Preparation method of sun-screening agent octyl triazinone

Abstract

The invention discloses a preparation method of a sun-screening agent octyl triazinone, octyl triazinone prepared by the preparation method and an application of octyl triazinone, and the method comprises the following steps: step 1, carrying out esterification reaction on p-nitrobenzoic acid and isooctyl alcohol to obtain a product I, 2, carrying out a hydrogenation reaction on the product I in the presence of a catalyst, filtering after the reaction is completed, and carrying out reduced pressure distillation to obtain a product II, and step 3, adding a solvent into the product II, heating to reflux, adding the solution A, carrying out a reaction, and carrying out post-treatment to obtain octyltriazinone. Cheap and easily available p-nitrobenzoic acid is used as a raw material, the sun-screening agent octyl triazinone is efficiently prepared through esterification, hydrogenation and coupling, meanwhile, iso-octyl p-aminobenzoate is obtained, the obtained octyl triazinone is high in chromatographic purity and yield, and the method has the advantages of being few in three wastes, low in cost, green, environmentally friendly, easy to operate, easy to control and the like.Easy realization of industrial production.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of sunscreen agent octyl triazone. Background technique [0002] Sunscreen agent octyl triazone is a new type of ultraviolet absorber. It has a large molecular structure and high ultraviolet absorption efficiency, and has a broad-spectrum sunscreen effect. Used as an additive in sunscreen products, it is the oil-soluble absorbent with the strongest UVB absorption capacity on the market today. It has high photostability, prevents the immunosuppressive effect induced by UVB, has strong water resistance, and has a good effect on skin keratin. affinity. As a sunscreen agent, octyltriazone has the advantages of high absorption rate and low addition amount. Usually in sunscreen care products, it only needs a very small dose to achieve a high SPF value and has excellent sunscreen effect. [0003] BASF company patent WO2012 / 127425 discloses a method for synthesizin...

AI Technical Summary

Problems solved by technology

The method has the following defects: the reaction route is long, the yield of intermediate I is 92.5%, the yield of intermediate II is 93.2%, the yield of intermediate III is 93.2%, the yield of product octyl triazone ketone is 91.6%, and the total yield is only 73.6% %; The preparation of intermediate II adopts chemical reduction method, which will produce a large amount of iron sludge and seriously pollute the environment; when intermediate III is prepared, it is difficult to control the substitution quantity of cyanuric chloride, thus causing the low yield of intermediate III, and the intermediate III is very sensitive to water and is easy to hydrolyze to produce impurities that are difficult to remove; more solvents are introduced in the whole preparation process, which creates hidden dangers for the final product's dissolved residue

The problem that this method exists is: when melamine is coupled with p-chlorobenzoic acid, the chlorine activity on the benzene ring is low, and it is difficult to react with the amino group on the melamine, so that the yield of intermediate I is low; In the process of sodium bisulfate catalyzed esterification with isooctyl alcohol, it is difficult to completely esterify the three carboxyl groups on the intermediate I at the same time, so that the finished product contains unesterified impurities, which brings difficulties to separation and purification. It also ultimately affects the yield and quality of the product

The patent does not provide a preparation method for methyl p-aminobenzoate, and the outsourcing price is relatively expensive and difficult to obtain; the use of various solvents such as xylene, toluene, methanol, ethanol, isooctyl alcohol, etc., poses a hidden danger to the solvent residue of subsequent products ; Use 10% sodium methylate to catalyze the transesterification reaction between intermediate I and isooctyl alcohol, which will inevitably increase the cost of product manufacturing and cause three wastes to pollute the environment; The finished product contains impurities that have not been completely transesterified, which brings difficulties to separation and purification, and ultimately affects product quality

Images