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4,4'-bis(4-nitrophenoxy)phenyl sulfide preparation method

A technology of nitrophenoxy and dihydroxydiphenyl sulfide, which is applied in the field of preparation of aromatic organic compounds and achieves the effects of less three wastes, convenient recovery and less investment

Inactive Publication Date: 2009-03-11
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] But the preparation method of 4,4'-bis(4-nitrophenoxy) diphenyl sulfide, there is no published patent or bibliographical information yet at present

Method used

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Experimental program
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Effect test

Embodiment 1

[0031] 21.8 grams (0.10 moles) of 4,4'-dihydroxydiphenyl sulfide, 34.7 grams (0.22 moles) of 4-chloronitrobenzene, 110.4 grams (0.80 moles) of potassium carbonate, 110 milliliters of N, N-dimethyl Phenyl formamide, 100 milliliters of xylene and 1000 milliliters of toluene were put into the reaction kettle, stirred, heated to reflux and separated from water for 18 hours, concentrated the reaction solution, recovered the solvent for recycling, cooled the reactant system, added water, and precipitated a solid product. Wash with hot water for 2 to 3 times, and dry to obtain 43.8 grams of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide, with a melting point of 152.9°C (such as figure 2 shown), the purity is 99.5%. According to the actual amount of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide and the theoretical amount (46.0 grams), the calculated 4,4'-bis( The yield of 4-nitrophenoxy)diphenylsulfide was 95.2%.

Embodiment 2

[0033] 21.8 grams (0.10 moles) of 4,4'-dihydroxydiphenyl sulfide, 44.5 grams (0.22 moles) of 4-bromonitrobenzene, 55.2 grams (0.40 moles) of potassium carbonate, 150 milliliters of N, N-dimethyl Acetamide, 550 milliliters of N,N-dimethylformamide and 700 milliliters of xylene were put into the reaction kettle, stirred, heated to reflux and separated from water for 4 hours, concentrated the reaction solution, recovered the solvent for recycling, and cooled the reactant system, add water, precipitate a solid product, wash with hot water 2 to 3 times, and dry to obtain 35.7 grams of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide with a purity of 98.5%. According to the actual The amount and theoretical amount of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide (46.0 g), calculated to give 4,4'-bis(4-nitrophenoxy)diphenyl sulfide The yield was 77.6%.

Embodiment 3

[0035] 21.8 grams (0.10 moles) of 4,4'-dihydroxydiphenyl sulfide, 31.5 grams (0.20 moles) of 4-chloronitrobenzene, 10.6 grams (0.10 moles) of sodium carbonate, 550 milliliters of N, N-dimethyl Put methyl formamide, 350 milliliters of N-methyl-2-pyrrolidone, 300 milliliters of xylene and 300 milliliters of dichlorobenzene into the reaction kettle, stir, heat to reflux and divide water for 10 hours, concentrate the reaction solution, recover the solvent to Recycle, cool the reactant system, add water, separate out the solid product, wash 2 to 3 times with hot water, and dry to obtain 44.9 grams of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide with a purity of 99.6%, based on the actual amount of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide and the theoretical amount (46.0 grams), the calculated 4,4'-bis(4-nitrophenoxy base) The yield of diphenyl sulfide was 97.6%.

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Abstract

The invention relates to a method for preparing 4, 4'-bis (4-nitrophenoxy) diphenyl sulfide ether which comprises the steps: (1) 4,4'-thiobis-phenol and 4-halogenated nitrobenzene with the mol ratio of 1.00 to between 2.00 and 2.22 are subjected to heating reflux water separation reaction for 4 to 18 hours in a system formed by a salt forming agent and an organic solvent; and (2) reaction liquid is concentrated, a reactant system is cooled, water is added to precipitate a solid product, and the 4, 4'-bis (4-nitrophenoxy) diphenyl sulfide ether is obtained through filtration, washing and drying. The method has simple operation, and high yield and purity of products, ensures that the solvent is convenient to reclaim and can be repeatedly used, has less three wastes, is environment-friendly,and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of preparation of aromatic organic compounds, in particular to a preparation method of 4,4'-bis(4-nitrophenoxy)diphenyl sulfide. Background technique [0002] Aromatic dinitro compounds are important raw materials for the preparation of aromatic di-primary amines, and aromatic di-primary amines are used for the preparation of high-temperature resistant polyimide resins, liquid crystal alignment agents, carbon fiber reinforced advanced composite material matrix resins, high-resistance It is an important raw material for impact epoxy resin curing agent, polyurethane chain extender, VLSI passivation coating and alpha particle barrier coating material, and printed electronic circuit board base material matrix resin or adhesive. [0003] Aromatic polyimide has excellent thermal stability, nuclear radiation resistance, excellent mechanical properties, electrical properties and resistance to organic solvents, and has been wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/20C07C319/20
CPCY02P20/582
Inventor 虞鑫海陈梅芳刘斌
Owner DONGHUA UNIV
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