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Preparation method of 4-(4-formyl phenoxy)benzaldehyde

A formylphenoxy, hydroxybenzaldehyde technology, applied in the field of preparation of 4-benzaldehyde, can solve the problems of difficulty in industrialization, high risk, low yield, etc., and achieves low price, low production cost, and easy raw materials. the effect

Active Publication Date: 2019-04-19
河北海力香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the problems of low yield, high risk and difficulty in realizing industrialization in the process for preparing 4-(4-formylphenoxy)benzaldehyde in the prior art, the present invention provides a 4-(4-formylphenoxy) Base) the preparation method of benzaldehyde

Method used

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  • Preparation method of 4-(4-formyl phenoxy)benzaldehyde
  • Preparation method of 4-(4-formyl phenoxy)benzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0050] A preparation method of 4-(4-formylphenoxy)benzaldehyde:

[0051] Step 1. Put 303kg of 4-hydroxybenzaldehyde, 240kg of potassium carbonate, 90.9g of phenothiazine, 121.2g of BHT, 1212kg of N,N-dimethylformamide and 242.4kg of toluene into an enamel reactor with a reflux device, stir and heat to 120 Incubate at ℃, reflux and dehydrate for 3 hours to obtain an intermediate solution;

[0052] Step 2. Add 299g 4-fluorobenzaldehyde dropwise to the intermediate solution, the dropping time is 0.5h, and the reaction is kept at 120°C for 16h, sampling HPLC detects that the 4-fluorobenzaldehyde content is less than 0.2%, the reaction is over, 4 -(4-Formylphenoxy)benzaldehyde solution;

[0053] Step: Distill toluene out under normal pressure, and stop distilling to the gas phase temperature of 145°C; reduce the temperature to 85°C, keep it warm and press filter, wash the filter cake with 200kg N,N-dimethylformamide, combine the filtrate and washing liquid, stir, Add 1212kg of hot water...

Embodiment 2

[0055] A preparation method of 4-(4-formylphenoxy)benzaldehyde:

[0056] Step 1. Put 303kg of 4-hydroxybenzaldehyde, 205.8kg of potassium carbonate, 151.5g of phenothiazine, 60.6g of BHT, 909kg of N,N-dimethylacetamide and 272.2kg of toluene into an enamel reactor with a reflux device, stir and heat to Keep warm at 130°C, reflux and dehydrate for 2 hours to obtain the intermediate solution;

[0057] Step 2. Add 304.9kg 4-fluorobenzaldehyde dropwise to the intermediate solution, the dropping time is 0.5h, and the reaction is kept at 130°C for 14h, sampling HPLC detects that the 4-fluorobenzaldehyde content is less than 0.2%, and the reaction is over. 4-(4-formylphenoxy)benzaldehyde solution;

[0058] Step: Distill toluene out under normal pressure, distill to the gas phase temperature of 145°C and stop; lower the temperature to 90°C, keep it hot and filter with pressure, wash the filter cake with 200kg N,N-dimethylformamide, combine the filtrate and washing liquid, stir, Add 1091kg ...

Embodiment 3

[0060] Step 1. Combine 303kg of 4-hydroxybenzaldehyde, 274.3kg of potassium carbonate, 33g of phenothiazine, 151.5g of BHT, 1515kg of N,N-dimethylformamide and dimethyl sulfoxide (mass ratio of 1:1) and 151.5 The mixture of kg toluene and xylene (the mass ratio is 1:1) is put into an enamel reactor with a reflux device, stirred and heated to 110°C for heat preservation, refluxed and dehydrated for 4 hours to obtain an intermediate solution;

[0061] Step 2: Add 293.3kg 4-fluorobenzaldehyde dropwise to the intermediate solution, the dropping time is 0.5h, and the reaction is kept at 110°C for 17h, sampling HPLC detects that the 4-fluorobenzaldehyde content is less than 0.2%, the reaction is over, 4-(4-formylphenoxy)benzaldehyde solution;

[0062] Step: Distill toluene out under normal pressure, distill to the gas phase temperature of 145°C and stop; lower the temperature to 80°C, keep it warm and press filter, wash the filter cake with 200kg N,N-dimethylformamide, combine the filtra...

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 4-(4-formyl phenoxy)benzaldehyde. The preparation method comprises the steps that 4-hydroxybenzaldehyde and potassium carbonate are adopted for reacting to generate potassium salt in presence of a polymer inhibitor and an antioxidant, water generated through the reaction is removed throughazeotropic reflux, and then the potassium salt with the water removed reacts with 4-fluorobenzaldehyde to obtain a 4-(4-formylphenoxy)benzaldehyde product. The purity and molar yield of the prepared 4-(4-formyl phenoxy)benzaldehyde product can reach 99% or above and 97% or above respectively, industrial production of 4-(4-formyl phenoxy)benzaldehyde is achieved, and the method has wide applicationprospects.

Description

Technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 4-(4-formylphenoxy)benzaldehyde. Background technique [0002] 4-(4-Formylphenoxy)benzaldehyde, the structural formula is: [0003] [0004] It is an important raw material for the preparation of new phenolic resin. The phenolic resin prepared from it has excellent insulation, heat resistance and processability. It is widely used in electronics, solar energy, photovoltaic power generation, aviation, aerospace, etc. field. [0005] At present, the main methods for synthesizing 4-(4-formylphenoxy)benzaldehyde are: (1) Using p-hydroxybenzaldehyde and p-bromobenzoic acid as raw materials, preparing 4-(4-formylphenoxy)benzaldehyde by etherification and then reduction. (4-Formylphenoxy)benzaldehyde, but lithium aluminum hydride and tetrahydrofuran are used in this synthesis method, which is dangerous and difficult to operate, making it difficult to achieve i...

Claims

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Application Information

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IPC IPC(8): C07C45/64C07C47/575
CPCC07C45/64C07C47/575
Inventor 张云堂李文革朱玉梅时红粉
Owner 河北海力香料股份有限公司
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