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Method for preparing 1, 1'-bi-2-naphthol through inorganic base assisted catalysis

A technology of catalytic preparation and inorganic base, which is applied in the field of chemical industry, can solve problems such as difficulties, and achieve the effects of reducing preparation costs, mild conditions, and accelerating the reaction rate

Active Publication Date: 2021-02-26
中唯炼焦技术国家工程研究中心有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method prepares 1,1'-bi-2-naphthol with high yield, but produces a large amount of waste water, which will bring great difficulties

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 45g of 2-naphthol, 333.5g of 1,2-dichloroethane, 150g of water, 0.31g of solid CuCl and 0.125g of NaOH in a 500ml four-neck flask with heating, stirring, thermometer, and reflux condenser device, and then Heat and control the temperature to 50-80°C, pass in oxygen at a flow rate of 100-500ml / min to oxidize, react for 7 hours, stop the reaction, cool down the reaction mixture solution, and filter to obtain 1,1'-bi-2-naphthol The crude product has a reaction yield of 90.2%, and the filtrate is distilled to recover the solvent for recycling. The crude product was beaten and washed with deionized water, filtered and washed until the solid pH = 6-7, and dried to obtain 40.6 g of the crude product washed with water of 1,1'-bi-2-naphthol. The crude product washed with water was recrystallized to obtain 31.6g of 1,1'-bi-2-naphthol product, the purity of liquid chromatography after drying was 99.2%, and the melting point was 216.4-217.7°C.

Embodiment 2

[0034] Add 45g of 2-naphthol, 333.5g of 1,2-dichloroethane, 150g of water, 0.31g of solid CuCl and 0.175g of KOH in a 500ml four-neck flask with heating, stirring, thermometer, and reflux condenser device, and then Heating to 50°C, and controlling the temperature at 50-80°C, passing in oxygen at a flow rate of 100-500ml / min for oxidation, the reaction was carried out for 7 hours, and the reaction was stopped, and the reaction mixed solution was cooled and filtered to obtain 1,1'-linked- The crude product of 2-naphthol has a reaction yield of 89.8%, and the filtrate is distilled to recover the solvent for recycling. The crude product was beaten and washed with deionized water, filtered, and washed until the pH of the solid was 6-7. After drying, 40.4 g of the crude 1,1’-bi-2-naphthol was obtained. The crude product washed with water was recrystallized to obtain 30.9 g of 1,1'-bi-2-naphthol product. The purity of liquid chromatography after drying was 99.1%, and the melting poin...

Embodiment 3

[0036]Add 45g of 2-naphthol, 333.5g of 1,2-dichloroethane, 150g of water, 0.31g of solid CuCl and Na 2 CO 3 0.331g, then heated to 50°C, and controlled at 50-80°C, and oxidized with oxygen at a flow rate of 100-500ml / min. The reaction was carried out for 7 hours, and the reaction was stopped. The reaction mixture solution was cooled and filtered to obtain 1,1 The crude product of '-linked-2-naphthol has a reaction yield of 88.9%, and the filtrate is distilled to recover the solvent for recycling. The crude product was beaten and washed with deionized water, filtered, and washed until the solid pH = 6-7. After drying, 40.0 g of the crude 1,1'-bi-2-naphthol was obtained. The crude product washed with water was recrystallized to obtain 29g of 1,1'-bi-2-naphthol product. After drying, the liquid chromatographic purity was 99.1%, and the melting point was 216.2-217.8°C.

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Abstract

The invention relates to a method for preparing 1, 1 '-bi-2-naphthol through inorganic base assisted catalysis. CuCl is used as a catalyst, and inorganic base assisted catalysis comprises the following steps: 1) adding 2-naphthol, 1, 2-dichloroethane, water, solid CuCl and inorganic base solid into a four-necked bottle, installing a thermometer on the four-necked bottle, stirring, and refluxing acondenser pipe; 2) starting to stir at normal pressure, heating and controlling the temperature to 50-80 DEG C, introducing oxygen for oxidation, and reacting for 6-12 hours to obtain a reaction mixedsolution after the reaction is finished; 3) cooling and filtering the reaction mixed solution to obtain a 1, 1 '-bi-2-naphthol crude product, and distilling the filtrate to recover the solvent for recycling; 4) pulping and washing the 1, 1 '-bi-2-naphthol crude product with deionized water, filtering and washing until the pH value of the solid is equal to 6-7, and drying to obtain a 1, 1 '-bi-2-naphthol washed crude product; and 5) recrystallizing the 1, 1 '-bi-2-naphthol washed crude product, filtering, and drying to obtain the white 1, 1 '-bi-2-naphthol product.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for preparing 1,1'-bi-2-naphthol through inorganic base-assisted catalysis. Background technique [0002] 1,1'-Dihydroxy-1,1'-binaphthyl (2,2'-Dihydroxy-1,1'-binaphthyl) is white needle-like crystal or powder, molecular formula C 20 h 14 o 2 , with a melting point of 215-218°C. Soluble in ether and lye, slightly soluble in alcohol, hardly soluble in chloroform, insoluble in water, can sublimate when reaching boiling point. 1,1'-bi-2-naphthol is a typical chiral compound, its molecule has strong surface asymmetry, and it is easy to split into high-purity enantiomers, with axis and plane asymmetry, The unique stereochemical properties such as rigidity and flexibility are the most researched C in recent years. 2 Axisymmetric aromatic compounds. [0003] Relevant reports at home and abroad that 2-naphthol prepares 1,1'-bi-2-naphthol through oxidative coupling are mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/16C07C39/14C07C37/70B01J27/10
CPCC07C37/16C07C37/685C07C37/70B01J27/10C07C39/14Y02P20/584
Inventor 李强王海波曲圣涛李鸿霖曲业芳
Owner 中唯炼焦技术国家工程研究中心有限责任公司