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Method for preparing wormer sec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

A technology of icaridin and insect repellent, applied in the field of preparation of insect repellent, can solve the problems of increased production cost, high product cost, high market price, etc., achieve less by-products, reduce the generation of by-products, reduce The effect of safety hazards

Active Publication Date: 2010-04-28
FUJIAN SENFA BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1), the market price of starting raw material 2-hydroxyethylpiperidine or 2-hydroxyethylpyridine is high, resulting in high product cost;
[0006] 2), when 2-hydroxyethylpiperidine and sec-butyl chloroformate are condensed, a large amount of organic solvents are used, which will not only cause harm to the human body, but also increase the production cost;
[0007] 3), high vacuum and high temperature are required to distill to obtain the finished product of icaridin under the condition of adding antioxidants, which requires high energy consumption

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1) Preparation of 2-hydroxyethylpyridine

[0033] Add 100g of 2-picoline, 20g of paraformaldehyde and 2g of sodium carbonate into the reaction flask, and stir the reaction at 100°C for 15h. The reaction solution was distilled under reduced pressure, and the 130-150°C / 10-20mmHg fraction was collected to obtain the product 2-hydroxyethylpyridine, 115.6g, with a chromatographic content of 98.9%.

[0034] 2) Preparation of 2-hydroxyethylpiperidine

[0035] Put 50g of 2-hydroxyethylpyridine, 250g of toluene and 2.5g of Raney nickel (SC-4100) into the autoclave, replace with nitrogen three times, and replace with hydrogen twice. Slowly raise the temperature to 60°C under stirring, and keep the hydrogen pressure at 4Mpa, react for 6h, and stop the reaction when the gas chromatography analysis shows that the content of 2-hydroxyethylpyridine is less than 1% of the total amount. The reaction solution was filtered to remove the catalyst, the toluene was recovered by distillatio...

Embodiment 3

[0046] 1) Preparation of 2-hydroxyethylpyridine

[0047] Add 100g of 2-picoline, 40g of paraformaldehyde and 3g of sodium carbonate into the reaction flask, and stir the reaction at 90°C for 16h. The reaction solution was distilled under reduced pressure, and the 130-150°C / 10-20mmHg fraction was collected to obtain the product 2-hydroxyethylpyridine, 115.3g, with a chromatographic content of 98.8%.

[0048] 2) Preparation of 2-hydroxyethylpiperidine

[0049] Put 50g of 2-hydroxyethylpyridine, 200g of tetrahydrofuran and 2g of Raney nickel (SC-4100) into the autoclave, replace with nitrogen three times, and replace with hydrogen twice. Slowly raise the temperature to 70°C under stirring, and keep the hydrogen pressure at 4Mpa, react for 7h, and stop the reaction when the gas chromatography analysis shows that the content of 2-hydroxyethylpyridine is less than 1% of the total amount. The reaction solution was filtered to remove the catalyst, and tetrahydrofuran was recovered b...

Embodiment 5

[0060] 1) Preparation of 2-hydroxyethylpyridine

[0061] Add 100g of 2-picoline, 30g of paraformaldehyde and 3g of potassium carbonate into the reaction flask, and stir the reaction at 80°C for 19h. The reaction solution was distilled under reduced pressure, and the 130-150°C / 10-20mmHg fraction was collected to obtain the product 2-hydroxyethylpyridine, 116.2g, with a chromatographic content of 98.6%.

[0062] 2) Preparation of 2-hydroxyethylpiperidine

[0063] Put 50g of 2-hydroxyethylpyridine, 100g of ethanol and 1.5g of Raney nickel (SC-4100) into the autoclave, replace with nitrogen for three times, and replace with hydrogen twice. Slowly raise the temperature to 80°C under stirring, and keep the hydrogen pressure at 4Mpa, react for 4h, and stop the reaction when the gas chromatography analysis shows that the content of 2-hydroxyethylpyridine is less than 1% of the total amount. The reaction solution was filtered to remove the catalyst, and the ethanol was recovered by d...

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Abstract

The invention discloses a method for preparing a wormer sec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate, which comprises the following three steps: firstly, taking 2-methylpyridine as a starting material to undergo a condensation reaction with paraformaldehyde to produce 2-hydroxyethyl pyridine in the presence of a catalyst sodium carbonate or potassium carbonate; secondly, dissolving the 2-hydroxyethyl pyridine into a solvent and adding a high-efficient hydrogenation catalyst for reaction with hydrogen for a certain time at a certain temperature and under a certain pressure to produce 2-hydroxyethyl piperidine; and finally, placing the 2-hydroxyethyl piperidine and aqueous slkali into a reaction bulb, controlling the reaction temperature, dropwise adding sec-butyl chloroformate dropwise under the condition of no solvent, and after reacting for certain time, performing acid cleaning, water rinsing and drying to directly produce a finished product of the sec-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate. The method is low in production cost, moderate in reaction conditions, less in side reaction, high in yield, good in product quality, simple and convenient in process and easy in operation.

Description

technical field [0001] The invention relates to a method for preparing an insect repellent, in particular to a method for preparing the insect repellent icaridin. Background technique [0002] Icaridin is also known as hydroxypiperate, isobutyl hydroxyethylpiperidine carboxylate, and its chemical name is 1-(1-carboxylate sec-butyl)-2-(2-hydroxyethyl)piperidine (CAS NO 87818-31-3), is a safe, effective and environmentally friendly insect repellant. It does not directly kill insects, but can effectively drive insects away without harming the user's health through the volatilization of odor, so that users can avoid the pain of mosquito bites, and can replace mosquito repellent with bad smell and high viscosity amine. Icaridin has been proven to be an effective insect repellent ingredient in the prevention and control of malaria, dengue hemorrhagic fever, yellow fever, West Nile virus, Lyme borreliosis (Lyme disease), forest encephalitis and other highly fatal play an importa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22A01N47/16A01P17/00
CPCY02P20/584
Inventor 许鹏翔
Owner FUJIAN SENFA BIOTECH
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