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Clean method for synthesis of phenylglyoxylic acid

A benzoylformic acid, clean technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylates, etc., can solve the problem that the total yield of the target product is not high, the benzoylformic acid method is backward, unfavorable and sustainable Development and other issues to achieve the effect of reducing the generation of organic by-products, lowering the cost, and improving the cleanliness

Inactive Publication Date: 2016-12-07
CHINA PETROLEUM & CHEM CORP +1
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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, etc.
Although the five-step reaction synthesis method of styrene also uses cheap styrene and hydrogen peroxide as raw materials, the entire process route is long and the reaction time is long, resulting in a low total yield of the target product. 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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  • Clean method for synthesis of phenylglyoxylic acid
  • Clean method for synthesis of phenylglyoxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 20mmol 48% hydrobromic acid at room temperature to a 500mL three-neck flask with 20mmol styrene and 100mL water, slowly add 200mmol 30% hydrogen peroxide dropwise, control the dropping time for 30min, stir at room temperature for 30min, heat up to 80°C, and react 10h. The organic and aqueous phases were separated on standing. The organic phase containing 2-bromoacetophenone was added to a reactor filled with 150 mL of water, hydrolyzed completely under the promotion of microwave, and the organic phase was separated from the water phase by standing. Place the organic phase containing 2-hydroxyacetophenone in a 500mL reactor, add 150g of water and 20mmol of 48% hydrobromic acid solution, and slowly add 16mmol of 30% hydrogen peroxide dropwise under stirring for 1h. After the addition, the temperature is slowly raised to React at 70°C for 6 hours, lower to room temperature and let stand to separate the organic phase from the water phase. The separated organic phase is...

Embodiment 2

[0036]Add 21mmol 48% hydrobromic acid at room temperature to a 500mL three-neck flask with 20mmol styrene and 100mL water, slowly add 200mmol 30% hydrogen peroxide dropwise, control the dropping time for 30min, stir at room temperature for 30min, heat up to 80°C, and react 10h. The organic and aqueous phases were separated on standing. Add the organic phase containing 2-bromoacetophenone into a reactor filled with 150 mL of water, complete hydrolysis under heating, and let stand to separate the organic phase and the water phase. Place the organic phase containing 2-hydroxyacetophenone in a 500mL reactor, add 150g of water and 20mmol of 48% hydrobromic acid solution, and slowly add 16mmol of 30% hydrogen peroxide dropwise under stirring for 1h. After the addition, the temperature is slowly raised to React at 90°C for 5 hours, lower to room temperature and let stand to separate the organic phase from the water phase. The separated organic phase is then distilled, refined and dr...

Embodiment 3

[0038] Add 20mmol 48% hydrobromic acid at room temperature to a 500mL three-necked flask with 20mmol styrene and 100mL water, slowly add 210mmol 30% hydrogen peroxide dropwise, control the dropping time for 60min, stir at room temperature for 30min, heat up to 80°C, and react 10h. The organic and aqueous phases were separated on standing. The organic phase containing 2-bromoacetophenone was added to a reactor filled with 150 mL of water, hydrolyzed completely under the promotion of microwave, and the organic phase was separated from the water phase by standing. Place the organic phase containing 2-hydroxyacetophenone in a 500mL reactor, add 150g of water and 20mmol of 48% hydrobromic acid solution, and slowly add 16mmol of 30% hydrogen peroxide dropwise under stirring for 1h. After the addition, the temperature is slowly raised to React at 90°C for 6 hours, lower to room temperature and let stand to separate the organic phase from the water phase. The separated organic phase ...

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Abstract

The invention discloses a clean method for synthesis of phenylglyoxylic acid. The clean method is an environmental economic method for high selectivity synthesis of phenylglyoxylic acid from styrene and hydrogen peroxide as base raw materials and water as a solvent. Under mild reaction conditions, styrene and hydrogen peroxide undergo a reaction under hydrobromic acid catalysis to produce 2-bromoacetophenone, under microwave action, the 2-bromoacetophenone is hydrolyzed to form 2-hydroxyacetophenone and the 2-hydroxyacetophenone is oxidized to form a desired compound. The clean method utilizes styrene as a reaction substrate, utilizes water as a reaction medium to replace an organic solvent in the whole reaction process, has a high reaction yield, good reaction selectivity, a low cost, simple processes, mild reaction conditions and high product purity, prevents severe environmental pollution and a high cost of the traditional method and is a method with environmental economy and an industrial application prospect.

Description

technical field [0001] The invention relates to the field of compound preparation methods, in particular to a cleaning method for synthesizing benzoylformic acid. Background technique [0002] Benzoylformic acid, also known as styrene acid, is a colorless or light yellow crystal with a melting point of 66°C, a boiling point of 147.5°C / 1.6kPa, a flash point of 147~151°C / 12mmHg, and a density of 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 an intermediate in the preparation of medicines and pesticides. In recent years, it has been found to be a sensitizer for fluorescent materials and a catalyst for organic oxidation reactions by complexing with metal elements, which has attracted more attention. [0005] In the preparation of...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/285
CPCC07C51/285C07C45/63C07C45/64C07C59/84C07C49/82C07C49/80
Inventor 彭新华江鸥郑学根朱四九绪浩舒
Owner CHINA PETROLEUM & CHEM CORP
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