A kind of synthetic method of 3,4,5-trimethoxybenzoic acid

A technology of trimethoxybenzoic acid and synthesis method, which is applied in chemical instruments and methods, separation/purification of carboxylic acid compounds, preparation of carboxylate salts, etc. , technological production difficulties and other problems, to achieve the effect of reducing waste water production, no ecological environmental risks, and overcoming high risk factors

Active Publication Date: 2020-06-05
WUFENG CHICHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1) Use tannic acid or gallic acid to methylate twice with dimethyl sulfate in an alkaline environment, and then go through a series of purification steps to obtain 3,4,5-trimethoxybenzoic acid with a content of about 98% Products, this method uses a large amount of highly toxic dimethyl sulfate, which poses a huge threat to the life and health of front-line operators, and produces a large amount of difficult-to-treat high-salt wastewater, which does not meet the requirements of green environmental protection;
[0006] 2) Ethyl 3,4,5-trimethoxybenzoate extracted from natural plants is used to obtain 3,4,5-trimethoxybenzoic acid after hydrolysis, but this method is not only limited by resources, but the yield is only About 75%, the cost is high, and the process production is very difficult;
[0007] 3) Using potassium permanganate and sodium hypochlorite to oxidize 3,4,5-trimethoxybenzaldehyde can obtain 3,4,5-trimethoxybenzoic acid, but the acquisition of 3,4,5-trimethoxybenzaldehyde is relatively Difficult, it needs to be prepared by bromination, methoxylation and methylation with p-hydroxybenzaldehyde, the process is complicated and the total yield is low

Method used

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  • A kind of synthetic method of 3,4,5-trimethoxybenzoic acid
  • A kind of synthetic method of 3,4,5-trimethoxybenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) Add 1313.2 mL (17 mol) of solvent N,N-dimethylformamide, 17 g (0.1 mol) of gallic acid, and catalyst potassium carbonate to the reaction flask protected by inert gas in sequence at 20~25 °C 41.4g (0.3mol) and 103.5g (1.15mol) of dimethyl carbonate, stirred for 0.5~1 hour to fully mix the materials.

[0026] 2) Heat the material in the reaction bottle to 110~120℃, and keep it warm for 8~10 hours.

[0027] 3) After the reaction is completed, initially recover the excess dimethyl carbonate by vacuum distillation at -0.1MPa, 75°C, and then raise the temperature to 90~100°C to distill N,N-dimethylformamide until the bottle forms mushy. The dimethyl carbonate and N,N-dimethylformamide recovered by vacuum distillation are reserved as raw materials in step 1) for recycling.

[0028] 4) Add 576 mL (32mol) of water and 0.84g (0.07mol) of activated carbon into the reaction flask, heat to 80-90°C, keep stirring for 0.5-1 hour, and stop heating.

[0029] 5) Filter the material...

Embodiment 2

[0031] 1) Add 1313.2 mL (17 mol) of solvent N,N-dimethylformamide, 17 g (0.1 mol) of gallic acid, and catalyst potassium carbonate to the reaction flask protected by inert gas in sequence at 20~25 °C 48.3g (0.35mol) and 103.5g (1.15mol) of dimethyl carbonate, stirred for 0.5~1 hour to fully mix the materials.

[0032] 2) Heat the material in the reaction bottle to 110~120℃, and keep it warm for 8~10 hours;

[0033] 3) After the reaction is completed, initially recover the excess dimethyl carbonate by vacuum distillation at -0.1MPa, 75°C, and then raise the temperature to 90~100°C to distill N,N-dimethylformamide until the bottle forms mushy. Dimethyl carbonate and N,N-dimethylformamide recovered by vacuum distillation are reserved as raw materials in step 1) for recycling;

[0034] 4) Add 576 mL (32mol) of water and 0.84g (0.07mol) of activated carbon into the reaction bottle, heat to 80~90℃, keep stirring for 0.5~1 hour, and stop heating;

[0035] 5) Filter the material wh...

Embodiment 3

[0037] 1) Add 1313.2 mL (17 mol) of solvent N,N-dimethylformamide, 17 g (0.1 mol) of gallic acid, and catalyst potassium carbonate to the reaction flask protected by inert gas in sequence at 20~25 °C 55.2g (0.4mol) and 103.5g (1.15mol) of dimethyl carbonate, stirred for 0.5~1 hour to fully mix the materials.

[0038] 2) Heat the material in the reaction bottle to 110~120℃, and keep it warm for 8~10 hours;

[0039] 3) After the reaction is completed, initially recover the excess dimethyl carbonate by vacuum distillation at -0.1MPa, 75°C, and then raise the temperature to 90~100°C to distill N,N-dimethylformamide until the bottle forms mushy. Dimethyl carbonate and N,N-dimethylformamide recovered by vacuum distillation are reserved as raw materials in step 1) for recycling;

[0040] 4) Add 576 mL (32mol) of water and 0.84g (0.07mol) of activated carbon into the reaction bottle, heat to 80~90℃, keep stirring for 0.5~1 hour, and stop heating;

[0041] 5) Filter the material whi...

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Abstract

The invention relates to a synthesis method of 3,4,5-trimethoxybenzoic acid. Under the condition of 110 to 120 DEG C, N, N-dimethylformamide is used as a solvent; under the catalysis condition of potassium carbonate, gallic acid and dimethyl carbonate are added in one step; the 3,4,5-trimethoxybenzoic acid is synthesized through methylation. The process has the advantages that the synthesis process is simple; the cost is low; the yield reaches 95 percent or higher; the product purity reaches 100.0 percent, and the like. The green methylation reagent of dimethyl carbonate is used for replacing highly toxic dimethyl sulfate; the high risk factor of the process is overcome; the process safety is improved to the maximum degree; the economic benefits are obvious; the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 3,4,5-trimethoxybenzoic acid, specifically using gallic acid and dimethyl carbonate as raw materials to synthesize the green color of 3,4,5-trimethoxybenzoic acid through methylation reaction The synthesis method belongs to the field of chemical synthesis. [0002] technical background [0003] 3,4,5-Trimethoxybenzoic acid is an important fine chemical product or pharmaceutical intermediate, which is widely used in the fields of medicine, dyestuff, food and fine chemical industry. In addition to being used as an additive for high-grade food, cigarettes and beverages, it can also be used to prepare trimethoxybenzoyl chloride, syringic acid and trimethoxybenzoate, etc., and it is also used as stomach medicine and heart disease medicine in medicine , anti-anxiety drugs, antipyretic drugs, drugs for treating schizophrenia, and important intermediates of antibacterial synergistic drugs, the market demand is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/21C07C51/367C07C51/43
CPCC07C51/367C07C51/43C07C65/21
Inventor 刘义稳陈清龙陈赤清毛业富
Owner WUFENG CHICHENG BIOTECH
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