Improved preparation method of nitenpyram

A kind of technology of nitenpyram and ethylamine

Inactive Publication Date: 2016-02-17
SHANGHAI JINJING CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] In summary, compared with 2-chloro-5-chloromethylpyridine, there are relatively few manufacturers of 2-chloro-5-aminomethylpyridine, and the raw materials are not easy to buy, while the raw materials in route 3 or route 4 are cheap, Low toxicity, easy to obtain, simple synthesis method, suitable for large-scale industrial production; other routes involve dimethyl sulfate or methyl isothiocyanate, which are highly toxic, easy to cause production safety, difficult to handle after-treatment, and easy to cause environmental pollution. Pollution

Method used

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  • Improved preparation method of nitenpyram

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Preparation of compound (b) 1,1,1-trichloro-2-nitroethane

[0041] 1. In a 5000L glass-lined reactor, add 2231kg ​​of 36% hydrochloric acid, cool below 10°C, add 978kg of sodium nitrate in batches, stir for 20min, and then add 3kg of tetrabutylammonium bromide;

[0042] 2. Add 970kg of vinylidene chloride dropwise, control the temperature at 10°C, and keep warm for 4 hours after the addition;

[0043] 3. After the reaction is completed, stand still for 30 minutes and separate into layers;

[0044] 4. Add 1000kg of tap water to the organic layer and stir for 30min, then stand still for 30min to separate the layers to obtain 1606.5kg of compound (b) 1,1,1-trichloro-2-nitroethane, GC=90%, molar yield 0.9;

[0045] Preparation of compound (c) 1,1-dichloro-2-nitroethylene

[0046] 1. In a 5000L glass-lined kettle, add 1606.5kg of the obtained compound (b), add 1000kg of tap water, and raise the temperature by 30-40°C;

[0047] 2. Then add 2100kg 8% NaHCO dropwise 3 About...

Embodiment 2

[0068] Preparation of compound (b) 1,1,1-trichloro-2-nitroethane

[0069] 1. In a 5000L glass-lined reactor, add 2231kg ​​of 36% hydrochloric acid, cool below 10°C, add 978kg of sodium nitrate in batches, stir for 20min, and then add 3kg of tetrabutylammonium bromide;

[0070] 2. Add 970kg of vinylidene chloride dropwise, control the temperature at 20°C, and keep warm for 3 hours after the addition;

[0071] 3. After the reaction is completed, stand still for 30 minutes and separate into layers;

[0072] 4. Add 1000kg of tap water to the organic layer and stir for 30min, then stand still for 30min to separate the layers to obtain 1606.5kg of compound (b) 1,1,1-trichloro-2-nitroethane, GC=90%, molar yield 0.9;

[0073] Preparation of compound (c) 1,1-dichloro-2-nitroethylene

[0074] 1. In a 5000L glass-lined kettle, add 1606.5kg of the obtained compound (b), add 1000kg of tap water, and raise the temperature by 30-40°C;

[0075] 2. Then add 2100kg 8% NaHCO dropwise 3 About...

Embodiment 3

[0096] Preparation of compound (b) 1,1,1-trichloro-2-nitroethane

[0097] 1. In a 5000L glass-lined reactor, add 2231kg ​​of 36% hydrochloric acid, cool below 10°C, add 978kg of sodium nitrate in batches, stir for 20min, and then add 3kg of tetrabutylammonium bromide;

[0098] 2. Add 970kg of vinylidene chloride dropwise, control the temperature at 25°C, and keep warm for 3 hours after the addition;

[0099] 3. After the reaction is completed, stand still for 30 minutes and separate into layers;

[0100] 4. Add 1000kg of tap water to the organic layer and stir for 30min, then stand still for 30min to separate the layers to obtain 1606.5kg of compound (b) 1,1,1-trichloro-2-nitroethane, GC=90%, molar yield 0.9;

[0101] Preparation of compound (c) 1,1-dichloro-2-nitroethylene

[0102] 1. In a 5000L glass-lined kettle, add 1606.5kg of the obtained compound (b), add 1000kg of tap water, and raise the temperature by 30-40°C;

[0103] 2. Then add 2100kg 8% NaHCO dropwise 3 About...

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Abstract

The invention relates to an improved preparation method of nitenpyram. The method comprises steps as follows: firstly, 1,1-dichloroethylene has a reaction with a nitration agent comprising hydrochloric acid and sodium nitrate to generate 1,1,1-trichlorine-2-nitroethane, and the 1,1,1-trichlorine-2-nitroethane has an elimination reaction with NaHCO3 to generate a 1,1-dichlorine-2-nitroethylene intermediate; secondly, 2-chlorine-5-chloromethylpyridine has a reaction with ethylamine, and an ethylamine intermediate is prepared; thirdly, the ethylamine intermediate has a reaction with 1,1-dichlorine-2-nitroethylene intermediate and monomethylamine, and the final product nitenpyram is generated. NaNO3 is used to replace traditional nitric acid to serve as a target phase transfer catalyst, the reaction selectivity is improved, the yield is higher, and the operation is safer.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an improved method for preparing nitenpyram. Background technique [0002] Nitenpyram (Nitenpyram) is another new type of nicotinamide insecticide following imidacloprid and acetamiprid. It has a nerve blocking effect on the synaptic receptors of pests. The effect of the method is unique systemic and osmotic action, excellent quick-acting and long-lasting effect, less dosage and low toxicity, so it is very important to study the synthesis process of nitenpyram. At present, nitenpyram The synthesis of generally mainly contains the following several synthetic routes. [0003] Route 1: [0004] [0005] Route 2: [0006] [0007] Route 3: [0008] [0009] Route 4: [0010] [0011] Route 5: [0012] [0013] In summary, compared with 2-chloro-5-chloromethylpyridine, there are relatively few manufacturers of 2-chloro-5-aminomethylpyridine, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 龙聪未马俊周仙配唐松青吕叶军
Owner SHANGHAI JINJING CHEM CO LTD
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