Method for preparing high-purity 1-aminoanthraquinone through catalytic hydrogenation

A technology of aminoanthraquinone and nitroanthraquinone, which is applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of no industrial value and high cost, and achieve good industrial value and solvent use. The effect of less quantity, low equipment requirements and low production cost

Active Publication Date: 2012-07-04
JIANGSU YABANG DYE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there are some green processes, such as hydrazine hydrate method, naphthoquinone method and electrochemical method to synthesize 1-aminoanthraquinone, but these methods have no industrial value due to their high cost.

Method used

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  • Method for preparing high-purity 1-aminoanthraquinone through catalytic hydrogenation
  • Method for preparing high-purity 1-aminoanthraquinone through catalytic hydrogenation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Insert electromagnetic stirring into a 2L normal-pressure hydrogenation glass reactor, and add 100 g of 1-nitroanthraquinone with a purity of 99.0%, 600 g of N, N-dimethylformamide (DMF), 3% palladium / Carbon catalyst 5.0g, feed hydrogen into the system, carry out hydrogenation reaction at room temperature. After 3 hours of hydrogenation (according to theoretical calculation, the amount of hydrogen intake is 1.18 mol), the flow of hydrogen was stopped. After the reducing solution was filtered to remove the catalyst, it was stirred in the air for 1 h, and placed in a freezer for 4 h to crystallize. Then the crystals precipitated from the reducing solution were filtered, weighed 63.5 g after drying, and its purity was detected by liquid chromatography. The content of 1-aminoanthraquinone was 99.4%. Apply the mother liquor and the catalyst mechanically, add 80 g of 1-nitroanthraquinone, repeat the above reaction and post-treatment process, and carry out liquid chromatogra...

Embodiment 2

[0020] In a 2L electromagnetically stirred hydrogenation pressure reactor, add 240g of 1-nitroanthraquinone with a purity of 99.0%, 600g of N,N-dimethylformamide (DMF), and 18.0g of Raney Ni catalyst, and pass through the system Inject hydrogen, and carry out hydrogenation reaction at 65°C. After 4 hours of hydrogenation, hydrogen flow was stopped. After the reducing solution was filtered to remove the catalyst, it was stirred in the air for 1 h and then stood at room temperature for 8 h to crystallize. Then the crystals precipitated from the reducing solution were filtered, dried and weighed to be 158g. The purity was detected by liquid chromatography, and the content of 1-aminoanthraquinone was 99.4%. Apply the mother liquor and catalyst mechanically, add 180g of 1-nitroanthraquinone, repeat the above reaction and post-treatment process (wherein, 3.0g of catalyst is added when applying mechanically for the seventh time), and carry out liquid phase analysis for each precipit...

Embodiment 3

[0022] In a 2L electromagnetically stirred hydrogenation pressure reactor, add 240g of 1-nitroanthraquinone with a purity of 99.0%, 500g of N,N-dimethylformamide (DMF), 300g of xylene, and 18.0g of Raney Ni catalyst, Introduce hydrogen into the system to carry out hydrogenation reaction at 80°C. After 3 hours of hydrogenation, hydrogen flow was stopped. After the reducing solution was filtered to remove the catalyst, it was stirred in the air for 1 h and then stood at room temperature for 6 h to crystallize. Then the crystals precipitated from the reducing solution were filtered, weighed 179g after drying, and its purity was detected by liquid chromatography. The content of 1-aminoanthraquinone was 99.5%. Apply the mother liquor and catalyst mechanically, add 204g of 1-nitroanthraquinone, repeat the above reaction and post-treatment process, and perform liquid chromatography detection on each precipitated crystal obtained by applying mechanically 8 times, and the content of 1...

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Abstract

The invention discloses a method for producing high-purity 1-aminoanthraquinone through catalytic hydrogenation. The method has the advantages of simple equipment, safe operation, low production cost and no pollution. The method comprises the following steps of: preforming hydrogenation on 1-nitroanthraquinone and a solvent in the presence of a catalyst in a reactor, filtering off the catalyst, stirring or standing a reducing solution in an oxidant, and obtaining 1-aminoanthraquinone through oxidation of a small amount of perhydrogenation product in the reducing solution to promote solution oversaturation to realize homogeneous crystallization, so that the high-purity 1-aminoanthraquinone is obtained; and continuously applying a motor solution of which crystals are filtered off, and the catalyst mechanically, and after multiple mechanical application, adding a diluent into the reducing solution to obtain 1-aminoanthraquinone crystals, wherein in the catalytic hydrogenation reaction, a weight ratio of the solvent to the 1-nitroanthraquinone is (1.0-10.0):1, and the reaction temperature ranges from normal temperature to 120DEG C. The purity of the obtained 1-aminoanthraquinone is over 99 percent, the total yield in the process is over 98 percent, and in the production process, the consumption of the solvent is low, three-waste emission is avoided, and the production process is clean.

Description

technical field [0001] The invention relates to a production process of a type of aromatic organic amine, in particular to a catalytic hydrogenation production process of a chemical intermediate 1-aminoanthraquinone. Background technique [0002] Anthraquinone dyes are the second largest category of dyes next to azo dyes, and 1-aminoanthraquinone is an important intermediate for the synthesis of anthraquinone dyes. It has the widest application and the largest consumption. The main raw material of acid and pyrazole anthraquinone occupies an extremely important position in the dye industry. With the increasing demand for 1-aminoanthraquinone, the output of low-quality 1-aminoanthraquinone in the domestic market has exceeded the demand, while the output of high-quality products is far from meeting the needs of export. In recent years, due to the "three wastes" and other reasons, the production of anthraquinone-based intermediates, anthraquinone-based vat and disperse dyes has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/36B01J23/44B01J25/02
Inventor 辛阳郑冬松贾树勇侯春燕马素琴王公应冯良荣
Owner JIANGSU YABANG DYE
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