CN113387862A - Synthetic method of glutarimide - Google Patents
Synthetic method of glutarimide Download PDFInfo
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- CN113387862A CN113387862A CN202110689779.2A CN202110689779A CN113387862A CN 113387862 A CN113387862 A CN 113387862A CN 202110689779 A CN202110689779 A CN 202110689779A CN 113387862 A CN113387862 A CN 113387862A
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- glutarimide
- reaction
- glutaric anhydride
- urea
- synthesizing
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing glutarimide, which comprises the following steps: glutaric anhydride and urea are subjected to imidization reaction in a solvent to obtain glutarimide. The molar yield of the invention can reach more than 90 percent, and the product purity can reach more than 98 percent. And cooling after the reaction is finished, crystallizing and separating out the product, and filtering to obtain the product. The filtered filtrate can be used for the next batch without any treatment. The process is simple to operate, safe and easy to control, realizes zero emission, and represents a sustainable development direction of clean production.
Description
Technical Field
The invention relates to a method for synthesizing glutarimide.
Background
Glutarimide, the molecular structural formula is:
glutarimide is an important organic intermediate, and N-bromoglutarimide prepared by bromination is a good bromination reagent; it can also be used for the production of optical resins for optical protective films. In recent years, many studies on glutarimide antibiotics have been carried out, and the antibiotics have various biological activities such as antifungal activity, antibacterial activity, antiprotozoal activity, antiviral activity, anti-tumor activity, immunosuppression activity and the like.
At present, two methods for synthesizing glutarimide are mainly used, one method is prepared by reacting glutaric acid or glutaric anhydride with ammonia water; the other is prepared by the reaction of butyrolactone and potassium cyanide. The first method uses a large amount of excessive ammonia water, produces a large amount of ammonia-containing wastewater in the production process and has low yield; the second method is expensive in raw materials and uses a highly toxic compound, namely potassium cyanide. Neither method is suitable for industrial production.
Disclosure of Invention
The invention aims to provide a method for synthesizing glutarimide, which adopts glutaric anhydride and urea to obtain the glutarimide through imidization reaction in a solvent. And cooling after the reaction is finished, crystallizing and separating out the product, and filtering to obtain the product. The filtered filtrate can be used for the next batch without any treatment. The process is simple to operate, safe and easy to control, realizes zero emission, and represents a sustainable development direction of clean production.
The invention aims to realize the synthesis method of glutarimide by the following technical scheme, and the molecular structural formula of the compound is as follows:
the synthesis method takes glutaric anhydride and urea as raw materials, imidization reaction is carried out in a solvent, and glutarimide is obtained with high yield by simple filtration after the reaction is finished. The molar yield of the invention can reach more than 90 percent, and the product purity can reach more than 98 percent.
Compared with the prior art, the invention has the following beneficial effects: the invention changes the reaction substrate, reconstructs a new synthesis route, avoids generating a large amount of waste water generated by the raw material ammonia water, reduces the production and management cost and essentially reduces the environmental protection pressure. Meanwhile, the production efficiency and the product quality are improved, and the clean production of the glutarimide is realized.
Detailed Description
The invention is further illustrated by the following examples of embodiments.
A method for synthesizing glutarimide, the molecular structural formula of the compound is as follows:
the synthesis method takes glutaric anhydride and urea as raw materials to carry out imidization reaction in a solvent. After the reaction is finished, glutarimide is obtained with high yield by simple filtration.
Further, the reaction temperature is 180 ℃ and the reaction time is 1-5 hours.
Further, the solvent is selected from o-dichlorobenzene. The mass of the solvent used was 5 times the mass of the glutaric anhydride.
Further, the molar ratio of glutaric anhydride to urea was 2: 1.
The reaction equation is as follows:
carbon dioxide generated by the reaction can timely escape from the reaction system, and water generated by the reaction is timely removed, so that the balance of the reaction is favorable for moving to the right. The invention uses a water separator, and removes the water generated by the reaction out of the reaction system by using the principle of azeotropic boiling of o-dichlorobenzene and water during reflux.
During the specific operation, firstly, the measured glutaric anhydride, urea and solvent are put into a reactor, stirred and heated until reflux, the reflux is divided into water for a period of time, the temperature is cooled to room temperature, the materials are discharged and filtered, the next batch of materials are used for feeding the filtrate, and the finished product is obtained after the filter cake is dried.
Example 1
In a 2000ml four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, a water separator and an electric jacket, 114g (1mol) of glutaric anhydride, 30g (0.5mol) of urea and 570g of o-dichlorobenzene were charged, and heating was started with stirring.
When the temperature rises to 180 ℃, liquid drops at the lower end of the condenser flow back, and flow back to the system through the water separator. And carrying out reflux reaction for 1 hour, and timely draining water in the water separator midway. And cooling to room temperature. Filtration and drying of the filter cake gave 83.5g of a pale grey powder. The liquid chromatography content was 95.47% with a molar yield of 73.89% based on glutaric anhydride.
Example 2
In a 2000ml four-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, a water separator and an electric jacket, 114g (1mol) of glutaric anhydride, 30g (0.5mol) of urea and 570g of o-dichlorobenzene were charged, and heating was started with stirring.
When the temperature rises to 180 ℃, liquid drops at the lower end of the condenser flow back, and flow back to the system through the water separator. And carrying out reflux reaction for 5 hours, and timely draining water in the water separator midway. And cooling to room temperature. Filtration and drying of the filter cake gave 97g of a pale grey powder. The liquid chromatography content was 98.51%, calculated as glutaric anhydride, and the molar yield was 85.84%.
467g of filtrate is reserved for use.
Example 3
In a 2000ml four-necked flask with mechanical stirring, thermometer, reflux condenser, water separator and electric mantle was placed 114g (1mol) of glutaric anhydride, 30g (0.5mol) of urea, 467g of the filtrate of example 2 and 103g of neo-o-dichlorobenzene, stirring was turned on and heating was started.
When the temperature rises to 180 ℃, liquid drops at the lower end of the condenser flow back, and flow back to the system through the water separator. And carrying out reflux reaction for 5 hours, and timely draining water in the water separator midway. And cooling to room temperature. Filtration and drying of the filter cake gave 104g of a pale grey powder. The content of liquid chromatography is 98.11%, and the molar yield is 92.03% in terms of glutaric anhydride.
Claims (4)
1. A method for synthesizing glutarimide, the molecular structural formula of the compound is as follows:
the method is characterized in that glutaric anhydride and urea are subjected to imidization reaction in a solvent to obtain glutarimide.
The reaction equation of the synthesis method is as follows:
2. the method of claim 1, wherein the solvent is ortho-dichlorobenzene. The mass of the solvent used was 5 times the mass of the glutaric anhydride.
3. A method for synthesizing glutarimide according to claim 1 wherein the mole ratio of glutaric anhydride to urea is 2: 1.
4. A method for synthesizing glutarimide according to claim 1 wherein the reaction temperature is 180 ℃ and the reaction time is 1-5 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110689779.2A CN113387862A (en) | 2021-06-22 | 2021-06-22 | Synthetic method of glutarimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110689779.2A CN113387862A (en) | 2021-06-22 | 2021-06-22 | Synthetic method of glutarimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113387862A true CN113387862A (en) | 2021-09-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110689779.2A Pending CN113387862A (en) | 2021-06-22 | 2021-06-22 | Synthetic method of glutarimide |
Country Status (1)
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| CN (1) | CN113387862A (en) |
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2021
- 2021-06-22 CN CN202110689779.2A patent/CN113387862A/en active Pending
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Inventor after: Zou Congwei Inventor after: Zhang Yan Inventor after: Li Fu Inventor after: Li Renshun Inventor after: Li Ming Inventor after: Niu Wei Inventor before: Zhang Yan Inventor before: Zou Congwei Inventor before: Li Fu Inventor before: Li Renshun Inventor before: Li Ming Inventor before: Niu Wei |
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