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Method for preparing insect repellant icaridin

A technology of icaridin and insect repellent, which is applied in the field of preparation of insect repellent, can solve the problems of increased preparation cost, inconvenient transportation, high purchase price, etc., achieves reduction of energy consumption and solvent loss, acceleration of reaction process, and reaction conditions mild effect

Active Publication Date: 2011-08-31
CHANGZHOU INST OF MATERIA MEDICA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The reaction raw material sec-butyl alcohol chloroformate used in the above two schemes is usually obtained by the reaction of sec-butanol and phosgene, but phosgene is a highly toxic gas, which is inconvenient to transport and requires immediate production and use. Put forward higher requirements; if directly buy sec-butyl alcohol chloroformate, because the purchase price is higher, the preparation cost is increased

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  • Method for preparing insect repellant icaridin
  • Method for preparing insect repellant icaridin
  • Method for preparing insect repellant icaridin

Examples

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Embodiment 1）

[0039] All reagents used in this example were purchased from Changzhou Chemical Reagent Co., Ltd., with a purity of ≥98%, and were not further processed before use.

[0040] See figure 1 , the synthetic method of the present embodiment specifically comprises the following steps:

[0041] ① Preparation of 2-piperidine ethanol:

[0042] In a stirred 1L stainless steel autoclave, add 100g of 2-ethanolpyridine, 400g of solvent toluene and 5g of catalyst Raney nickel (SC-4100), close the autoclave, replace the air in the autoclave with nitrogen three times, and then use hydrogen Replace the gas in the reactor twice; then fill in hydrogen to make the reaction pressure in the reactor reach 4MPa, and slowly raise the temperature to 60°C under stirring, so that one of the products is a catalytic hydrogenation reaction of 2-piperidine ethanol, continue After stirring and reacting for 6 hours, a small amount of reaction liquid in the reactor was taken for detection, and gas chromatogra...

Embodiment 2）

[0076] All the other synthetic methods of the present embodiment are the same as in Example 1, except that:

[0077] In step 2., also comprise the purifying operation of sec-butyl chloroformate, after organic phase filtration removes desiccant anhydrous sodium sulfate, the solvent dichloromethane in the filtrate is evaporated earlier and reclaims mechanically, then remaining organic matter underpressure distillation, The fraction at 148-152°C / 5mmHg was collected to obtain 182 g of sec-butyl chloroformate with a yield of 91%. The purity of sec-butyl chloroformate was 98.4% as detected by GC.

[0078] In step ③, when synthesizing icaridin, the amount of solvent methylene chloride added is 40L, and the temperature in the reaction kettle drops to 0°C, and 14.0kg of sec-butyl chloroformate refined according to the method of step ② is added dropwise The reacted mixed material was washed with purified water twice and washed with saturated brine once, dried over anhydrous sodium sulfa...

Embodiment 3）

[0081] All the other synthetic methods of the present embodiment are the same as in Example 1, except that:

[0082] In step ②, the source material of chloroformic acid group is bis(trichloromethyl)carbonate. The chemical formula of bis(trichloromethyl)carbonate is Cl 3 COCO 2 CCl 3 , also known as triphosgene or solid phosgene, is a white crystal with a phosgene-like odor. One molecule of triphosgene can be decomposed into three molecules of phosgene. When triphosgene reacts with sec-butanol to prepare sec-butyl chloroformate, it first becomes phosgene, and the phosgene just generated reacts with sec-butanol immediately to generate hydrogen chloride gas and sec-butyl chloroformate, and the reaction formula is as follows:

[0083]

[0084] During preparation, under good ventilation conditions, add 112g (1.5mol) of sec-butanol, 500mL of solvent methylene chloride, 118g of catalyst pyridine and 150g (0.5mol) of bis(trichloromethyl) carbonate In the 2L three-necked bottle...

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Abstract

The invention discloses a method for preparing an insect repellant icaridin, which comprises the following three steps of: performing low pressure catalytic hydrogenation reduction to convert 2-pyridineethanol into 2-piperidineethanol by taking active nickel as a catalyst; reacting a raw material of isobutanol with chloroform chloroformate or triphosgene under the catalysis of organic base to obtain sec-butyl alcohol chloroformate; and performing one-step condensation on the obtained sec-butyl alcohol chloroformate and the 2-piperidineethanol in a specified organic solvent to obtain crude icaridin, and rectifying to obtain the finished product with the purity of more than or equal to 97 percent. The method is easy to operate, and has a few side reactions, small three-waste amount and high yield.

Description

technical field [0001] The invention relates to a preparation method of an insect repellent, in particular to a preparation method of the insect repellent icaridin. Background technique [0002] The insect repellent Icaridin (Icaridin) is also known as hydroxypiperate, and its chemical name is 2-(2-hydroxyethyl)piperidine-1-carboxylate sec-butyl ester (CAS No.: 119515-38-7). The structural formula is as follows: [0003] [0004] In February 2001, the World Health Organization (WHO) made the following 5 points of evaluation on icaridin: 1. Icaridin has good safety and meets the requirements of cosmetic properties (cosmetics properties). Its single or compound preparations It will not cause damage to common home improvement materials, including plastics, paints, metal decorative foils and paints; 2. Icaridin has been tested under normal and normal conditions, and has shown excellent repellent effects on many mosquitoes that infect malaria. Its effect is better than stand...

Claims

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Application Information

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IPC IPC(8): C07D211/22
Inventor 何浩明赵德元朱岩
Owner CHANGZHOU INST OF MATERIA MEDICA
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