Green synthesis method of 9, 9-bis (4-hydroxy) fluorene

A synthesis method and phenol technology, which is applied in the field of synthesis of bisphenol fluorene, can solve the problems of difficult industrialization, non-environmental protection, and high phenol content, and achieve the effects of reducing phenol content, reducing environmental pressure, and high selectivity

Active Publication Date: 2015-06-10
DALIAN TRICO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Either the phenol is recovered by distillation after neutralization, and the efficiency is extremely low; or it is directly discarded, and the amount of phenol in the wastewater is extremely high, which does not meet the requirements of environmental protection and is difficult to industrialize

Method used

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  • Green synthesis method of 9, 9-bis (4-hydroxy) fluorene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 10 grams of 9-fluorenone (0.055mol), 21 grams of phenol (0.22mol), and 16 grams of toluene to a 100ml flask equipped with a mechanical stirrer, a thermometer, and a condenser. Stir and place it in a water bath, then add 1.5 grams of Concentrated sulfuric acid, control the temperature at about 20 degrees, slowly add 0.37 g of 3-mercaptopropionic acid (0.0035 mol), after the addition, react at 20 ° C for 2 hours, slowly raise the temperature to 30 ° C and continue the reaction for 1 hour. After the system completely turned into a pure white slurry, liquid phase analysis was carried out, and the reaction of 9-fluorenone was complete, with a liquid phase content of 95% (excluding phenol). After adding 30 grams of toluene, cool down to room temperature and filter, and the filter cake is washed with a small amount of toluene. The filter cake was beaten in 5% sodium hydroxide solution with a mass ratio of 1:1, filtered, and dried to obtain 18.1 grams of pure white solid wi...

Embodiment 2

[0033] To a 100ml flask equipped with a mechanical stirrer, a thermometer, and a condenser, add 10 grams of 9-fluorenone (0.055mol), 31.5 grams of phenol (0.33mol), and 16 grams of dichloroethane in sequence, place them in a water bath with stirring, and add 2.5 grams of concentrated sulfuric acid, control the temperature at about 20°C, slowly add 0.37 grams of 3-mercaptopropionic acid (0.0035mol), after the addition, react at 20°C for 2 hours, slowly raise the temperature to 30°C and continue the reaction for 1 hour. After the system completely turned into a pure white slurry, liquid phase analysis was carried out, and the reaction of 9-fluorenone was complete, with a liquid phase content of 95% (excluding phenol). After adding 30 grams of dichloroethane, cool down to room temperature and filter, and the filter cake is washed with a small amount of dichloroethane. The filter cake was beaten in a 5% sodium hydroxide solution with a mass ratio of 1:1, filtered, and dried to obt...

example 3

[0036] Add 10 grams of 9-fluorenone (0.055mol), 21 grams of phenol (0.22mol), and 16 grams of toluene to a 100ml flask equipped with a mechanical stirrer, a thermometer, and a condenser. Stir and place it in a water bath, then add 2.5 grams of Concentrated sulfuric acid, control the temperature at about 20°C, slowly add 0.185 g of 3-mercaptopropionic acid (0.0018mol), after the addition, react at 20°C for 2 hours, slowly raise the temperature to 60°C and continue the reaction for 2 hours. After the system completely turned into a pure white slurry, liquid phase analysis was carried out, and the reaction of 9-fluorenone was complete, with a liquid phase content of 95% (excluding phenol). After adding 30 grams of toluene, cool down to room temperature and filter, and the filter cake is washed with a small amount of toluene. The filter cake was beaten in 5% sodium hydroxide solution with a mass ratio of 1:1, filtered, and dried to obtain 18.1 grams of pure white solid with a yiel...

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Abstract

The invention discloses a synthesis method of fluorene-9-bisphenol, in particular to a green synthesis method of 9, 9-bis (4-hydroxy) fluorine. The method comprises the steps of enabling phenol and 9-fluorenone to react in an organic solvent in a concentrated sulfuric acid acidic medium condition under the catalysis of 3-thiohydracrylic acid, wherein the mole ratio of the phenol to the concentrated sulfuric acid to the 3-thiohydracrylic acid to the 9-fluorenone is (2-8): (0.1-0.6): (0.01-0.1): 1, the reaction temperature is -5 to 80 DEG C, and the reaction time is 2-8h; after the completion of the reaction, cooling to room temperature, filtrating, and washing a filter cake with the organic solvent; combining filtrate, and then adding the 9-fluorenone, the phenol, the concentrated sulfuric acid and the 3-thiohydracrylic acid into the filtrate sequentially to carry out circular reaction. In the synthesis process, since the organic solvent is used, the dosage of the phenol can be greatly reduced, the excessive phenol can be directly recycled through the filtrate, the efficiency of the system can be improved, and the discharge of acidic wastewater and the phenol can be reduced; meanwhile, the fluorene-9-bisphenol can be synthesized with high yield and high selectivity.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a synthesis method of bisphenol fluorene. Background technique [0002] 9,9-bis(4-hydroxyphenyl)fluorene (bisphenol fluorene) can improve the heat resistance of the polymer due to its unique structure, and has good optical properties and formability, and it also has excellent transparency and High refractive index and easy solubility, so it has become a raw material or modifier for the synthesis of new heat-resistant polycarbonate, epoxy resin and polyester. It is used in military aircraft structural materials, missile warheads, engine nozzles and housings. , Aerospace, electronics, and automobile industries have been widely used, and the polymers thus prepared can be used as heat-resistant materials, separation membrane materials, and optical materials, etc., and have attracted great attention abroad in recent years. [0003] P. W. MORGAN discovered that phenol and ketone com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/17C07C37/20
CPCC07C37/20C07C2603/18C07C39/17
Inventor 王军伟刘杰赵国荣王越
Owner DALIAN TRICO CHEM
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