High-yield production process for 1,3-diphenyl propanedione compound

Abstract

The invention discloses a high-yield production process for a 1,3-diphenyl propanedione compound. The production process comprises the steps that a benzoate compound A, a catalyst and a solvent I areadded into a reaction kettle, then an acetophenone compound B is dropwise added into the reaction kettle at the set temperature for reaction, and after reaction, a final product is prepared through acidification, washing, desolvation and recrystallization. The production process has the characteristics that a mixed basic catalyst is adopted, compared with sodium methylate and a traditional process, the yield is increased by 10-15% and is greater than or equal to 85.0%, the production operation is easy, the environmental pollution is small, the product color is light, the distinctive aromatic odor is achieved, the quality is good, the market competitiveness is high, and the industrialization promotion is easy.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a production process for high-yield 1,3-diphenylpropanedione compounds. Background technique [0002] In recent years, the amount of ultraviolet radiation has been increasing with the destruction of the ozone layer. Among them, the near ultraviolet light of 320-400nm (UV-A for short) will cause radiation damage to the human body, induce gene mutation and cause skin cancer. In order to protect the human body from excessive ultraviolet radiation, ultraviolet absorbers with safe and efficient absorption of ultraviolet radiation are widely used in cosmetics, hair care products, fabric treatment and detergents. UV absorbers include known 1,3-diphenylpropanedione compounds such as butylmethoxydibenzoylmethane (Parsol 1789, avobenzone), which is a compound used exclusively in skin care cosmetics. An anti-UV-A ultraviolet light absorber, Parsol 1789 was originally developed and produced by...

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Problems solved by technology

However, sodium amide is prone to side reactions such as ammonolysis in the reaction process, and the product yield is low; sodium hydride and sodium react violently with water, and the safety hazard is very large in the production process, and the requirements for equipment are also high; and sodium amide and hydrogenation Sodium is expensive, the cost required for large-scale production is high, and there is no price advantage in the market

[0005] (2) Condensation of p-tert-butylbenzaldehyde and p-methoxyacetophenone under the action of sodium methoxide to generate 3-[4-tert-butylphenyl]-1-(4-methoxyphenyl)-2 -propene-1-one; then through halogen addition, sodium methoxide dehalogenation synthesis (Synthetic Chemistry, 2008,16(3):342-343; Eur.Pat.Appl.994092), the yield of this method is higher, but Bromine or chlorine gas is needed in the synthesis of this method, which not only requires high equipment, but also causes serious harm to people and the environment.

[0006] (3) Using p-tert-butylacetophenone and p-methoxybenzoyl chloride as raw materials, carry out acylation reaction to generate avobenzone (WO2006100225). In this method of synthesis, CuCl needs to be used as a catalyst, and the reaction time is up to 20h , post-processing is cumbersome, and more toxic reagents such as chloroform are needed

[0007] The above-mentioned methods all have their own advantages and disadvantages. Therefore, it is still necessary to continue to explore new synthetic methods to meet the industry's demand for high-quality, low-priced 1,3-diphenylpropanedione compounds

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