Method of lipase-catalyzed preparing 1-phenyl-1, 2-ethanediol

A technology for catalytic preparation of ethylene glycol, which is applied in fermentation and other fields, can solve the problems of severe equipment corrosion, complicated process steps, and bromide application restrictions, and achieve the effects of saving raw materials, mild reaction conditions, and simple operation

Inactive Publication Date: 2008-05-21
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the process of this method is mature, the process steps are complicated, and the intermediate steps require a large amount of solvent and water, which will produce a large amount of industrial pollution and cause serious corrosion to the equipment, which does not meet the requirements of today's atomic economic reaction and green chemistry.
At the same time, there will be residual bromide in the product, which greatly limits the application in the field of fragrance and medicine

Method used

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  • Method of lipase-catalyzed preparing 1-phenyl-1, 2-ethanediol
  • Method of lipase-catalyzed preparing 1-phenyl-1, 2-ethanediol
  • Method of lipase-catalyzed preparing 1-phenyl-1, 2-ethanediol

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Experimental program
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Effect test

Embodiment 1

[0022] In a 100ml flask, add 5ml (0.043mol) styrene, 1ml formic acid, 3ml solvent benzene, 0.0500g catalyst Novozym435;

[0023] Slowly start adding 5ml of 15% hydrogen peroxide dropwise in a constant temperature water bath with a magnetic stirring temperature of 30°C, complete the dropwise addition in 1 hour, and then continue the reaction at 30°C for 18 hours;

[0024] After the reaction was completed, 10ml of ethyl acetate was added to extract the layers, and the organic layer was washed with anhydrous Na 2 SO 4 dry;

[0025] Rotary steaming under reduced pressure at 60°C can obtain 1-phenyl-1,2-ethanediol with a content of 75.69%, and the conversion rate of styrene is 94.3%.

Embodiment 2

[0027] In a 100ml flask, add 3ml solvent benzene, 5ml (0.043mol) styrene, 2ml formic acid, 0.0500g catalyst Novozym435;

[0028] Slowly start adding 7.5ml of 30% hydrogen peroxide dropwise in a constant temperature water bath with a magnetic stirring temperature of 50°C, and the dropwise addition is completed in about 1 hour, and then continue to react at a temperature of 50°C for 23 hours;

[0029] Add 10ml of ethyl acetate after the reaction to extract and separate the layers, and the organic phase is washed with anhydrous Na 2 SO 4 dry;

[0030] Finally, rotary evaporation under reduced pressure at 60°C can obtain 1-phenyl-1,2-ethanediol with a content of 70.67%, and the conversion rate of styrene is 96.4%.

Embodiment 3

[0031] Embodiment 3 (solvent-free operation)

[0032] Add 5ml (0.043mol) styrene, 0.5ml formic acid, 0.0500g catalyst Novozym435 in 100ml flask;

[0033] Slowly start adding 5ml of 40% hydrogen peroxide dropwise in a constant temperature water bath with a magnetic stirring temperature of 45°C, and the dropwise addition is completed in about 1 hour, and then continue to react at a temperature of 45°C for 30 hours;

[0034] Add 10ml of ethyl acetate after the reaction to extract and separate the layers, and the organic phase is washed with anhydrous Na 2 SO 4 dry;

[0035] Finally, rotary evaporation under reduced pressure at 60°C can obtain 1-phenyl-1,2-ethanediol with a content of 56.68%, and the conversion rate of styrene is 91.3%.

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Abstract

The invention relates to a method for catalyzing and preparing 1-phenyl-1, 2-glycol with lipase; according to the method, styrene, solution, and organic acid are added into a reaction container and then mixed evenly; and then catalyst is added for a constant-temperature water bath; excessive sodium dioxide is added for reaction and after the reaction, ethyl acetate is added for extraction and delamination; the solution is evaporated by drying and depressurization to obtain the 1-phenyl-1,2-glycol. The method is characterized by simple operation and moderate reaction conditions; the added organic acid can be recycled in the reaction which avoids producing large amounts of industrial pollution and at the same time the raw materials are saved and the cost is reduced; the catalyst can be recycled after reaction and another raw material of sodium dioxide can be converted into water without pollution after reaction, which accords with the requirements of the present green chemistry and atomic economics. At the same time no halides exists in the outcome and in this way, the1-phenyl-1, 2-glycol can be used in spice and medicine industries in a safer way.

Description

technical field [0001] The invention relates to a method for preparing 1-phenyl-1,2-ethanediol by enzymatic catalysis Background technique [0002] 1-Phenyl-1,2-ethylene glycol has a weak floral smell and can be used in the fragrance industry. It is an essence for modulating orange, lily, clove, hyacinth and other fragrances, used in cosmetics; it is also an important organic Synthetic intermediates. Among them, (s)-1-phenyl-1,2-ethanediol is not only an indispensable chiral additive in liquid crystal materials. It is also an important intermediate for the preparation of optically active medicines and functional materials. The structure of 1-phenyl-1,2-ethanediol is: [0003] [0004] The current method of industrial production of 1-phenyl-1,2-ethanediol: 1,2-dibromophenylethane is produced by the reaction of styrene and bromine, and then hydrolyzed to obtain 1-phenyl-1,2-ethane diol. Specifically: add styrene to petroleum ether, add bromine dropwise under cooling, c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22
Inventor 吾满江·艾力李超哈丽丹·买买提夏木西卡玛尔阿依夏木古丽·努尔艾买提
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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