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Benzoyl formic acid synthesis method

A technology of benzoylformic acid and a synthesis method, applied in the field of compound synthesis of organic chemistry, can solve the problems of expensive raw materials, serious environmental pollution, long reaction time and the like, and achieve the effects of improving cleanliness, reducing complexity and short reaction time

Inactive Publication Date: 2016-02-17
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, the main methods for producing benzoylformic acid include benzoyl nitrile hydrolysis, mandelic acid oxidation, and Friedel-Crafts acylation. The traditional method has expensive raw materials, serious environmental pollution, and great corrosion to equipment. It does not have environmental and economic characteristics.
The latest patents CN201110345076.4 and CN201110345118.4 report a five-step reaction synthesis method for styrene, using cheap styrene and hydrogen peroxide as basic raw materials, which improves the clean behavior of the preparation reaction, but the entire process technical route is relatively complicated, and the use of volatile organic Solvent medium, and the reaction time is long, resulting in low overall yield of the target product

Method used

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  • Benzoyl formic acid synthesis method

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Experimental program
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Effect test

Embodiment 1

[0036]Pipette 10mmol styrene and add it into a three-necked flask. Add 10mL of acetonitrile, 0.10g of hydrotalcite, and slowly dropwise add 2.4mL of hydrogen peroxide under constant stirring. After the dropwise addition, stir for a while, then slowly heat to 60°C and cool down to room temperature after the reaction. Add 10mL of water, 0.50mmol of cerium ammonium nitrate, and 1.00g of N-bromosuccinimide to the reaction mixture after filtering out the hydrotalcite, control the reaction at 30°C to complete the reaction, and separate α-hydroxyacetophenone by distillation under reduced pressure . In the reactor equipped with α-hydroxyacetophenone, add 10mL of water and 10mmol of 48% hydrobromic acid under constant stirring, and slowly add 80mmol of 30% hydrogen peroxide dropwise. After the addition, slowly raise the temperature to 90°C, and slowly cool down after the reaction To room temperature, the organic phase and the aqueous phase are separated by standing, and the separated ...

Embodiment 2

[0038] Pipette 10 mmol styrene into the reactor. Add 10mL of acetonitrile and 0.10g of hydrotalcite under continuous stirring, and slowly add 2.5mL of hydrogen peroxide dropwise. After the dropwise addition, slowly raise the temperature to 60°C to complete the reaction. After filtering out the mixed solution of hydrotalcite, add 5 mL of water, 0.5 mmol of cerium ammonium nitrate, and 1.00 g of N-bromosuccinimide under stirring, control the temperature at 40°C to complete the reaction, and distill α-hydroxyacetophenone under reduced pressure. Add it into a reactor with 10mL of water, add 10mmol of 48% hydrobromic acid with stirring, then slowly add 100mmol of 30% hydrogen peroxide dropwise at room temperature, after the addition, slowly raise the temperature to 90°C to complete the reaction. The organic phase was separated at room temperature, distilled, purified and dried. The total yield of benzoylformic acid was 71.3%, and the HPLC purity was 98.7%.

Embodiment 3

[0040] Pipette 10mmol of styrene into the reactor, add 10mL of n-hexane and 0.10g of hydrotalcite successively under continuous stirring, slowly add 2.4mL of hydrogen peroxide dropwise, after the dropwise addition, slowly heat up to 60°C and react until the styrene is completely converted , cooled to room temperature, and after the hydrotalcite was separated, 10mL of acetonitrile and water mixed solution, 0.6mmol of cerium ammonium nitrate, 1.00g of N-bromosuccinimide were added successively, and the reaction was completed at 50°C, and α- Hydroxyacetophenone. Add the separated α-hydroxyacetophenone into a reactor with 10mL of water, add 10mmol 48% hydrobromic acid under continuous stirring, and then slowly add 100mmol 30% hydrogen peroxide dropwise, and then slowly raise the temperature until the reflux reaction ends. The organic phase was separated at room temperature, and after distillation, purification and drying, the total yield of benzoylformic acid was 79.3%, and the HP...

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Abstract

The present invention discloses a benzoyl formic acid synthesis method comprising the following steps: styrene is used as a starting material for implementation of hydrogen peroxide catalytic epoxidation reaction to produce styrene oxide intermediate, alpha-Hydroxyphenylacetone is obtained by hydrolysis of styrene oxide, and the generated alpha-Hydroxyphenylacetone is further oxidized into the desired product benzoyl formic acid. Advantages of the method are that: by use of the method using a solid base for hydrogen peroxide catalytic oxidation of the styrene substrate to form a styrene oxide precursor material, the use of hydrobromic acid is avoided, industrial production reaction cleanability is improved, product preparation selectivity, overall yield and product purity are improved, reaction condition is mild, reaction time is short, the complexity of the reaction process is reduced and industrialization is easy.

Description

technical field [0001] The invention relates to a synthesis method of benzoylformic acid, which is mainly applied in the technical field of compound synthesis of organic chemistry. Background technique [0002] Benzoylformic acid, also known as acetophenone 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...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/285
CPCC07C51/285C07C45/58C07D301/12C07D303/04C07C59/84C07C49/82
Inventor 彭新华江鸥吴雪平郑学根荣媛朱四九彭成军绪浩舒付潇
Owner CHINA PETROLEUM & CHEM CORP
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