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Preparation method of trans-D-chrysanthemic acid

A technology of trans chrysanthemic acid and mixed chrysanthemic acid, which is applied in the preparation of carboxylate salts, organic compounds, organic chemical methods, etc., can solve the problem that dextamine is not available for purchase, and achieve less solvent, Split the effect of high selectivity and low energy consumption

Inactive Publication Date: 2010-06-09
沈阳古德科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Chloramphenicol market is gradually shrinking with global restrictions on Chloramphenicol production and production bans are likely in the near future
As the main resolving agent raw material of the existing chrysanthemic acid series products, dexaamine may face the dilemma of being out of stock

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 21.6 grams of D-phenylglycine ethyl ester hydrochloride in 100 milliliters of water, add a solution consisting of 33.6 grams of trans chrysanthemic acid and 100 milliliters of toluene, adjust the pH to 5-7 with sodium bicarbonate or sodium carbonate, and fully Stir for 30 minutes, centrifuge to collect the precipitated D-(-)phenylglycinate ethyl ester trans-D-chrysanthemum acid double salt, adjust the water phase of the double salt filtrate to a pH value of 1 to 4, and divide the water phase as the dissolved water of the double salt . The double salt was placed in an aqueous hydrochloric acid solution with a pH of 1 to 4, stirred for 30 minutes, and allowed to stand for stratification to obtain 13.6 grams of trans-D-chrysanthemic acid with an optical purity of 90%, which was 81% of the theoretical yield, and the aqueous phase was D -Phenylglycine ethyl ester hydrochloride solution is set into the next batch for recycling.

Embodiment 2

[0022] Taking D-phenylglycine methyl ester hydrochloride as D-(-) phenylglycine ester hydrochloride, operating under the same conditions as in Example 1, to obtain 12.8 grams of trans-D-chrysanthemic acid with an optical purity of 90%, which is theoretical 76% of the yield. Recover 13.8 grams of D-(-)phenylglycinate hydrochloride, the recovery rate is 77%.

Embodiment 3

[0024] Using D-phenylglycine isopropyl ester hydrochloride as D-(-) phenylglycine ester hydrochloride, and operating under the same conditions as in Example 1, 13.8 grams of trans-D-chrysanthemic acid with an optical purity of 86% were obtained. 82% of theoretical yield. 15.9 g of D-(-)phenylglycinate hydrochloride was recovered, with a recovery rate of 89%.

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Abstract

A preparation method of trans-D-chrysanthemic acid relates to an improvement of the preparation method of trans-D-chrysanthemic acid. The invention provides a preparation method with easy operation of trans-D-chrysanthemic acid. The method of the invention comprises the following steps: (1) dissolving D-(-)phenylglycine ester.HCl in water, dissolving mixed trans-chrysanthemic acid in organic solvent; or after dissolving mixed trans-chrysanthemic acid in organic solvent, once adding D-(-)phenylglycine ester.HCl; mixing the two solutions, adjusting the pH value to 5-9 with weak base, wherein the molar ratio of mixed trans-chrysanthemic acid to D-(-)phenylglycine ester.HCl is 1.5-2.5:1; (2) precipitating D-(-)phenylglycine ester.trans-D-chrysanthemic acid double salt at 0-40 DEG C; (3) separating the double salt generated in the step (2), placing in an acidic aqueous solution with the pH value of 1-4, standing for standby; and separating to obtain the trans-D-chrysanthemic acid product, neutralizing the acidic aqueous solution of D-(-)phenylglycine ethyl ester with weak base to recycle D-(-)phenylglycine ester.HCl.

Description

Technical field: [0001] The present invention relates to the improvement of the preparation method of trans-D-chrysanthemic acid. Background technique: [0002] At present, the active ingredients widely used in household sanitation insecticides are pyrethroids represented by allethrin, which are highly efficient and low in toxicity, and are harmless to humans and animals. The key intermediate for the synthesis of such insecticides is chrysanthemic acid , it has a variety of isomers, among which the permethrin ester formed by trans chrysanthemic acid has the highest insecticidal effect, and the common method to obtain trans chrysanthemic acid is to separate and obtain it . Such as: (R)-(+)-1-amino-1,4a-dimethyl-7-isopropyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene (South China Journal of Polytechnic University, 27 (3), 100-105, 1999), L-lysine (German patent 2043137, 1971), ephedrine (European patent 68736, 1981), (-)-cis-benzyl-( 2-hydroxymethylcyclohexyl) amine (Japanese...

Claims

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Application Information

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IPC IPC(8): C07C61/37C07C51/487C07B57/00
Inventor 黄春宝
Owner 沈阳古德科技有限公司
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