Preparation method of 4,4'-dihydroxy-3,3'-diamino diphenyl ketone

A technology of diaminobenzophenone and dinitrobenzophenone, which is applied in the field of preparation of 4,4'-dihydroxy-3,3'-diaminobenzophenone, can solve the problem that does not have industrial production value, raw materials are not easy to obtain, and the process is complicated, so as to achieve the effect of high purity and yield, low production cost and simple process

Inactive Publication Date: 2015-04-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are few reports on the synthesis of 4,4'-dihydroxy-3,3'-diaminobenzophenone, but there are reports on the synthesis of its third intermediate
As we all know, although there are many synthetic methods of 4,4'-DDT, the production of this kind of substance has been banned as early as the 1970s because of its toxicity, difficult degradation and the ability to accumulate in organisms.
The process of preparing the target product by this method is complicated, the raw materials are not easy to obtain, and the environmental pollution is relatively large, so it has no industrial production value

Method used

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  • Preparation method of 4,4'-dihydroxy-3,3'-diamino diphenyl ketone
  • Preparation method of 4,4'-dihydroxy-3,3'-diamino diphenyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Add a mass concentration of 60% ethanol aqueous solution and 2.2g (0.055mol) NaOH solid to a four-neck flask equipped with a condenser tube, a thermometer and a stirring paddle and mix evenly. After the mixed solution is heated to 60°C, add Add 3.41g (0.01mol) 4,4'-dichloro-3,3'-dinitrobenzophenone, and maintain the temperature at 60°C for 24 hours to obtain an orange-red slurry, add 100ml Water completely dissolves the slurry to form an orange-red transparent solution, then adjusts the pH of the system to 1-2 with acid to completely change the sodium phenate into hydroxyl, filters and washes the product to be neutral, and then places it in an oven at a temperature of 80°C to dry it to obtain Orange-yellow powdery solid, the yield of the crude product obtained after weighing and calculation is 93.42%, and the purity is 88.10%. The product can be purified by recrystallizing the hydrolyzate with DMF and isopropanol. The product obtained after recrystallization is determin...

Embodiment 2

[0052] Add a mass concentration of 80% ethanol aqueous solution and 2.2g (0.055mol) NaOH solid to a four-neck flask equipped with a condenser tube, a thermometer and a stirring paddle and mix evenly. After the mixed solution is heated to 75°C, add Add 3.41g (0.01mol) of 4,4'-dichloro-3,3'-dinitrobenzophenone, and maintain the temperature at 75°C for 24 hours to obtain an orange-red slurry, add 100ml to the system Water completely dissolves the slurry to form an orange-red transparent solution, then adjusts the pH of the system to 1-2 with acid to completely change the sodium phenate into hydroxyl, filters and washes the product to be neutral, and then places it in an oven at a temperature of 80°C to dry it to obtain Orange powdery solid, the yield of the crude product obtained after weighing and calculation is 96.05%, and the purity is 89.92%.

Embodiment 3

[0054] Add a mass concentration of 50% ethanol aqueous solution and 3.2g (0.08mol) NaOH solid to a four-neck flask equipped with a condenser tube, a thermometer and a stirring paddle and mix evenly. After the mixed solution is heated to 100°C, add Add 3.41g (0.01mol) 4,4'-dichloro-3,3'-dinitrobenzophenone, and maintain the temperature at 100°C for 24 hours to obtain an orange-red slurry, add 100ml Water completely dissolves the slurry to form an orange-red transparent solution, then adjusts the pH of the system to 1-2 with acid to completely change the sodium phenate into hydroxyl, filters and washes the product to be neutral, and then places it in an oven at a temperature of 80°C to dry it to obtain Orange solid particles, the yield of the crude product is 95.34%, and the purity is 90.32%.

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Abstract

The invention discloses a preparation method of 4,4'-dihydroxy-3,3'-diamino diphenyl ketone. The preparation method is characterized in that common organic reagents (chlorobenzene and parachlorobenzoyl chloride) are used as raw materials to prepare the target product through organic reactions in four steps. Particularly, pollution-free 4,4'-dichloro-3,3'-dinitro diphenyl ketone with high industrial application value is adopted to prepare 4,4'-dihydroxy-3,3'-dinitro diphenyl ketone which is a hydrolyzate, and 4,4'-dihydroxy-3,3'- diamino diphenyl ketone is prepared by using pollution-free hydrazine hydrate reducing method which is simple in process.

Description

technical field [0001] The invention relates to a preparation method of 4,4'-dihydroxy-3,3'-diaminobenzophenone, belonging to the technical field of organic synthesis. Background technique [0002] 4,4'-dihydroxy-3,3'-diaminobenzophenone is an important intermediate in organic synthesis, widely used in the fields of agricultural chemistry, medicine, and dyes, and its hydrochloride can also be used as a monomer It has wide application value in the synthesis of poly-p-phenylene benzobisoxazole fiber (PBO). [0003] There are few reports on the synthesis of 4,4'-dihydroxy-3,3'-diaminobenzophenone, but there are reports on the synthesis of its third intermediate product. According to researchers such as Sibrikov S.G. and Kazin V.N., under the condition of N,N-dimethylformamide (DMF) as solvent, NaNO 2 Oxidation of 2,2-bis(3-nitro-4-chlorophenyl)-1,1,1-trichloroethane to 4,4'-dihydroxy-3,3'-dinitrobenzophenone . And 2,2-bis(3-nitro-4-chlorophenyl)-1,1,1-trichloroethane is der...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22
Inventor 蒋文伟雷丹
Owner SICHUAN UNIV
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