A kind of method preparing halogenated aniline by catalytic hydrogenation of halogenated nitrobenzene

A halogenated nitrobenzene, catalytic hydrogenation technology, applied in the preparation of amino compounds, catalyst activation/preparation, preparation of amino hydroxyl compounds, etc., can solve problems such as catalytic performance decline, sulfide loss, etc., to achieve improved quality, good stability , reduce the effect of separation and purification

Active Publication Date: 2019-06-14
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the literature [Q.Zhang, X.Li, etal.Chin.J.Chem.Eng.,2014,22(10):1111–1116] reported that the Pd / C catalyst treated with sulfide at 36 The application of hydrogenation of nitrobenzene to chloroaniline reaction, the literature pointed out that this type of catalyst is prone to sulfide loss during the hydrogenation reaction, which will lead to a decrease in the catalytic performance of this type of catalyst during recycling

Method used

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  • A kind of method preparing halogenated aniline by catalytic hydrogenation of halogenated nitrobenzene
  • A kind of method preparing halogenated aniline by catalytic hydrogenation of halogenated nitrobenzene
  • A kind of method preparing halogenated aniline by catalytic hydrogenation of halogenated nitrobenzene

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Embodiment 1

[0033] Weigh 10g of carbon material, the particle size of the carbon material is 800 mesh, and the specific surface area is 1400m 2 / g, the average pore diameter is 3nm, and the ash content is 0.3wt%. It is mixed with 0.6g elemental sulfur evenly, and treated at 1000°C for 5h under nitrogen atmosphere to obtain sulfur-doped carbon material. Then, the above-mentioned sulfur-doped carbon material was prepared into a slurry at a temperature of 80° C. in 100 ml of deionized water, and 10 ml of H 2 PdCl 4 solution (the Pd content is 0.02g / ml), stirred for 2.5h; the pH value of the solution was adjusted to 8 with 10wt% NaOH solution, and the temperature was lowered to room temperature, filtered, and the filter cake was washed to neutrality with deionized water; The filter cake was configured into a slurry at 80°C, 2ml of 85% hydrazine hydrate solution was added dropwise, stirred for 2 hours, filtered, the filter cake was washed with deionized water until neutral, and vacuum-dried a...

Embodiment 2

[0035] Weigh 10g of carbon material, the particle size of the carbon material is 1000 mesh, and the specific surface area is 1200m 2 / g, the average pore diameter is 2.5nm, the ash content is 3.0wt%, it is placed in H 2In the S / Ar mixed gas (volume ratio 1 / 10), the mixed gas flow rate is 2 L / h, and the sulfur-doped carbon material is obtained by treating at 800° C. for 10 h. Prepare the above-mentioned sulfur-doped carbon material in 100ml of deionized water to make a slurry at a temperature of 60°C, and slowly add 6ml of H 2 PtCl 6 solution (Pt content is 0.05g / ml), stirred for 2h; the pH value of the solution was adjusted to 8.5 with 10wt% KOH solution, and the temperature was lowered to room temperature, filtered, and the filter cake was washed to neutrality with deionized water; The cake was prepared into a slurry at 60°C, 10ml of formaldehyde was added dropwise, stirred for 2 hours, filtered, the filter cake was washed with deionized water until neutral, and dried in va...

Embodiment 3

[0037] Weigh 10g of carbon material, the particle size of the carbon material is 100 mesh, and the specific surface area is 1600m 2 / g, average pore diameter 10nm, ash content 0.1wt%, mix it with 4g thiophene evenly, and treat it at 1200°C for 3h under a helium atmosphere to obtain a sulfur-doped carbon material. Prepare the above-mentioned sulfur-doped carbon material in 100ml of deionized water to make a slurry at a temperature of 40°C, and slowly add 10ml of RuCl 3 solution (the Ru content is 0.005g / ml), stirred for 4h; the pH value of the solution was adjusted to 9 with ammonia water, and the temperature was lowered to room temperature, filtered, and the filter cake was washed with deionized water until neutral; Prepare a slurry, add dropwise 30ml of formic acid, stir for 4h, filter,

[0038] The filter cake was washed with deionized water until neutral, and dried in vacuum at 80° C. to obtain a sulfur-doped carbon material-supported ruthenium catalyst.

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Abstract

The invention discloses a method for preparing halogenated aniline from halogenated nitrobenzene through catalytic hydrogenation. The method comprises the following steps: in a reaction kettle, performing liquid phase catalytic hydrogenation reaction to halogenated nitrobenzene under the action of a sulfur-doped carbon material loaded noble metal catalyst, to obtain halogenated aniline shown in the formula (II), wherein the loading quantity of noble metal in the sulfur-doped carbon material loaded noble metal catalyst is 0.1-5wt%. In the method, the catalyst has good stability, the hydrogenation halogen removal side effect can be effectively inhibited under the condition of having no added halogen removal inhibitor, and the product selectivity is high.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing halogenated aniline by highly selective hydrogenation by using sulfur-doped carbon material loaded noble metal as catalyst and halogenated nitrobenzene as raw material. (2) Background technology [0002] The reduction of halogenated aromatic nitro compounds to synthesize halogenated anilines is an important organic reaction. The reduction methods include chemical reduction methods (iron powder reduction method, alkali sulfide reduction method and hydrazine hydrate reduction method, etc.), electrolytic reduction method and catalytic hydrogenation. Restoration, etc. Among them, the catalytic hydrogenation reduction method has attracted much attention due to its advantages of simple operation process, high product yield, good product quality and low energy consumption. It is an environmentally friendly green process. However, in practical applications, the catalytic hydrogenation method has the probl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/36C07C211/52C07C213/02C07C217/84C07C227/04C07C229/60C07C231/12C07C233/43B01J27/22B01J23/42B01J23/44B01J23/46B01J37/20B01J37/02B01J37/16
CPCB01J23/42B01J23/44B01J23/462B01J23/464B01J23/466B01J23/468B01J27/22B01J37/0201B01J37/16B01J37/20C07C209/365C07C213/02C07C227/04C07C231/12C07C211/52C07C217/84C07C229/60C07C233/43
Inventor 张群峰李康卢春山马磊丰枫许孝良李小年
Owner ZHEJIANG UNIV OF TECH
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