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Preparation method of 4,4'-dinitrodiphenyl ether

A technology of dinitrodiphenyl ether and p-nitrochlorobenzene, which is applied in 4 fields to achieve the effects of improving safety and stability, low solubility, and improving product quality

Active Publication Date: 2013-11-06
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The technical problem to be solved is to reduce the reaction temperature, improve the yield of one-step reaction, and reduce environmental pollution problems

Method used

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  • Preparation method of 4,4'-dinitrodiphenyl ether
  • Preparation method of 4,4'-dinitrodiphenyl ether
  • Preparation method of 4,4'-dinitrodiphenyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1. Preparation of crude product

[0041] Add 0.1mol (15.75g) p-nitrochlorobenzene, 80mL isopropanol and 20mL tert-butanol to a 250mL three-necked flask equipped with a spherical condenser, stirrer and thermometer, start stirring, and raise the temperature of the oil bath within half an hour. To 83°C, the solvent has been refluxed at this time, add 0.12mol (4.8g) NaOH and 0.005mol (0.96g) CuI solid, heat preservation reaction for 6 hours, stop heating and stirring, naturally cool down to normal temperature and filter, the obtained filtrate is recycled using molecular sieves Stored after removing water, the filter cake was washed with 10wt% NaOH solution at 95°C and filtered while hot, and washed several times with distilled water. The washed filter cake was placed in an oven and dried at 60°C for 4 hours to obtain 11.53 g of crude DNDPE as a yellow solid product.

[0042] 2. Refined

[0043] Gained crude product is put into the 250mL three-neck flask that spherical cond...

Embodiment 2

[0045] In step 1, the solvent used was 60 mL of recovered filtrate, and 32 mL of isopropanol and 8 mL of tert-butanol were added. Other conditions were the same as in Example 1, and the reaction was continued. 11.35 g of DNDPE was obtained with a yield of 87.3%.

Embodiment 3

[0047] In step 1, the oil bath temperatures were 75°C, 80°C, and 85°C, and other conditions were the same as in Example 1, and the yields were 79.3%, 81.6%, and 80.3%, respectively.

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Abstract

The invention discloses a preparation method of 4,4'-dinitrodiphenyl ether. The preparation method comprises the following steps of: adding nitrochlorobenzene, NaOH and CuI to solvents, stirring and mixing the materials uniformly and raising the temperature to 75-85 DEG C, preserving heat and stirring to react for 4-8 hours and then stopping heating and stirring, naturally cooling the reactant to the normal temperature and then filtering the reactant, washing the filter cake with a NaOH solution with mass concentration being 10% and at 95 DEG C, drying the filter cake and recrystallizing the filter cake with ethyl acetate, thus obtaining the product. The preparation method has the following beneficial effects that: CuI is used as the catalyst, thus reducing the reaction temperature, increasing the yield, reducing the traditional reaction temperature, namely 140 DEG C, to 70-90 DEG C, improving the safety and stability in the production process and reducing byproducts.

Description

1. Technical field [0001] The invention relates to a preparation method of a fine chemical intermediate, in particular to a preparation method of 4,4'-dinitrodiphenyl ether. 2. Background technology [0002] 4,4'-Dinitrodiphenyl ether (DEDPE) is an important fine chemical intermediate, which can replace carcinogenic benzidine for the production of azo dyes and reactive dyes. etc., are superior to benzidine dyes. Its reduction product 4,4'-diaminodiphenyl ether (4,4'-ODA) is used to produce polyimide resin, polymaleimide resin, polyamide-imide resin, polyester-polyethylene Main monomer of amine resin etc. 4,4'-ODA is also the raw material for the synthesis of 3,3',4,4'-tetraaminodiphenyl ether, which is used to prepare a series of new high-temperature-resistant heterocyclic polymers such as polybenzimidazole, polyimidazolepyridine , The main monomer of polyphenylquinoline. DEDPE is an important intermediate with high added value. With the continuous expansion of its appli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/38C07C201/12
Inventor 冯乙巳王除非叶加久郑波程月
Owner HEFEI UNIV OF TECH