CN112209914A - Method for preparing vinyl sulfate by adopting micro-flow field reaction technology - Google Patents
Method for preparing vinyl sulfate by adopting micro-flow field reaction technology Download PDFInfo
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- CN112209914A CN112209914A CN202011130428.XA CN202011130428A CN112209914A CN 112209914 A CN112209914 A CN 112209914A CN 202011130428 A CN202011130428 A CN 202011130428A CN 112209914 A CN112209914 A CN 112209914A
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00889—Mixing
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/0095—Control aspects
- B01J2219/00952—Sensing operations
- B01J2219/00954—Measured properties
- B01J2219/00961—Temperature
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/0095—Control aspects
- B01J2219/00984—Residence time
Abstract
The invention discloses a method for preparing dimethyl sulfate by adopting a micro-flow field reaction technology, which takes ethylene sulfite and persulfate as raw materials, adds a metal ruthenium catalyst, and prepares the dimethyl sulfate by utilizing a micro-channel modular reaction device, wherein the micro-channel modular reaction device comprises a micro-structure mixer and a micro-structure reactor which are sequentially connected through a pipeline, and the method comprises the following steps: (1) dissolving ethylene sulfite and a metal ruthenium catalyst in a solvent to obtain a mixed solution for later use; (2) preparing persulfate into aqueous solution for later use; (3) and mixing the prepared two solutions by a microstructure mixer, injecting the mixed solutions into a microstructure reactor for reaction, and collecting a product after the reaction to obtain the dimethyl sulfate. The preparation method disclosed by the invention has the advantages of environmental friendliness, safety, high efficiency, high reaction speed and the like.
Description
Technical Field
The invention belongs to the field of development of a vinyl sulfate process, and particularly relates to a process for efficiently preparing vinyl sulfate by adopting a micro-flow field reaction technology.
Background
The ethylene sulfate (DTD) is an additive which can enable the using effect of the lithium ion battery electrolyte to be better. After the vinyl sulfate is added into the electrolyte of the lithium ion battery, the reduction of the initial capacity of the battery can be inhibited, the initial discharge capacity is increased, the expansion of the battery after high-temperature placement can be reduced, and the charge and discharge performance and the cycle number of the battery are improved. The preparation method of the vinyl sulfate disclosed at present has the defects of high yield and purity, high water content and acid value, high preparation cost and the like.
Disclosure of Invention
The purpose of the invention is as follows: the invention provides a process for efficiently preparing vinyl sulfate, in particular to a process for efficiently synthesizing the vinyl sulfate by taking ethylene sulfite as a raw material and adopting persulfate oxidation continuous flow under the action of a ruthenium metal catalyst. The method has the characteristics of high catalytic efficiency, high yield and purity of the target compound, less industrial wastewater discharge and the like.
The technical scheme is as follows: in order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing dimethyl sulfate by adopting a micro-flow field reaction technology is characterized in that vinyl sulfite and persulfate are used as raw materials, a metal ruthenium catalyst is added, and the raw materials are prepared by utilizing a micro-channel modular reaction device, wherein the micro-channel modular reaction device comprises a micro-structure mixer and a micro-structure reactor which are sequentially connected through a pipeline, and the method comprises the following steps:
(1) dissolving ethylene sulfite and a metal ruthenium catalyst in a solvent to obtain a mixed solution for later use;
(2) preparing persulfate into aqueous solution for later use;
(3) and mixing the prepared two solutions by a microstructure mixer, injecting the mixed solutions into a microstructure reactor for reaction, and collecting a product after the reaction to obtain the dimethyl sulfate.
Preferably, in step (1), the solvent is acetonitrile, ethanol, dichloromethane, dimethyl sulfoxide, n.n-dimethylformamide, tetrahydrofuran or N-methylpyrrolidone, preferably acetonitrile.
Preferably, in step (1), the metallic ruthenium catalyst is ruthenium trichloride, ruthenium tricarbonyl dichloride dimer, ruthenium acetylacetonate or ruthenium acetate, preferably ruthenium trichloride.
Preferably, in the step (2), the persulfate is sodium persulfate, potassium persulfate or ammonium persulfate, preferably ammonium persulfate.
Preferably, the molar ratio of the ethylene sulfite, the persulfate and the metallic ruthenium catalyst is 1: (1.0-2.0):(0.05-0.15).
Preferably, in the step (3), the reaction temperature of the micro-structure reactor is-20 to 50 ℃, preferably 0 to 20 ℃, the reaction residence time is 1 to 20min, preferably 3 to 10min, the flow rate of a mixed solution obtained by mixing through a micro-mixer is 0.1 to 5mL/min, preferably 0.5 to 3mL/min, and the volume of the micro-structure reactor is 5 to 50mL, preferably 5 to 10 mL.
As a preferred scheme, the microchannel modular reaction device further comprises a raw material storage tank 1, a raw material storage tank 2 and a product collector, wherein the discharge ports of the raw material storage tank 1 and the raw material storage tank 2 are connected with the feed port of the microstructure mixer, and the discharge port of the microstructure reactor is connected with the feed port of the product collector.
Has the advantages that: the method takes the metal ruthenium as the catalyst, and has the characteristics of high catalytic efficiency, mild reaction conditions, high yield of the target compound, convenient operation and the like. Therefore, the preparation method has the advantages of environmental protection, safety, high efficiency, easily obtained raw materials, low price, no residue of highly toxic reactants, high reaction speed and the like.
The foregoing is only an overview of the technical solutions of the present invention, and in order to make the technical means of the present invention more clearly understood and to be implemented according to the content of the description, the following is a detailed description of preferred embodiments of the present invention.
Drawings
FIG. 1 is a schematic view of a microchannel modular reactor apparatus according to the present invention;
Detailed Description
The following detailed description of embodiments of the present invention is provided in connection with the accompanying drawings and examples. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) are dissolved in 50mL of acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL of water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 95.4%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 95.13%.1H NMR(400MHz,Chloroform-d)δ4.45(s,1H)；13C NMR(100MHz,Common NMR Solvents)δ69.26；HRMS(ESI-TOF):m/z calcd for C2H4O4S[M+H]+124.9879,Found 124.9895.
Example 2
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) were dissolved in 50mL of acetonitrile, and the mixture was placed in a raw material tank 1, and sodium persulfate (0.13mol) was dissolved in 50mL of water in a raw material tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 85.7%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 94.32%.
Example 3
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) were dissolved in 50mL of acetonitrile, and the mixture was placed in a raw material tank 1, and potassium persulfate (0.13mol) was dissolved in 50mL of water in a raw material tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 88.3%. The product was analyzed by liquid chromatography and showed 95.15% vinyl sulfate content.
Example 4
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) are dissolved in 50mL of acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL of water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 20 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 90.3%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 90.24%.
Example 5
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) are dissolved in 50mL of acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL of water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at the temperature of minus 10 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 78.6%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 96.25%.
Example 6
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) are dissolved in 50mL of acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL of water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 95.1%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 97.15%.
Example 7
Ethylene sulfite (0.1mol) and ruthenium trichloride (0.01mol) are dissolved in 50mL of acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL of water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 94.17%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 96.85%.
Example 8
Ethylene sulfite (0.1mol) and ruthenium trichloride (1mmol) are dissolved in 50mL acetonitrile and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 1mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 94.32%. The product was analyzed by liquid chromatography, and the result showed that the vinyl sulfate content was 94.17%.
Example 9
Ethylene sulfite (0.1mol) and ruthenium acetylacetonate (1mmol) were dissolved in 50mL of acetonitrile, and the solution was prepared by placing the solution in a raw material tank 1 and ammonium persulfate (0.13mol) in 50mL of water in a raw material tank 2. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge hole of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 73.1%. The product was analyzed by liquid chromatography and showed 86.42% vinyl sulfate content.
Example 10
Ethylene sulfite (0.1mol) and ruthenium trichloride (1mmol) are dissolved in 50mL tetrahydrofuran and placed in a raw material storage tank 1, and ammonium persulfate (0.13mol) is dissolved in 50mL water in a raw material storage tank 2 to prepare a solution. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 5min at 0 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, standing and layering reaction liquid, taking an organic layer, washing the organic layer twice by using distilled water, and drying to obtain the vinyl sulfate with the yield of 80.3%. The product was analyzed by liquid chromatography and showed a vinyl sulfate content of 76.49%.
Comparative example
Dissolving ethylene sulfite (0.1mol) and ruthenium trichloride (1mmol) in 50mL tetrahydrofuran, placing the solution in a round-bottom flask, dissolving ammonium persulfate (0.13mol) in 50mL water to prepare a solution, adding an ammonium persulfate aqueous solution into the round-bottom flask, stirring at room temperature for 5 hours, standing the reaction solution for layering, taking an organic layer, washing the organic layer twice with distilled water, and drying to obtain the vinyl sulfate with the yield of 64.2%. The product was analyzed by liquid chromatography and showed 59.49% vinyl sulfate content.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. A method for preparing dimethyl sulfate by adopting a micro-flow field reaction technology is characterized in that vinyl sulfite and persulfate are used as raw materials, a metal ruthenium catalyst is added, and the method is prepared by utilizing a micro-channel modular reaction device, wherein the micro-channel modular reaction device comprises a micro-structure mixer and a micro-structure reactor which are sequentially connected through a pipeline, and the method comprises the following steps:
(1) dissolving ethylene sulfite and a metal ruthenium catalyst in a solvent to obtain a mixed solution for later use;
(2) preparing persulfate into aqueous solution for later use;
(3) and mixing the prepared two solutions by a microstructure mixer, injecting the mixed solutions into a microstructure reactor for reaction, and collecting a product after the reaction to obtain the dimethyl sulfate.
2. The method for preparing dimethyl sulfate by using micro flow field reaction technology as claimed in claim 1, wherein in the step (1), the solvent is acetonitrile, ethanol, dichloromethane, dimethyl sulfoxide, n.n-dimethylformamide, tetrahydrofuran or N-methylpyrrolidone.
3. The method for preparing dimethyl sulfate by using micro-flow field reaction technology as claimed in claim 1, wherein in step (1), the metallic ruthenium catalyst is ruthenium trichloride, ruthenium tricarbonyl dichlorohydrin dimer, ruthenium acetylacetonate or ruthenium acetate.
4. The method for preparing dimethyl sulfate by using the micro-flow field reaction technology as claimed in claim 1, wherein in the step (2), the persulfate is sodium persulfate, potassium persulfate or ammonium persulfate.
5. The method for preparing dimethyl sulfate by using the micro-flow field reaction technology as claimed in claim 1, wherein the molar ratio of the vinyl sulfite, the persulfate and the metallic ruthenium catalyst is 1 (1.0-2.0) to (0.05-0.15).
6. The method for preparing dimethyl sulfate by using the micro-flow field reaction technology as claimed in claim 1, wherein in the step (3), the reaction temperature of the micro-structure reactor is-20 to 50 ℃, the reaction residence time is 1 to 20min, the flow rate of the mixed solution obtained after mixing by the micro-mixer is 0.1 to 5mL/min, and the volume of the micro-structure reactor is 5 to 50 mL.
7. The method for preparing dimethyl sulfate by using the micro-flow field reaction technology as claimed in claim 1, wherein the micro-channel modular reaction device further comprises a raw material storage tank 1, a raw material storage tank 2 and a product collector, the discharge ports of the raw material storage tank 1 and the raw material storage tank 2 are connected with the feed port of the micro-structure mixer, and the discharge port of the micro-structure reactor is connected with the feed port of the product collector.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114195757A (en) * | 2022-01-05 | 2022-03-18 | 香河昆仑新能源材料股份有限公司 | Method for synthesizing vinyl sulfate |
| CN114210351A (en) * | 2021-12-29 | 2022-03-22 | 重庆敏恒科技有限公司 | Catalyst for synthesizing vinyl sulfate and vinyl sulfate synthesis method |
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| CN114210351B (en) * | 2021-12-29 | 2023-06-30 | 重庆敏恒科技有限公司 | Catalyst for synthesizing vinyl sulfate and method for synthesizing vinyl sulfate |
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