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High selectivity synthesis method of benzoyl formic acid

A technology of benzoylformic acid and its synthesis method, which is applied in the field of highly selective synthesis of benzoylformic acid, can solve the problems of unfavorable large-scale industrial production sustainable development, backward benzoylformic acid method, serious environmental pollution, etc., and achieve Reduce waste water discharge, improve product yield and purity, and reduce environmental pollution

Inactive Publication Date: 2012-02-08
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 research reports on the synthesis methods of benzoylformic acid in China, 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
  • High selectivity synthesis method of benzoyl formic acid
  • High selectivity synthesis method of benzoyl formic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 1. At 10-25°C, add 150mL of water, 10.40g of styrene and 35.42g of tetrabutylammonium bromide into a 500mL three-necked flask, slowly add 39.67g of hydrogen peroxide solution with a mass fraction of 30% under stirring, and control the drop Adding time is 1-1.5h. After the dropwise addition, slowly raise the temperature to 60-70°C for 10-13h. After the reaction, cool down to room temperature. Separate the organic phase and the water phase by standing still, and extract the organic phase with ethyl acetate for 2 -3 times, the extracts were combined, the solvent was distilled off under reduced pressure at 0.3-0.5MPa, 40-45°C, and then recrystallized with dichloromethane to obtain 18.90g of α-bromoacetophenone;

[0047] 2. Add the generated α-bromoacetophenone into a reactor containing 14.72g of ethylene glycol and 0.04g of p-toluenesulfonic acid, and react at 80-90°C for 30-40h. Extract the liquid with ethyl acetate for 2-3 times, combine the extracts, distill the extracts...

Embodiment 2

[0052] 1. At 10-25°C, add 150mL of water, 10.40g of styrene and 41.86g of tetrabutylammonium bromide into a 500mL three-necked flask, slowly add 39.67g of hydrogen peroxide solution with a mass fraction of 30% under stirring, and control the drop Adding time is 1-1.5h. After the dropwise addition, slowly raise the temperature to 60-70°C for 10-13h. After the reaction, cool down to room temperature. Separate the organic phase and the water phase by standing still, and extract the organic phase with ethyl acetate for 2 -3 times, the extracts were combined, the solvent was distilled off under reduced pressure at 0.3-0.5MPa, 40-45°C, and then recrystallized with dichloromethane to obtain 19.10g of α-bromoacetophenone;

[0053] 2. Add the generated α-bromoacetophenone into a reactor containing 16.07g of ethylene glycol and 0.04g of p-toluenesulfonic acid, and react at 80-90°C for 30-40h. Extract the liquid with ethyl acetate for 2-3 times, combine the extracts, distill the extracts...

Embodiment 3

[0058] 1. At 10-25°C, add 150mL of water, 10.40g of styrene and 41.86g of tetrabutylammonium bromide into a 500mL three-necked flask, slowly add 45.33g of hydrogen peroxide solution with a mass fraction of 30% under stirring, and control the drop Adding time is 1-1.5h. After the dropwise addition, slowly raise the temperature to 60-70°C for 10-13h. After the reaction, cool down to room temperature. Separate the organic phase and the water phase by standing still, and extract the organic phase with ethyl acetate for 2 -3 times, the extracts were combined, the solvent was distilled off under reduced pressure at 0.3-0.5MPa, 40-45°C, and then recrystallized with dichloromethane to obtain 19.36g of α-bromoacetophenone;

[0059] 2. Add the generated α-bromoacetophenone into a reactor containing 18.10g of ethylene glycol and 0.04g of p-toluenesulfonic acid, and react at 80-90°C for 30-40h. Extract the liquid with ethyl acetate for 2-3 times, combine the extracts, distill the extracts...

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Abstract

The invention discloses a high selectivity synthesis method of benzoyl formic acid. With styrene as raw material, addition oxidation reaction is carried out in a mixed system of H2O2 and tetrabutyl ammonium bromide to obtain alpha-bromoacetophenone; then ethylene glycol and para-toluenesulfonic acid are added, reflow reaction is carried out to generate alpha-bromoacetophenone ethylene glycol; thegenerated alpha-bromoacetophenone ethylene glycol is hydrolyzed in potassium carbonate solution to generate alpha-hydroxyacetophenone ethylene glycol; the alpha-bromoacetophenone ethylene glycol reacts in the mixed system of H2O2 an tetrabutyl ammonium bromide to obtain 2-phenyl-1,3-dioxolame-2-carboxylic acid, and then deprotection reaction is carried out with oxalic acid to generate target product benzoyl formic acid. The synthesis method disclosed by the invention has high reaction yield, good reaction selectivity, low cost, simple technological process, mild reaction conditions and high product purity, and the defects of the traditional technological method that environment is severely polluted and cost is high are overcome, thus the synthesis method disclosed by the invention has industrial-scale production prospect.

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. The structural formulas of benzoylformic acid are: [0003] [0004] Benzoylformic acid is mainly used as an intermediate raw material for the preparation of medicines and pesticides. In recent years, it has been found that it can be used as a sensitizer for fluorescent materials and a catalyst for organic oxidation reactions by complexing with metal elemen...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/373
Inventor 彭新华戴志宏荣媛
Owner HEFEI UNIV OF TECH
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