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Preparation method of terephthalylidene dicamphor sulfonic acid sun-screening agent

A technology of xylylene biscamphorsulfonic acid and camphorsulfonic acid, which is applied in the fields of sulfonic acid preparation and organic chemistry, can solve the problems of difficult stirring, poor solubility, difficult filtration, etc., and achieves low cost and simple equipment , the effect of easy mixing

Inactive Publication Date: 2017-06-13
广州星业科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Existing technologies, such as patent US4585597, mainly use sodium methoxide solid as a catalyst, but due to the large amount of use, the solubility in toluene is poor, it is easy to viscous, and it is not easy to stir, so a large amount of toluene needs to be used as a solvent
Moreover, a large amount of viscous solids are precipitated during the production process, which is not easy to filter, and toluene needs to be poured out, which is not easy to operate

Method used

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  • Preparation method of terephthalylidene dicamphor sulfonic acid sun-screening agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 1000ml four-necked round bottom flask, add 60g camphorsulfonic acid, 116ml mass content of 25% sodium methylate methanol solution and 310ml cyclohexane, nitrogen protection, stir at 75°C for 60min, and reclaim the low boiling point solvent with a water separator; then Add dropwise a methanol-cyclohexane solution containing 17.6g of terephthalaldehyde, wherein the volume ratio of methanol to cyclohexane is 1:6; keep warm at 70°C for 80min, and recover the low boiling point solvent; after the reaction is completed, add 280ml of water and wash with concentrated hydrochloric acid Adjust the pH to 2 and raise the temperature to 90°C, then separate the liquids and recover cyclohexane; add 250ml of ethanol to the water layer, cool it to -15°C, and then filter with suction to obtain a white solid, which is then vacuum-dried to obtain p-xylylene Dicamphorsulfonic acid sunscreen agent 42.7g, its mass content as determined by HPLC is 99.74%.

Embodiment 2

[0030] In a 1000ml four-necked round bottom flask, add 60g camphorsulfonic acid, 120ml mass content of 30% sodium methylate methanol solution and 460ml cyclohexane, nitrogen protection, react at 65°C for 120min, and reclaim the low boiling point solvent with a water separator; then Add dropwise a methanol-cyclohexane solution containing 17.4g of terephthalaldehyde, wherein the volume ratio of methanol to cyclohexane is 1:6; keep warm at 75°C for 30 minutes, and recover the low boiling point solvent; after the reaction is completed, add 410ml of water and wash with concentrated hydrochloric acid Adjust the pH to 1, and raise the temperature to 90°C, then separate the liquid and recover cyclohexane; add 300ml of acetone to the water layer, cool down to -10°C, and filter with suction to obtain a white solid terexylylene biscamphorsulfonic acid sunscreen 45.0g, its mass content determined by HPLC is 99.68%.

Embodiment 3

[0032] In a 1000ml four-necked round bottom flask, add 68g camphorsulfonic acid, 130ml mass content of 28% sodium methylate methanol solution and 350ml cyclohexane, nitrogen protection, react at 65°C for 20min, and reclaim the low boiling point solvent with a water separator; then Add dropwise methanol-cyclohexane solution containing 17.6g of terephthalaldehyde, the volume ratio of methanol to cyclohexane is 1:5; keep warm at 65°C for 100min, and recover the low boiling point solvent; after the reaction is completed, add 350ml of water and adjust with concentrated hydrochloric acid pH = 3, and heated up to 90°C, then separated and recovered cyclohexane; the water layer was directly cooled to 25°C at low temperature, and suction filtered to obtain 32 g of white solid terexylylene biscamphorsulfonic acid sunscreen, which was determined by HPLC The mass content is 99.89%.

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Abstract

The invention belongs to the field of producing fine chemicals and discloses a preparation method of a terephthalylidene dicamphor sulfonic acid sun-screening agent. The preparation method comprises the following steps: stirring camphor sulfonic acid, a methanol solution of sodium methylate and cyclohexane by using a water segregator at the temperature being 65-75 DEG C to carry out reaction for 20-120min, and recovering methanol; dropwise adding a cyclohexane-methanol mixed solution of terephthalic aldehyde, continuously stirring by using the water segregator at the temperature being 65-75 DEG C to carry out reaction for 30-120min, and recovering methanol; and then adding water, carrying out acidification with acid, carrying out layering by rising temperature, and carrying out crystallization and pumping filtration on a water layer to obtain a product with the HPLC purity being larger than 99 percent. The technology greatly simplifies operation and flow and is simple to operate.

Description

technical field [0001] The invention belongs to the field of fine chemical production, and in particular relates to a preparation method of a terexylylene dicamphorsulfonic acid sunscreen agent containing a p-phenylene diolefin structure. Background technique [0002] Terexylylene biscamphorsulfonic acid containing p-phenylene structure is a kind of ultraviolet UVA sunscreen agent, which belongs to water-soluble chemical sunscreen agent. It is one of the most effective UVA sunscreen agents today, with low skin absorption rate and obtained Approved by the US FDA, it has a wide range of uses in the field of cosmetics. [0003] At present, terephthalmethylene biscamphorsulfonic acid is mainly prepared by the following method. Terephthalaldehyde and camphorsulfonic acid are reacted under alkaline conditions, and then acidified to obtain the product. as follows: [0004] [0005] Existing technologies, such as patent US4585597, mainly use sodium methoxide solid as a catalyst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/22C07C309/24
CPCC07C303/22C07C309/24
Inventor 胡伟孟巨光
Owner 广州星业科技股份有限公司
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