CN111689926A - Preparation method, product and application of 3-methyl-1, 4, 2-dioxazole-5-ketone - Google Patents
Preparation method, product and application of 3-methyl-1, 4, 2-dioxazole-5-ketone Download PDFInfo
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- CN111689926A CN111689926A CN202010672318.XA CN202010672318A CN111689926A CN 111689926 A CN111689926 A CN 111689926A CN 202010672318 A CN202010672318 A CN 202010672318A CN 111689926 A CN111689926 A CN 111689926A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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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
Abstract
The invention discloses a preparation method, a product and application of 3-methyl-1, 4, 2-dioxazole-5-ketone, which are characterized by comprising the following steps: adding acetohydroxamic acid, dimethyl carbonate and a catalyst into a reaction flask, heating to 110 ℃, reacting while distilling off a byproduct methanol, performing reduced pressure distillation on the reaction solution after 4 hours of reaction, and collecting a fraction with the temperature of 89 ℃/10mmHg to obtain the 3-methyl-1, 4, 2-dioxazol-5-one. The method synthesizes the 3-methyl-1, 4, 2-dioxazole-5-ketone by using an ester exchange method, has few byproducts, can separate the catalyst by filtration, greatly reduces the later purification steps, and is easy to obtain a high-purity product.
Description
Technical Field
The invention belongs to the technical field of electrolyte additives of rechargeable lithium ion battery systems, and particularly relates to a preparation method of 3-methyl-1, 4, 2-bisoxazole-5-ketone, 3-methyl-1, 4, 2-bisoxazole-5-ketone prepared by the method and application thereof.
Background
In recent years, the development of new energy industry in China is rapid, and particularly, the development of electric automobiles represented by power lithium ion batteries is rapid. However, the power type lithium ion battery has the problems of long charging time, short endurance mileage and the like, and the problem is broken through, and a novel additive is developed to be a strategy with higher cost performance.
Chinese patent application No. CN201810377636.6, No. 2018.04.25, No. CN110400968A, No. 2019.11.01 disclose a nonaqueous electrolyte comprising a lithium salt, an organic solvent and an additive containing dioxazolones, a power battery containing the same and a vehicle containing the power battery, wherein the additive has a structure shown in formula (1) and formula (1)
Wherein R is an electron withdrawing group; r is one of halogen atom, nitryl, nitrile group, halogenated alkyl with 1-5 carbon atoms, nitroalkyl with 1-5 carbon atoms and cyanoalkyl with 1-5 carbon atoms, wherein the halogen atom is one of F, Cl, Br and I. When the electrolyte is used for a battery, the additive not only has good oxidation resistance, but also has good film forming performance, and the battery still shows good cycle performance at a high voltage of 4.4V, so that the electrolyte shows better high-pressure stability and high-temperature stability compared with the electrolyte added with the film forming additive in the prior art. The temperature and voltage of the high nickel anode or the silicon-carbon cathode during use are improved, so that the bottleneck problems of quick charge, high endurance and the like are solved. However, the above scheme discloses only the electrolyte additives of the dioxazalone type with electron withdrawing group, and the electrolyte additives of the dioxazalone type with electron donating group are less disclosed in the scheme and the prior art.
Disclosure of Invention
1. Technical problem to be solved
Aiming at the problems that the prior art only discloses a bisoxazolone electrolyte additive with an electron-withdrawing group, and the bisoxazolone electrolyte additive with an electron-donating group type is less disclosed in the technical scheme and the prior technical data, the invention aims to provide a preparation method of 3-methyl-1, 4, 2-bisoxazolone-5-ketone, the 3-methyl-1, 4, 2-bisoxazolone-5-ketone prepared by the method and the application thereof in the field of lithium ion batteries, the preparation method is simple and easy to implement, byproducts are easy to separate, and the yield and purity are high, so that the method is suitable for large-scale production and preparation.
2. Technical scheme
In order to achieve the purpose, the invention adopts the following technical scheme:
the preparation method of 3-methyl-1, 4, 2-dioxazole-5-ketone is characterized by comprising the following steps: adding acetohydroxamic acid, dimethyl carbonate and a catalyst into a reaction flask, heating to 110 ℃, reacting while distilling off a byproduct methanol, performing reduced pressure distillation on the reaction solution after reacting for 4 hours, and collecting a fraction with the temperature of 89 ℃/10mmHg to obtain 3-methyl-1, 4, 2-dioxazol-5-one; the reaction formula is as follows:
in a specific embodiment of the invention, the molar ratio of the acetohydroxamic acid to the dimethyl carbonate is 1: 2-3; preferably, the molar ratio of the acetohydroxamic acid to the dimethyl carbonate is 1 to (2-2.9); 1: 2-2.8; 1: 2-2.7; 1: 2-2.6; 1: 2-2.5; 1: 2-2.4; 1: 2-2.3; 1: 2-2.2; 1: 2-2.1; 1: 2.1-3; 1: 2.1-2.9; 1: 2.1-2.8; 1: 2.1-2.7; 1: 2.1-2.6; 1: 2.1-2.5; 1: 2.1-2.4; 1: 2.1-2.3; 1: 2.1-2.2; 1: 2.2-3; 1: 2.2-2.9; 1: 2.2-2.8; 1: 2.2-2.7; 1: 2.2-2.6; 1: 2.2-2.5; 1: 2.2-2.4; 1: 2.2-2.3; 1: 2.3-3; 1: 2.3-2.9; 1: 2.3-2.8; 1: 2.3-2.7; 1: 2.3-2.6; 1: 2.3-2.5; 1: 2.3-2.4; 1: 2.4-3; 1: 2.4-2.9; 1: 2.4-2.8; 1: 2.4-2.7; 1: 2.4-2.6; 1: 2.4-2.5; 1: 2.5-3; 1: 2.6-3; 1: 2.7-3; 1: 2.8-3 and 1: 2.9-3.
In a specific embodiment of the invention, the catalyst is a mixture of malondialdehyde and calcium hydroxide; the molar ratio of the malondialdehyde to the calcium hydroxide is (2-2.1) to 1; preferably the molar ratio of malondialdehyde to calcium hydroxide is 2.01: 1; 2.02: 1; 2.03: 1; 2.04: 1; 2.05: 1; 2.06: 1; 2.07: 1; 2.08: 1; 2.09: 1.
In a particular embodiment of the invention, the catalyst is a mixture of dialdehyde and barium hydroxide; the molar ratio of the malondialdehyde to the barium hydroxide is (2-2.1) to 1; preferably the molar ratio of malondialdehyde to barium hydroxide is 2.01: 1, 2.02: 1, 2.03: 1, 2.04: 1, 2.05: 1, 2.06: 1, 2.07: 1, 2.08: 1, 2.09: 1.
In a specific embodiment of the invention, the amount of the catalyst is 1-5% of the mass of the acetohydroxamic acid; preferably, the dosage of the catalyst is 1-4%, 1-3%, 1-2%, 2-5%, 2-4%, 3-5% and 4-5% of the mass of the acetohydroxamic acid.
The reaction principle for preparing 3-methyl-1, 4, 2-dinazole-5-ketone is as follows: 1. when the mixture of malondialdehyde and calcium hydroxide is used as a catalyst, malondialdehyde and calcium hydroxide generate malondialdehyde calcium at the temperature of 110 ℃; reacting calcium malondialdehyde with dimethyl carbonate to produce an active intermediate, namely methoxycarbonylmalondialdehyde, and reacting the methoxycarbonylmalondialdehyde with acetylhydroxamic acid to generate a target product, namely 3-methyl-1, 4, 2-dioxazole-5-ketone; 3. when the mixture of malondialdehyde and barium hydroxide is used as a catalyst, malondialdehyde and barium hydroxide generate malondialdehyde barium at the temperature of 110 ℃, the malondialdehyde barium reacts with dimethyl carbonate to generate an active intermediate methoxycarbonylmalondialdehyde, and then the methoxycarbonylmalondialdehyde reacts with acetohydroxamic acid to generate a target product 3-methyl-1, 4, 2-dioxazole-5-ketone.
Another object of the present invention is to provide 3-methyl-1, 4, 2-dioxazol-5-one prepared by the above-mentioned method.
The invention also aims to provide application of the 3-methyl-1, 4, 2-bisoxazol-5-one in the field of electrolyte additives, in particular application of the 3-methyl-1, 4, 2-bisoxazol-5-one serving as the electrolyte additive in rechargeable lithium ion battery systems.
Acetohydroxamic acid, also known as acetohydroxamic acid, N-Hydroxyacetamide, tradename Eudragit, formula C2H5NO2Molecular weight: 75.07, CAS number: 546-88-3, structural formula
White crystal or crystalline powder (feed additive grade is orange red); almost odorless; slightly bitter in taste; changing color when meeting light; moisture absorption is easy; easily soluble in water and absolute ethyl alcohol; the aqueous solution is in acid-regulating reaction. The product is used as a rumen microorganism urease inhibitor in the feed industry, is used as a ruminant feed additive, is also used as a urease competitive inhibitor in medicine, is called as Junshitong in the trade name, is used as a chelating agent and an extracting agent in the metallurgical industry, and is used for extracting and identifying metal ions and the like.
Dimethyl carbonate (alternatively called methyl carbonate, DMC), also called methyl carbonate, ethane carbonate, of the formula (CH)3O)2CO is colorless, transparent, slightly odorous and slightly sweet liquid with low toxicity, excellent environmental protection performance and wide application, has the melting point of 4 ℃, the boiling point of 90.1 ℃ and the density of 1.069g/cm3, is difficult to dissolve in water, but can be mixed and dissolved with almost all organic solvents such as alcohol, ether, ketone and the like. DMC was azeotroped with methanol at atmospheric pressure with an azeotropic temperature of 63.8 ℃. The molecular structure contains carbonyl, methyl, methoxy and other functional groups, has various reaction properties, and has the characteristics of safe and convenient use, less pollution, easy transportation and the like in production.
3. Advantageous effects
Compared with the prior art, the invention has the beneficial effects that: the prior art discloses that the reaction of acetohydroxamic acid and carbonyl diimidazole generates the dioxazalone materials, but a large amount of by-product imidazole is generated, so that the purification is difficult in the later purification; the 3-methyl-1, 4, 2-dioxazole-5-ketone is synthesized by using an ester exchange method, the by-products are few, the catalyst can be separated by filtration, and the later purification steps are greatly reduced, so that a high-purity product is easily obtained; the methyl functional group in the 3-methyl-1, 4, 2-dinazole-5-ketone obtained by the invention is an electronic group.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects solved by the present invention more apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The present invention will be further illustrated by the following examples.
Example 1
3-methyl-1, 4, 2-dinazole-5-ketone, and the preparation method thereof comprises the following steps: first, 100 g of acetohydroxamic acid, 240 g of dimethyl carbonate and 2.4 g of catalyst, wherein 1.59 g of malondialdehyde and 0.81 g of calcium hydroxide are contained, are added into a reaction bottle, then the reaction bottle is heated to 110 ℃, the byproduct methanol is distilled off while the reaction is carried out, after 4 hours of reaction, the reaction liquid is decompressed and distilled, and the fraction of 89 ℃/10mmHg is collected, thus obtaining 109 g of 3-methyl-1, 4, 2-dioxazole-5-ketone with 81 percent yield and 99.7 percent purity.
Example 2
3-methyl-1, 4, 2-dinazole-5-ketone, and the preparation method thereof comprises the following steps: firstly, 200 g of acetohydroxamic acid, 720 g of dimethyl carbonate and 10 g of catalyst, wherein the weight of glyoxal is 5.2 g and the weight of barium hydroxide is 6 g, are added into a reaction bottle, then are heated to 110 ℃, the byproduct methanol is distilled while the reaction is carried out, after 4 hours of reaction, the reaction liquid is decompressed and distilled, and the fraction of 89 ℃/10mmHg is collected, thereby obtaining 227 g of 3-methyl-1, 4, 2-dioxazole-5-ketone with 85 percent of yield and 99.2 percent of purity.
Example 3
3-methyl-1, 4, 2-dinazole-5-ketone, and the preparation method thereof comprises the following steps: firstly, 200 g of acetohydroxamic acid, 700 g of dimethyl carbonate and 6 g of catalyst, wherein the content of malondialdehyde is 4 g and the content of calcium hydroxide is 2 g, are added into a reaction bottle, then the reaction is heated to 110 ℃, the byproduct methanol is distilled off while the reaction is carried out, after 4 hours of reaction, the reaction liquid is distilled under reduced pressure, and the fraction with 89 ℃/10mmHg is collected, thus obtaining 219 g of 3-methyl-1, 4, 2-dinazole-5-ketone with the yield of 82 percent and the purity of 99.5 percent.
Example 4
3-methyl-1, 4, 2-dinazole-5-ketone, and the preparation method thereof comprises the following steps: first 150 g of acetohydroxamic acid, 525 g of dimethyl carbonate and 4 g of catalyst containing 2.7 g of malondialdehyde and 1.3 g of calcium hydroxide are added. After charging into a reaction flask and heating to 110 ℃ to distill off by-product methanol while reacting for 4 hours, the reaction solution was distilled under reduced pressure, and a fraction of 89 ℃/10mmHg was collected to obtain 164 g of 3-methyl-1, 4, 2-dioxazol-5-one in a yield of 82% and a purity of 99.1%.
Example 5
3-methyl-1, 4, 2-dinazole-5-ketone, and the preparation method thereof comprises the following steps: firstly, 150 g of acetohydroxamic acid, 500 g of dimethyl carbonate and 7 g of catalyst, wherein the content of malondialdehyde is 4.6 g and the content of barium hydroxide is 2.3 g, are added into a reaction bottle, then the reaction bottle is heated to 110 ℃, the byproduct methanol is distilled off while the reaction is carried out, after 4 hours of reaction, the reaction liquid is subjected to reduced pressure distillation, the fraction with 89 ℃/10mmHg is collected, 166 g of 3-methyl-1, 4, 2-dioxazole-5-ketone is obtained, the yield is 83 percent, and the purity is 99.0 percent.
The foregoing examples are illustrative only, and serve to explain some of the features of the present disclosure. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. And that advances in science and technology will result in the substitution of potential equivalents for the inaccurate representation of language, and such changes should also be construed where possible to be covered by the appended claims.
Claims (10)
- A process for producing 3-methyl-1, 4, 2-bisoxazol-5-one, characterized by comprising the steps of: adding acetohydroxamic acid, dimethyl carbonate and a catalyst into a reaction flask, heating to 110 ℃, reacting while distilling off a byproduct methanol, performing reduced pressure distillation on the reaction solution after reacting for 4 hours, and collecting a fraction with the temperature of 89 ℃/10mmHg to obtain 3-methyl-1, 4, 2-dioxazol-5-one; the reaction formula is as follows:
- 2. the process for producing 3-methyl-1, 4, 2-dioxazol-5-one according to claim 1, wherein: the molar ratio of the acetohydroxamic acid to the dimethyl carbonate is 1: 2-3.
- 3. The process for producing 3-methyl-1, 4, 2-bisoxazol-5-one according to claim 1 or 2, characterized in that: the catalyst is a mixture of malondialdehyde and calcium hydroxide.
- 4. The process for producing 3-methyl-1, 4, 2-dioxazol-5-one according to claim 3, wherein: the molar ratio of the malondialdehyde to the calcium hydroxide is (2-2.1) to 1.
- 5. The process for producing 3-methyl-1, 4, 2-dioxazol-5-one according to claim 3, wherein: the dosage of the catalyst is 1-5% of the mass of the acetohydroxamic acid.
- 6. The process for producing 3-methyl-1, 4, 2-bisoxazol-5-one according to claim 1 or 2, characterized in that: the catalyst is a mixture of dialdehyde and barium hydroxide.
- 7. The process for producing 3-methyl-1, 4, 2-dioxazol-5-one according to claim 6, wherein: the molar ratio of the malondialdehyde to the barium hydroxide is (2-2.1) to 1.
- 8. The process for producing 3-methyl-1, 4, 2-dioxazol-5-one according to claim 6, wherein: the dosage of the catalyst is 1-5% of the mass of the acetohydroxamic acid.
- 3-methyl-1, 4, 2-bisoxazol-5-one characterized in that: 3-methyl-1, 4, 2-bisoxazol-5-one obtained by the process for preparing 3-methyl-1, 4, 2-bisoxazol-5-one as claimed in any of claims 1 to 8.
- 10. Use of 3-methyl-1, 4, 2-bisoxazol-5-one according to claim 9 in electrolyte additives, in particular 3-methyl-1, 4, 2-bisoxazol-5-one as electrolyte additive in rechargeable lithium ion battery systems.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115707691A (en) * | 2021-08-20 | 2023-02-21 | 张家港市国泰华荣化工新材料有限公司 | Phenoxymethyl-1,4,2-dioxazole-5-ketone and preparation method thereof |
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| JP2008308495A (en) * | 2007-05-17 | 2008-12-25 | Kissei Pharmaceut Co Ltd | New catechol derivative, medicinal composition containing the same and its use |
| CN108336405A (en) * | 2017-12-18 | 2018-07-27 | 合肥国轩高科动力能源有限公司 | A kind of lithium-sulfur cell function electrolyte and preparation method thereof |
| CN110291676A (en) * | 2017-02-17 | 2019-09-27 | 明斯特威斯特法伦威廉大学 | Electrolyte additive for lithium-ion battery systems |
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| DE4326510A1 (en) * | 1993-08-06 | 1995-02-09 | Bayer Ag | Process for the preparation of cyclohexene derivatives |
| JP2008308495A (en) * | 2007-05-17 | 2008-12-25 | Kissei Pharmaceut Co Ltd | New catechol derivative, medicinal composition containing the same and its use |
| CN110291676A (en) * | 2017-02-17 | 2019-09-27 | 明斯特威斯特法伦威廉大学 | Electrolyte additive for lithium-ion battery systems |
| CN108336405A (en) * | 2017-12-18 | 2018-07-27 | 合肥国轩高科动力能源有限公司 | A kind of lithium-sulfur cell function electrolyte and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115707691A (en) * | 2021-08-20 | 2023-02-21 | 张家港市国泰华荣化工新材料有限公司 | Phenoxymethyl-1,4,2-dioxazole-5-ketone and preparation method thereof |
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