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Preparation method of 2-hydroxy-1, 4-naphthoquinone

A hydroxyl and naphthoquinone technology, applied in the field of organic chemical synthesis, can solve the problems of complex preparation process, difficult purification, low yield, etc., and achieve the effects of simple synthesis process, no environmental pollution, and low reaction cost

Inactive Publication Date: 2010-06-30
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Yan Yan et al. reported in 2004 to prepare HNQ by oxidizing naphthol with oxygen, with a yield of 62%, but they all used organic solvent methanol, a large amount of volatile organic reagent methanol as a solvent, and there is a safety hazard of explosion in a pure oxygen environment
[0005] There are many reports on the chemical synthesis of 2-hydroxyl 1-4 naphthoquinone (HNQ), but its preparation process is very complicated, and the yield is low, it is very difficult to purify, and there are fewer reports with naphthol as the reactant

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Step 1: Dissolve 0.050g of cobalt phthalocyanine (chemically pure) and 0.432g of naphthol (chemically pure) in 4.32g of [HMIM]PF 6 In the ionic liquid, put 0.60g NaOH (chemically pure) into the reaction kettle, stir and mix evenly, and then fill with 0.96g of oxygen, and the oxygen filling pressure is 0.5Mpa.

[0021] Step 2: React the reactor at a constant temperature of 30°C for 2 hours. After the reaction, let it stand and cool to room temperature, then pour out the supernatant, add 1.0mol / L HCl dropwise until the pH of the solution is 3.0, and the precipitated product is suction filtered , 2-hydroxyl-1,4-naphthoquinone (HNQ) was obtained by vacuum drying, the yield was 58%, the drying pressure was 0.05Mpa, and the drying temperature was 40°C.

[0022] Step 3: recycle the cobalt phthalocyanine catalyst that has been precipitated after standing, and the recovered catalyst is tested for activity, and no obvious decrease in catalytic activity is found.

Embodiment 2

[0024] Step 1: Dissolve 0.036g of copper phthalocyanine (chemically pure) and 0.144g of naphthol (chemically pure) in 7.2g of [OMIM]BF 4 In the ionic liquid, put 0.4g KOH (chemically pure) into the reaction kettle, stir and mix evenly, and then fill with 1.6g of oxygen, and the oxygen filling pressure is 1.0Mpa.

[0025] Step 2: React the reactor at a constant temperature of 70°C for 8 hours. After the reaction, let it stand and cool to room temperature, then pour out the supernatant, and add 2.0mol / L of H 2 SO 4 When the pH of the solution was 2.5, the precipitated product was suction-filtered and vacuum-dried to obtain 2-hydroxy-1,4-naphthoquinone (HNQ) with a yield of 72%. The drying pressure was 0.06Mpa and the drying temperature was 50°C.

[0026] Step 3: Recycle the copper phthalocyanine catalyst that has been left to settle and recycle it. The activity of the recovered catalyst is tested, and no obvious reduction in catalytic activity is found.

Embodiment 3

[0028] Step 1: Dissolve 0.150 g of cobalt phthalocyanine (chemically pure) and 0.350 g of naphthol (chemically pure) in 6.00 g of [OMIM]Tf 2 In the N ionic liquid, put 4.0g KOH (chemically pure) into the reaction kettle, stir and mix evenly, then fill with 2.4g oxygen, and the pressure of oxygen filling is 1.5Mpa.

[0029] The second step: React the reactor at a constant temperature of 90°C for 6 hours. After the reaction, let it stand and cool to room temperature, then pour out the supernatant, add 3.0mol / L HCl dropwise until the solution pH=3.0, and the precipitated product is suction filtered , 2-hydroxyl-1,4-naphthoquinone (HNQ) was obtained by vacuum drying, the yield was 70%, the drying pressure was 0.07Mpa, and the drying temperature was 40°C.

[0030] Step 3: recycle the cobalt phthalocyanine catalyst that has been precipitated after standing, and the recovered catalyst is tested for activity, and no obvious decrease in catalytic activity is found.

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PUM

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Abstract

The invention discloses a preparation method of 2-hydroxy-1, 4-naphthoquinone, which is characterized by mixing naphthol and hydroxide, taking metal phthalocyanine dissolved by hydrophobic ionic liquid as catalyst to have oxygenic reaction, and leaching and drying the reactant to prepare 2-hydroxy-1, 4-naphthoquinone. Compared with the prior art, the invention has simple synthesis process, low cost and easy taking of raw material, low reaction cost and high yield, and the catalyst can be recycled to used and can not pollute environment.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of 2-hydroxyl-1,4-naphthoquinone. Background technique [0002] 2-Hydroxy 1-4 naphthoquinone (HNQ) can prevent the formation of HIV-1 type protease, prevent and treat AIDS (AIDS), and has the drug effect of anti-tumor and cancer treatment. In addition, the unique reversible redox reaction of quinone phenols in HNQ can be used as an electron conversion intermediate in biofuel cells, and has been widely used in various biochemical fuel cell research. [0003] Yan Yan et al. from Jilin University reported in the internationally renowned journal "Journal of Molecular Catalysis A: Chemical" 157 volume 65-72 in 2000 that iron porphyrin was used as a catalyst to oxidize naphthol with hydrogen peroxide to prepare HNQ with a yield of 57%. [0004] Yan Yan et al. reported in 2004 to prepare HNQ by oxidizing naphthol with oxygen, with a yield of 62%,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/32C07C46/08B01J31/22
CPCY02P20/584
Inventor 单永奎单冲冲赵新华朱海燕张新华王平
Owner EAST CHINA NORMAL UNIV
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