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Environment-friendly asymmetric synthetic method of (R)-phenyl ethylene glycol

A technology of phenylethylene glycol and its synthesis method, which is applied in the field of direct catalytic oxidation of styrene to prepare phenylethylene glycol, achieving the effects of low environmental risk, high atom economy, and simple process

Inactive Publication Date: 2015-05-27
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem solved by the present invention is to overcome the existing defects in the preparation of (R)-phenylethylene glycol and provide a green asymmetric synthesis method for (R)-phenylethylene glycol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A kind of green asymmetric synthetic method of (R)-phenyl glycol, comprises the steps:

[0024] 1) Take a certain amount of styrene, add 0.3 times its mass of catalyst and 1.2 times its mass of 40% hydrogen peroxide in sequence, and react at 55°C for 1.8 hours to obtain a reaction mixture;

[0025]The preparation method of the catalyst is as follows: take a certain amount of S-nicotine, add octadecane bromide 2.25 times its mass, reflux in toluene at 115°C for 20 hours, and distill off the solvent under reduced pressure to obtain a yellow viscous chiral ionic liquid , while stirring, dropwise added to the phosphotungstic acid solution with a mass percentage concentration of 6%, the stirring speed was 400r / min, the mass of the phosphotungstic acid solution was 20 times the mass of S-nicotine, and particles with a particle size of 0.4mm were generated A yellow precipitate, filtered and dried to obtain the catalyst;

[0026] The amount of toluene used is 12 times the mass...

Embodiment 2

[0031] A kind of green asymmetric synthetic method of (R)-phenyl glycol, comprises the steps:

[0032] 1) Take a certain amount of styrene, add 0.15 times its mass of catalyst and 0.8 times its mass of 27.5% hydrogen peroxide in sequence, and react at 50°C for 1 hour to obtain a reaction mixture;

[0033] The preparation method of the catalyst is as follows: take a certain amount of S-nicotine, add octadecane bromide 2.05 times its mass, reflux in toluene at 110°C for 16 hours, and distill off the solvent under reduced pressure to obtain a yellow viscous chiral ionic liquid , while stirring, dropwise added to the phosphotungstic acid solution with a mass percentage concentration of 2%, the stirring speed was 300r / min, the mass of the phosphotungstic acid solution was 18 times the mass of S-nicotine, and particles with a particle size of 0.2mm were generated A yellow precipitate, filtered and dried to obtain the catalyst;

[0034] The amount of toluene used is 10 times the mas...

Embodiment 3

[0039] A kind of green asymmetric synthetic method of (R)-phenyl glycol, comprises the steps:

[0040] 1) Take a certain amount of styrene, sequentially add 0.25 times its mass of catalyst and 1.0 times its mass of 35% hydrogen peroxide, and react at 52°C for 1.5 hours to obtain a reaction mixture;

[0041] The preparation method of the catalyst is as follows: take a certain amount of S-nicotine, add octadecane bromide 2.15 times its mass, reflux in toluene at 113°C for 18 hours, and distill off the solvent under reduced pressure to obtain a yellow viscous chiral ionic liquid , while stirring, dropwise added to the phosphotungstic acid solution with a mass percentage concentration of 4%, the stirring speed was 350r / min, the mass of the phosphotungstic acid solution was 19 times the mass of S-nicotine, and particles with a particle size of 0.3mm were generated A yellow precipitate, filtered and dried to obtain the catalyst;

[0042] The amount of toluene used is 11 times the m...

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PUM

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Abstract

The invention discloses an environment-friendly asymmetric synthetic method of (R)-phenyl ethylene glycol and belongs to the technical field of asymmetric synthesis. By taking styrene as a raw material, optically pure (R)-phenyl ethylene glycol is prepared by direct catalytic oxidization. The (R)-phenyl ethylene glycol has a relatively high atom economy. Moreover, by taking a low-toxicity harmless phosphotungstic chiral ionic liquid as a catalyst and H2O2 as a green oxidizing agent, the yield of the (R)-phenyl ethylene glycol is 67-82% and the enantiomeric purity is 96-100%e. e. After reaction, the catalyst is easily separated from byproducts, and the recovered catalyst precipitate can be recycled. The method disclosed by the invention is simple in process, high in production efficiency, low in cost and small in environmental risk and meets the requirements of environment-friendly chemical industry.

Description

technical field [0001] The invention relates to a green asymmetric synthesis method of (R)-phenylethylene glycol, belongs to the technical field of asymmetric catalytic synthesis, and specifically relates to a method for preparing (R)-phenylethylene glycol by direct catalytic oxidation of styrene method. Background technique [0002] Chirality is ubiquitous in nature and the human body. The isomers that are enantiomers have similar structures and properties, but they show significant differences in pharmacology, toxicology and functional effects. The industrial methods to obtain such optically active compounds are mainly indirect resolution and direct synthesis. The former utilizes resolving agents such as amino acids, alkaloids, and chiral acids to react with racemates to generate derivatives with large differences in properties. The substances are further separated, while the latter uses highly selective catalysts such as biological enzymes, chiral catalysts, etc., so tha...

Claims

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Application Information

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IPC IPC(8): C07C33/26C07C29/05
CPCY02P20/584C07C29/05
Inventor 梁栋胡志勇朱海林郭建峰马雪梅曹端林
Owner ZHONGBEI UNIV
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