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Preparation of pesticide 2-(2-hydroxyethyl)-piperidine-1-carbonate-1-methyl isopropyl ester

A kind of technology of hydroxyphenidate and pesticide, applied in the field of preparation of hydroxyphenidate, can solve the problems such as impurity and side reaction process are not clearly pointed out, 2-ethanol piperidine does not report preparation method, is unfavorable for large-scale operation and the like , to achieve the effect of improving the total yield of the reaction, reducing the amount of impurities generated, and being easy to operate.

Inactive Publication Date: 2008-12-17
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The weak point of this patent is: (1) starting material 2-ethanol piperidine does not report definite preparation method
(2) The total yield of hydroxyphenidate synthesis reported in this patent is only 49%, and the impurities and side reaction process are not clearly pointed out.
(3) The crude product of Hydroxyphenidate is low in purity, and high-vacuum rectification is required to obtain the finished product of Hydroxyphenidate, resulting in high energy consumption in the production process
(4) The temperature required for the reaction is minus 20 degrees, which is not conducive to large-scale industrial operation

Method used

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  • Preparation of pesticide 2-(2-hydroxyethyl)-piperidine-1-carbonate-1-methyl isopropyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Preparation of 2-ethanol piperidine

[0035] 200g (99%, mol) of 2-ethanolpyridine, 400g of methanol, and 10g of 10% Pd / C were respectively put into a 1-liter high-pressure hydrogenation kettle, replaced with nitrogen three times, and then replaced with hydrogen three times. Slowly heat up under stirring, keep the hydrogen pressure at 5Mpa, keep the kettle temperature at 90°C, and react for 10 hours. Gas chromatography analysis shows that the 2-ethanol pyridine content is less than 0.5%, and the reaction is completed and cooled to below 30°C. The hydrogen was vented, the reaction solution was filtered to remove the catalyst, and the filtrate was decompressed to recover methanol for mechanical use. The residue was 2-ethanol piperidine, 202 g, with a content of 99.2%.

[0036] (2) Preparation of Hydroxyphenidate Crude Product

[0037] Take 100g (99.2%, 0.769mol) of 2-ethanolpiperidine and 200g of toluene, put them into a 1-liter reaction flask equipped with a condense...

Embodiment 2

[0041] (1) Preparation of 2-ethanol piperidine

[0042] 200g (99%, mol) of 2-ethanolpyridine, 400g of ethanol, and 10g of 10% Pd / C were respectively put into a 1-liter high-pressure hydrogenation kettle, replaced with nitrogen three times, and then replaced with hydrogen three times. Slowly heat up under stirring, keep the hydrogen pressure at 5Mpa, keep the kettle temperature at 90°C, and react for 10 hours. Gas chromatography analysis shows that the 2-ethanol pyridine content is less than 0.5%, and the reaction is completed and cooled to below 30°C. The hydrogen was vented, the reaction solution was filtered to remove the catalyst, and the filtrate was decompressed to recover methanol for mechanical use. The residue was 2-ethanol piperidine, 200 g, with a content of 99.3%.

[0043] (2) Preparation of Hydroxyphenidate Crude Product

[0044] Take 100g (99.2%, 0.769mol) of 2-ethanolpiperidine and 200g of cyclohexane, put them into a 1-liter reaction flask equipped with a conde...

Embodiment 3

[0048] (1) Preparation of 2-ethanol piperidine

[0049] 200g (99%, mol) of 2-ethanolpyridine, 400g of isopropanol, and 10g of 10% Pd / C were respectively put into a 1-liter high-pressure hydrogenation kettle, replaced with nitrogen three times, and then replaced with hydrogen three times. Slowly heat up under stirring, keep the hydrogen pressure at 5Mpa, keep the kettle temperature at 90°C, and react for 10 hours. Gas chromatography analysis shows that the 2-ethanol pyridine content is less than 0.5%, and the reaction is completed and cooled to below 30°C. The hydrogen was vented, the reaction solution was filtered to remove the catalyst, the filtrate was decompressed to recover methanol and used mechanically, and the residue was 2-ethanol piperidine, 204g, with a content of 99.1%.

[0050] (2) Preparation of Hydroxyphenidate Crude Product

[0051] Take 100g (99.1%, 0.769mol) of 2-ethanolpiperidine and 200g of methylcyclohexane, put them into a 1-liter reaction flask equipped wi...

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Abstract

The invention discloses a method for preparing insecticide Picaridin, which comprises three steps as follows: firstly, 2-ethanolpyridine is dissolved in a polar solvent and reacts with hydrogen under the function of a hydrogenation catalyst and at certain pressure and temperature to obtain a 2-thanolpyridine reaction solution; then the obtained 2-thanolpyridine is dissolved in a non-polar solvent, reaction temperature is controlled, and simultaneously, sec-Butyl chloroformate and sig water is added by dripping; crude Picaridin is obtained after the treatments of acid washing, water washing and desolution, finally the crude Picaridin is distilled under the function of an antioxidant and under the condition of vacuum and high temperature to obtain finished Picaridin. The invention has the advantages of low cost input, few side reaction, high overall yield, simple technique and easy operation.

Description

technical field [0001] The present invention relates to a kind of insecticide, especially refers to the preparation method of hydroperidate. Background technique [0002] Hydroxyphenidate is the common name for 2-(2-hydroxyethyl)-piperidine-1-carbonate-1-methylisopropyl ester. It is a safe, effective and environmentally friendly insecticide that can replace DEET with bad smell and high viscosity. Hydroxyphenidate has the following advantages: it is widely applicable and effective against mosquitoes, lice, sandflies and horseflies, etc.; it is mild to the skin, non-sticky, and has no bad smell; it will not damage plastics, fibers, paints and adhesives; Can be used during breastfeeding and breastfeeding; safe for children over 2 years old. [0003] Hydroxyphenidate was first developed by Bayer Corporation of Germany, and the application documents of U.S. Patent US4900834 (1988) disclosed the synthetic method of series of compounds such as Hydroxyphenidyl, wherein Hydroxyphen...

Claims

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Application Information

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IPC IPC(8): C07D211/22C07D211/92A01P7/00
Inventor 王永峰陶伟周耀德
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD