CN111892542A - Method for synthesizing imidazole film-forming ionic liquid - Google Patents
Method for synthesizing imidazole film-forming ionic liquid Download PDFInfo
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Abstract
A method for synthesizing imidazole film-forming ionic liquid belongs to the technical field of compound synthesis, and comprises the following steps: A. reacting phosgene with acetylene alcohol or vinyl alcohol to obtain a liquid product; B. under the condition of nitrogen, triethylene glycol monomethyl ether and triethylamine are added into toluene, methane sulfonic acid chloride is added under ice bath, and a solid product is obtained after reaction; C. adding sodium into toluene under the condition of nitrogen, heating until the sodium is molten, stirring to room temperature, then controlling the temperature to be 0-5 ℃, adding N, N-dimethylethanolamine, reacting for 30-40min at the room temperature, and then controlling the temperature to be 0-5 ℃, adding the solid product obtained in the step B, and reacting at the room temperature to obtain a liquid product; D. and C, under the condition of nitrogen, dissolving imidazole in a solvent, adding the liquid product obtained in the step C, cooling to 0 ℃, dropwise adding the liquid product obtained in the step A, controlling the temperature to be 5-10 ℃, stirring for 2-5h, carrying out suction filtration, controlling the pH value of filtrate to be 7.1-7.3, drying, and carrying out reduced pressure distillation to obtain the product. The synthesis method is simple, the reaction condition is mild and stable, and the product yield and purity are high.
Description
Technical Field
The invention belongs to the technical field of compound synthesis, and particularly relates to a synthesis method of imidazole film-forming ionic liquid.
Background
Commercial lithium batteries use an organic solution as an electrolyte, and although factors such as conductivity have been improved significantly, they are flammable and may cause leakage when used improperly. Therefore, in order to improve the safety of the lithium ion battery, it is necessary to improve the stability of the electrolyte of the lithium ion battery.
The ionic liquid as a novel electrolyte solvent has the advantages of wide electrochemical window, no vapor pressure, high electrochemical stability, wide liquid process, no pollution, easy recovery and the like. The application research of the ionic liquid in the electrolyte of the lithium ion battery at present can be divided into two types according to the volume fraction of the ionic liquid in the electrolyte: 1) the ionic liquid is used as an electrolyte solvent of the lithium ion battery; 2) the ionic liquid is used as an additive. In view of the existing research situation, the ionic liquid is used for replacing or partially replacing the carbonate solvent for the lithium ion battery, so that the safety problem of the lithium ion battery is hopefully solved, and the ionic liquid becomes the best choice for replacing the traditional organic electrolyte. Wherein, the imidazole ionic liquid has small viscosity and high conductivity (up to 10)-2S/cm), and the like, and has good application effect in the lithium ion battery. However, the synthesis technology of the imidazole ionic liquid is not mature at present, and the industrial production of the imidazole ionic liquid is not realized.
Disclosure of Invention
The invention aims to provide a method for synthesizing imidazole film-forming ionic liquid, in particular to a synthetic compound
And compounds
The method of (1).
The technical scheme adopted by the invention for realizing the purpose is as follows:
the method for synthesizing the imidazole film-forming ionic liquid comprises the following steps:
A. adding phosgene into a reactor, stirring, cooling to 10-15 ℃, dropwise adding acetylene alcohol or vinyl alcohol for 1.5-3h, keeping the temperature for 2-3h after dropwise adding, carrying out reduced pressure distillation, filtering, and fractionating to obtain a liquid product;
B. under the condition of nitrogen, adding triethylene glycol monomethyl ether and triethylamine into toluene, adding methane sulfonic acid chloride under ice bath, reacting for 8-10h, performing suction filtration, and decompressing filtrate to remove toluene to obtain a solid product for later use;
C. adding sodium into toluene under the condition of nitrogen, heating until the sodium is molten, stirring to room temperature, then controlling the temperature to be 0-5 ℃, adding N, N-dimethylethanolamine, reacting for 30-40min at the room temperature, then controlling the temperature to be 0-5 ℃, adding the solid product obtained in the step B, reacting for 20-24h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain a liquid product for later use;
D. and C, under the condition of nitrogen, dissolving imidazole in a solvent, adding the liquid product obtained in the step C, cooling to 0 ℃, dropwise adding the liquid product obtained in the step A for 0.5-1h, controlling the temperature to be 5-10 ℃, stirring for 2-5h, performing suction filtration, controlling the pH value of filtrate to be 7.1-7.3, drying, and performing reduced pressure distillation to obtain the product.
In the step A, the molar ratio of phosgene to acetylene alcohol or vinyl alcohol is (1.0-1.3): 1.
in the step B, the mass ratio of triethylene glycol monomethyl ether, triethylamine and methane sulfonyl chloride is 1 (0.7-0.75): (0.8-0.85).
In the step C, the mass ratio of sodium to N, N-dimethylethanolamine to the solid product is 1; (4-4.3): (9.5-10).
In the step D, the mass ratio of imidazole to the liquid product in the step C to the liquid product in the step A is 1: (2.1-3.2): (0.9-1.8).
The invention has the beneficial effects that:
the method has the advantages of cheap and easily obtained raw materials, simple and easy synthetic method, low energy consumption, mild and stable reaction conditions, short reaction time and high product yield.
Drawings
FIG. 1 is a 1H map of the synthesis of 1H-imidazole-1-carboxylic acid acetylene ester according to the invention.
FIG. 2 is a 13C map of the synthesis of 1H-imidazole-1-carboxylic acid acetylene ester according to the invention.
FIG. 3 is a 1H map of the present invention for the synthesis of vinyl 1H-imidazole-1-carboxylate.
FIG. 4 is a 13C map of the inventive synthesis of vinyl 1H-imidazole-1-carboxylate.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
A. Adding 1mol of phosgene into a reactor, stirring and cooling to 10 ℃, dropwise adding 1mol of acetylene alcohol into the reactor for 2 hours, preserving the temperature for 3 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 98.9g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 115g of triethylamine are added into toluene, 132g of methane sulfonic acid chloride is added under ice bath, the reaction is carried out for 8 hours, the filtration is carried out, the toluene is removed under reduced pressure from the filtrate, and 236.9g of solid product is obtained for standby;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 0 ℃, adding 92g of N, N-dimethylethanolamine, reacting for 30min at the room temperature, then controlling the temperature to be 0 ℃, adding 219g of the obtained solid product, reacting for 20h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 157.3g of liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 105g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 45g of the liquid product obtained in the step A is dropwise added, the dropwise adding time is 0.5H, then the temperature is controlled to 6 ℃, stirring is carried out for 4H, suction filtration is carried out, the pH value of filtrate is controlled to 7.1, drying and reduced pressure distillation are carried out, 55.9g of the product is obtained (the yield is 95.2%), gas phase method detection is carried out, the solvent is dichloromethane, and the product is identified to be 1H-imidazole-1-acetylene formate through 1H-NMR and 13C-NMR characterization analysis, and the product is shown in figure 1 and figure 2.
Example 2
A. Adding 1mol of phosgene into a reactor, stirring and cooling to 12 ℃, dropwise adding 1.2mol of acetylene alcohol into the reactor for 1.5 hours, keeping the temperature for 2.5 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 100.6g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 117g of triethylamine are added into toluene, 134g of methane sulfonic acid chloride is added under ice bath, the mixture reacts for 9 hours, the filtration is carried out, and the toluene is removed from the filtrate under reduced pressure to obtain 237.8g of solid product for later use;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 1 ℃, adding 95g of N, N-dimethylethanolamine, reacting for 40min at the room temperature, then controlling the temperature to be 3 ℃, adding 225g of the obtained solid product, reacting for 23h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 159.1g of a liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 120g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 45g of the liquid product obtained in the step A is dropwise added, the dropwise adding time is 1H, then the temperature is controlled to be 7 ℃, stirring is carried out for 3H, suction filtration is carried out, the pH value of filtrate is controlled to be 7.3, drying and reduced pressure distillation are carried out, 74.8g of a product (the yield is 95.5%) is obtained, the solvent is dichloromethane, and the product is identified to be 1H-imidazole-1-acetylene formate through 1H-NMR and 13C-NMR characterization analysis.
Example 3
A. Adding 1mol of phosgene into a reactor, stirring and cooling to 15 ℃, dropwise adding 1.1mol of acetylene alcohol for 2.5 hours, keeping the temperature for 3 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 99.4g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 118g of triethylamine are added into toluene, 139g of methanesulfonic acid chloride is added under ice bath, the mixture reacts for 10 hours, the filtration is carried out, and the toluene is removed from the filtrate under reduced pressure to obtain 237.2g of a solid product for later use;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 2 ℃, adding 98.9g of N, N-dimethylethanolamine, reacting for 35min at the room temperature, then controlling the temperature to be 5 ℃, adding 230g of the obtained solid product, reacting for 22h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 167.5g of a liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 160g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 80g of the liquid product obtained in the step A is dropwise added, the dropwise adding time is 40min, then the temperature is controlled to be 5 ℃, stirring is carried out for 2H, suction filtration is carried out, the pH value of filtrate is controlled to be 7.2, drying and reduced pressure distillation are carried out, 94.9g of the product is obtained (the yield is 95.6%), gas phase method detection is carried out, the solvent is dichloromethane, and the product is identified to be 1H-imidazole-1-acetylene formate through 1H-NMR and 13C-NMR characterization analysis.
Example 4
A. Adding 1mol of phosgene into a reactor, stirring and cooling to 13 ℃, dropwise adding 1.3mol of vinyl alcohol into the reactor for 3 hours, preserving the temperature for 2 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 102.2g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 121g of triethylamine are added into toluene, 135g of methanesulfonic acid chloride is added under ice bath, the mixture reacts for 8.5h, the filtration is carried out, the toluene is removed under reduced pressure, and 237.6g of solid product is obtained for later use;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 3 ℃, adding 93g of N, N-dimethylethanolamine, reacting for 32min at the room temperature, then controlling the temperature to be 4 ℃, adding 223g of the obtained solid product, reacting for 25h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 155.5g of a liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 140g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 90g of the liquid product obtained in the step A is dropwise added, the dropwise adding time is 50min, then the temperature is controlled to be 8 ℃, stirring is carried out for 5H, suction filtration is carried out, the pH value of filtrate is controlled to be 7.2, drying and reduced pressure distillation are carried out, 96.8g of the product is obtained (the yield is 95.4%), gas phase method detection is carried out, the solvent is dichloromethane, and the product is identified as 1H-imidazole-1-vinyl formate through 1H-NMR and 13C-NMR characterization analysis.
Example 5
A. Adding 1mol of phosgene into a reactor, stirring and cooling to 13 ℃, dropwise adding 1.2mol of vinyl alcohol into the reactor for 3 hours, preserving the temperature for 2 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 101.7g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 123g of triethylamine are added into toluene, 138g of methane sulfonic acid chloride is added under ice bath, the mixture reacts for 9.5 hours, the filtration is carried out, the toluene is removed under reduced pressure from the filtrate, and 237.4g of solid product is obtained for standby;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 4 ℃, adding 94g of N, N-dimethylethanolamine, reacting for 38min at the room temperature, then controlling the temperature to be 1 ℃, adding 228g of the obtained solid product, reacting for 24h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 157.2g of a liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 130g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 70g of the liquid product obtained in the step A is dropwise added, the dropwise adding time is 45min, then the temperature is controlled to be 10 ℃, stirring is carried out for 2H, suction filtration is carried out, the pH value of filtrate is controlled to be 7.1, drying and reduced pressure distillation are carried out, 86.8g of the product is obtained (the yield is 95.6%), gas phase method detection is carried out, the solvent is dichloromethane, and the product is identified to be 1H-imidazole-1-vinyl formate through 1H-NMR and 13C-NMR characterization analysis, and the reference is made in figures 3 and.
Example 6
A. Adding 1mol of phosgene into a reactor, stirring, cooling to 11 ℃, dropwise adding 1.1mol of vinyl alcohol into the reactor for 2.5 hours, preserving heat for 2.5 hours after dropwise adding, carrying out reduced pressure distillation, filtering and fractionating to obtain 101.9g of liquid product;
B. under the condition of nitrogen, 164g of triethylene glycol monomethyl ether and 120g of triethylamine are added into toluene, 136g of methanesulfonic acid chloride is added under ice bath, the mixture reacts for 9 hours, the filtration is carried out, the toluene is removed under reduced pressure from the filtrate, and 237.5g of solid product is obtained for standby;
C. under the condition of nitrogen, adding 23g of sodium into toluene, heating to melt the sodium, stirring to room temperature, then controlling the temperature to be 5 ℃, adding 96g of N, N-dimethylethanolamine, reacting for 35min at the room temperature, then controlling the temperature to be 2 ℃, adding 226g of the obtained solid product, reacting for 21h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain 160.2g of a liquid product for later use;
D. under the condition of nitrogen, 50g of imidazole is dissolved in dichloromethane, 150g of the liquid product obtained in the step C is added, the temperature is reduced to 0 ℃, 50g of the liquid product obtained in the step A is dropwise added for 30min, then the temperature is controlled to be 9 ℃, stirring is carried out for 3H, suction filtration is carried out, the pH value of filtrate is controlled to be 7.3, drying and reduced pressure distillation are carried out, 61.7g of the product is obtained (the yield is 95.2%), gas phase method detection is carried out, the solvent is dichloromethane, and the product is identified as 1H-imidazole-1-vinyl formate through 1H-NMR and 13C-NMR characterization analysis.
Claims (5)
1. The method for synthesizing the imidazole film-forming ionic liquid is characterized by comprising the following steps of:
A. adding phosgene into a reactor, stirring, cooling to 10-15 ℃, dropwise adding acetylene alcohol or vinyl alcohol for 1.5-3h, keeping the temperature for 2-3h after dropwise adding, carrying out reduced pressure distillation, filtering, and fractionating to obtain a liquid product;
B. under the condition of nitrogen, adding triethylene glycol monomethyl ether and triethylamine into toluene, adding methane sulfonic acid chloride under ice bath, reacting for 8-10h, performing suction filtration, and decompressing filtrate to remove toluene to obtain a solid product for later use;
C. adding sodium into toluene under the condition of nitrogen, heating until the sodium is molten, stirring to room temperature, then controlling the temperature to be 0-5 ℃, adding N, N-dimethylethanolamine, reacting for 30-40min at the room temperature, then controlling the temperature to be 0-5 ℃, adding the solid product obtained in the step B, reacting for 20-24h at the room temperature, adding water, separating liquid, drying an organic phase, and then distilling under reduced pressure to remove toluene to obtain a liquid product for later use;
D. and C, under the condition of nitrogen, dissolving imidazole in a solvent, adding the liquid product obtained in the step C, cooling to 0 ℃, dropwise adding the liquid product obtained in the step A for 0.5-1h, controlling the temperature to be 5-10 ℃, stirring for 2-5h, performing suction filtration, controlling the pH value of filtrate to be 7.1-7.3, drying, and performing reduced pressure distillation to obtain the product.
2. The method for synthesizing the imidazole-based film-forming ionic liquid according to claim 1, wherein in the step A, the molar ratio of phosgene to acetylene alcohol or vinyl alcohol is (1.0-1.3): 1.
3. the method for synthesizing the imidazole-based film-forming ionic liquid according to claim 1, wherein in the step B, the mass ratio of triethylene glycol monomethyl ether, triethylamine and methanesulfonyl chloride is 1 (0.7-0.75): (0.8-0.85).
4. The method for synthesizing the imidazole-based film-forming ionic liquid according to claim 1, wherein in the step C, the mass ratio of sodium to N, N-dimethylethanolamine to the solid product is 1; (4-4.3): (9.5-10).
5. The method for synthesizing the imidazole-based film-forming ionic liquid according to claim 1, wherein in the step D, the mass ratio of imidazole to the liquid product in the step C to the liquid product in the step A is 1: (2.1-3.2): (0.9-1.8).
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| US20030228334A1 (en) * | 2002-06-03 | 2003-12-11 | Mmp, Inc. | Mattifying oil-in-water emulsion |
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| Title |
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| 刘学英: "脂肪酶催化合成（S）-吲哚洛芬及其与小分子相互作用机理", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 马思渝等: "乙醛—乙烯醇、乙烯酮—乙炔醇异构化研究", 《物理化学学报》 * |
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