CN112812043A - Synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine - Google Patents
Synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine Download PDFInfo
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- CN112812043A CN112812043A CN201911129199.7A CN201911129199A CN112812043A CN 112812043 A CN112812043 A CN 112812043A CN 201911129199 A CN201911129199 A CN 201911129199A CN 112812043 A CN112812043 A CN 112812043A
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- dichloromethane
- methyl hydroxylamine
- room temperature
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- dimethyl sulfonyl
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- VABYABGJKGDHAP-UHFFFAOYSA-N S(=O)(=O)(C)ON(OC)OS(=O)(=O)C Chemical compound S(=O)(=O)(C)ON(OC)OS(=O)(=O)C VABYABGJKGDHAP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000001308 synthesis method Methods 0.000 title claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 62
- 238000003756 stirring Methods 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 11
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000010791 quenching Methods 0.000 claims abstract description 6
- 230000000171 quenching effect Effects 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000009987 spinning Methods 0.000 claims abstract description 3
- 238000000967 suction filtration Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- -1 N-dodecylpyridine hexafluorophosphate Chemical compound 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000012071 phase Substances 0.000 abstract description 6
- 239000002000 Electrolyte additive Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 238000001228 spectrum Methods 0.000 description 19
- 239000000654 additive Substances 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004451 qualitative analysis Methods 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 4
- 229910001416 lithium ion Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine belongs to the technical field of battery electrolyte additives, and comprises the steps of adding dichloromethane, organic alkali and methoxyamine hydrochloride into a reactor, starting stirring, dropwise adding methylsulfonyl chloride at room temperature, completing dropwise addition within 1.5-2h, then stirring at room temperature for reacting for 6.5-7.5h, then quenching the reaction with water, layering the system, extracting the water phase with dichloromethane, combining organic phases, washing the organic phase with saturated sodium chloride for 20-30min, drying, performing suction filtration, and spinning out the solvent to obtain the N, N-dimethyl sulfonyl-O-methyl hydroxylamine. The method has the advantages of simple synthetic route, easy control of reaction, mild reaction and higher yield and purity of the obtained product.
Description
Technical Field
The invention belongs to the technical field of battery electrolyte additives, and discloses a synthesis method of a battery electrolyte additive N, N-dimethyl sulfonyl-O-methyl hydroxylamine, which is used for synthesizing a battery-grade N, N-dimethyl sulfonyl-O-methyl hydroxylamine, improving the conductivity and oxidation potential of the battery electrolyte and improving the corrosion resistance.
Background
Along with the rapid development of economy, the demand for energy is continuously increased, and lithium ion batteries as new energy are more and more concerned by people according to the demand for sustainable development.
The lithium ion battery has the characteristics of high capacity, high power and the like, but is still restricted by different degrees in the aspects of cycle efficiency, cycle life, safety performance and the like, and people have put forward higher requirements on the lithium ion battery. In order to meet different requirements, a small amount of additives are generally added into the lithium ion battery electrolyte to improve the performance of the battery, such as an overcharge-preventing additive, an SEI (solid electrolyte interphase) film performance improving additive, an electrolyte low-temperature performance improving additive, an electrolyte thermal stability improving additive and the like.
The N, N-dimethyl sulfonyl-O-methyl hydroxylamine has good characteristics, can be used as an additive in battery electrolyte, and plays a role in improving the performance of the battery. The existing method for synthesizing the N, N-dimethyl sulfonyl-O-methyl hydroxylamine is complex and is not ideal in synthesis yield and purity, so that the research on the method for efficiently synthesizing the N, N-dimethyl sulfonyl-O-methyl hydroxylamine has important significance.
Disclosure of Invention
The invention aims to provide a method for synthesizing battery-grade N, N-dimethyl sulfonyl-O-methyl hydroxylamine, which has the advantages of simple synthetic route, easy control of reaction, mild reaction and higher yield and purity of the obtained product.
The technical scheme adopted by the invention for realizing the purpose is as follows:
adding dichloromethane, organic base and methoxylamine hydrochloride into a reactor, starting stirring, dropwise adding methylsulfonyl chloride at room temperature, completing the dropwise addition for 1.5-2h, then stirring at room temperature for reaction for 6.5-7.5h, then quenching the reaction with water, layering the system, extracting the aqueous phase with dichloromethane, combining the organic phases, washing the organic phase with saturated sodium chloride for 20-30min, drying, carrying out suction filtration, and spinning out the solvent to obtain the N, N-dimethylsulfonyl-O-methylhydroxylamine.
The molar ratio of the methoxylamine hydrochloride, the organic base and the methylsulfonyl chloride is 1: (3.1-3.5): (2.0-2.4).
The organic base is triethylamine or pyridine or a mixture of triethylamine and N-dodecyl pyridine hexafluorophosphate.
The content of the N-dodecyl pyridine hexafluorophosphate is 0.05 to 0.1 percent of the mass of the triethylamine.
The amount of dichloromethane added was 450-500ml based on 1mol of methoxyamine hydrochloride.
The condition of solvent extraction is controlled at 25-30 deg.C and-0.06 Mpa.
Drying is carried out by using anhydrous sodium sulfate.
The invention has the beneficial effects that:
the synthesis method is simple, the synthesis process is mild and stable, the yield of the synthesized product is high and reaches over 90 percent, and the purity is high and reaches 99.9 percent.
Drawings
FIG. 1 is a graph of the H spectrum of N, N-dimethylsulfonyl-O-methylhydroxylamine of the present invention.
FIG. 2 is a C spectrum of N, N-dimethylsulfonyl-O-methylhydroxylamine of the present invention.
FIG. 3 is a mass spectrum of N, N-dimethylsulfonyl-O-methylhydroxylamine of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples.
The synthetic route of the invention is as follows:
detailed description of the preferred embodiments
1. Reagent
| Name of reagent | Grade specification | Suppliers of goods |
| Methylene dichloride | Analytical purity | TIANJIN SAFE REAGENT TECHNOLOGY Co.,Ltd. |
| Methoxylamine hydrochloride | Analytical purity | SHANGHAI ALADDIN BIOCHEMICAL TECHNOLOGY Co.,Ltd. |
| Pyridine compound | Analytical purity | TIANJIN DAMAO CHEMICAL REAGENT FACTORY |
| Triethylamine | Analytical purity | Tianjin City Jing Jiang Gong Ltd |
| Anhydrous sodium sulfate | Analytical purity | TIANJIN DAMAO CHEMICAL REAGENT FACTORY |
| Sodium chloride | Analytical purity | TIANJIN DAMAO CHEMICAL REAGENT FACTORY |
2. Instrument for measuring the position of a moving object
| Name of instrument | Suppliers of goods |
| Reactor with a reactor shell | Acciaierie e Ltd |
| Heat collection type magnetic stirrer | Zhengzhou purple Tuo instruments & Equipment Co Ltd |
| Electronic balance | Shijiazhuang Botong high-tech limited |
| Separating funnel | Shijiazhuang Botong high-tech limited |
| Rotary evaporator | Shanghai' an pavilion electronic instrument factory |
| SHZ-D (III) circulating water vacuum pump | GONGYI KERUI INSTRUMENT Co.,Ltd. |
| Gas chromatograph | Yiancao International trade company of Beijing |
| Mass spectrometer | Agilent Technologies Co., Ltd. |
| Nuclear magnetic resonance apparatus | Bruke (Beijing) science and technology Co., Ltd |
Example 1
Adding 450mL of dichloromethane, 3.1mol of triethylamine and 1mol of methoxyamine hydrochloride into a reactor, starting stirring, dropwise adding 2.0mol of methylsulfonyl chloride at room temperature, finishing dropping for 1.5h, then stirring and reacting for 6.5h at room temperature, then quenching the reaction with water, layering the system, and extracting the aqueous phase with 60mL of dichloromethane by 3 times. The organic phases were combined, washed with saturated sodium chloride for 20min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 183.37g of product.
The product is detected by a gas chromatograph, and the detection purity is 99.90%. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a spectrum mass and the like, and the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
example 2
480mL of dichloromethane, 3.2mol of pyridine and 1mol of methoxyamine hydrochloride are added into a reactor, stirring is started, 2.2mol of methylsulfonyl chloride is added dropwise at room temperature, 1.7h of the mixture is completed, then the reaction is stirred at room temperature for 7h, the reaction is quenched by water, the system is separated, and the water phase is extracted by dichloromethane 60mL by 3 times. The organic phases were combined, washed with saturated sodium chloride for 25min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 183.45g of product.
The product is detected by a gas chromatograph, and the detection purity is 99.92%. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a spectrum mass and the like, and the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
example 3
Adding 450mL of dichloromethane, 3.3mol of triethylamine and 1mol of methoxyamine hydrochloride into a reactor, starting stirring, dropwise adding 2.3mol of methylsulfonyl chloride at room temperature, finishing dropping for 1.6h, then stirring at room temperature for reacting for 7.2h, then quenching the reaction with water, layering the system, and extracting the aqueous phase with 60mL of dichloromethane by 3 times. The organic phases were combined, washed with saturated sodium chloride for 23min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 183.41g of product.
The product is detected by a gas chromatograph, and the detection purity is 99.91%. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a spectrum mass and the like, and the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
example 4
Adding 500mL of dichloromethane, 3.5mol of pyridine and 1mol of methoxyamine hydrochloride into a reactor, starting stirring, dropwise adding 2.4mol of methylsulfonyl chloride at room temperature, finishing dropping for 2h, then stirring and reacting for 6.8h at room temperature, then quenching the reaction with water, demixing the system, and extracting the water phase with 60mL of dichloromethane by 3 times. The organic phases were combined, washed with saturated sodium chloride for 30min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 183.32g of product.
The product is detected by a gas chromatograph, and the detection purity is 99.90%. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a spectrum mass and the like, and the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
example 5
470mL of dichloromethane, 3.4mol of triethylamine and 1mol of methoxyamine hydrochloride are added into a reactor, stirring is started, 2.1mol of methanesulfonyl chloride is added dropwise at room temperature, 1.8h of the mixture is finished, then the mixture is stirred and reacted for 7.5h at room temperature, the reaction is quenched by water, the system is separated, and the water phase is extracted for 3 times by 60mL of dichloromethane. The organic phases were combined, washed with saturated sodium chloride for 28min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 183.38g of product.
The product is detected by a gas chromatograph, and the detection purity is 99.90%. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a spectrum mass and the like, and the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
example 6
The N-dodecyl pyridine hexafluorophosphate used in the invention can be a commercial product or prepared by the following method: taking pyridine and bromododecane according to a mass ratio of 1: 3.1 mixing in a reactor, refluxing in a water bath at 65 ℃ and stirring with electric power, reacting for 5 hours, adding 0.3mol KPF6Heating, stirring and refluxing for 6 hours in an acetone phase, filtering, and evaporating the acetone under reduced pressure to obtain a reddish brown liquid, namely the N-dodecyl pyridine hexafluorophosphate.
470mL of dichloromethane, 3.4mol of triethylamine and N-dodecyl pyridine hexafluorophosphate (N-dodecyl pyridine hexafluorophosphate is 0.08 percent of the mass of triethylamine) in total and 1mol of methoxyamine hydrochloride are added into a reactor, stirring is started, 2.1mol of methylsulfonyl chloride is added dropwise at room temperature, the solution is stirred and reacted for 7.5 hours at room temperature, then the reaction is quenched by water, the system is layered, and the water phase is extracted for 3 times by 60mL of dichloromethane. The organic phases were combined, washed with saturated sodium chloride for 28min, dried, filtered and the solvent (25 ℃ C., -0.06MPa) was spun off to give 195.39g of product.
The purity of the product detected by a gas chromatograph is 99.93 percent. Through qualitative analysis, specific structure characterization is carried out by using a spectrum C, a spectrum H, a mass spectrum and the like, and referring to figures 1-3, the obtained product is identified to be N, N-dimethyl sulfonyl-O-methyl hydroxylamine, and the structural formula is as follows:
Claims (7)
- the synthesis method of the N, N-dimethyl sulfonyl-O-methyl hydroxylamine is characterized by adding dichloromethane, organic base and methoxylamine hydrochloride into a reactor, starting stirring, dropwise adding methylsulfonyl chloride at room temperature, completing dropwise addition for 1.5-2h, then stirring at room temperature for 6.5-7.5h, then quenching the reaction with water, layering the system, extracting the aqueous phase with dichloromethane, combining the organic phases, washing the organic phase with saturated sodium chloride for 20-30min, drying, carrying out suction filtration, and spinning out the solvent to obtain the N, N-dimethyl sulfonyl-O-methyl hydroxylamine.
- 2. The method of claim 1 wherein the molar ratio of methoxylamine hydrochloride, organic base and methylsulfonyl chloride is 1: (3.1-3.5): (2.0-2.4).
- 3. The method of claim 1 wherein the organic base is triethylamine or pyridine or a mixture of triethylamine and N-dodecylpyridine hexafluorophosphate.
- 4. The method for synthesizing N, N-dimethylsulfonyl-O-methylhydroxylamine according to claim 3, wherein the content of N-dodecylpyridine hexafluorophosphate is 0.05-0.1% by mass of triethylamine.
- 5. The method for synthesizing N, N-dimethylsulfonyl-O-methylhydroxylamine as claimed in claim 1, wherein the amount of dichloromethane is 450-500ml based on 1mol of methoxyamine hydrochloride.
- 6. The method for synthesizing N, N-dimethylsulfonyl-O-methylhydroxylamine according to claim 1, wherein the solvent is spun off at a temperature of 25 to 30 ℃ and a pressure of-0.06 MPa.
- 7. The method of synthesizing N, N-dimethylsulfonyl-O-methylhydroxylamine of claim 1 wherein the drying is over anhydrous sodium sulfate.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911129199.7A CN112812043A (en) | 2019-11-18 | 2019-11-18 | Synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine |
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|---|---|---|---|
| CN201911129199.7A CN112812043A (en) | 2019-11-18 | 2019-11-18 | Synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine |
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| CN201911129199.7A Pending CN112812043A (en) | 2019-11-18 | 2019-11-18 | Synthesis method of N, N-dimethyl sulfonyl-O-methyl hydroxylamine |
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| Country | Link |
|---|---|
| CN (1) | CN112812043A (en) |
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2019
- 2019-11-18 CN CN201911129199.7A patent/CN112812043A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| CHEMISCHER INFORMATIONSDIENST: "Chemischer Informationsdienst", CHEMISCHER INFORMATIONSDIENST, vol. 13, no. 14, pages 53 * |
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