CN115806540A - Preparation method of ethylene sulfite - Google Patents
Preparation method of ethylene sulfite Download PDFInfo
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- CN115806540A CN115806540A CN202211444391.7A CN202211444391A CN115806540A CN 115806540 A CN115806540 A CN 115806540A CN 202211444391 A CN202211444391 A CN 202211444391A CN 115806540 A CN115806540 A CN 115806540A
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- sulfite
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- ethylene
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- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 135
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 51
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 239000012043 crude product Substances 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000007792 addition Methods 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 230000007935 neutral effect Effects 0.000 claims abstract description 8
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- RBBXSUBZFUWCAV-UHFFFAOYSA-N ethenyl hydrogen sulfite Chemical compound OS(=O)OC=C RBBXSUBZFUWCAV-UHFFFAOYSA-N 0.000 claims description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000002994 raw material Substances 0.000 abstract description 8
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000010606 normalization Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of chemical synthesis, and particularly discloses a preparation method of ethylene sulfite. The method comprises the following steps: mixing a certain amount of ethylene glycol and a dichloromethane solvent in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1:1-1.2; and S2, when the dropwise addition of the thionyl chloride is finished, stirring the mixture for reaction for a period of time, and then heating the mixture to 40 ℃. Subsequently, the dichloromethane solvent in the dichloromethane replacement system is added dropwise thereto, when the volume of the dropwise added dichloromethane solvent is 1 to 2 times the volume of the initially added dichloromethane solvent, the replacement is stopped, and the reaction is stirred for a while. And (3) washing the reaction product, adjusting the pH to be neutral, separating liquid, taking a lower organic phase, drying, and performing rotary evaporation to obtain a crude product of the ethylene sulfite. And rectifying to obtain the high-purity ethylene sulfite. The method has the advantages of few reaction raw material types, simple and convenient operation, low energy consumption and high purity of the prepared ethylene sulfite crude product.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of ethylene sulfite.
Background
The ethylene sulfite is an important organic chemical product, is also an intermediate for synthesizing other chemical products, and can be used as a solvent or an additive of the electrolyte of the lithium ion secondary battery.
The current methods for preparing the ethylene sulfite mainly comprise the following steps: (1) Ethylene oxide is reacted with sulfur dioxide to produce ethylene sulfite. (2) Preparing the ethylene sulfite by using a polyethylene glycol sulfite depolymerization method. (3) The ethylene glycol reacts with the dimethyl sulfite to prepare the ethylene sulfite. The vinyl sulfite produced by the above method contains a large amount of impurities, and the vinyl sulfite is not suitable for use as a solvent or additive for an electrolyte of a lithium ion secondary battery, which may affect the storage stability of the electrolyte.
Disclosure of Invention
The invention aims to provide a preparation method of vinyl sulfite, which effectively solves the problem of low purity of the vinyl sulfite in the preparation method of the vinyl sulfite in the prior art.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a preparation method of ethylene sulfite comprises the following steps:
s1, mixing a certain amount of ethylene glycol and a dichloromethane solvent in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1:1-1.2;
s2, when the dropwise addition of the thionyl chloride is finished, stirring for reaction for a period of time, and heating to 40 ℃;
s3, when the temperature reaches 40 ℃, dropwise adding a dichloromethane solvent in a dichloromethane replacement system, stopping replacement when the volume of the dropwise added dichloromethane solvent is 1-2 times of the volume of the initially added dichloromethane solvent, and stirring for reaction for a period of time;
s4, washing the reaction product, adjusting the pH to be neutral, separating liquid, and taking a lower organic phase;
s5, drying the organic phase by using anhydrous magnesium sulfate, and performing rotary evaporation to recover dichloromethane to obtain a crude product of the ethylene sulfite;
s6, rectifying the crude product of the ethylene sulfite to obtain high-purity ethylene sulfite.
Further, in step S1, the volume ratio of ethylene glycol to methylene chloride solvent is 1:5.
Further, in step S2, the stirring reaction time was 1 hour.
Further, in step S3, the stirring reaction time was 0.5h.
Further, in step S3, the volume of the dichloromethane solvent added dropwise is 2 times the volume of the dichloromethane solvent initially added, which is the volume of the dichloromethane solvent in step S1.
Further, in step S4, the reaction product is washed with water and ph is adjusted to neutral with sodium hydroxide solution.
Further, in step S5, the rotary evaporation is performed under reduced pressure.
The beneficial technical effects of the invention are as follows:
(1) The reaction raw materials only comprise thionyl chloride, ethylene glycol and a dichloromethane solvent, and the variety of the raw materials used in the reaction is small; the reaction is simple and convenient to operate, the reaction raw materials are mixed at room temperature, the reaction is continued at the solvent boiling point temperature of 40 ℃, and the solvent is evaporated in a rotary mode after the reaction is finished. The preparation process is simple, the reaction is easy to complete, the energy consumption is low, and the purity of the prepared ethylene sulfite crude product is high.
(2) According to the invention, through a specific preparation method and specific reaction raw materials and the dosage ratio of the reaction raw materials, the obtained ethylene sulfite crude product has high quality yield and purity, the quality yield reaches more than 98%, the purity reaches 99.53%, and compared with the prior art, the method has unexpected technical effects.
Drawings
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
FIG. 1 is a GC spectrum of the purity analysis of the crude vinyl sulfite obtained in example 1 of the present invention;
FIG. 2 is a GC spectrum of the purity analysis of the crude vinyl sulfite obtained in example 2 of the present invention;
FIG. 3 is a GC spectrum of the purity analysis of the crude vinyl sulfite obtained in example 3 of the present invention.
Detailed Description
Example 1
S1, mixing ethylene glycol and a dichloromethane solvent in a volume ratio of 1:5 in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1:1.
And S2, when the dropwise addition of the thionyl chloride is finished, stirring the mixture for reaction for 1 hour, and then heating the mixture to 40 ℃.
And S3, when the temperature reaches 40 ℃, dropwise adding a dichloromethane solvent in the dichloromethane replacement system, stopping replacement when the volume of the dropwise added dichloromethane solvent is 1 time of the volume of the initially added dichloromethane solvent in the step S1, and stirring for reaction for 0.5h.
And S4, washing the reaction product, adjusting the pH to be neutral by using a sodium hydroxide solution, separating liquid, and taking a lower-layer organic phase.
And S5, drying the organic phase by using anhydrous magnesium sulfate, and carrying out reduced pressure rotary evaporation to recover dichloromethane to obtain a crude product of the ethylene sulfite. The purity of the crude product is analyzed by a gas chromatography-hydrogen flame ion detector, as shown in figure 1 and table 1, after normalization treatment, the purity of the crude product of the ethylene sulfite is 98.56%, and the mass yield reaches more than 70%.
Mass yield = actual yield purity/theoretical yield.
S6, rectifying the crude product of the ethylene sulfite to obtain high-purity ethylene sulfite.
Table 1 analytical results of fig. 1
Example 2
S1, mixing ethylene glycol and a dichloromethane solvent in a volume ratio of 1:5 in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1.2.
And S2, when the dropwise addition of the thionyl chloride is finished, stirring the mixture for reaction for 1 hour, and then heating the mixture to 40 ℃.
And S3, when the temperature reaches 40 ℃, dropwise adding a dichloromethane solvent in the dichloromethane replacement system, stopping replacement when the volume of the dropwise added dichloromethane solvent is 1 time of the volume of the initially added dichloromethane solvent in the step S1, and stirring for reaction for 0.5h.
And S4, washing the reaction product, adjusting the pH to be neutral by using a sodium hydroxide solution, separating liquid, and taking a lower-layer organic phase.
And S5, drying the organic phase by using anhydrous magnesium sulfate, and carrying out reduced pressure rotary evaporation to recover dichloromethane to obtain a crude product of the ethylene sulfite. The purity of the crude product was analyzed by gas chromatography-hydrogen flame ion detector, as shown in fig. 2 and table 2, after normalization treatment, the purity of the crude product of ethylene sulfite was 97.50%, and the mass yield was more than 80%.
Mass yield = actual yield purity/theoretical yield.
S6, rectifying the crude product of the ethylene sulfite to obtain high-purity ethylene sulfite.
Table 2 analysis results of fig. 2
Example 3
S1, mixing ethylene glycol and a dichloromethane solvent in a volume ratio of 1:5 in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1.2.
S2, when the dropwise addition of the thionyl chloride is finished, stirring for reaction for 1 hour, and then heating to 40 ℃.
And S3, when the temperature reaches 40 ℃, dropwise adding a dichloromethane solvent in the dichloromethane replacement system, stopping replacement when the volume of the dropwise added dichloromethane solvent is 2 times of the volume of the initially added dichloromethane solvent in the step S1, and stirring for reaction for 0.5h.
And S4, washing the reaction product, adjusting the pH to be neutral by using a sodium hydroxide solution, separating liquid, and taking a lower-layer organic phase.
And S5, drying the organic phase by using anhydrous magnesium sulfate, and carrying out rotary evaporation under reduced pressure to recover dichloromethane to obtain a crude product of the ethylene sulfite. The purity of the crude product was analyzed by gas chromatography-hydrogen flame ion detector, as shown in fig. 3 and table 3, after normalization treatment, the purity of the crude product of ethylene sulfite was 99.53%, and the mass yield was more than 98%.
Mass yield = actual yield purity/theoretical yield.
S6, rectifying the crude product of the ethylene sulfite to obtain high-purity ethylene sulfite.
Table 3 analysis results of fig. 3
According to the preparation method of the ethylene sulfite provided by the invention, only thionyl chloride, ethylene glycol and dichloromethane solvents are used as reaction raw materials, the reaction raw materials are few in types, the energy consumption is low, the process is simple, the operation is simple and convenient, the reaction is easy to complete, and the obtained crude ethylene sulfite is high in purity and yield. The purity of the ethylene sulfite crude product is analyzed by a gas chromatography-hydrogen flame ion detector, after normalization treatment, the purity of the crude product can reach as high as 99.53 percent without calculating a solvent peak, and the mass yield can reach more than 98 percent.
It is to be understood that the above description is not intended to limit the present invention, and the present invention is not limited to the above examples, and those skilled in the art may make modifications, alterations, additions or substitutions within the spirit and scope of the present invention.
Claims (7)
1. The preparation method of the ethylene sulfite is characterized by comprising the following steps:
s1, mixing a certain amount of ethylene glycol and a dichloromethane solvent in a reaction kettle, and then dropwise adding thionyl chloride into the mixture at room temperature, wherein the molar ratio of the ethylene glycol to the thionyl chloride is 1:1-1.2;
s2, when the dropwise addition of the thionyl chloride is finished, stirring and reacting for a period of time, and then heating to 40 ℃;
s3, when the temperature reaches 40 ℃, dropwise adding a dichloromethane solvent in a dichloromethane replacement system, stopping replacement when the volume of the dropwise added dichloromethane solvent is 1-2 times of the volume of the initially added dichloromethane solvent, and stirring for reaction for a period of time;
s4, washing the reaction product, adjusting the pH to be neutral, separating liquid, and taking a lower organic phase;
s5, drying the organic phase by using anhydrous magnesium sulfate, and performing rotary evaporation to recover dichloromethane to obtain a crude product of the ethylene sulfite;
s6, rectifying the crude product of the ethylene sulfite to obtain high-purity ethylene sulfite.
2. The method for producing vinyl sulfite according to claim 1, wherein in step S1, the volume ratio of ethylene glycol to methylene chloride solvent is 1:5.
3. The method for producing vinyl sulfite according to claim 2, wherein in the step S2, the stirring reaction time is 1 hour.
4. The method for producing vinyl sulfite according to claim 3, wherein in the step S3, the stirring reaction time is 0.5h.
5. The method of producing vinyl sulfite according to claim 4, wherein in the step S3, the volume of the dropwise addition of the methylene chloride solvent is 2 times the volume of the initially added methylene chloride solvent, which is the volume of the methylene chloride solvent in the step S1.
6. The method according to claim 5, wherein in step S4, the pH of the reaction product is adjusted to neutral by sodium hydroxide solution after washing with water.
7. The method for producing vinyl sulfite according to claim 6, wherein in the step S5, the rotary evaporation is performed under reduced pressure.
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2022
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