Method for preparation of m-aminobenzenesulfonic acid by catalytic hydrogenation

A technology of aminobenzenesulfonic acid and catalytic hydrogenation, which is applied in the preparation of sulfonic acid, organic chemistry, chemical recovery, etc., can solve the problems of reduced utilization rate of hydrogenation kettle, lack of production cost, large utilization rate of equipment, etc., and achieves improved equipment utilization. Utilization, overcoming pollution and energy consumption, the effect of reducing catalyst cost

Active Publication Date: 2014-05-21
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Industrially, the traditional methods for preparing sulfanilic acid are iron powder reduction method and electrolytic synthesis of sulfanilic acid, but these methods are replaced by catalytic hydrogenation method because of heavy pollution or cannot be recycled.
[0003] Literature [Application of Modified Skeleton Nickel Catalyst in 3NBSA Hydrogenation to Prepare M-Sulphonic Acid, Shen Xiaofeng, Journal of Shenyang Institute of Chemical Technology, 2007(12), 21(4): 276-278] and [Liquid Phase Catalytic Hydrogenation Method Synthesis of 2-aminobenzenesulfonic acid, Yan Xinhuan et al., Dyestuff Industry, 2001 (4), 38 (2): 40-41] respectively used two catalysts, the modified framework nickel and the self-made palladium carbon, which were introduced in these two articles Although the method is easy to carry out the reaction, it has the disadvantages of too few times of catalyst application and high cost.
The cause of the deactivation of the catalyst is that the impurity 3,3'-diaminodiphenylsulfide will be produced during the hydrogenation reduct

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation of embodiment 1Pt-Ru / C catalyst

[0019] 0.28g chloroplatinic acid (H 2 PtCl 6 6H 2 O) Dissolve in 2ml of concentrated hydrochloric acid, add 20ml of water to dilute; dissolve 0.19g of ruthenium chloride in 10ml of water, mix the two solutions for use. Add 120ml of water and 9g of nitric acid-treated activated carbon into a 250ml four-necked bottle (with a stirrer, thermometer, condenser and dropping funnel), and add the pre-prepared chloroplatinic acid-chlorinated For the mixed solution of ruthenium, control the dropwise addition time for about 1 hour, and continue to stir for 30 minutes after the dropwise addition to make it completely permeate on the activated carbon. Use saturated sodium carbonate solution to adjust the pH value between 7 and 8, add 2ml of 85% hydrazine hydrate, heat up to 90°C, keep warm for 1 hour, then cool down to 25°C, filter, wash with water until neutral, and suction filter until no water drips . The obtained catalyst is ...

Embodiment 2

[0022] Add 150ml of water to 150g of sodium m-nitrobenzene sulfonate, heat to dissolve, add 3g of activated carbon to boil, perform hot filtration, and adjust the pH value of the obtained filtrate to between 7.5 and 8.5 with 20% aqueous sodium hydroxide solution. In an autoclave with a volume of 500ml, add the treated sodium m-nitrobenzenesulfonate solution, add 1.0g of 1%Pt-Ru / C (Pt:Ru=5:1) catalyst prepared as in Example 1, and seal . After replacing 3 times with nitrogen and 5 times with hydrogen, adjust the hydrogen pressure to 1.0 MPa, and carry out hydrogenation reduction at a temperature of 90°C. The hydrogen absorption time is 85 minutes, until the reaction no longer consumes hydrogen as the end point (the hydrogen pressure does not drop for 1 hour continuously) ). The material is discharged, filtered, and the solid catalyst is washed with water and recovered for the next reaction. The pH value of the filtrate adjusted with 30% sulfuric acid was 2, and the white prec...

Embodiment 3

[0024] Add 150ml of water to 100g of sodium m-nitrobenzenesulfonate, heat to dissolve, add 3g of activated carbon to boil, and perform hot filtration. The obtained filtrate is adjusted to a pH value between 7.5 and 8.5 with 30% aqueous sodium hydroxide solution. In an autoclave with a volume of 500ml, add the treated sodium m-nitrobenzenesulfonate solution, add 0.15g of 10%Pt-Ru / C (Pt:Ru=1:1) catalyst prepared as in Example 1, and seal . After replacing 3 times with nitrogen and 5 times with hydrogen, adjust the hydrogen pressure to 0.8MPa, and carry out hydrogenation and reduction at a temperature of 80°C. The hydrogen absorption time is 75 minutes until the reaction no longer consumes hydrogen as the end point (the hydrogen pressure does not drop for 1 hour continuously) ). Aftertreatment is the same as embodiment 2. The resulting filtrate pH value was adjusted to 2 with 20% sulfuric acid, and the precipitated white precipitate was m-aminobenzenesulfonic acid solid. Analys...

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PUM

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Abstract

Belonging to the field of fine chemical industry, the invention in particular relates to a method for preparation of m-aminobenzenesulfonic acid by catalytic hydrogenation. The method includes: taking sodium m-nitrobenzene sulfonate as the raw material, adding water for dissolving, boiling the mixture by activated carbon, conducting hot filtration, adjusting the pH value of the filtrate to 7.5-8.5 by a sodium hydroxide aqueous solution, employing Pt-Ru/C as a catalyst to perform hydrogenation reduction for preparation of m-aminobenzenesulfonic acid, ending the hydrogenation reduction reaction when the hydrogen pressure no longer changes, filtering out the Pt-Ru/C catalyst at the end of the reaction, firstly washing the catalyst by ethanol, then carrying out washing recycling, with the recycled catalyst being able to be applied over 50 times and still having a conversion rate and selectivity up to 99%; and subjecting the obtained filtrate to acid precipitation to pH of 2, thus obtaining a white crystal, i.e. the target product m-aminobenzenesulfonic acid. The method provided by the invention lowers the catalyst cost, improves the utilization rate of equipment, and also overcomes the problems of pollution and energy consumption in the regeneration process of the catalyst.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and in particular relates to a method for preparing m-aminobenzenesulfonic acid by catalytic hydrogenation. Background technique [0002] Aminobenzenesulfonic acid is an important chemical intermediate, widely used in the production of dyes, medicines, pesticides, developers and other industries. Industrially, the traditional methods for preparing sulfanilic acid are iron powder reduction method and electrolytic synthesis of sulfanilic acid, but these methods are replaced by catalytic hydrogenation method because of heavy pollution or cannot be recycled. [0003] Literature [Application of Modified Skeleton Nickel Catalyst in 3NBSA Hydrogenation to Prepare M-Sulphonic Acid, Shen Xiaofeng, Journal of Shenyang Institute of Chemical Technology, 2007(12), 21(4): 276-278] and [Liquid Phase Catalytic Hydrogenation Method Synthesis of 2-aminobenzenesulfonic acid, Yan Xinhuan et al., Dyestuff Indus...

Claims

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Application Information

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IPC IPC(8): C07C309/46C07C303/22
CPCY02P20/584
Inventor 白雪松李付刚
Owner 中国中化股份有限公司
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