Method for synthesizing 1-nitroanthraquinone by nitration of nitrogen pentoxide

A technology of dinitrogen pentoxide and nitroanthraquinone is applied in the field of dye intermediates, which can solve problems such as environmental pollution, and achieve the effects of cost reduction, less three wastes and good selectivity

Active Publication Date: 2015-04-08
NANJING UNIV OF SCI & TECH
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Problems solved by technology

[0005] In the above-mentioned method of nitrating and synthesizing 1-nitroanthraquinone with nitric acid mixed acid as a nitrating agent, not only a large amount of waste acid will be produced, but also a large amount of waste residue will be produced in the refining process, causing serious environmental pollution
In the new green Kyodai nitration system, although the yield and selectivity are high, the choice of catalyst is the main factor limiting the practical application of this method

Method used

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  • Method for synthesizing 1-nitroanthraquinone by nitration of nitrogen pentoxide
  • Method for synthesizing 1-nitroanthraquinone by nitration of nitrogen pentoxide

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preparation example Construction

[0016] The preparation process of 1-nitroanthraquinone of the present invention is as figure 1 As shown, the equation is as follows:

[0017]

Embodiment 1

[0019] Step 1. Nitrification process:

[0020] Weigh 4.16 g (0.02 mol) of anthraquinone into a four-necked flask, add 0.48 g (0.005 mol) of methanesulfonic acid, measure 50 mL of dichloromethane and pour it into the four-necked flask, and stir Add 3.24 g (0.03 mol) of dinitrogen pentoxide, and stir the reaction at 0 °C for 1.0 h. After the reaction, neutralize with saturated aqueous sodium bicarbonate solution to pH 6~8, add a small amount of water to wash, distill off the organic solvent, filter with suction, and dry the filter cake to obtain the nitrated compound of anthraquinone, which is determined by liquid phase. The content of base anthraquinone is 86%.

[0021] Step 2. The refining of 1-nitroanthraquinone:

[0022] Weigh 2.5 g of the solid obtained in step 1, place it in a 50 mL four-neck flask, add 5 mL of N,N-dimethylformamide and 0.03 g of urea (the amount is 1.2% of the mass of nitroanthraquinone), Stir, heat to 90 °C, react for 4.0 h, cool naturally, precipitat...

Embodiment 2

[0024] Step 1. Nitrification process:

[0025] Weigh 4.16 g (0.02 mol) of anthraquinone into a four-necked flask, add 0.54 g (0.004 mol) of ferric chloride, measure 50 mL of dichloromethane and pour it into the four-necked flask, and stir Add 3.24 g (0.03 mol) of dinitrogen pentoxide, and stir the reaction at -10 °C for 2.0 h. After the reaction, neutralize with saturated aqueous sodium bicarbonate solution to pH 6~8, add a small amount of water to wash, distill off the organic solvent, filter with suction, and dry the filter cake to obtain the nitrated compound of anthraquinone, which is determined by liquid phase. The content of base anthraquinone is 80%.

[0026] Step 2. The refining of 1-nitroanthraquinone:

[0027] Weigh 2.5 g of the solid obtained in step 1, place it in a 50 mL four-neck flask, add 5 mL of N,N-dimethylformamide and 0.03 g of urea (the amount is 1.2% of the mass of nitroanthraquinone), Stir, heat to 90 °C, react for 4.0 h, cool naturally, precipitate a...

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Abstract

The invention discloses a method for synthesizing 1-nitroanthraquinone by nitration of nitrogen pentoxide. According to the method, nitrogen pentoxide serves as a catalyst to nitrate anthraquinone to synthesize 1-nitroanthraquinone, and the content of 1-nitroanthraquinone in obtained nitride reaches above 85%. N2O5 in the method is a novel green nitration agent. An N2O5 / organic solvent body is a mild nitration system and has the characteristics of mild reaction conditions, high reaction rate, reaction in a non-acid medium, good selectivity, high yield, little waste gas, waste water and industrial residue, and the like. The method is high in yield, the purity of prepared 1-nitroanthraquinone is greater than 96%, and the preparation method has a good industrial production value.

Description

technical field [0001] The invention relates to a dye intermediate, in particular to a method for synthesizing 1-nitroanthraquinone by using dinitrogen pentoxide green nitrating agent to nitrate anthraquinone. Background technique [0002] 1-Nitroanthraquinone is one of the most important anthraquinone derivatives, which is mainly used in the synthesis of 1-aminoanthraquinone bromine for the manufacture of vat dyes and reactive dyes. At present, the focus is still on the direct nitration method of anthraquinone. Anthraquinone obtained by nitration is a relatively complex mixture containing 1-nitroanthraquinone, 2-nitroanthraquinone, 1,5-dinitroanthraquinone and 1,8-dinitroanthraquinone and not involved in Reactive anthraquinone and other components. [0003] The preparation method of 1-nitroanthraquinone developed from the pure nitric acid nitration method in the 1930s and 1940s to the nitric acid mixed acid nitration method in the 1970s and 1980s, and then to the indu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/47C07C201/08C07C201/16
Inventor 罗军魏紫霄杨艳
Owner NANJING UNIV OF SCI & TECH
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