CN114621187A - Synthetic method of imidacloprid - Google Patents
Synthetic method of imidacloprid Download PDFInfo
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- CN114621187A CN114621187A CN202011427116.5A CN202011427116A CN114621187A CN 114621187 A CN114621187 A CN 114621187A CN 202011427116 A CN202011427116 A CN 202011427116A CN 114621187 A CN114621187 A CN 114621187A
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- Prior art keywords
- imidacloprid
- dropwise adding
- imidazolidine
- synthesizing
- nitroguanidine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Abstract
The invention provides a synthetic method of imidacloprid, which comprises the steps of mixing nitroguanidine and sulfuric acid, dropwise adding ethylenediamine, heating and synthesizing an intermediate imidazolidine; adding acetonitrile, imidazolidine, potassium carbonate and cesium chloride, mixing a little, dropwise adding acetonitrile solution dissolved with 2-chloro-5-chloromethyl pyridine, heating for reflux reaction, and filtering to obtain the imidacloprid product. The imidacloprid product is obtained through two-step reaction, and the content and yield of the imidacloprid product are both improved to 95 percent; the reaction temperature is reduced, the reflux time is reduced, and the energy consumption is reduced; the preparation method is safe and environment-friendly, is suitable for industrial production, and has wide application prospect.
Description
Technical Field
The invention relates to a synthetic method of imidacloprid, belonging to the technical field of organic synthesis.
Background
Imidacloprid is a nitro methylene systemic insecticide, belongs to chloronicotinyl insecticides, is also called neonicotinyl insecticides, and has a chemical formula C9H10ClN5O2. Has the advantages of broad spectrum, high efficiency, low toxicity, low residue, difficult resistance generation of pests, and multiple effects of contact poisoning, stomach poisoning, systemic absorption and the like. After the pests contact the pesticide, normal conduction of central nerves is blocked, so that the pests die in paralysis. The product has good quick action, has higher control effect 1 day after being applied, and has a residual period as long as about 25 days. The pesticide effect and the temperature are in positive correlation, the temperature is high, the insecticidal effect is good, and the insecticidal composition is mainly used for preventing and controlling the pests with piercing-sucking mouthparts. However, in the current industrial synthetic method of imidacloprid, various raw materials are simply mixed with a solvent and a catalyst and then directly reacted, and the problems of long reaction period, high energy consumption, excessive byproducts and low yield are generally existed.
Disclosure of Invention
The invention aims to solve the defects of the conventional imidacloprid synthesis method and provides a safe and efficient imidacloprid synthesis method which can be industrially produced in batch.
The technical solution of the invention is as follows: a synthetic method of imidacloprid specifically comprises the following steps:
1) adding nitroguanidine and sulfuric acid into a reaction kettle, gradually dropwise adding ethylenediamine, heating to 70 ℃ after dropwise adding, reacting, filtering, washing and drying after the reaction is finished to obtain an intermediate imidazolidine;
2) adding acetonitrile into a reaction kettle, mixing the imidazolidine prepared in the step 1), potassium carbonate and cesium chloride, gradually dropwise adding an acetonitrile solution in which 2-chloro-5-chloromethylpyridine is dissolved, heating and refluxing for 4 hours after dropwise adding, filtering, washing filter residues with acetonitrile, combining the filtrate, and desolventizing to obtain a brown solid imidacloprid product.
The water content of the nitroguanidine in the step 1) is 50 percent.
The mass concentration of the sulfuric acid in the step 1) is 70%.
The mass ratio of nitroguanidine, ethylenediamine and sulfuric acid in the step 1) is 1:1: 0.8.
The mass ratio of imidazolidine to 2-chloro-5-chloromethylpyridine in said step 2) is 1: 0.7.
Compared with the prior art, the invention has the advantages that:
1) the content of imidacloprid is improved to 95 percent, and the yield is improved to 95 percent;
2) the reaction temperature is reduced, the reflux time is reduced, and the energy consumption is reduced;
3) the preparation method is safe and environment-friendly, and is suitable for industrial production.
Detailed Description
The technical scheme of the invention is further illustrated by the following examples. The technical solutions and the related parameters given in the following embodiments are only exemplary and are intended to be used for explaining the present invention, and should not be construed as limiting the present invention.
The embodiment discloses a method for synthesizing imidacloprid, wherein nitroguanidine and ethylenediamine are adopted for reaction, and the generated intermediate is prepared into imidacloprid by reacting with 2-chloro-5-chloromethyl pyridine, which comprises the following steps:
sequentially adding nitroguanidine and 70% sulfuric acid into a 1000ml four-neck flask, dropwise adding ethylenediamine, heating to 70 ℃ for reaction, filtering, washing and drying after the sampling reaction is finished to obtain an intermediate product imidazolidine; adding acetonitrile, imidazolidine, potassium carbonate and cesium chloride into a 1000ml four-neck flask, mixing a little, dropwise adding acetonitrile solution dissolved with 2-chloro-5-chloromethyl pyridine, heating for reflux reaction for 4 hours, filtering, washing filter residues with acetonitrile, combining filtrates, desolventizing to obtain an imidacloprid product, and determining that the imidacloprid yield is 95%.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (5)
1. The synthetic method of imidacloprid is characterized by comprising the following steps:
1) adding nitroguanidine and sulfuric acid into a reaction kettle, gradually dropwise adding ethylenediamine, heating to 70 ℃ after dropwise adding, reacting, filtering, washing and drying after the reaction is finished to obtain an intermediate imidazolidine;
2) adding acetonitrile into a reaction kettle, mixing the imidazolidine prepared in the step 1), potassium carbonate and cesium chloride, gradually dropwise adding an acetonitrile solution in which 2-chloro-5-chloromethylpyridine is dissolved, heating and refluxing for 4 hours after dropwise adding, filtering, washing filter residues with acetonitrile, combining the filtrate, and desolventizing to obtain a brown solid imidacloprid product.
2. The method for synthesizing imidacloprid as claimed in claim 1, wherein the water content of nitroguanidine in the step 1) is 50%.
3. The method for synthesizing imidacloprid as claimed in claim 1, wherein the mass concentration of the sulfuric acid in the step 1) is 70%.
4. The method for synthesizing imidacloprid as claimed in claim 1, wherein the ratio of the amounts of nitroguanidine, ethylenediamine and sulfuric acid in step 1) is 1:1: 0.8.
5. The method for synthesizing imidacloprid as claimed in claim 1, wherein the mass ratio of the imidazolidine to the 2-chloro-5-chloromethylpyridine in step 2) is 1: 0.7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011427116.5A CN114621187A (en) | 2020-12-09 | 2020-12-09 | Synthetic method of imidacloprid |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011427116.5A CN114621187A (en) | 2020-12-09 | 2020-12-09 | Synthetic method of imidacloprid |
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| CN114621187A true CN114621187A (en) | 2022-06-14 |
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| CN202011427116.5A Pending CN114621187A (en) | 2020-12-09 | 2020-12-09 | Synthetic method of imidacloprid |
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Citations (8)
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|---|---|---|---|---|
| CN103073535A (en) * | 2013-01-30 | 2013-05-01 | 山东省联合农药工业有限公司 | Synthetic method of imidacloprid |
| CN103641815A (en) * | 2013-11-21 | 2014-03-19 | 青岛佰众化工技术有限公司 | Production improvement process of imidacloprid |
| CN104672212A (en) * | 2013-11-26 | 2015-06-03 | 嘉兴学院 | Method for synthesizing imidacloprid employing cascade reaction |
| CN105924428A (en) * | 2016-06-29 | 2016-09-07 | 南通天泽化工有限公司 | Method for synthesizing imidacloprid |
| CN109180641A (en) * | 2018-10-22 | 2019-01-11 | 江苏长青农化股份有限公司 | A kind of preparation method of imidacloprid |
| CN110818686A (en) * | 2019-11-15 | 2020-02-21 | 江苏扬农化工集团有限公司 | Synthetic method of imidacloprid |
| WO2020058807A1 (en) * | 2018-09-17 | 2020-03-26 | Upl Ltd | A manufacturing process for 2-nitroimino heterocyclic compounds |
| CN110981809A (en) * | 2019-12-23 | 2020-04-10 | 南通天泽化工有限公司 | Method for synthesizing imidazolidine |
-
2020
- 2020-12-09 CN CN202011427116.5A patent/CN114621187A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073535A (en) * | 2013-01-30 | 2013-05-01 | 山东省联合农药工业有限公司 | Synthetic method of imidacloprid |
| CN103641815A (en) * | 2013-11-21 | 2014-03-19 | 青岛佰众化工技术有限公司 | Production improvement process of imidacloprid |
| CN104672212A (en) * | 2013-11-26 | 2015-06-03 | 嘉兴学院 | Method for synthesizing imidacloprid employing cascade reaction |
| CN105924428A (en) * | 2016-06-29 | 2016-09-07 | 南通天泽化工有限公司 | Method for synthesizing imidacloprid |
| WO2020058807A1 (en) * | 2018-09-17 | 2020-03-26 | Upl Ltd | A manufacturing process for 2-nitroimino heterocyclic compounds |
| CN109180641A (en) * | 2018-10-22 | 2019-01-11 | 江苏长青农化股份有限公司 | A kind of preparation method of imidacloprid |
| CN110818686A (en) * | 2019-11-15 | 2020-02-21 | 江苏扬农化工集团有限公司 | Synthetic method of imidacloprid |
| CN110981809A (en) * | 2019-12-23 | 2020-04-10 | 南通天泽化工有限公司 | Method for synthesizing imidazolidine |
Non-Patent Citations (2)
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| 章瑛等: "基于串联反应的吡虫啉新合成工艺研究", 化学通报, vol. 77, no. 9, pages 919 - 921 * |
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