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Method for converting arylamine polyhalide

A polychlorinated aromatic amine and compound technology, which is applied in the preparation of organic compounds, the preparation of amino compounds, chemical instruments and methods, etc., to achieve the effect of reducing environmental pollution and improving yield

Active Publication Date: 2014-04-02
SHANDONG QINGYUAN GROUP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the hydrodehalogenation of trihalogenated arylamine compounds in the literature at present, especially the organic pigment intermediate - a chloroaniline compound that is 2,5-dimethoxy-4- The rectification residue of chloroaniline is used as raw material to carry out partial hydrodehalogenation reaction to convert polychlorinated aniline compounds rich in it into monochloroaniline compounds for recycling.

Method used

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  • Method for converting arylamine polyhalide
  • Method for converting arylamine polyhalide

Examples

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Effect test

Embodiment 1

[0023] This example is used to illustrate the preparation of the catalyst.

[0024] According to the final composition of the catalyst, an appropriate amount of Group VIII metal chloride (such as palladium chloride) was weighed and dissolved in 20 ml of concentrated hydrochloric acid, and diluted to 100 ml with water. Take 50ml of the prepared mixed solution, add it to 100g of activated carbon carrier treated with nitric acid, soak it at 25°C for 8 hours, filter it, evaporate it to dryness on a water bath in an evaporating dish, and finally place it in an oven for drying at 120°C. That is, an activated carbon-supported catalyst with Group VIII metal as an active component is obtained. The catalyst needs to pass through H before use 2 reduction.

Embodiment 2

[0026] This example illustrates the effect of the method of the invention.

[0027] Add 100 grams of 2,4,6-trichloroaniline, 0.38 grams of activated carbon-supported palladium catalyst (containing 0.1% by weight of palladium), 300 ml of ethanol solvent, and 10 grams of sodium hydroxide into a 1 L autoclave. Under the hydrogen pressure of 3.5MPa, the temperature was controlled at 120° C., stirred, and a partial hydrodechlorination reaction was carried out. After the reaction was carried out for 4 hours, 85 grams of the final reaction product were obtained, including 12% of dichloroaniline and 88% of monochloroaniline.

Embodiment 3

[0029] Add 100 grams of 2,6-dichloroaniline, 0.2 grams of activated carbon-supported palladium catalyst (containing 0.1% by weight of palladium), 300 ml of ethanol solvent, and 10 grams of sodium hydroxide into a 1 L autoclave. Under the hydrogen pressure of 2.5 MPa, the temperature was controlled at 100° C., stirred, and a partial hydrodechlorination reaction was carried out. After the reaction was carried out for 5 hours, 80 g of the final reaction product was obtained, of which 100% monochloroaniline.

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Abstract

The invention provides transformation method for poly-halogenated aromatic amine compound. In the method, a hydrodechlorination reaction is carried out on the poly-chloraniline compound (I) rich in the rectification residue, with the existence of H2, liquid solvent and alkali, by taking the rectification residue generated in the process of synthesizing 2, 5 dimethoxy-4-chloraniline as raw materials and by adopting a support catalyst with group VIII metals as active components. The method has the advantage that the rectification residue generated in the process of synthesizing 2, 5 dimethoxy-4-chloraniline can be recycled at utmost, so that the environmental pollution caused by the discharge of rectification residue is reduced.

Description

technical field [0001] The present invention relates to a method for converting polyhalogenated arylamine compounds, in particular to a rectification residue produced in the production process of monohalogenated aniline compounds—that is, 2,5-dimethoxy-4-chloroaniline As a raw material, the polychlorinated aniline compounds rich in it are converted into monochloroaniline compounds through partial hydrodehalogenation and recycled. Background technique [0002] As a chloroaniline compound, 2,5-dimethoxy-4-chloroaniline is an important organic pigment intermediate, which can be used to prepare permanent yellow HR (dye index number C.I.PigmentYellow 83 (21108) by diazotization reaction )) and permanent pink FBB-B (dye index number C.I.Pigment Red 146 (12485), used for advanced ink and plastic products. [0003] The starting material for 2,5-dimethoxy-4-chloroaniline is hydroquinone. Hydroquinone undergoes etherification (ie methylation) reaction to become p-xylylene dimethyl e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/52C07C209/74B01J23/89B01J23/40
Inventor 王广建钟立梅丁浩
Owner SHANDONG QINGYUAN GROUP CO LTD
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