Synthesis process of hydroxyl pinacolone retinoate

A synthesis process and retinoic acid ester technology, applied in metal/metal oxide/metal hydroxide catalysts, organic chemistry, physical/chemical process catalysts, etc., can solve the problem of chlorinated alkane residues, low domestic output and high price and other problems, to achieve the effects of pollution control, high reaction yield and simple operation.

Active Publication Date: 2022-01-04
南京先达医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] With the development of the cosmetics field, the usage of hydroxypinacolone retinoic acid ester has been increasing, but the source of this material is mainly imported from abroad, and the domestic production is extremely low. less, it is difficult to meet the demand of the market, and the current hydroxy pinacolone retinoate is expensive, and the preparation process uses chloropinacolone as the inspiration raw material, which can easily cause the residue of chlorinated alkanes in the raw material. Strictly prohibited in the field of cosmetics

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A synthesis process of hydroxypinacolone retinoate, comprising:

[0027] Retinoic acid and hydroxypinacolone are condensed under the action of a water-absorbing catalyst to obtain hydroxypinacolone retinoate. The water-absorbing catalyst adopts a shell-core catalyst with vermiculite as the core and titanium-aluminum oxide as the medium Hole shell.

[0028] The molar ratio of the micro-A acid to hydroxy pinazone is 1:1.1.

[0029] The mass ratio of the retinoic acid to the water absorption catalyst is 1:0.3.

[0030] The condensation reaction is carried out in isopropanol, and the concentration of tretinoin in isopropanol is 100g / L.

[0031] After the condensation reaction is completed, the water-absorbing catalyst is taken out, and the organic phase is spin-dried and crystallized to obtain golden yellow crystals; the organic phase is removed by evaporation, and then the residue is put into n-heptane and stirred evenly, heated to 50° C. to dissolve, Then filter and co...

Embodiment 2

[0037] A synthesis process of hydroxypinacolone retinoate, comprising:

[0038] Retinoic acid and hydroxypinacolone are condensed under the action of a water-absorbing catalyst to obtain hydroxypinacolone retinoate. The water-absorbing catalyst adopts a shell-core catalyst with vermiculite as the core and titanium-aluminum oxide as the medium Hole shell.

[0039] The molar ratio of the micro-A acid to hydroxy pinazone is 1:1.3.

[0040] The mass ratio of the retinoic acid to the water absorption catalyst is 1:0.5.

[0041] The condensation reaction is carried out in isopropanol, and the concentration of tretinoin in isopropanol is 200g / L.

[0042] After the condensation reaction, the water-absorbing catalyst was taken out, the organic phase was spin-dried and crystallized to obtain golden yellow crystals, the organic phase was removed by evaporation, and then the residue was put into n-heptane and stirred evenly, heated to 60°C to dissolve, Then filter and cool down to 15°C...

Embodiment 3

[0048] A synthesis process of hydroxypinacolone retinoate, comprising:

[0049] Retinoic acid and hydroxypinacolone are condensed under the action of a water-absorbing catalyst to obtain hydroxypinacolone retinoate. The water-absorbing catalyst adopts a shell-core catalyst with vermiculite as the core and titanium-aluminum oxide as the medium Hole shell.

[0050] The molar ratio of the micro-A acid to hydroxy pinazone is 1:1.2.

[0051] The mass ratio of the retinoic acid to the water absorption catalyst is 1:0.4.

[0052] The condensation reaction is carried out in isopropanol, and the concentration of the retinoic acid in isopropanol is 150g / L.

[0053] After the condensation reaction is completed, the water-absorbing catalyst is taken out, and the organic phase is spin-dried and crystallized to obtain golden yellow crystals; the organic phase is removed by evaporation, and then the residue is put into n-heptane and stirred evenly, heated to 55° C. to dissolve, Then filte...

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PUM

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Abstract

The invention belongs to the field of synthesis, and particularly relates to a synthesis process of hydroxyl pinacolone retinoate, the synthesis process comprises the following steps: carrying out condensation reaction on tretinoin and hydroxyl pinacolone under the action of a water absorption catalyst to obtain hydroxyl pinacolone retinoate, wherein the water absorption catalyst adopts a shell-core catalyst, vermiculite is used as an inner core, and titanium aluminum oxide is used as a mesoporous shell layer. According to the synthesis process, the defects in the prior art are overcome, distilled water generated in the reaction process is rapidly absorbed by utilizing the water absorption catalyst, and stable esterification reaction is formed under the catalytic action of titanium oxide.

Description

technical field [0001] The invention belongs to the field of synthesis, and in particular relates to a synthesis process of hydroxy pinacolone retinoate. Background technique [0002] Hydroxypinacolone retinoate is a derivative of retinol, which can directly bind to cell retinoic acid receptors, has the function of regulating the metabolism of the epidermis and stratum corneum, can resist aging, reduce seborrhea, and dilute the epidermis Pigment can prevent skin aging, treat acne, whiten and lighten spots, etc. While ensuring the powerful effect of retinoic acid, it greatly reduces its irritation. It is mainly used for anti-aging, anti-wrinkle and prevention of acne recurrence. [0003] With the development of the field of cosmetics, the usage of hydroxypinacolone retinoate is continuously increasing, but the source of this material is mainly imported from abroad, and the domestic production is very small, which is difficult to meet the demand of the market. At the same tim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38B01J21/06B01J21/04B01J21/16
CPCC07D309/38B01J21/063B01J21/04B01J23/002B01J35/008B01J21/16Y02P20/584
Inventor 曹璨李祥祥王兆敏
Owner 南京先达医药科技有限公司
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