Method for preparing o-chloroaniline by catalytic hydrogenation

A technology for catalytic hydrogenation and o-chloroaniline, which is applied in the preparation of aniline and o-chloroaniline, can solve the problems of high energy consumption, complex reduction route, and additional filtration in the electrochemical reduction method, and achieve large-scale Effects of industrialized production, reduced post-treatment process, and reduction of coupling compounds

Inactive Publication Date: 2010-07-14
JIANGSU KANGHENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The iron powder reduction method produces a large amount of iron sludge, which seriously pollutes the environment; the alkali sulfide reduction method has disadvantages such as complex reduction routes, low product yield, and large waste liquid; the electrochemical reduction method consumes too much energy; the catalytic hydrogenation method has a reaction route Short, low energy consumption, environmental protection and other advantages
However, in the process of preparing o-chloroaniline by catalytic hydrogenation of o-nitrochlorobenzene, the side reactions of hydrogenation and dechl

Method used

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  • Method for preparing o-chloroaniline by catalytic hydrogenation

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Experimental program
Comparison scheme
Effect test

Embodiment a

[0017] Prior art: 150g of o-nitrochlorobenzene and 300ml of methanol are added to the autoclave, and 7.5g of Raney-Ni catalyst (Ni / Al) and 1.50g of triethylamine are added simultaneously, the autoclave is closed, the hydrogen valve is opened, and the Pass hydrogen into the kettle, ventilate 3 times, adjust the pressure of the kettle to 1.0MPa, stir and heat up to 55-65°C to react, so that the pressure does not change (about 3h), take a sample, and the result of gas chromatography analysis shows that the content of o-chloroaniline is 97.50% . The obtained main product o-chloroaniline was mixed with impurities, and after the catalyst and some insolubles were filtered out, the solvent was recovered and the water was distilled off to obtain 102 g of refined o-chloroaniline (yield 85%, GC99.9%). The residue is about 20.0g, and the residue contains 1-3 / 100 of the coupling compound, which is attached to the rectification tower and is difficult to clean when the rectification tower is...

Embodiment b

[0019] The technology of the present invention: 150g of o-nitrochlorobenzene, 300ml of ethyl acetate are added in the autoclave, 7.5g of Raney-Ni catalyst (Ni / C) is added simultaneously, 1.50g of triethylamine, the airtight autoclave is opened, the hydrogen valve is opened, Introduce hydrogen into the autoclave, ventilate 3 times, adjust the pressure of the autoclave to 1.0MPa, stir and raise the temperature to 55-65°C to react, so that the pressure does not change (about 3h), take a sample, analyze the results by gas chromatography, the content of o-chloroaniline 98.50%. The ethyl acetate phase was obtained by liquid separation, the solvent was recovered and rectified to obtain 110 g of refined o-chloroaniline (yield 90%, GC99.9%). The residue is about 10.0g, and due to the use of ethyl acetate solvent and neutral catalyst, there is no need to filter, just a simple liquid separation, and the coupling compound in the reaction is only 1 / 2 or even less than that of the prior art...

Embodiment 1

[0021] Add 50 g of o-nitrochlorobenzene and 200 ml of ethyl acetate into the autoclave, add 2.5 g of Raney-Ni catalyst (Ni / C) and 1.0 g of dicyandiamide at the same time, close the autoclave, open the hydrogen valve, and inject Pass in hydrogen, ventilate 3 times, adjust the pressure of the kettle to 1.0MPa, stir and heat up to 55-65°C to react (replenish hydrogen repeatedly), so that the pressure does not change, take a sample, and the result of gas chromatography analysis shows that the content of o-chloroaniline is 97.80%. The ethyl acetate phase was obtained by liquid separation, and after the solvent was recovered, rectification obtained 36.5 g of refined o-chloroaniline and impurities (yield 90%, GC99.9%). Impurities remain in the kettle, and after testing, the coupling compound in the impurities is less than 1 / 100.

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Abstract

The invention discloses a method for preparing o-chloroaniline by catalytic hydrogenation. O-nitrochlorobenzene, ethyl acetate solution, a dechlorination inhibitor and hydrogen are subjected to catalytic hydrogenation synthetic reaction under the effect of a catalyst at the temperature of 25-90 DEG C to obtain the o-chloroaniline. For better technical effects, the o-nitrochlorobenzene, ethyl acetate solution, dechlorination inhibitor are continuously delivered to a fixed bed reactor by a metering pump, inlet amount of hydrogen is controlled by a flow meter, and catalytic hydrogenation synthetic reaction is conducted in the fixed bed reactor. The fixed bed reactor which uses Ni alloy as the catalyst and a neutral carrier as a catalyst carrier is used for controlling the inlet amount of raw materials and hydrogen and the catalyst, thus reducing cost and improving efficiency. In the invention, dechlorination reaction can be effectively inhibited, subsequent processing steps of the principal product are simplified, coupling compounds generated in reaction are little, the selectivity of o-chloroaniline is above 99%, and the dechlorinating amount is below 0.3%. The invention has the advantages of mass industrial production and environment protection.

Description

technical field [0001] The invention relates to a method for preparing aniline, in particular to a method for preparing o-chloroaniline by catalytic hydrogenation, and belongs to the field of preparing o-chloroaniline. Background technique [0002] O-chloroaniline is an important dye intermediate, pharmaceutical intermediate, solvent, antifungal agent and reagent, etc. It is widely used in the production of fine chemicals such as pesticides, dyes, and medicine. Traditional nitro reduction methods mainly include iron powder reduction method, alkali sulfide reduction method, catalytic hydrogenation reduction method, and electrochemical reduction method. The iron powder reduction method produces a large amount of iron sludge, which seriously pollutes the environment; the alkali sulfide reduction method has disadvantages such as complex reduction routes, low product yield, and large waste liquid; the electrochemical reduction method consumes too much energy; the catalytic hydrog...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/36
Inventor 邱志刚
Owner JIANGSU KANGHENG CHEM
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