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Synthesis method of 4, 4 '-diaminodiphenyl ether

A technology of diaminodiphenyl ether and synthesis method, which is applied in the field of synthesis of 4,4'-diaminodiphenyl ether, can solve the problems of poor selectivity, low yield, high temperature and high pressure required for reaction conditions, and achieves low production cost , high yield, easy to large-scale industrial production effect

Pending Publication Date: 2022-02-25
SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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  • Description
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  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to provide a synthetic method of 4,4'-diaminodiphenyl ether, which can solve the problem of high temperature and high pressure, poor selectivity, Technical problem with low yield

Method used

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  • Synthesis method of 4, 4 '-diaminodiphenyl ether
  • Synthesis method of 4, 4 '-diaminodiphenyl ether
  • Synthesis method of 4, 4 '-diaminodiphenyl ether

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Embodiment 1

[0040] Embodiment 1: the synthetic method of 4,4'-diaminodiphenyl ether

[0041] In a 1000mL reaction flask, add 258g of tetrahydrofuran (99%), 51.6g of diphenyl ether (99%, 0.3mol), 102.0g of ammonia (25%, 1.5mol), 3.6g of potassium bromide (99%, 0.03mol), 5.8g of cuprous iodide (99%, 0.03mol), 12.1g of ligand L2 (99%, 0.03mol), 68.0g of hydrogen peroxide (30%, 0.6mol); The reaction was carried out under stirring, the stirring speed was 600rpm, and the heat preservation reaction was 6hr; after the reaction was completed, the liquid was separated, washed with water, and the organic layer was recovered from the solvent and then crystallized with methanol to obtain 57.3g of 4,4'-diaminodiphenyl ether with a content of 99.8% , yield 95.2%;

[0042] Wherein, the structural formula of ligand L2 is:

Embodiment 2

[0043] Embodiment 2: the synthetic method of 4,4'-diaminodiphenyl ether

[0044] Add 516g of dichloromethane (99%), 51.6g of diphenyl ether (99%, 0.3mol), 204.0g of ammonia (25%, 3mol), 3.1g of sodium bromide (99% , 0.03mol), 4.1g of copper chloride (99%, 0.03mol), 12.1g of ligand L2 (99%, 0.03mol), 51.0g of hydrogen peroxide (30%, 0.45mol); The reaction was carried out with stirring, the stirring speed was 600 rpm, and the heat preservation reaction was 12 hours; after the reaction, the liquid was separated, washed with water, and the organic layer was recovered from the solvent and then crystallized with methanol to obtain 58.1 g of 4,4'-diaminodiphenyl ether with a content of 99.8%. Yield 96.5%;

[0045] Wherein, the structural formula of ligand L2 is:

Embodiment 3

[0046] Embodiment 3: the synthetic method of 4,4'-diaminodiphenyl ether

[0047] In a 1000mL reaction flask, add 258g of tetrahydrofuran (99%), 51.6g of diphenyl ether (99%, 0.3mol), 102.0g of ammonia (25%, 1.5mol), 3.6g of potassium bromide (99%, 0.03mol), 5.8g of cuprous iodide (99%, 0.03mol), 8.0g of ligand L1 (99%, 0.03mol), 68.0g of hydrogen peroxide (30%, 0.6mol); Stirring reaction, stirring speed 600rpm, heat preservation reaction 24hr; After the reaction, separate liquid, wash with water, recover the solvent in the organic layer, crystallize with methanol to obtain 35.5g of 4,4'-diaminodiphenyl ether, the content is 99.2%, the yield 58.6%;

[0048] Wherein, the structural formula of ligand L1 is:

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Abstract

The invention discloses a synthesis method of 4, 4 '-diaminodiphenyl ether, the synthesis method comprises the following step: taking diphenyl ether, hydrogen peroxide, ammonia water and bromide as initial raw materials, synthesizing the 4, 4'-diaminodiphenyl ether through one-step reaction in the presence of a solvent, a catalyst and a ligand. The technical problems that high temperature and high pressure are needed for reaction conditions, the selectivity is poor and the yield is low in an existing 4, 4 '-diaminodiphenyl ether synthesis process are solved; the adopted Mannich alkali ligand has strong power supply property and large steric hindrance, and is coordinated with the copper salt, so that the catalytic effect of the copper salt can be remarkably improved; the adopted brominated salt enables diphenyl ether to be subjected to an oxidative bromination reaction to generate the 4, 4 '-dibromodiphenyl ether intermediate. The synthesis process can be completed at the room temperature, the reaction condition is mild, selectivity is good, aftertreatment purification is simple, the yield is high, and the product quality is good.

Description

technical field [0001] The invention belongs to the technical field of fine chemical organic materials, in particular to a synthesis method of 4,4'-diaminodiphenyl ether. Background technique [0002] 4,4'-diaminodiphenyl ether is an important fine chemical intermediate, which can be used industrially to synthesize engineering plastic polyimide, polyetherimide, polyesterimide and other high temperature resistant polymer materials, and also It can be used as a raw material and crosslinking agent for synthetic polymers such as high-performance heat-resistant epoxy resin polyurethane; it can also be used to replace carcinogenic benzidine to produce azo dyes, reactive dyes and fragrances. Therefore, it is of great significance to study the synthesis of 4,4'-diaminodiphenyl ether. Industrially, there are two main routes for the synthesis of 4,4’-diaminodiphenyl ether. [0003] Route 1: Patent CN112876367A reports a synthesis method of 4,4'-diaminodiphenyl ether, which uses diph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/02
CPCC07C213/02C07C217/90
Inventor 朱叶峰裴晓东骆艳华杨修光吴忠凯王凡
Owner SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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