Method for synthesizing 2, 3, 5-trimethylbenzoquinone

A technology of trimethylbenzoquinone and trimethylphenol, applied in the field of vitamin E synthesis, can solve problems such as difficult direct application, uneconomical, difficult to dissolve, etc., achieve simple process operation, improve reaction effect, and prevent rapid decomposition Effect

Active Publication Date: 2022-02-01
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cost of ionic liquid is high, the viscosity of the system is high, and the ionic liquid is mixed with the distillation residue after distillation, so it is difficult to apply directly
[0009] CN102633614B discloses that copper chloride, ferric chloride (or cobalt chloride) and triethylamine hydrochloride are mixed to prepare a composite catalyst, and hydrogen peroxide is used to oxidize 2,3,6-trimethylphenol to synthesize 2,3,5-trimethylphenol quinone, but the molar ratio of hydrogen peroxide to 2,3,6-trimethylphenol is as high as 30 or more, resulting in high raw material cost of hydrogen peroxide and uneconomical
[0010] CN102108047B discloses that under the catalysis of copper halide and lithium halide, a phase transfer catalyst is added, water is used as the reaction medium, and pure oxygen or oxygen-enriched gas is used for oxidation reaction, but the price of lithium halide is relatively expensive, which makes the production cost rise. At the same time, the reaction raw materials 2, 3,6-Trimethylphenol is difficult to dissolve, the system is viscous, and the mass and heat transfer effect is not good
[0011] The conversion rate of 2,3,6-trimethylphenol in the above methods cannot reach 100%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 12g of n-butanol to a 100mL four-necked flask with an electric stirrer, a thermometer and a reflux condenser placed in a constant temperature water bath, start stirring, add 5.45g of 2,3,6-trimethylphenol (0.04 mol), after dissolving completely, add 0.545g of polyvinylpyrrolidone and 0.032mol of copper chloride in turn, heat up to 65°C, slowly add 0.16mol of hydrogen peroxide with a mass percentage concentration of 30% with a constant pressure funnel, and the dropping time is controlled at 15min . After the dropwise addition, the reaction was continued at 65°C for 4h. Then stand still, cool and separate, take the organic phase, wash the organic phase with deionized water, and detect with the internal standard method of gas chromatography (internal standard: ethyl benzoate), the result is 2,3,6-trimethylphenol raw material The conversion rate was 100%, and the yield of 2,3,5-trimethylbenzoquinone was 74.0%.

Embodiment 2

[0026] Add 16g n-hexanol to a 100ml four-neck flask with an electric stirrer, thermometer and reflux condenser placed in a constant temperature water bath, start stirring, add 2,3,6-trimethylphenol 5.45g (0.04 mol), after dissolving completely, add polyvinylpyrrolidone 0.545g, cupric chloride 0.032mol and ferric chloride 0.032mol successively, heat up to 65 ℃, slowly add the hydrogen peroxide 0.16mol of 30% mass percentage concentration with constant pressure funnel, The dropping time was controlled at 15min. After the dropwise addition, the reaction was continued at 65°C for 4h. Then stand still, cool and separate, take the organic phase, wash the organic phase with deionized water, and detect with the internal standard method of gas chromatography (internal standard: ethyl benzoate), the result is 2,3,6-trimethylphenol raw material The conversion rate is 100%, and the yield of 2,3,5-trimethylbenzoquinone is 91.3%.

Embodiment 3

[0028] Reaction apparatus and operation method are with embodiment 2. The difference is that the amount of polyvinylpyrrolidone added is 0.275g, and as a result, the conversion rate of 2,3,6-trimethylphenol raw material is 100%, and the yield of 2,3,5-trimethylbenzoquinone is 88.5%.

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PUM

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Abstract

The invention discloses a method for synthesizing 2, 3, 5-trimethylbenzoquinone, and relates to the technical field of vitamin E synthesis. The method comprises the following steps: dissolving 2, 3, 6-trimethylphenol in an organic solvent, adding copper chloride, ferric chloride and polyvinylpyrrolidone to form a composite catalyst, heating to a reaction temperature, and dropwise adding a hydrogen peroxide aqueous solution to carry out an oxidation reaction so as to synthesize 2, 3, 5-trimethylbenzoquinone. The polyvinylpyrrolidone is added into a reaction system, has relatively strong complexing ability, and can be used for complexing metal ions, playing a role in promoting catalysis and improving the reaction effect, so that the conversion rate of 2, 3, 6-trimethylphenol reaches 100%, and the problem that 2, 3, 6-trimethylphenol which is not completely reacted is removed from a reaction product 2, 3, 5-trimethylbenzoquinone is avoided; meanwhile, polyvinylpyrrolidone can be complexed with hydrogen peroxide, the effect of stabilizing the hydrogen peroxide is achieved, the hydrogen peroxide is prevented from being decomposed too fast under heating, and therefore the consumption of the hydrogen peroxide is reduced. The process is simple and safe to operate and low in cost.

Description

technical field [0001] The invention relates to the technical field of vitamin E synthesis, in particular to a method for synthesizing 2,3,5-trimethylbenzoquinone by one-step oxidation of 2,3,6-trimethylphenol through hydrogen peroxide. Background technique [0002] 2,3,5-Trimethylbenzoquinone is an important intermediate in the production of synthetic vitamin E. Synthetic vitamin E is prepared by condensation reaction of 2,3,5-trimethylhydroquinone and isophytic alcohol, while 2,3,5-trimethylhydroquinone is obtained from 2,3,5-trimethylhydroquinone Benzoquinone is obtained by hydrogenation reduction. At present, the synthesis of 2,3,5-trimethylbenzoquinone mainly adopts the process route of oxidation reaction using 2,3,6-trimethylphenol as raw material. [0003] The early synthesis method of 2,3,5-trimethylbenzoquinone was to sulfonate 2,3,6-trimethylphenol into 4-sulfo-2,3,6-trimethylphenol through sulfuric acid, and then use MnO 2 Oxidation to 2,3,5-trimethylbenzoquino...

Claims

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Application Information

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IPC IPC(8): C07C46/06C07C50/02B01J31/30B01J31/06
CPCC07C46/06B01J31/30B01J31/06C07C2601/16B01J2231/70C07C50/02Y02P20/584
Inventor 黎四芳叶家婧
Owner XIAMEN UNIV
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