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Method for preparing trimethylbenzoquinone with resin-supported catalyst

A technology of trimethylbenzoquinone and trimethylphenol, applied in the field of producing trimethylbenzoquinone, can solve the problems of long reaction time, large energy consumption, unfavorable industrialization, etc., and achieve good mechanical strength, good thermal stability, The effect that is not easy to lose

Active Publication Date: 2010-03-10
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When recycling and reusing the catalyst, a large amount of energy consumption is required, which is quite unfavorable from an economic point of view
In addition, due to the low catalyst activity and long reaction time, large-scale reactors are required
[0005] In US4828762A, the above method has been improved, water and 5-10 carbon aliphatic alcohols are used as solvents to solve the problem of separating TMBQ and catalyzer, but the conversion rate of reaction is still low, the recovery and use of catalyzer The process is also very complicated, and the corrosion of the catalyst to the reaction vessel is not improved at the same time, the reaction time is long and the yield is low
[0006] Also in Japanese Patent Laid-Open Nos. 225137 / 1984, 81135 / 1985, 255745 / 1985, 255746 / 1985, and 17532 / 1986, copper and alkali metal complexes (e.g., LiCuCl 3 , KCuCl 3 , or NH 4 CuCl 3 ) to catalyze this oxidation reaction, although the conversion rate and yield have been improved, but the operation process also has disadvantages. For example, the prepared catalyst, that is, copper and alkali metal halide complex, is used as a When using a solvent, it is difficult to separate the catalyst from the solvent, which is not conducive to industrialization

Method used

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  • Method for preparing trimethylbenzoquinone with resin-supported catalyst
  • Method for preparing trimethylbenzoquinone with resin-supported catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 2.0g of macroporous anion exchange resin (D301) supported catalyst ([Cu 2+ ] / [N] molar ratio = 0.5), 20.0 g n-butanol and 1.36 g trimethylphenol (0.01 mol), add a certain oxygen pressure (1 bar), and stir vigorously (1000 rpm) at the same time. The reaction was maintained at 100°C for 8 hours. After the reaction, the molar yield of trimethylbenzoquinone was determined to be 94.5% by liquid chromatography.

Embodiment 2

[0032] After the completion of Example 1, the stirring was stopped, and the solvent was directly poured out by the decant method. The residual solids were washed three times with the solvent to become the recovered catalyst.

[0033] Add the recovered catalyst, 20.0 g n-butanol and 1.36 g TMP (0.01 mol) into a 100 ml four-neck flask, add a certain oxygen pressure (1 bar), and stir vigorously (1000 rpm) at the same time. The temperature was maintained at 60° C. and the reaction was conducted for 6 hours. After the reaction, the molar yield of trimethyl benzoquinone was 92.4% as determined by liquid chromatography.

Embodiment 3

[0035] In a 100ml four-necked flask was added 2.0g of gel anion exchange resin (201) supported catalyst ([Cu 2+ ] / [N] molar ratio = 0.25), 20.0 g ethylene glycol butyl ether and 1.36 g TMP (0.01 mol), add a certain oxygen pressure (1 bar), and stir vigorously (1000 rpm) at the same time. Maintain the temperature at 80° C. and react for 21 hours. After the completion of the reaction, the molar yield of trimethyl benzoquinone was calibrated by liquid chromatography to be 64.5%.

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Abstract

The invention relates to a new preparation method of trimethylbenzoquinone. The method use one or two of n-butyl alcohol, n-pentanol, isopentyl alcohol, hexanol, 2-hexanol, diethylene glycolmonobutylether, diethylene glycolmonobutylether, dimethoxyethane, diethylene glycoldimethylether and acetylacetonate as solvent and gelatinous resin or macroporous resin-supported transition metal complex as catalyst. Trimethylbenzoquinone is prepared by oxidizing trimethylphenol at 0-150 DEG C adopting molecular oxygen, oxygen-enriched gas or air as oxidant wherein the molar ratio of trimethylphenol to catalyst is 100:1-1:1, the weight ratio of trimethylphenol to alcohol is 50:1-1:50, and the resin-supported transition metal catalyst is D201, D301, D002, 201, 301 or 002 resin. The best advantage of the catalyst is that the catalyst can be used in the fixed bed and trickle bed and can be used for continuous operation.

Description

Technical field [0001] The invention relates to a method for preparing trimethylbenzoquinone. The method uses molecular oxygen or oxygen-enriched gas to oxidize trimethyl phenol under the conditions of alcohol and other solvents with a resin-supported transition metal complex as a catalyst to generate trimethyl benzoquinone. At the same time, the catalyst involved in the present invention can be recycled and reused, and a method for reusing the catalyst after the reaction is reported. Background technique [0002] 2,3,5-Trimethylbenzoquinone (TMBQ) is an important intermediate in the synthesis of vitamin E, mainly used for the synthesis of the main ring of vitamin E. Due to the importance of trimethylbenzoquinone in the chemical and pharmaceutical fields, the oxidation of 2,3,6-trimethylphenol (TMP) to 2,3,5-trimethylbenzoquinone has long been a chemical industry A hot spot in the field of research. For the oxidation of trimethylphenol, quite a lot of patents and documents hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/04C07C46/08B01J31/22
CPCY02P20/50
Inventor 李浩然陈志荣姚加阮月垒毛建拥管俊胡柏剡
Owner ZHEJIANG UNIV
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