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A kind of method for preparing 1,1'-bi-2-naphthol by inorganic base-assisted catalysis

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

Active Publication Date: 2022-07-05
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] 45g of 2-naphthol, 333.5g of 1,2-dichloroethane, 150g of water, 0.31g of solid CuCl and 0.125g of NaOH were added to a 500ml four-necked flask equipped with heating, stirring, thermometer and reflux condenser, and then Heating and controlling the temperature to 50~80℃, feeding oxygen with a flow rate of 100~500ml / min for oxidation, the reaction was carried out for 7 hours, the reaction was stopped, and the reaction mixture solution was cooled and filtered 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 pulped and washed with deionized water, filtered and washed to a solid pH of 6 to 7, and dried to obtain 40.6 g of 1,1'-bi-2-naphthol washed crude product. The washed crude product was recrystallized to obtain 31.6 g of 1,1'-bi-2-naphthol product, the liquid chromatographic purity after drying was 99.2%, and the melting point was 216.4-217.7°C.

Embodiment 2

[0034] 45g of 2-naphthol, 333.5g of 1,2-dichloroethane, 150g of water, 0.31g of solid CuCl and 0.175g of KOH were added to a 500ml four-necked flask equipped with heating, stirring, thermometer and reflux condenser, and then Heating to 50°C, and controlling the temperature to 50-80°C, feeding oxygen with a flow rate of 100-500ml / min for oxidation, the reaction was carried out for 7 hours, the reaction was stopped, and the reaction mixture solution was cooled and filtered to obtain 1,1'-linked- The 2-naphthol crude product has a reaction yield of 89.8%, and the filtrate is distilled to recover the solvent for recycling. The crude product was pulped and washed with deionized water, filtered, and washed to a solid pH of 6 to 7. After drying, 40.4 g of 1,1'-bi-2-naphthol washed crude product was obtained. The washed crude product was recrystallized to obtain 30.9 g of 1,1'-bi-2-naphthol product. After drying, the liquid chromatography purity was 99.1%, and the melting point was 21...

Embodiment 3

[0036]In a 500ml four-necked flask equipped with heating, stirring, thermometer and reflux condenser, add 2-naphthol 45g, 1,2-dichloroethane 333.5g, 150g water, solid CuCl 0.31g and Na 2 CO 3 0.331g, then heated to 50 ℃, and the temperature was controlled at 50-80 ℃, and oxygen with a flow rate of 100-500ml / min was introduced for oxidation, the reaction was carried out for 7 hours, the reaction was stopped, and the reaction mixture solution was cooled and filtered to obtain 1,1 '-bi-2-naphthol crude product, the reaction yield is 88.9%, and the filtrate is distilled to recover the solvent for recycling. The crude product was pulped and washed with deionized water, filtered, and washed to a solid pH of 6 to 7. After drying, 40.0 g of 1,1'-bi-2-naphthol washed crude product was obtained. The washed crude product was recrystallized to obtain 29 g 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 is used as assisted catalysis. 1) 2-naphthol, 1,2-dichloroethane, Water, solid CuCl and inorganic alkali solids are added to a four-necked flask, and a thermometer, stirring and reflux condenser are installed on the four-necked flask; 2) Start stirring at normal pressure, heat and control the temperature to 50-80°C, and introduce oxygen Oxidation was carried out, the reaction was carried out for 6-12 hours, and the reaction was completed to obtain a reaction mixture solution; 3) the reaction mixture solution was cooled and filtered to obtain a crude product of 1,1'-bi-2-naphthol, and the filtrate was distilled to recover the solvent for recycling; 4) 1 , 1'-linked-2-naphthol crude product is washed with deionized water by beating, filtration and washing to solid pH=6~7, after drying, 1,1'-linked-2-naphthol crude product is obtained by washing; 5) 1, The crude 1'-linked-2-naphthol was washed with water for recrystallization, filtered and dried to obtain a white 1,1'-linked-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'-Bi-2-naphthol (2,2'-Dihydroxy-1,1'-binaphthyl) is white needle crystal or powder, molecular formula C 20 H 14 O 2 , the melting point is 215-218 ℃. Soluble in ether and lye, slightly soluble in alcohol, insoluble in chloroform, insoluble in water, and sublimable when it reaches the boiling point. 1,1'-Bi-2-naphthol is a typical chiral compound, its molecule has strong surface asymmetry, it is easy to be split into high-purity enantiomers, and has axial and surface asymmetry, The unique stereochemical properties such as rigidity and flexibility are the most studied C in recent years. 2 Axisymmetric aromatic compounds. [0003] Relevant reports at home and abroad for the preparation of 1,1'-bi-2-naphthol by oxidative coupling from 2-naphthol The main techniq...

Claims

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Application Information

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Patent Type & Authority Patents(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