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A kind of synthetic method of avobenzone

A synthesis method and avobenzone technology are applied in the synthesis field of avobenzone, and can solve the problems of unsatisfactory total reaction yield, difficult industrialization implementation, low total reaction yield and the like, so as to prevent thermal decomposition and desorption. Acid phenomenon, beneficial to industrial production, easy to handle

Active Publication Date: 2017-02-01
JIANGXI YONGTONG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among these two routes, the intermediate synthetic route in the first route is relatively long, the total reaction yield is low, and the total reaction time is also long, so it is difficult to implement industrially; while the intermediate synthetic route of the second reaction route is simple, and the technology has been relatively low. Mature, mild reaction conditions, but the overall reaction yield is not ideal

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A kind of synthetic method of avobenzone of the present invention comprises the following steps:

[0017] 1), the alkylation reaction takes toluene and chloro-tert-butane as raw materials, uses aluminum chloride as a catalyst, the reaction temperature is 23.5° C., and the reaction time is 85 minutes to obtain p-tert-butyltoluene; chloro-tert-butyl toluene and The mol ratio of toluene is 1:1.6, and the yield that finally obtains p-tert-butyltoluene is 86.5%, and the purity is 98%;

[0018] 2), potassium permanganate is used as an oxidizing agent in the oxidation reaction, and the p-tert-butyltoluene obtained in step 1) is oxidized into p-tert-butylbenzoic acid; the reaction temperature is 85°C, and the reaction time is 8.5h, and p-tert-butyl The mol ratio of methyl toluene and potassium permanganate is 1:3, and the potassium permanganate oxidant is dropped into the reaction system in 5 times, 1.2 molar parts are dropped into for the first time, 0.8 molar parts are droppe...

Embodiment 2

[0023] A kind of synthetic method of avobenzone of the present invention comprises the following steps:

[0024] 1), the alkylation reaction takes toluene and chloro-tert-butane as raw materials, uses aluminum chloride as a catalyst, the reaction temperature is 23.5° C., and the reaction time is 85 minutes to obtain p-tert-butyltoluene; chloro-tert-butyl toluene and The mol ratio of toluene is 1:1.5, and the yield that finally obtains p-tert-butyltoluene is 83%, and the purity is 98%;

[0025] 2), potassium permanganate is used as an oxidizing agent in the oxidation reaction, and the p-tert-butyltoluene obtained in step 1) is oxidized into p-tert-butylbenzoic acid; the reaction temperature is 85°C, and the reaction time is 8.5h, and p-tert-butyl The molar ratio of methyl toluene to potassium permanganate is 1:3, and the potassium permanganate oxidant is added in 5 to 8 times. Preferably, the potassium permanganate oxidant of 3 molar parts is put into the reaction system in 6 ...

Embodiment 3

[0030] A kind of synthetic method of avobenzone of the present invention comprises the following steps:

[0031] 1), the alkylation reaction takes toluene and chloro-tert-butane as raw materials, uses aluminum trichloride as a catalyst, the reaction temperature is 23.5° C., and the reaction time is 85 minutes to obtain p-tert-butyltoluene; wherein, chloro-tert-butyl The molar ratio of alkane to toluene is 1:1.6, and finally the yield of p-tert-butyltoluene is 86.5%, and the purity is 98%;

[0032] 2), potassium permanganate is used as an oxidizing agent in the oxidation reaction, and the p-tert-butyltoluene obtained in step 1) is oxidized into p-tert-butylbenzoic acid; the reaction temperature is 85°C, and the reaction time is 8.5h, and p-tert-butyl The mol ratio of methyl toluene and potassium permanganate is 1:3, and the potassium permanganate oxidant is dropped into the reaction system in 6 times, and 0.9 mole part is dropped into for the first time, and 0.6 mole part is dr...

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Abstract

The invention discloses a synthetic method of avobenzone. The avobenzone is prepared by subjecting phenetole and methylbenzene, as starting materials, to alkylation, oxidation, esterification, acylation and condensation reaction. During oxidation, the oxidant potassium permanganate is added to a reaction system six times, thus thermal decomposition and deacidification of the potassium permanganate is avoided, and reaction yield is higher. During esterification, with methylsulphonic acid as catalyst, P-tert-butyl benzoic acid and methanol are subjected to reflux reaction for 8 hours according to a molar ratio: 1:7; the methanol is added in two stages for reaction, and the problem that water diversion fails in the reaction process is solved. During acylation, phosphotungstic acid is used as catalyst, reaction selectivity is improved, post-reaction treatment is simpler, and reaction yield is higher; the phosphotungstic acid is recyclable, thus cost is saved and industrial production is more benefited.

Description

technical field [0001] The invention relates to a synthetic method of avobenzone. Background technique [0002] Avobezone is a synthetic UV absorber with a chemical name of 4-tert-butyl-4'-methoxy-dibenzoylmethane, also known as Bassoon 1789, sunscreen BMDM (UV- A). It is a good UV-A (>320nm) type ultraviolet absorber, which can block all-band (320-400nm) UVA, and is an efficient broad-spectrum oil-soluble UVA filter, compounded with other UVB sunscreens , which provides full UVA and UVB protection for the prevention of photoinduced skin cancer. [0003] At present, there are mainly two synthetic routes of avobenzone. Route 1 uses tert-butylbenzoyl chloride and 2-trimethylsiloxy-2-tolylethylene as reaction intermediates, copper chloride as a catalyst, and methylene chloride as a solvent, and reacts for 21 hours to obtain avobenzone Case; Route 2 uses methoxyacetophenone and methyl p-tert-butylbenzoate as reaction intermediates, and sodium amide as catalyst, and reacts...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C45/72
CPCY02P20/584
Inventor 刘忠春
Owner JIANGXI YONGTONG TECH