Preparation method of 4-alkylresorcinol

A technology of alkylresorcinol and acylresorcinol, which is applied in the field of preparation of 4-alkylresorcinol, can solve the problems of high environmental pressure, high operation requirements, and many by-products, and reduce production Cost, ease of post-processing, effect of reducing by-products

Inactive Publication Date: 2018-03-16
SPEC CHEM IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the prior art, in the preparation of 4-alkyl resorcinols, there are generally low product yields, low raw material conversion rates, many by-products, high operating requirements, complicated post-processing, high costs, and relatively high environmental pressures. shortcoming

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 165.0g resorcinol (1.5mol) in the 2.0L four-necked flask, then add 1.0L cyclohexane, then add 132.2g n-butyric acid (1.5mol), add 245.3g zinc chloride (1.8mol) under stirring . After the addition, heat to reflux and stir, the water separator separates the water produced by the reaction, and GC tracks until the reaction is complete. Zinc chloride was separated, the organic phase was washed with water and saturated sodium bicarbonate, and concentrated to obtain 218.0 g of 4-butyryl resorcinol with a yield of 80.6%.

[0023] Add 90.1g (0.5mol) of 4-butyryl resorcinol to a 1.0L four-necked flask, add 500ml of acetic acid, 10% wet Pd / C (20.0g), under nitrogen protection, heat to 110°C, add 157.7 g ammonium formate (2.5mol), followed by GC until the end of the reaction. Add 2.0L of dichloromethane to the reaction solution, filter and recover Pd / C, wash the filtrate with water, wash with saturated sodium bicarbonate, dry over anhydrous sodium sulfate, and concentrate to ...

Embodiment 2

[0025] Add 165.0 g of resorcinol (1.5 mol) to a 2.0 L four-necked flask, then add 1.0 L of toluene, then add 158.6 g of n-butyric acid (1.8 mol), and add 245.3 g of zinc chloride (1.8 mol) under stirring. After the addition, heat to reflux and stir, the water separator separates the water produced by the reaction, and GC tracks until the reaction is complete. Zinc chloride was separated, the organic phase was washed with water and saturated sodium bicarbonate, and concentrated to obtain 241.5 g of 4-butyryl resorcinol with a yield of 89.3%.

[0026] Add 90.1g (0.5mol) of 4-butyryl resorcinol to a 1.0L autoclave, add 500ml of methanol, 10% wet Pd / C (20.0g), heat to 80°C, and feed hydrogen at a pressure of 1.5MPa , GC tracking to the end of the reaction. The reaction solution was filtered to recover Pd / C, and the filtrate was concentrated to obtain a light brown-red oily liquid, which was recrystallized from dichloromethane and n-hexane to obtain 72.3 g of 4-butylresorcinol, GC...

Embodiment 3

[0028] Add 165.0 g of resorcinol (1.5 mol) to a 2.0 L four-necked flask, then add 1.0 L of xylene, then add 158.6 g of n-butyric acid (1.8 mol), and add 245.3 g of zinc chloride (1.8 mol) under stirring. After the addition, heat to reflux and stir, the water separator separates the water produced by the reaction, and GC tracks until the reaction is complete. Zinc chloride was separated, the organic phase was washed with water and saturated sodium bicarbonate, and concentrated to obtain 232.0 g of 4-butyryl resorcinol with a yield of 85.8%.

[0029] Add 90.1g (0.5mol) of 4-butyryl resorcinol to a 1.0L autoclave, add 500ml of methanol, Raney nickel (20.0g), heat to 80°C, feed hydrogen, pressure 1.5MPa, GC tracking to The reaction is over. The reaction solution was filtered to recover Raney nickel, and the filtrate was concentrated to obtain a light brown-red oily liquid, which was recrystallized from dichloromethane and n-hexane to obtain 54.2 g of 4-butylresorcinol, GC>99.0%, ...

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PUM

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Abstract

The invention discloses a preparation method of 4-alkylresorcinol. The preparation method comprises the steps: carrying out a reaction on resorcinol and alkyl acid to prepare acyl resorcinol, and then, catalyzing a hydrogenation reaction to obtain 4-alkylresorcinol. By using the method, the dosages of a catalyst and alkyl groups are controlled in an acylation process, so that the yield is remarkably increased, byproducts are reduced, and the production cost is reduced; and hydrogen reduction is adopted in a reduction process, and a high-toxicity and high-pollution zinc amalgam reducing agent is prevented from being used, so that the preparation method is green and environment-friendly; and the aftertreatment is simple, the prepared product is high in purity, the total yield of the two steps reaches up to 77%, and the preparation method has a remarkable significance for industrial production of 4-alkylresorcinol.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a preparation method of 4-alkylresorcinol. Background technique [0002] The exploration of whitening raw materials in the cosmetics industry has never stopped. In the past ten years, a class of resorcinol derivatives has been found to have a super strong potential whitening effect: in vitro experiments have also proved that it is tens or even hundreds of times stronger than VC, and its whitening ability has been clinically confirmed. It has the same whitening ability as hydroquinone. The most important thing is that the whitening speed is fast and consumers like it. After more than ten years of continuous understanding of the properties and safety of these raw materials, they are gradually being licensed by various countries and gradually used in cosmetics. [0003] Since some ingredients have been approved globally, the country will gradually refer to the introdu...

Claims

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Application Information

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IPC IPC(8): C07C39/08C07C37/00C07C51/60C07C53/42C07C45/46C07C49/825
CPCC07C37/002C07C45/46C07C51/60C07C53/42C07C49/825C07C39/08
Inventor 徐金荣查建生
Owner SPEC CHEM IND INC
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