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High-activity bifunctional catalyst for preparing chiral epoxy alkane and diol and application thereof

A bifunctional catalyst and alkylene oxide technology, which is applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, hydrolysis preparation, etc., can solve the problem of prolonging reaction time, reducing reaction efficiency, poor solubility, etc. problem, to achieve the effect of high product enantioselectivity and high catalytic activity

Active Publication Date: 2013-08-14
SHENYANG GOLD JYOUKI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It is reported above that trivalent cobalt catalysts are easily reduced to divalent cobalt compounds without catalytic activity during the reaction process, which usually requires prolonged reaction time, which reduces reaction efficiency and increases the cost in large-scale production.
In addition, these catalysts are poorly soluble in some alkylene oxides, requiring additional addition of organic solvents

Method used

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  • High-activity bifunctional catalyst for preparing chiral epoxy alkane and diol and application thereof
  • High-activity bifunctional catalyst for preparing chiral epoxy alkane and diol and application thereof
  • High-activity bifunctional catalyst for preparing chiral epoxy alkane and diol and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Compound b: In a 100mL round bottom flask, dissolve compound a (3.60g, 10.0mmol) and anhydrous potassium carbonate (1.5g, 12.0mmol) in 50mL refined acetonitrile, add refined diethylamine (1.7mL, 12.0mmol), Reacted at 80°C for 24 h, followed the reaction by TLC until no raw materials remained, stopped the reaction, cooled the reaction liquid to room temperature, filtered, and removed the solvent under reduced pressure to obtain the crude product as a white turbid liquid. Dissolve it in 10ml of ethyl acetate, add 40mL of 2mol / L dilute hydrochloric acid solution, and stir vigorously for 0.5h. Separate the aqueous phase, extract the organic phase with water (20mL×3), combine the aqueous phases, slowly add saturated sodium bicarbonate solution to make it alkaline to pH=8, and extract with dichloromethane (50mL×3). The combined organic phases were washed with saturated brine (200 mL×1), dried over anhydrous sodium sulfate, and the solvent was removed under reduced p...

Embodiment 2

[0055] Add alkylene oxide and the prepared catalyst in a flask with a volume of 200mL, and after cooling to 0°C, slowly add water dropwise. , stop responding. A small amount of the reaction solution was taken for NMR analysis. Distill unreacted alkylene oxide under normal pressure or reduced pressure, weigh and calculate the yield, and analyze its optical purity with gas phase or liquid chromatography; carry out vacuum distillation on the residual liquid to obtain diol products, weigh and calculate the yield, and use gas phase or liquid chromatography to analyze its optical purity; Or liquid chromatography to analyze its optical purity.

[0056] The results are shown in Table 1-6.

[0057] Table 1 Table 2 table 3 Table 4

[0058] table 5 Table 6

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Abstract

The invention relates to a high-activity bifunctional catalyst for preparing chiral epoxy alkane and diol and application thereof. The catalyst is a tetradentate Schiff-base cobalt complex, and a molecule of the catalyst at least contains one quaternary ammonium or phosphonium salt group. Due to the quaternary ammonium or phosphonium salt group, on one hand, the solubility of the catalyst in a reaction system can be improved; and on the other hand, a role in stabilizing trivalent cobalt ions is played, and the trivalent cobalt ions are effectively inhibited from being transformed into inactive divalent cobalt ions. The catalyst can efficiently catalyze the hydrolytic kinetic resolution reaction of a variety of racemic-end-position epoxy alkanes at a lower concentration so as to prepare high-optical-purity end-position epoxy alkanes and corresponding chiral diol products.

Description

Technical field: [0001] The present invention relates to the catalyst that is used for preparing chiral end position alkylene oxide and diol, specifically, relates to the high activity bifunctional catalyst and application thereof of preparation chiral alkylene oxide and diol, can be used for high-efficiency catalytic racemization Hydrolytic Kinetic Resolution of Terminal Alkylene Oxides to Prepare Alkylene Oxide and Corresponding Diol Products in High Optical Purity. Background technique [0002] As an important class of synthetic intermediates, chiral alkylene oxides are widely used in the preparation of medicines and pesticides. At present, the methods for preparing chiral terminal alkylene oxides are mainly divided into the following two types: 1. Epoxidation of terminal olefins under the action of chiral catalysts; 2. Hydrolysis kinetic resolution of racemic terminal alkylene oxides point. The first method for preparing chiral end-position alkylene oxide has low produ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/19C07C201/12C07F15/06C07C29/10C07C33/46C07C31/42C07D301/32C07C43/23C07B53/00C07D303/22C07D303/04C07C33/025B01J31/22C07C43/13C07D303/23C07C33/14C07C33/26C07C41/26C07C31/20C07D303/08
Inventor 任伟民于凯徐桅吕小兵
Owner SHENYANG GOLD JYOUKI TECH
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