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High-selectivity synthesis method of benzoyl formic acid

A technology of benzoylformic acid and a synthesis method, which is applied in the field of highly selective synthesis of benzoylformic acid, can solve problems such as unfavorable large-scale industrial production sustainable development, backward production method of benzoylformic acid, serious environmental pollution, and the like, Achieve the effect of improving product yield and purity, reducing production costs and reducing environmental pollution

Inactive Publication Date: 2013-07-31
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have expensive raw materials, serious environmental pollution, and great corrosion to equipment. These shortcomings are not conducive to the sustainable development of large-scale industrial production.
At present, there are few domestic research reports on the synthesis method of benzoylformic acid, and the main methods for producing benzoylformic acid are backward and cause great environmental pollution.

Method used

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  • High-selectivity synthesis method of benzoyl formic acid
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  • High-selectivity synthesis method of benzoyl formic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 150.00g of water, 10.40g of styrene and 35.46g of tetrabutylammonium bromide into a 500mL three-necked flask, add 22.67g of hydrogen peroxide solution with a mass fraction of 30% dropwise at 10-25°C under stirring, and control the dropping time to 1 -1.5h, after the dripping, raise the temperature to 80-100°C, continue the reaction for 10-13 hours, after the end of the reaction, cool down to room temperature, extract the reaction solution with ethyl acetate for 2-3 times, combine the extracts for 0.3-0.5 MPa, 40-45 ℃ decompression distillation to remove the solvent, and finally recrystallized from dichloromethane to obtain α-bromophenylethanol;

[0044] Slowly add 22.67g of 30% hydrogen peroxide solution dropwise into α-bromophenylethanol. After the dropwise addition, react at room temperature for 18-23h. After the reaction, separate the organic phase and the aqueous phase by standing still. Extract the organic phase with ethyl acetate for 2-3 times, combine the ext...

Embodiment 2

[0050] Add 150.00g of water, 10.40g of styrene and 35.46g of tetrabutylammonium bromide into a 500mL three-necked flask, add 21.53g of hydrogen peroxide solution with a mass fraction of 30% dropwise at 10-25°C under stirring, and control the dropping time to 1 -1.5h, after the dripping, raise the temperature to 80-100°C, continue the reaction for 10-13 hours, after the end of the reaction, cool down to room temperature, extract the reaction solution with ethyl acetate for 2-3 times, combine the extracts for 0.3-0.5 MPa, 40-45 ℃ decompression distillation to remove the solvent, and finally recrystallized from dichloromethane to obtain α-bromophenylethanol;

[0051] Slowly add 22.67g of 30% hydrogen peroxide solution dropwise into α-bromophenylethanol. After the dropwise addition, react at room temperature for 18-23h. After the reaction, separate the organic phase and the aqueous phase by standing still. Extract the organic phase with ethyl acetate for 2-3 times, combine the ext...

Embodiment 3

[0056] Add 150.00g of water, 10.40g of styrene and 45.08g of tetrabutylammonium bromide into a 500mL three-necked flask, add 22.67g of hydrogen peroxide solution with a mass fraction of 30% dropwise at 10-25°C under stirring, and control the dropping time to 1 -1.5h, after the dripping, raise the temperature to 80-100°C, continue the reaction for 10-13 hours, after the end of the reaction, cool down to room temperature, extract the reaction solution with ethyl acetate for 2-3 times, combine the extracts for 0.3-0.5 MPa, 40-45 ℃ decompression distillation to remove the solvent, and finally recrystallized from dichloromethane to obtain α-bromophenylethanol;

[0057] Slowly add 22.67g of 30% hydrogen peroxide solution dropwise into α-bromophenylethanol. After the dropwise addition, react at room temperature for 18-23h. After the reaction, separate the organic phase and the aqueous phase by standing still. Extract the organic phase with ethyl acetate for 2-3 times, combine the ext...

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Abstract

The invention discloses a high-selectivity synthesis method of benzoyl formic acid, which comprises the following steps: oxidizing styrene, which serves as the raw material, in a H2O2 / tetrabutylammonium bromide mixed system to generate alpha-bromophenethyl alcohol; oxidizing the generated alpha-bromophenethyl alcohol with H2O2 to generate alpha-bromoacetophenone; hydrolyzing the alpha-bromoacetophenone under alkaline conditions to generate alpha-hydroxyacetophenone; and oxidizing the alpha-hydroxyacetophenone with H2O2 to generate the target product benzoyl formic acid. In the invention, oxydol is used as an oxidant, and the byproduct is water, thereby reducing the generation of the organic byproducts and the discharge amount of inorganic salt (acid) waste water. Compared with other inorganic heavy metallic salt and inorganic mineral acid oxidization methods, the method disclosed by the invention enhances the cleanness of industrial preparation reaction, and reduces the environmental pollution. The invention enhances the product yield and purity: the yield is enhanced by nearly 13%, the total yield is up to 93.7%, and the product purity exceeds 95%; and other indexes are correspondingly enhanced.

Description

1. Technical field [0001] The present invention relates to a process for the preparation of known compounds, in particular to a highly selective synthesis of benzoylformic acid. 2. Background technology [0002] Benzoylformic acid, also known as phenylglyoxylic acid, is a colorless or light yellow crystal with a melting point of 66°C, a boiling point of 147.5°C / 1.6kPa, and a flash point of 147-151°C / 12mmHg , density ρ=1.38g / cm 3 , distilled and decomposed under normal pressure, soluble in water, acid, ether and hot carbon tetrachloride; its molecular formula is C 8 h 6 o 3 , the relative molecular mass is 150.13. [0003] The structural formula of benzoylformic acid is as follows: [0004] [0005] In the preparation of medicine, more than 50 kinds of chemical raw materials can be directly synthesized by using benzoylformic acid as a raw material. For example, methyl (b) benzoylformate is the drug orphenium bromide for the treatment of gastric and duodenal ulcers, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/84C07C51/373C07C69/738C07C67/08
Inventor 彭新华戴志宏董雄辎
Owner HEFEI UNIV OF TECH
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