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Method for synthesizing hydroquinone by phenol hydroxylation

A technology of hydroquinone and phenol hydroxyl group, which is applied in the field of phenol hydroxylation to synthesize hydroquinone, can solve the problems of high content of by-products and tar, low selectivity of phenol-hydroquinone, etc., and achieve high content of by-products and tar Low, good utilization rate, and the effect of increasing added value

Pending Publication Date: 2020-12-25
江西兄弟医药有限公司
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method currently has the problems of low phenol conversion rate and hydroquinone selectivity, and high content of by-products and tar.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 7.0g of TS-1 catalyst, 65.0g of phenol, and 40.0g of methanol into a 250mL four-neck flask, circulate cooling and reflux, magnetically stir at 300r / min, heat up to boiling, slowly add 10.0g of 50% hydrogen peroxide solution dropwise, dropwise for 2h, Stop the test after 2 hours of heat preservation reaction, and take samples for chromatographic detection and analysis. The conversion rate of phenol was 21.3%, the selectivity of hydroquinone was 82.7%, the para-ortho ratio was 2.35, the effective utilization rate of hydrogen peroxide was 66.7%, and the selectivity of tar was 21.5%.

Embodiment 2

[0033] Add 7.0g of TS-1 catalyst, 65.0g of phenol, and 50.0g of methanol into a 250mL four-neck flask, circulate cooling and reflux, stir magnetically at 300r / min, heat up to boiling, slowly add 10.0g of 50% hydrogen peroxide solution dropwise, dropwise for 2h, Stop the test after 2 hours of heat preservation reaction, and take samples for chromatographic detection and analysis. The phenol conversion rate was 22.8%, the diphenol selectivity was 83.6%, the ortho ratio was 2.47, the hydrogen peroxide effective utilization rate was 67.4%, and the tar selectivity was 20.6%.

Embodiment 3

[0035]Add 7.0g of TS-1 catalyst, 65.0g of phenol, 50.0g of methanol, and 0.8g of sulfuric acid into a 250mL four-neck flask, circulate cooling and reflux, stir magnetically at 300r / min, heat up to boiling, and slowly add 10.0g of 50% hydrogen peroxide solution dropwise, Add dropwise for 2 hours, keep warm for 2 hours, stop the test, and sample for chromatographic analysis. The phenol conversion rate was 25.5%, the diphenol selectivity was 89.1%, the ortho ratio was 2.50, the hydrogen peroxide effective utilization rate was 83.9%, and the tar selectivity was 16.5%.

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Abstract

The invention relates to a method for synthesizing hydroquinone by phenol hydroxylation. According to the method, hydroxylation reaction is carried out on phenol and hydrogen peroxide in a system of asolvent and an acidic reagent under the action of a TS-1 catalyst to synthesize hydroquinone. The method specifically comprises the steps of (1) adding a TS-1 catalyst, phenol, a solvent and an acidic reagent into a four-neck flask, carrying out circulating cooling reflux, continuously stirring, and heating; and (2) dropwise adding hydrogen peroxide with the concentration of 30% or 50%, and carrying out heat preservation reaction after dropwise adding to obtain hydroquinone. According to the method, the proportion of hydroquinone in the product generated by phenol hydroxylation can be remarkably increased, and the content of generated by-products and tar is reduced.

Description

technical field [0001] The invention relates to a method for synthesizing hydroquinone by phenol hydroxylation. Background technique [0002] Hydroquinone is an important fine chemical intermediate, which is widely used in dyestuff, medicine, fragrance, chemical industry and other industries. Hydroquinone production methods include aniline oxidation method, p-diisopropylbenzene oxidation method, o-chlorophenol hydrolysis method, epoxide dehydrogenation method, etc. Due to the long process of these methods, serious equipment corrosion, many wastes and high cost, the domestic It has been phased out and replaced by phenol hydroxylation. [0003] The phenol hydroxylation method uses phenol and hydrogen peroxide as raw materials, generates catechol and hydroquinone under the action of a catalyst, and produces a small amount of tar as a by-product. At present, the technological processes that have been industrialized include: the French Rhone-Poulenc method, the Japanese Ube Ind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/08C07C37/58
CPCC07C37/58C07C39/08
Inventor 张秋华钟友坤周中平
Owner 江西兄弟医药有限公司
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