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Synthesis process method of avobenzone

A process method and avobenzone technology are applied in the field of preparing avobenzone, can solve the problems of separation and purification of avobenzone, the total yield is only 87-90.5%, etc. The effect of equipment requirements

Pending Publication Date: 2021-12-07
马鞍山科思化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this patent does not separate and purify the product avobenzone. The inventor repeated the synthesis method of this patent many times and found that the GC purity is 90-95%, and the total yield of separation and purification is only 87-90.5%.

Method used

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  • Synthesis process method of avobenzone
  • Synthesis process method of avobenzone
  • Synthesis process method of avobenzone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Embodiment 1

[0081] Under the protection of nitrogen, add 98.0g of 30% potassium methylate methanol solution into a dry and clean four-necked flask, control the temperature of the kettle at 25-28°C, and drop 60.0g of liquid p-methoxyacetophenone into the methanol within 1h In the potassium solution, after the dropwise addition, the heat preservation reaction was continued for 30 minutes to obtain 158.0 g of potassium p-methoxystyrene alcohol salt solution, which was transferred to the condensation process for later use.

[0082] Under nitrogen protection, add 600.0g o-xylene and 80.0g methyl p-tert-butylbenzoate into a 2000mL four-neck flask equipped with a stirrer, thermometer and decompression reflux water separation device, and the water pump controls the vacuum degree in the kettle to 18 ~25mmHg, the temperature of the kettle is controlled at 80~85°C, add 158.0g of p-methoxystyrene alcohol potassium salt solution dropwise, and methanol is extracted at the same time. The time of dropping...

experiment example 1

[0098] Get the p-methoxystyrene alcohol potassium salt that obtains in embodiment 1 and carry out nuclear magnetic resonance spectrum analysis, use INOVA400MHz high-resolution nuclear magnetic resonance spectrometer, TMS is internal standard, CDCl 3 for the solvent. The NMR spectra of p-methoxyacetophenone and potassium salt of p-methoxystyryl alcohol are as follows figure 1 shown.

[0099] from figure 1 As can be seen in the figure, after the reaction finishes, the resonance peak δ(2.55, 3H) representing the hydrogen atom on the methyl group connected to the carbonyl in p-methoxyacetophenone almost disappears, and a representative p-methoxystyrene appears. Resonant peaks δ(4.15, H) and δ(4.60, H) of the hydrogen atom on the enol bond in potassium alkoxide. δ(3.76, H) is the hydrogen on the methoxy group, and δ(6.92, 2H) and δ(7.65, 2H) are the hydrogens on the benzene ring, indicating that the reaction has yielded potassium p-methoxystyrene alkoxide.

experiment example 2

[0101] The crude product of avobenzone obtained after hydrolysis, neutralization and separation of the organic phase in Example 1 was analyzed by gas chromatography. The chromatographic column for chromatographic analysis is HP-5, nitrogen is used as carrier gas, the detector is flame ionization detector (FID), and the detector temperature is 300°C. The column oven was kept at 60°C for 3 minutes, then raised to 280°C at a rate of 30°C / min, and kept for 10 minutes. Chromatograms such as figure 2 shown. Wherein, the 26.087min place corresponds to the retention time of avobenzone, and the 5min place is the solvent o-xylene for dissolving the sample, the solvent is not counted, and the purity of avobenzone in the crude product is 98.7999%, illustrating the process in the present invention Control can effectively improve the selectivity of the target product and greatly reduce the formation of by-products.

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Abstract

The invention provide sa synthesis process method of avobenzone, p-methoxyacetophenone and p-tert-butyl benzoate are adopted as raw materials and react step by step, so that the reaction process and side reaction are effectively controlled, the reaction yield is greatly improved, the productivity is improved and the side reaction is inhibited under the condition of not changing the feeding amount, and the yield of the avobenzone is improved. The method has the advantages of effective reduction of the impurity product content, mild reaction conditions, multi-angle simplification of the reaction process, reduction of the equipment requirements, reduction of the generation of three wastes, and facilitating the industrial production of avobenzone.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a method for preparing an organic intermediate, in particular to a method for preparing avobenzone. Background technique [0002] Traditionally, the ultraviolet spectrum is divided into three regions. The long-wave ultraviolet rays with a wavelength of 320-400nm are called UV-A, the medium-wave ultraviolet rays with a wavelength of 280-320nm are called UV-B, and the short-wave ultraviolet rays with a wavelength of 200-280nm are called UV-A. Ultraviolet light is called UV-C. UV-A has the strongest penetrating power, and the amount reaching the surface is 100 times that of UV-B. It can cause sunburn and sunburn, and can strengthen the damage of UV-B to the skin. It can penetrate to the dermis and is the skin The main cause of aging; UV-B is the most carcinogenic, and the effect of sunburn and sunburn is 1000 times that of UV-A; UV-C can be blocked by the ozone layer, but with...

Claims

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Application Information

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IPC IPC(8): C07C41/26C07C43/23C07C49/84C07C45/68
CPCC07C41/26C07C45/68C07C43/23C07C49/84
Inventor 刘启发杨建钟世强菜程凯
Owner 马鞍山科思化学有限公司
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