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Application of rhodium monatomic catalyst in reaction for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene

A chloronitrobenzene and catalyst technology, which is applied in the preparation of amino compounds, the preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve problems such as catalyst stability enhancement and dechlorination, and achieve superior catalytic activity, dechlorination side effects. Effects of reduced reaction and mild reaction conditions

Inactive Publication Date: 2021-05-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] On the other hand, the dechlorination is inhibited by the modification of the prepared alloy catalyst. Mahata et al. added metal Cu to the Pt / AC catalyst to catalyze the selective hydrogenation of p-chloronitrobenzene, and found that the addition of Cu to the Pt / AC catalyst After that, its catalytic activity remained basically unchanged, but the selectivity of p-chloroaniline was greatly improved (>99%), and the stability of the catalyst was obviously strengthened. The only disadvantage was that there was still dechlorination

Method used

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  • Application of rhodium monatomic catalyst in reaction for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene
  • Application of rhodium monatomic catalyst in reaction for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene
  • Application of rhodium monatomic catalyst in reaction for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Single atom 0.1wt% Rh-Al 2 o 3 Preparation of -C catalyst

[0033] Weigh 5.2g of aluminum nitrate nonahydrate and dissolve it in 20mL of water, and add 1.152g of terephthalic acid to it, add 0.8mL of RhCl 3 solution (10mg Rh / mL), ultrasonicated for 10min, transferred to a 50mL hydrothermal reactor, placed in a temperature-programmed oven, set the heating rate at 1°C / min, heated at 220°C for 72h, and then slowly lowered to room temperature , filter, H 2 O. Wash with ethanol three times, and then put the sample into a 60°C oven to dry to obtain the Rh-MIL-53(Al) material. After grinding, the Rh-MIL-53(Al) sample was transferred into a tube furnace, raised to a pyrolysis temperature of 600 °C at a heating rate of 5 °C / min, and pyrolyzed for 5 h in a nitrogen atmosphere. After natural cooling, it was obtained Rh-Al 2 o 3 -C precursor. Subsequently, the dried precursor was transferred into a tube furnace under 10% H 2 / Ar atmosphere at 300 ℃ for reduction, the heatin...

Embodiment 2

[0044] The monoatomic 0.1wt% Rh-Al prepared in the above example 1 2 o 3 -C catalyst is used to catalyze the selective hydrogenation of m-chloronitrobenzene to prepare m-chloroaniline reaction. First, take 78.78mg m-chloronitrobenzene, 30mg catalyst and 2mL toluene in a 10mL autoclave at room temperature, and feed N 2 Replace 3 times, then pass H 2 Replace 3 times, let H 2 The pressure is 2Mpa. Put the reaction kettle into the water bath, turn on the stirring, and start the reaction when the temperature of the water bath rises to 40°C. After reacting for 3 hours, cool down, take an appropriate amount of the reaction solution and centrifuge it for gas chromatography analysis.

Embodiment 3

[0046] Catalytic reaction performance comparison

[0047] The 0.1wt%Rh-Al prepared in Example 1 of the present invention 2 o 3 -C, 0.1wt% Rh / γ-Al prepared in Comparative Example 1 2 o 3 Compared with the reaction performance of the 0.1wt%Rh / C catalyst prepared in Comparative Example 2 to catalyze the selective hydrogenation of m-chloronitrobenzene to prepare m-chloroaniline, see Table 1. Reaction condition is with embodiment 4.

[0048] Catalytic reaction performance comparison of different catalysts in table 1

[0049]

[0050] As can be seen from Table 1 ("-" means not detected), the monoatomic 0.1wt% Rh-Al prepared in Example 1 of the present invention 2 o 3 The -C catalyst has the highest reactivity and selectivity to m-chloroaniline.

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Abstract

The invention provides application of a rhodium monatomic catalyst in preparation of m-chloroaniline through selective hydrogenation of m-chloronitrobenzene, wherein the conversion rate and the selectivity of m-chloroaniline can reach 99% or above under mild conditions. The catalyst is composed of a carrier with MOF as a precursor and an active component loaded on the carrier, wherein the active component is precious metal rhodium. According to the invention, the reaction system is simple, the reaction conditions are mild, and the catalyst and the solvent are easy to separate and recover; and the rhodium monatomic catalyst provided by the invention is novel in structure, metal is uniformly dispersed on the carrier, and the rhodium monatomic catalyst has relatively high reaction rate and good stability when being applied to a reaction for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene, and has wide application in the field of utilization for preparing m-chloroaniline through selective hydrogenation of m-chloronitrobenzene.

Description

technical field [0001] The invention relates to the field of catalytic hydrogenation, in particular to the application of a rhodium single atom (SAC) catalyst in the selective hydrogenation of m-chloronitrobenzene to prepare m-chloroaniline. Background technique [0002] m-Chloroaniline is an important class of organic intermediates, mainly used in the synthesis of pesticides, dyes, pharmaceuticals and other chemical products. In industry, m-chloroaniline is generally prepared by reduction of m-chloronitrobenzene. At present, the methods for m-chloronitrobenzene reduction to m-chloroaniline mainly include iron powder reduction method, electrochemical reduction method, alkali sulfide reduction method, catalytic addition Hydrogen reduction method, etc., the first three methods will produce a large amount of industrial waste liquid in the production process, which seriously pollutes the environment and tends to be eliminated, while catalytic hydrogenation reduction method has t...

Claims

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Application Information

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IPC IPC(8): B01J23/46C07C209/36C07C211/52
CPCB01J23/464C07C209/365C07C211/52
Inventor 罗文豪王伟银林露王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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