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Method for synthesizing diphenoquinone derivative under catalysis of supported semiconductor

A diphenyldiquinone and semiconductor technology, which is applied in the field of preparation of diphenyldiquinone derivatives, can solve time-consuming and labor-intensive problems, and achieve the effects of low energy consumption, high conversion rate, and high yield

Inactive Publication Date: 2015-07-22
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Or use oxygen as an oxidant, this method needs to continuously blow in oxygen, which is time-consuming and labor-intensive

Method used

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  • Method for synthesizing diphenoquinone derivative under catalysis of supported semiconductor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Using 1.0% Au / CeO 2 Catalyzed Preparation of 3,3',5,5'-Tetramethyl-4,4'-Biphendioquinone

[0017] Step (1) weighs 2.00gCeO in a beaker 2 Nano-powder as carrier, add 20.0mL of lysine solution with a concentration of 0.53mol / L as a stabilizer, stir rapidly, add 10.0mL of HAuCl with a concentration of 0.01mol / L 4 The solution was used as the loaded metal source, stirred vigorously for 30 minutes, and 7 mL of NaBH with a concentration of 0.035 mol / L was added dropwise at a rate of 1 drop / s. 4 The solution is restored. After stirring for 5 minutes, let it stand for 24 hours. The mixed solution was filtered with a Buchner funnel, and the filter cake was dried in a vacuum oven at 60° C. for 12 hours. Grinding to obtain a semiconductor-supported gold catalyst, that is, Au / CeO with a loading of 1.0% 2 catalyst. Step (2) Add 1.22g of 10mmol 2,6-dimethylphenol into the reaction vessel, then add 5mL of ethanol solvent until completely dissolved, add 2mL of 30% hydro...

Embodiment 2

[0018] Example 2: Using 1.0% Au / ZrO 2 Catalytic Preparation of 3,3',5,5'-tetra-tert-butyl-4,4'-biphenyldiquinone

[0019] Step (1) weighs 2.00gZrO in a beaker 2 Nano powder as carrier, add 20.0mL of lysine solution with a concentration of 0.53mol / L as a stabilizer, stir rapidly, add 10.0mL of HAuCl with a concentration of 0.01mol / L 4 The solution was used as the loaded metal source, stirred vigorously for 30 minutes, and 7 mL of NaBH with a concentration of 0.035 mol / L was added dropwise at a rate of 1 drop / s. 4 The solution is restored. After stirring for 5 minutes, let it stand for 24 hours. The mixed solution was filtered with a Buchner funnel, and the filter cake was dried in a vacuum oven at 60° C. for 12 hours. Grinding to obtain a semiconductor-supported gold catalyst, that is, Au / ZrO with a loading of 1.0% 2 catalyst. Step (2) Add 1.22g of 10mmol 2,6-di-tert-butylphenol into the reaction vessel, then add 5mL of ethanol solvent until completely dissolved, add 2mL o...

Embodiment 3

[0020] Example 3: Using 1.0% Au / H 2 Ti 3 o 7 Catalyzed Preparation of 3,3',5,5'-Tetramethyl-4,4'-Biphendioquinone

[0021] Step (1) weigh 2.00gH in a beaker 2 Ti 3 o 7 Nanotube powder as carrier, add 20.0mL of lysine solution with a concentration of 0.53mol / L as a stabilizer, stir rapidly, add 10.0mL of HAuCl with a concentration of 0.01mol / L 4 The solution was used as the loaded metal source, stirred vigorously for 30 minutes, and 7 mL of NaBH with a concentration of 0.035 mol / L was added dropwise at a rate of 1 drop / s. 4 The solution is restored. After stirring for 5 minutes, let it stand for 24 hours. The mixed solution was filtered with a Buchner funnel, and the filter cake was dried in a vacuum oven at 60° C. for 12 hours. Grinding to obtain a semiconductor-supported gold catalyst, that is, Au / H with a loading of 1.0% 2 Ti 3 o 7 catalyst. Step (2) Add 1.22g of 10mmol 2,6-dimethylphenol into the reaction vessel, then add 5mL of ethanol solvent until completely d...

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Abstract

The invention discloses a method for preparing diphenoquinone and a derivative thereof in an acetonitrile solution under the catalysis of a semiconductor supported precious metal material. The diphenoquinone derivative is prepared through efficient catalysis of alkylphenol oxidation coupling at normal temperature for 4-6h with the semiconductor supported precious metal material as a catalyst, alkylphenol as a reaction substrate and hydrogen peroxide as an oxidant. The above reaction can be represented by general formula (1). In the general formula (1), R1 and R2 are C1-12 straight chain or branched chain alkyl groups, and can be same to or different from each other. The heterogeneous catalyst is used in the reaction, is easy to separate, and can be reused above 10 times. The method also has the advantages of simple operation of the synthesis reaction, easily available raw material, high reaction selectivity, high conversion rate, high yield, small pollution, safety, low price, environmental protection and low energy consumption.

Description

technical field [0001] The invention belongs to the technical field of preparation of diphenyldiquinone derivatives, and in particular relates to a method for preparing diphenyldiquinone derivatives by catalyzing alkylphenols in an acetonitrile solution. Background technique [0002] Tetraalkylbiphenyldiquinone is an active intermediate with great application value in the fine chemical industry. It can be used to make organic photoconductors and electron transport materials, so it is an important intermediate for liquid crystal materials. After different modifications, it can be used to synthesize a variety of hydroxyaryl ethers; it can also use polymer technology to generate a variety of block, telechelic, graft, star and comb macromolecular polymers, or to prepare PPO (polyphenylene oxide) / Epoxy (epoxy resin) laminate material for high-frequency printed circuit boards. It has excellent heat resistance and good mechanical properties, so it can be used as a flame retarda...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/08C07C46/06
CPCC07C46/06C07C50/08
Inventor 郭成郝琳蔡达李子平吕梦远王建强
Owner NANJING TECH UNIV