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Novel 4-butylresorcinol synthesis method

A technology of butyl resorcinol and butyryl resorcinol, which is applied in the field of synthesis of 4-butyl resorcinol, can solve the problems of easy safety accidents, high risk factor, a large amount of waste acid and mercury-containing solids. Waste and other problems, to avoid high-pressure dangerous reaction, high yield effect

Pending Publication Date: 2022-02-11
河南旭瑞新材料科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] At present, the industrialization process of this product mainly adopts zinc amalgam method for reduction, which will produce a large amount of waste acid and mercury-containing solid waste; there are other reports in the literature that hydrogen is used for reduction under high pressure conditions. This process has a high risk factor and is very prone to safety accidents.

Method used

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  • Novel 4-butylresorcinol synthesis method
  • Novel 4-butylresorcinol synthesis method
  • Novel 4-butylresorcinol synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Synthesis of 4-butyrylresorcinol

[0040] Add resorcinol (220g, 1.0 eq), toluene (700 mL), zinc chloride (350 g, 1.3 eq), butyric acid (220 g, 1.25 eq) into a 2000 mL three-necked flask, connect to the water separator, and heat up to 105-110°C heat preservation reaction for 4-6 hours, HPLC central control, after the reaction, add 500g of water to the reaction bottle to obtain a red solution, heat up and distill toluene until no more drops out, then cool down to room temperature, each time Extracted 2-3 times with 200ml of ethyl acetate, combined the organic phases, concentrated to dryness, the obtained oil was recrystallized with ethanol water, and dried to obtain the target intermediate product with a weight of 305g and a yield of 84.7%.

[0041] Synthesis of 4-Butylresorcinol

[0042] In a 100 mL three-neck flask, add 4-butyrylresorcinol (10 g, 1.0eq), 5% Pd / C (0.1g, 0.01X), methanol (40 ml, 4V), PMHS (10 mL , the hydrogen content is not less than 1.5%, 4-5eq hydrog...

Embodiment 2

[0044] The synthesis steps of 4-butyryl resorcinol in this example are the same as those in Example 1.

[0045] The difference between this embodiment and embodiment 1 is: the synthesis of 4-butylresorcinol

[0046] In a 100 mL three-neck flask, add 4-butyrylresorcinol (10 g, 1.0eq), 5% Pd / C (0.05g, 0.005X), ethanol (30 ml, 3V), PMHS ((10 mL, the hydrogen content is not less than 1.5%, 4-5eq hydrogen equivalent), heated to 60°C and stirred for 6 hours, the reaction in the HPLC control was completed, filtered palladium carbon, and then concentrated to dryness with an oil pump under reduced pressure, PE / EA (1: 0~10:1) was purified by column chromatography as the eluent to obtain 7 g of the product, the HPLC purity was 98.6%, and the yield was 75.6%.

Embodiment 3

[0048] The synthesis steps of 4-butyryl resorcinol in this example are the same as those in Example 1.

[0049] The difference between this embodiment and embodiment 1 is: the synthesis of 4-butylresorcinol

[0050] In a 2000 mL three-neck flask, add 4-butyrylresorcinol (300 g, 1.0eq), 5% Pd / C (2g, 0.007X), methanol (1200 ml, 4V), PMHS ((320 mL , the hydrogen content is greater than 1.7%, the hydrogen equivalent is greater than 5 eq), the temperature is raised to 50°C and stirred for 3-4 hours, the reaction in the HPLC control is completed, the palladium carbon is removed by nitrogen pressure filtration, the mother liquor is first evaporated to methanol at normal pressure, and then decompressed with an oil pump Concentrate to dryness, use n-hexane as a solvent for the oily matter, decolorize and recrystallize with activated carbon to obtain 201 g of the product, the HPLC purity is 99.1%, and the yield is 72.3%.

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Abstract

The invention provides a novel 4-butylresorcinol synthesis method, and belongs to the technical field of chemical synthesis, the synthesis method comprises the following steps: by taking 4-butyryl resorcinol as a raw material, polymethylhydrosiloxane as a hydrogen source and palladium-carbon as a catalyst, heating and stirring to react in an alcohol solvent under the normal pressure condition; and after the HPLC central control reaction is finished, filtering palladium on carbon, concentrating a mother liquor, and recrystallizing and purifying the obtained oily substance to obtain the 4-butylresorcinol. According to the invention, generation of waste acid and mercury-containing solid waste is effectively avoided; hydrogenation reduction is realized at normal pressure, so that high-pressure dangerous reaction is avoided; and the conversion rate of the final product is high, and hundred-kilogram-level amplified production is realized.

Description

Technical field [0001] The invention relates to the technical field of chemical synthesis, and specifically relates to a new synthesis method of 4-butylresorcinol. Background technique [0002] Whitening is the eternal pursuit of Oriental women, and the cosmetics industry has never stopped exploring whitening raw materials. There are endless raw materials for whitening and lightening spots on the market, from traditional raw materials (vitamin C derivatives, fruit acid, kojic acid and its dipalmitate, β-arbutin) to later tranexamic acid, α-arbutin, There are hundreds of kinds of various extracts, etc. However, it usually takes two or three months for these raw materials to take initial effect, and consumers tend to lose patience. [0003] As a new whitening ingredient, 4-butylresorcinol can effectively inhibit the activity of tyrosinase in the skin, block the formation of melanin, and accelerate the decomposition and excretion of melanin by directly combining with tyrosine...

Claims

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Application Information

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IPC IPC(8): C07C37/00C07C39/08C07C45/46C07C49/825
CPCC07C45/46C07C37/002C07C49/825C07C39/08
Inventor 马可望王志刚蒋腾飞周永增
Owner 河南旭瑞新材料科技有限公司
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