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Despinning method of left-handed trans-inulin alkyl ester

A technology of L-trans chrysanthemum acid alkyl ester and racemic chrysanthemum acid alkyl ester, which is applied in the racemization field of L-trans chrysanthemum acid alkyl ester, which can solve the problems of large amount of waste water, complex process and high production cost

Inactive Publication Date: 2018-07-13
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method reported in the literature, such as Pesticides. 1993.32 (2) P42, uses L-trans chrysanthemic acid as a raw material for racemization to obtain racemic chrysanthemic acid, but this method requires enzymatic hydrolysis of the L-trans chrysanthemic acid alkyl ester Saponification and acidification to obtain L-trans chrysanthemic acid and then racemization, the process is complicated, the production cost is high, and the amount of waste water is large

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 150g (0.824mol) of L-trans-chrysanthemum acid methyl ester, 28.05g (0.115mol) of 3-bromopropyltrimethoxysilane, 550g of toluene, put into a 1000ml dry four-necked bottle, start stirring, and heat up to 45°C , 36 g (0.247 mol) of di-tert-butyl peroxide was added dropwise, the dropwise addition was completed, and the reaction was kept for 2 hours. Cool down to 20°C, add 100g of water, stir and wash with water for 30min, separate layers, desolventize the oil layer to 120°C, -0.09Mpa, and obtain 146g of racemic methyl chrysanthemic acid, content 95%, trans-(+) methyl chrysanthemic acid The content is 48.2%, the content of trans-(-) methyl chrysanthemum is 47.7%, and the content of cis (±) methyl chrysanthene is 4.1%.

Embodiment 2

[0018] 150g (0.824mol) of L-trans-chrysanthemum acid methyl ester, 14.4g (0.117mol) of acetyl bromide, 700g of toluene, put into a 1500ml dry four-necked bottle, start stirring, raise the temperature to 45°C, add di-tert-peroxide dropwise 36g (0.247mol) of butyl, the dropwise addition is completed, and the reaction is kept for 2h. Cool down to 20°C, add 100g of water, stir and wash with water for 30min, separate layers, desolventize the oil layer to 120°C, -0.09Mpa, and obtain 142g of racemic methyl chrysanthemic acid, content 94.6%, trans-(+) methyl chrysanthemic acid The content is 46.8%, the content of trans-(-) methyl chrysanthemum is 48.3%, and the content of cis (±) methyl chrysanthene is 4.9%.

Embodiment 3

[0020] 161.5g (0.824mol) of left-handed trans-chrysanthemum acid ethyl ester, 28.05g (0.115mol) of 3-bromopropyltrimethoxysilane, and 600g of heptane were put into a 1000ml dry four-necked bottle, started stirring, and raised the temperature to 45 ℃, 22.3 g (0.247 mol) of tert-butyl hydroperoxide was added dropwise, and the dropwise addition was completed, and the reaction was kept for 2 hours. Cool down to 20°C, add 100g of water, stir and wash with water for 30min, separate layers, desolventize the oil layer to 120°C, -0.09Mpa, and obtain 148g of racemic ethyl chrysanthemic acid, content 95.6%, trans-(+) ethyl chrysanthemic acid The content is 48.1%, the trans-(-) ethyl chrysanthemum acid content is 47.2%, and the cis (±) chrysanthemic acid ethyl ester content is 4.7%.

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Abstract

The invention discloses a despinning method of left-handed trans-inulin alkyl ester. The despinning method comprises the following steps: performing despinning reaction on the left-handed trans-inulinalkyl ester, peroxide and a bromine-containing compound in a solvent at 40 to 50 DEG C for 1 to 2 h, adding water for washing, and desolventizing an oil layer to obtain the despun inulin alkyl ester.The despinning method aims to directly despin the low-pharmaceutical-effect left-handed trans-inulin alkyl ester which is a byproduct obtained by enzyme hydrolysis by a one-step method to obtain despun chrysanthemic acid, so as to realize comprehensive cyclic utilization of raw materials, reduce the production cost and reduce the wastewater amount; through selection of a proper chemical initiatorand a catalyst, the despinning yield is increased; the content of trans-(+) inulin alkyl ester is 45 to 48 percent; the content of trans-(-) inulin alkyl ester is 45 to 48 percent; the content of cis(+ / -)inulin alkyl ester is 4 to 6 percent. Therefore, the effect of despinning the left-handed trans-inulin alkyl ester is achieved; moreover, reaction processes are reduced, the production cost is reduced, and the treatment capacity of wastewater is reduced.

Description

technical field [0001] The invention relates to a racemization method of L-trans-chrysanthemum acid alkyl ester, which belongs to the synthesis method of cyclopropane carboxylic acid derivatives Background technique [0002] Alkyl chrysanthemum acid, 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate, is an important intermediate of pyrethroid insecticides. In its molecule, there are cis and trans isomers relative to the plane of cyclopropane, and two chiral carbon atoms on the ring, so there are four optical isomers, trans-(+) alkyl chrysanthemum acid The insecticidal activity of the formed permethrin is the highest, followed by cis-(+) chrysanthemic acid, and the other two are less effective. In the process of enzymatic hydrolysis and synthesis to obtain trans-(+) alkyl chrysanthemic acid, the obtained trans-(-) alkyl chrysanthemic acid with lower drug efficacy is directly racemized to obtain the racemate alkyl chrysanthemic acid, There is no literature report. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/747C07C67/62C07C67/48
CPCC07B2200/09C07C67/48C07C67/62C07C69/747
Inventor 周其奎姜友法王宝林孙迎东冯广军王振锋
Owner JIANGSU YANGNONG CHEM
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