Synthetic process for amino aromatic hydrocarbon compound

A technology of aromatic compounds and aminoaromatics, which is applied in the field of synthesis of aminoaromatic compounds, can solve the problems of producing highly toxic nitrogen oxides, spending a lot of money to recover nitric acid, endangering biological health, etc., achieving fast speed, improving purity and yield , the effect of high industrial safety

Inactive Publication Date: 2015-08-19
ANHUI SHENGYUAN CHEM
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0006] This process has the advantages of reliable process conditions and stable product quality, but objectively existing problems limit or even stop the existence and development of this type of old process: (1) in the nitration reaction process, the amount of nitric acid is often large, and the reaction ends. It takes a lot of energy and expense to recycle the nitric acid before concentrating the waste acid, which will produce highly toxic nitrogen oxides, pollute the air, and endanger the health of organisms; (2) The iron powder used in the iron powder reduction process is greatly excessive. Hot water washes the aminoaromatic compound (III) adhering to the iron sludge, and the amount of iron sludge and waste water is very large, which is very serious to environmental pollution. At present, this kind of high energy consumption, large amount of solid waste and waste water, and very serious environmental pollution The reduction method has been clearly listed as an elimination or immediate elimination process by the national industrial policy, and all domestic manufacturers who use the iron powder reduction method are ordered to stop production and develop a new low-energy, high-environmental nitro reduction process that can replace the iron powder reduction method

Method used

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  • Synthetic process for amino aromatic hydrocarbon compound
  • Synthetic process for amino aromatic hydrocarbon compound
  • Synthetic process for amino aromatic hydrocarbon compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Preparation of nitration reaction solution:

[0049] Reaction solution-1: Weigh 78g of benzene as reaction solution-1;

[0050] Reaction solution-2: Weigh 96.9g (65%) of nitric acid and 78.8g (98%) of concentrated sulfuric acid and mix, keep the temperature of the mixing process not exceeding 15°C, and use it as reaction solution-2;

[0051] (2) Synthesis of nitrobenzene:

[0052] Keep the temperature of the micro-reactor at 20°C, add the reaction solution-1 and the reaction solution-2 into the micro-reactor through the syringe pumps-1 and -2 respectively, the flow rate of the reaction solution-1 is 20mL / min, the flow rate of the reaction solution-2 The flow rate is 22 mL / min, and at this time, the molar ratio of nitric acid to benzene added is 1.05:1. After the reaction was complete, 236g of water was added and filtered to obtain 113.2g of nitrobenzene product. The nuclear magnetic resonance spectrum data of described nitrobenzene compound is as: 1 HNMR (500MHz...

Embodiment 2

[0058] (1) Preparation of nitration reaction solution:

[0059] Reaction solution-1: weigh 165g of p-acetamidoanisole and mix with 825g (98%) concentrated sulfuric acid as reaction solution-1;

[0060] Reaction solution-2: Weigh 67.0g (95%) nitric acid as reaction solution-2;

[0061] (2) Synthesis of 2-nitro-4-acetamidoanisole:

[0062] Keep the temperature of the microreactor at 50°C, and add the reaction solution-1 and the reaction solution-2 into the microreactor through the syringe pumps-1 and -2 respectively, the flow rate of the reaction solution-1 is 10mL / min, and the flow rate of the reaction solution-2 The flow rate is 95mL / min, at this time, the molar ratio of nitric acid to benzene added is 1.01:1. After the reaction was completed, 3300 g of water was added and filtered to obtain 205.8 g of 2-nitro-4-acetamidoanisole product. The NMR spectrum data of the 2-nitro-4-acetamidoanisole compound are as follows: 1 HNMR (500MHz, CDCl 3 ): δ1.62(s,2H), 4.20(s,3H), 7.42...

Embodiment 3

[0068] Reaction solution-1: Weigh 108g of anisole as reaction solution-1;

[0069] Reaction solution-2: Weigh 63g (95%) nitric acid and 108g (98%) concentrated sulfuric acid and mix, keep the temperature during the mixing process not exceeding 15°C, and use it as reaction solution-2;

[0070] (2) Synthesis of nitroanisole:

[0071] The temperature of the microreactor was kept at 10°C, and the reaction solution-1 and the reaction solution-2 were added to the microreactor through the syringe pumps-1 and -2 respectively. The flow rate of the reaction solution-1 was 10mL / min, and the flow rate of the reaction solution-2 was The flow rate was 9.5mL / min. At this time, the molar ratio of nitric acid and anisole was 1:1. After the reaction was completed, 324g of water was added and filtered to obtain 150g of mixed nitroanisole product.

[0072] (3) Preparation of reduction reaction solution

[0073] Reaction solution-3: Mix 150g of mixed nitroanisole obtained in the previous step wi...

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Abstract

The invention discloses a synthetic process for an amino aromatic hydrocarbon compound. The process comprises the following steps: pre-preparing reaction solutions -1 and -2 by using an aromatic hydrocarbon compound (I), concentrated sulphuric acid and concentrated nitric acid, respectively pumping the solutions in a micro reactor, heating to react, cooling the reaction liquid, and pos-treating to obtain a nitryl aromatic hydrocarbon compound (II); mixing the nitryl aromatic hydrocarbon compound (II), a catalyst and a solvent as a reaction solution -3; respectively pumping the reaction solution -3 and hydrogen into the micro reactor, heating to react, cooling the reaction liquid and post-treating to obtain the amino aromatic hydrocarbon compound (III). The process disclosed by the invention is less in use level of nitric acid, convenient to concentrate and apply waste acid; in the nitrification reaction process, the heat release is little, and the nitration product nitryl aromatic hydrocarbon compound (II) is quickly transferred. The reaction phenomenon is stable without intense heat release and even material punching of a common kettle nitration reaction, so that the safety of nitration reaction is improved; the process is easy to realize industrialization, simple to operate and high in industrial safety degree and meets the environmental requirements.

Description

technical field [0001] The invention relates to a preparation method of organic compounds, in particular to a synthesis process of aminoaromatic compounds. Background technique [0002] Aminoaromatic compound (III) is a class of organic synthesis intermediates, and has a wide range of applications in the fields of dyes, pesticides, medicines, and fragrances. One of the main intermediates for the synthesis of disperse blue dyes, p-aminobenzenesulfonic acid is a synthetic reactive dye p-(β-sulfate ethyl sulfone) aniline (commonly known as "reduced product"), o-aminotoluene can be used to synthesize dinitromethanol, etc. Wait. Studying the synthesis methods of these compounds and developing new processes with high efficiency, low energy consumption and environmental protection are of great significance for national chemical production and global environmental protection. [0003] The technology currently used in the industrialized large-scale production of aminoaromatic compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/46C07C211/47C07C211/52C07C209/36C07C233/43C07C231/12C07C217/84C07C215/76C07C213/02
CPCY02P20/584
Inventor 韩君邱宇飞邵玉田
Owner ANHUI SHENGYUAN CHEM
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