A kind of synthetic method of tert-butyl hydroquinone

A technology of tert-butyl hydroquinone and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of uninspected catalyst recycling activity, high process cost, high environmental protection pressure, etc. problems, to achieve the effect of green and clean production process, low process cost and high product purity

Active Publication Date: 2022-04-12
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN102173981A discloses a method for synthesizing tert-butylhydroquinone with macroporous sulfonic acid resin as catalyst and xylene / ketone as mixed solvent, but the recycling activity of the catalyst has not been investigated
The process of preparing tertiary butyl hydroquinone with liquid acid and other catalytic systems will be gradually eliminated due to problems such as high process cost, poor product quality, and high environmental protection pressure.

Method used

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  • A kind of synthetic method of tert-butyl hydroquinone
  • A kind of synthetic method of tert-butyl hydroquinone
  • A kind of synthetic method of tert-butyl hydroquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Weigh 3.0g of hydroquinone, 0.6g of catalyst sulfamic acid, 12.0g of xylene, and 4.0g of tert-butanol in a heatable pressure-resistant reactor, heat the oil bath to 150°C and react for 4 hours;

[0032] (2) add ethanol to dissolve crude product after reaction finishes cooling, leave standstill and separate catalyst with Buchner funnel suction filtration, gained filtrate carries out gas chromatography analysis and detection with internal standard method, and wherein the transformation rate of raw material hydroquinone is 86.4%, The yield of the target product tert-butylhydroquinone was 57.8%, the yield of the side-reactant 2,5-di-tert-butylphenol was 17.2%, and the rest were a small amount of ethers and quinones. After the filtrate is desolvated, the product tert-butylhydroquinone can be obtained by washing or recrystallization.

Embodiment 2

[0034] (1) Weigh 3.0g hydroquinone, 0.6g catalyst sulfamic acid, 12.0g toluene, 3.0g tert-butanol, 1.0g 1,4-dioxane in a heatable pressure reactor, oil bath After heating to 120°C, react for 12 hours;

[0035] (2) Add ethanol to dissolve crude product after reaction finishes cooling, leave standstill and separate catalyst with Buchner funnel suction filtration, gained filtrate carries out gas chromatography analysis and detection with internal standard method, and wherein the transformation rate of raw material hydroquinone is 86.7%, The yield of the target product tert-butylhydroquinone was 55.2%, the yield of the by-product 2,5-di-tert-butylphenol was 4.6%, and the rest were a small amount of ethers and quinones. After the filtrate is precipitated, the TBHQ product can be obtained by washing or recrystallization.

Embodiment 3

[0037] (1) Weigh 3.0g hydroquinone, 0.6g catalyst sulfamic acid, 12.0g toluene, 3.0g tert-butanol, 1.0g 1,4-dioxane in a heatable pressure reactor, oil bath After heating to 135°C, react for 4 hours;

[0038] (2) Add ethanol to dissolve crude product after reaction finishes cooling, leave standstill and separate catalyst with Buchner funnel suction filtration, gained filtrate carries out gas chromatography analysis and detection with internal standard method, wherein the conversion rate of raw material hydroquinone is 73.9%, The yield of target product tert-butylhydroquinone was 48.1%, the yield of side-reactant 2,5-di-tert-butylphenol was 9.2%, and the rest were a small amount of ethers and quinones. After the filtrate is precipitated, the TBHQ product can be obtained by washing or recrystallization.

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Abstract

The invention discloses a synthesis method of tert-butyl hydroquinone, which relates to tert-butyl hydroquinone. A method for synthesizing tert-butylhydroquinone with simple process and low cost is provided. 1) Catalyst sulfamic acid, solvent toluene or xylene, tert-butanol, hydroquinone, 1,4-dioxane are sequentially added to a heatable pressure reactor to react, and the temperature of the reaction is 120 ~150 ℃, the reaction time is 4~12h; 2) After the reaction, add ethanol and filter to remove the catalyst sulfamic acid, and remove the solvent to obtain the crude product; 3) Purify the crude product obtained in step 2) to obtain the product characteristic Butylhydroquinone. It overcomes the shortcomings of the existing synthesis process that requires the use of a highly corrosive catalyst, high process cost, serious environmental pollution, and low reaction selectivity.

Description

technical field [0001] The invention relates to a method for synthesizing tert-butyl hydroquinone. Background technique [0002] Tert-Butylhydroquinone (tert-Butylhydroquinone), also known as tert-butylhydroquinone or tert-butylhydroquinone, referred to as TBHQ, is an antioxidant, white powder crystal, with a special smell, melting point 126.5 ~ 128.5 ℃ , boiling point 300°C. It has good antioxidant effect and can enhance the stability of oil during the shelf life. Tertiary butyl hydroquinone is a safe and efficient edible oil antioxidant allowed by the state, suitable for vegetable oil, lard, etc. Its antioxidant performance is superior, and it has stronger antioxidant capacity than ethoxyquin, BHA, propyl gallate and vitamin C; it can also effectively inhibit the growth of microorganisms such as fungi. Tertiary butyl hydroquinone will not combine with metal ions in the product to develop color, and it can also be used in combination with BHT and BHA to greatly enhance t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/16C07C39/08
CPCC07C37/16C07C39/08
Inventor 吐松洪伟图叶李艺高玉兴陈学云尹应武
Owner XIAMEN UNIV
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