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Preparation method of clethodim and intermediate thereof

A technology for clethodim and intermediates, applied in the field of clethodim preparation, can solve the problems of affecting the yield and product quality, increasing the burden of wastewater treatment, high ammonia nitrogen content, etc., achieving easy separation and purification, increasing the burden of wastewater treatment, and high purity Effect

Inactive Publication Date: 2020-06-02
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound Ⅵ is the same substance as the compound Ⅴ in US6300281. In this process, the synthesis of the compound Ⅵ from the compound Ⅳ has long and cumbersome process steps. Although the amine catalyst can improve the rearrangement selectivity, the improvement is limited, and the reaction still produces relatively high There are many by-product impurities, and the impurities will be converted into tar in the subsequent hydrolysis rearrangement, which affects the yield and product quality. The yield of compound VI is about 80% according to its report
Furthermore, the use of amine catalysts leads to high ammonia nitrogen content in wastewater, requiring special removal of ammonia nitrogen, which increases the burden of wastewater treatment

Method used

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  • Preparation method of clethodim and intermediate thereof
  • Preparation method of clethodim and intermediate thereof
  • Preparation method of clethodim and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] 1. Refer to the method of patent 201710535450.4 to prepare 6-ethylthio-3-hepten-2-one toluene solution.

[0057] 2. Put 45g of sodium methoxide methanol solution with a mass concentration of 30% into a 500ml three-necked flask, distill off the methanol, then add 250g of toluene and 40g of diethyl malonate, stir for 1h, and then dropwise add 30wt% of 6-Ethylthio-3-hepten-2-one toluene solution 137g, dropwise time is 1h, after dropping, keep warm at 40°C for 1h for cyclization reaction, after reaction, heat up to 70°C for dealcoholization, and add 120g of toluene at the same time, After dealcoholization is finished, obtain the mixture of 240g compound A and toluene, compound A structural formula is as follows:

[0058] .

[0059] 3. Filter the mixture of compound A and toluene obtained above to remove impurities, put the obtained compound A into a three-necked flask filled with 200g of toluene, and pass hydrogen chloride gas into the reaction solution at 15°C until the...

Embodiment 2

[0064] 1. Refer to the method of patent 201710535450.4 to prepare 6-ethylthio-3-hepten-2-one toluene solution.

[0065] 2. Put 45g of sodium methoxide methanol solution with a mass concentration of 30% into a 500ml three-necked flask, distill off the methanol, then add 250g of benzene and 33g of dimethyl malonate, stir for 1h, and then add dropwise 30wt% of 137g of 6-ethylthio-3-hepten-2-one toluene solution, the time of dropping is 1h, and after the dropping is completed, the cyclization reaction is kept at 40°C for 1h, and after the reaction, the temperature is raised to 70°C for dealcoholization, and 120g of benzene is added at the same time. After dealcoholization is completed, obtain the mixture of 225g compound A and benzene, compound A structural formula is as follows:

[0066]

[0067] 3. Filter the compound A and benzene mixture obtained above to remove impurities, put the obtained compound A into a three-necked flask with 200 g of benzene, and feed hydrogen bromid...

Embodiment 3

[0072] 1. Refer to the method of patent 201710535450.4 to prepare 6-ethylthio-3-hepten-2-one toluene solution.

[0073] 2. Put 45g of sodium methoxide methanol solution with a mass concentration of 30% into a 500ml three-necked flask, distill off the methanol, then add 250g of toluene and 19g of methyl acetate, and then add dropwise 6-ethylthio with a content of 30wt% at 40°C - 3-hepten-2-one toluene solution 137g, dropwise time is 1h, after dropping, keep warm at 40°C for 1h, heat up to 70°C to remove solvent, add 120g toluene at the same time, after dealcoholization , obtain the mixture of 190g compound A and toluene, compound A structural formula is as follows:

[0074]

[0075] 3. Filter the mixture of compound A and toluene obtained above to remove impurities, put the obtained compound A into a three-necked flask equipped with 200g toluene, add 30wt% hydrochloric acid solution to the reaction solution at 0°C until pH3 left and right, standing and stratifying, and the ...

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Abstract

The invention discloses a preparation method of clethodim and an intermediate thereof. The preparation method of the intermediate comprises the step of acidifying a compound A to obtain a compound B.According to the invention, the compound B is obtained by acidifying the compound A, and reacts to obtain a compound D, and the compound D reacts to obtain clethodim, so that the reaction condition are mild, the operation is simple, the preparation process of the compounds A-D does not require separation, water washing, layering, rearrangement and other operations, the clethodim preparation process flow is simplified, the reaction time is shortened, the production efficiency is improved, the post-treatment is simple, water washing, layering and other processes are not needed, separation and purification are facilitated, the wastewater treatment burden is not increased, three wastes are reduced, the production cost is reduced, the environmental protection requirement is met, and the methodis suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing a clethodim intermediate, and also relates to a method for preparing clethodim by using the intermediate, belonging to the technical field of clethodim preparation. Background technique [0002] Clethodim, the chemical name is 2-{1-[(3-chloro-2-allyl)oxy]iminopropyl}-5-[2-(ethylthio)propyl]-3-hydroxy -2-Cyclohexen-1-one is a broad-spectrum post-emergence herbicide that releases grass weeds in broadleaf crops. It has a strong killing effect on annual and perennial grass weeds, and is mainly suitable for soybeans It can control more than 40 kinds of crops such as cotton, peanut, watermelon and more than 30 kinds of gramineous weeds such as barnyard grass. [0003] At present, there are few reports on the synthetic routes of clethodim, and the yields are not high. In 2001, the patent US6300281 reported the specific preparation method of clethodim. The steps are: using crotonaldehyde and ethanethiol as raw ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/20C07C323/22C07C323/55C07C323/47
CPCC07C319/20C07C323/22C07C323/47C07C323/55C07C2601/16
Inventor 孙国庆侯永生绳敏胡义山邹宗加贺瑞军李顺仁
Owner SHANDONG RUNBO BIOTECH CO LTD
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