hours, performing suction filtration to obtain filtrate, performing reduced pressure distillation, recovering the dichloromethane in the solvent, and taking the rest as the ethylene sulfite.
Vinyl sulfate Synthesis step of obtaining the above-mentionedEthylene sulfite and lithium heteropolyblue salt Li3PMo12O40According to the mass ratio of 1: 2 to methylene chloride recovered as a solvent, and reacted at room temperature for 8 hours, the solvent methylene chloride was distilled off under reduced pressure, and the resulting solid was recrystallized to obtain vinyl sulfate containing heteropolyblue lithium salt of example 1.
Example 2
Embodiment 2 discloses a method for preparing vinyl sulfate for a lithium battery, which includes the following steps:
deprotonation of the polyacid H3PW12O40And lithium hydroxide solution according to the mass ratio of 1: 3, fusing and reacting, and drying the obtained solid at the temperature of 40-60 ℃ to obtain heteropoly blue lithium salt Li3 PW12O40.
And a step of synthesizing the ethylene sulfite, namely adding 400 ml of dichloromethane into a stainless steel reaction kettle at the reaction temperature of 0-3 ℃, adding 80 g of ethylene glycol into the dichloromethane, slowly dropwise adding 200 g of thionyl chloride, keeping the reaction kettle at room temperature for reacting for 4 hours, adding 160 g of triethylamine into the reaction kettle, continuing to react for 3 hours, performing suction filtration to obtain filtrate, performing reduced pressure distillation, recovering the dichloromethane in the solvent, and taking the rest as the ethylene sulfite.
A step of synthesizing vinyl sulfate, namely synthesizing the obtained vinyl sulfite and heteropolyblue lithium salt Li3PW12O40According to the mass ratio of 1: 2 to dichloromethane, and reacted at room temperature for 8 hours, the solvent dichloromethane was distilled off under reduced pressure, and the resulting solid was recrystallized to obtain vinyl sulfate containing heteropolyblue lithium salt of example 2.
Example 3
Embodiment 3 discloses a method for preparing vinyl sulfate for a lithium battery, which includes the following steps:
deprotonation of the polyacid H4SiW12O40And lithium hydroxide solution according to the mass ratio of 1: 4, fusing for reaction, and carrying out solid reaction at the temperature of 40-60 DEG CDrying to obtain heteropoly blue lithium salt Li4SiW12O40.
And a step of synthesizing the ethylene sulfite, namely adding 400 ml of dichloromethane into a stainless steel reaction kettle at the reaction temperature of 0-3 ℃, adding 80 g of ethylene glycol into the dichloromethane, slowly dropwise adding 200 g of thionyl chloride, keeping the reaction kettle at room temperature for reacting for 4 hours, adding 160 g of triethylamine into the reaction kettle, continuing to react for 3 hours, performing suction filtration to obtain filtrate, performing reduced pressure distillation, recovering the dichloromethane in the solvent, and taking the rest as the ethylene sulfite.
A step of synthesizing vinyl sulfate, namely synthesizing the obtained vinyl sulfite and heteropolyblue lithium salt Li4SiW12O40According to the mass ratio of 1: 2 to methylene chloride as a solvent, and reacted at room temperature for 8 hours, the methylene chloride as the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized to obtain vinyl sulfate containing lithium heteropolyblue salt of example 3.
Example 4
Embodiment 4 discloses a method for preparing vinyl sulfate for a lithium battery, which includes the following steps:
deprotonation of the polyacid H3SiMo12O40And lithium hydroxide solution according to the mass ratio of 1: 4, reacting, drying the obtained solid at the temperature of 40-60 ℃ to obtain heteropoly blue lithium salt Li3SiMo12O40.
And a step of synthesizing the ethylene sulfite, namely adding 400 ml of dichloromethane into a stainless steel reaction kettle at the reaction temperature of 0-3 ℃, adding 80 g of ethylene glycol into the dichloromethane, slowly dropwise adding 200 g of thionyl chloride, keeping the reaction kettle at room temperature for reacting for 4 hours, adding 160 g of triethylamine into the reaction kettle, continuing to react for 3 hours, performing suction filtration to obtain filtrate, performing reduced pressure distillation, recovering the dichloromethane in the solvent, and taking the rest as the ethylene sulfite.
A step of synthesizing vinyl sulfate, namely synthesizing the obtained vinyl sulfite and heteropolyblue lithium salt Li3SiMo12O40According to the mass ratio of 1: 2 to methylene chloride as a solvent, and reacted at room temperature for 8 hours, the methylene chloride as the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized to obtain vinyl sulfate containing lithium heteropolyblue salt of example 4.
Comparative example 1
Comparative example 1 discloses a method for preparing vinyl sulfate for a lithium battery, comprising the steps of:
and a step of synthesizing the ethylene sulfite, namely adding 400 ml of dichloromethane into a stainless steel reaction kettle at the reaction temperature of 0-3 ℃, adding 80 g of ethylene glycol into the dichloromethane, slowly dropwise adding 200 g of thionyl chloride, keeping the reaction kettle at room temperature for reacting for 4 hours, adding 160 g of triethylamine into the reaction kettle, continuing to react for 3 hours, performing suction filtration to obtain filtrate, performing reduced pressure distillation, recovering the dichloromethane in the solvent, and taking the rest as the ethylene sulfite.
A step of synthesizing vinyl sulfate, namely, mixing the vinyl sulfite and dibenzoyl peroxide obtained in the step of synthesizing the vinyl sulfite according to the mass ratio of 1: 2 to dichloromethane, and reacted at room temperature for 8 hours, the dichloromethane solvent was distilled off under reduced pressure, and the resulting solid was recrystallized to obtain vinyl sulfate of comparative example 1.
The vinyl sulfates obtained in examples 1 to 4 and comparative example 1 were subjected to purity and content testing of lithium salt of heteropolyblue, the results of which are shown in table 1 below:
TABLE 1
As can be seen from Table 1, the purity of the vinyl sulfate prepared by the method can reach or even exceed that of the vinyl sulfate prepared by the prior art, and the impurities contained in the vinyl sulfate are heteropoly blue lithium salt substances which are just additives and compositions required in the electrolyte for preparing the lithium battery, namely, for the preparation of the lithium battery electrolyte, the vinyl sulfate prepared by the method of the invention has no impurities influencing the effect of the electrolyte, and is very suitable for the preparation of the lithium battery electrolyte.
Claims (5)
1. A preparation method of vinyl sulfate for a lithium battery is characterized by comprising the following steps:
deprotonation of the polyacid in the presence of H3XY12O40Or H4XY12O40Reacting the polyacid with a lithium hydroxide solution, and drying the solid obtained by the reaction at the temperature of 40-60 ℃ to obtain heteropoly blue lithium salt Li3XY12O40Or Li4XY12O40Wherein, X is Si or P, Y is W or Mo;
a step of synthesizing ethylene sulfite, namely adding dichloromethane into a stainless steel reaction kettle at a reaction temperature of 0-3 ℃, adding ethylene glycol into the dichloromethane, and then dropwise adding thionyl chloride; then keeping the reaction kettle at room temperature for reacting for 4 hours, adding triethylamine into the reaction kettle, continuing to react for 3 hours, carrying out suction filtration on the reaction kettle after the reaction is finished, carrying out reduced pressure distillation on the filtrate obtained by the suction filtration to recover dichloromethane in the solvent, wherein the rest part of the solvent is the ethylene sulfite;
a step of synthesizing vinyl sulfate, namely, deprotonating the polyacid lithium salt obtained in the step of deprotonating the polyacid and synthesizing the vinyl sulfite obtained in the step of synthesizing the vinyl sulfite according to the mass ratio of 1: 2, adding the mixture into dichloromethane recovered in the step of synthesizing the vinyl sulfite, reacting at room temperature for 8 hours, removing the dichloromethane by reduced pressure distillation after the reaction is finished to obtain residual solid, and recrystallizing the residual solid to obtain the vinyl sulfite containing the heteropolyblue lithium salt.
2. The method of claim 1, wherein the vinyl sulfate is selected from the group consisting of: in the step of synthesizing the ethylene sulfite, the ethylene glycol is added into the dichloromethane in a ratio of 20 g per 100 ml of dichloromethane.
3. The method of claim 1 or 2, wherein the vinyl sulfate is selected from the group consisting of: in the step of synthesizing the ethylene sulfite, 50 g of thionyl chloride is dropwise added to every 100 ml of dichloromethane in the proportion of dropwise adding the thionyl chloride.
4. The method of claim 3, wherein the vinyl sulfate is selected from the group consisting of: in the step of synthesizing the ethylene sulfite, the thionyl chloride is dripped into the reaction kettle at the speed that the weight of each thionyl chloride drop is not more than 1 g.
5. The method of claim 1 or 2, wherein the vinyl sulfate is selected from the group consisting of: in the step of synthesizing the ethylene sulfite, the triethylamine is added into a reaction kettle in a proportion that 40 g of triethylamine is added into every 100 ml of dichloromethane.
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Citations (3)
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| JP2009285583A (en) * | 2008-05-29 | 2009-12-10 | Sanyo Chem Ind Ltd | Catalyst for oxidation reaction |
| CN102983362A (en) * | 2012-12-20 | 2013-03-20 | 中国东方电气集团有限公司 | Low-temperature electrolyte for LiFePO4 (lithium iron phosphate) lithium-ion batteries |
| CN103012366A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for oxidizing thiophene sulfides |
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- 2021-11-05 CN CN202111304960.3A patent/CN114105938B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009285583A (en) * | 2008-05-29 | 2009-12-10 | Sanyo Chem Ind Ltd | Catalyst for oxidation reaction |
| CN103012366A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for oxidizing thiophene sulfides |
| CN102983362A (en) * | 2012-12-20 | 2013-03-20 | 中国东方电气集团有限公司 | Low-temperature electrolyte for LiFePO4 (lithium iron phosphate) lithium-ion batteries |
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| 曹小华等: "杂多酸型化合物及其研究展望", 《化工中间体》 * |
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