A green and simple preparation method of 2,3,5-trimethylbenzoquinone (tmbq)

A technology of trimethylbenzoquinone and trimethylphenol, which is applied in the field of green and simple preparation of 2,3,5-trimethylbenzoquinone, can solve the problem that it is difficult to remove by-products, and the products cannot be crystallized. Pure products and other problems, to achieve the effect of low reaction equipment requirements, reduced production costs, high purity and yield

Inactive Publication Date: 2014-10-22
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

We also tried to use this method to prepare TMBQ, and found that after the reaction was completed, orange-yellow needle crystals could not be obtained, and the product after evaporating the solvent was always oily, and the reaction was monitored by high-performance thin-layer chromatography (TLC). Shows a dark by-product point under the main spot, which is difficult to remove by conventional chemical methods, so the product cannot form a crystalline pure product

Method used

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  • A green and simple preparation method of 2,3,5-trimethylbenzoquinone (tmbq)
  • A green and simple preparation method of 2,3,5-trimethylbenzoquinone (tmbq)
  • A green and simple preparation method of 2,3,5-trimethylbenzoquinone (tmbq)

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Weigh 0.03 mol of 2,3,6-trimethylphenol into a 250 mL three-necked flask, add 35 mL of petroleum ether and place it on a constant temperature oil bath with temperature controlled at 30°C. When the raw material is dissolved and the temperature is constant, add 4 times the equivalent of 50% sulfuric acid aqueous solution dropwise. The rate of addition should not be too fast. The rate of addition can be controlled by a constant pressure dropping funnel. After the addition is completed, keep warm for 30 minutes. Then measure 6 times the equivalent of 30% hydrogen peroxide, and add it dropwise to the above reaction system, and react at 30°C for half an hour after the addition is completed. The reaction produces a large amount of earthy matter, after the end, let it stand for stratification, filter to remove the solid, separate the water phase and petroleum ether phase, and then extract the water phase with petroleum ether for 3 times, combine the organic phase, and successive...

Embodiment 2

[0039] Weigh 0.03 mol of 2,3,6-trimethylphenol into a 250 mL three-necked flask, add 35 mL of petroleum ether and place it on a constant temperature oil bath with temperature controlled at 30°C. When the raw material is dissolved and the temperature is constant, add 4 times the equivalent of 50% sulfuric acid aqueous solution dropwise. The rate of addition should not be too fast. The rate of addition can be controlled by a constant pressure dropping funnel. After the addition is completed, keep warm for 30 minutes. Measure 6 times the equivalent of acetic acid and 30% hydrogen peroxide (acetic acid and hydrogen peroxide are equal equivalents), mix them in a 50mL constant pressure dropping funnel, and add them drop by drop to the above reaction system. React at 30°C for half an hour. After the reaction, the layers were left to stand, and the water phase and petroleum ether phase were separated, and the water phase was extracted with petroleum ether for 3 times, and the organic ...

Embodiment 3

[0041] Weigh 0.03 mol of 2,3,6-trimethylphenol into a 250 mL three-necked flask, add 35 mL of petroleum ether and place it on a constant temperature oil bath with temperature controlled at 30°C. When the raw material is dissolved and the temperature is constant, add 2 times the equivalent of 50% sulfuric acid aqueous solution dropwise. The dropping rate should not be too fast. The dropping rate can be controlled by a constant pressure dropping funnel. After the dropping is completed, keep warm for 30 minutes. Measure 6 times the equivalent of acetic acid and 30% hydrogen peroxide (acetic acid and hydrogen peroxide are equal equivalents), mix them in a 50mL constant pressure dropping funnel, and add them drop by drop to the above reaction system. React at 30°C for half an hour. After the reaction, the layers were left to stand, and the water phase and petroleum ether phase were separated, and the water phase was extracted with petroleum ether for 3 times, and the organic phase ...

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Abstract

The invention discloses a preparation method for 2,3,5-trimethylbenzoquinone, which comprises the following steps of: dropwise adding a mixed solution of 50 percent of sulfuric acid and oxidant-glacial acetic acid at the temperature of 30 DEG C by taking 2,3,6-trimethylphenol as a raw material and petroleum ether as a solvent; standing after reaction is ended to separate out upper layer organic phases; extracting an aqueous phase by using the petroleum ether; merging the organic phases and then washing to be nearly neutral; evaporating to remove the organic phases; cooling; and performing vacuum drying to obtain the 2,3,5-trimethylbenzoquinone. The yield is higher than 86 percent, and the purity is higher than 98.5 percent. The preparation method for the 2,3,5-trimethylbenzoquinone has the advantages that the used raw materials are wide in source, the cost is low, the reaction time is short, the energy consumption is low, the post-processing operation is simple, and the product yield and the purity are higher. Meanwhile, reagents capable of polluting the environment, such as heavy metal and concentrated acid, used by a traditional method are omitted by the preparation method for the 2,3,5-trimethylbenzoquinone; the used solvent can also be repeatedly and mechanically used, therefore, the production cost is reduced, and meanwhile, the environmental pollution is avoided, and the requirement of the green and environmental protection of the modern industrial production is met. In a word, the preparation method has the advantages that the environment cannot be polluted, the requirement on reaction equipment is low and the production cost is low, and is extremely suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a green and simple preparation method of 2,3,5-trimethylbenzoquinone (TMBQ). Background technique [0002] 2,3,5-trimethylbenzoquinone (TMBQ for short) is an important intermediate in the synthesis of vitamin E—2,3,5-trimethylhydroquinone (2,3,5- Trimethylhydroquinone, referred to as TMHQ) precursor compound. Since vitamin E is an important fat-soluble biological antioxidant, it has been widely used in medicine, health products, food, cosmetics, animal husbandry and other fields, and the demand for vitamin E in domestic and foreign markets has increased sharply. However, my country's vitamin E mainly depends on imports, and 2,3,5-trimethylbenzoquinone is the key factor restricting the production of vitamin E. Therefore, the synthesis of its important intermediates has greater application value and higher economic benefits. [0003] The synthesis methods ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/02C07C46/06
Inventor 李荀臧恒昌施雷雷
Owner SHANDONG UNIV
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