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Synthesis method for disperse dye intermediate

A technology of disperse dyes and synthesis methods, which is applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc. It can solve the problems of large amount of three wastes, many by-products, and difficult temperature control, etc., and achieves obvious technological advantages. The effect of high conversion rate of hydrogen reduction and few side reactions

Inactive Publication Date: 2018-08-24
JIANGSU DAOBO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Adopt the 1st route to prepare 3-amino-4-methoxyacetanilide, although this route is mature in technology and stable in quality, the price of 2,4-dinitrochlorobenzene is high, and the preparation cost of the product is high
Using the second route to prepare 3-amino-4-methoxyacetanilide, the heat generated in the nitration reaction is large, the temperature is not easy to control, there are many by-products, and the amount of three wastes is large.

Method used

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  • Synthesis method for disperse dye intermediate
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  • Synthesis method for disperse dye intermediate

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preparation example Construction

[0032] The synthesis method described in the present invention undergoes three unit reaction processes of hydrogenation reduction, etherification and acylation, using 2,4-dinitrophenol as a raw material, using methanol as a solvent, adding a certain amount of catalyst, and introducing hydrogen to generate reduction Reaction generates 2,4-diaminophenol; The resulting 2,4-diaminophenol and methyl iodide are in the catalyst methyl tributyl methyl ammonium carbonate; Chloromethane is used as a solvent, and the acylation reaction with acetic anhydride generates the target product 3-amino-4-methoxyacetanilide. Concrete reaction steps are as follows:

[0033] 1. Hydrogenation reduction reaction: Put methanol, 2,4-dinitrophenol, and Pd / C catalyst into high pressure in turn, start stirring and record, after stirring for 5 minutes, replace the pressure vessel with nitrogen for 5 times, heat up, and open the hydrogen valve Fill the kettle with hydrogen, the reaction temperature is 60-65...

Embodiment 1

[0039] Step 1,2, the synthesis of 4-diaminophenol

[0040] In a 1000ml autoclave, put 100g of 2,4-dinitrophenol, 202ml of methanol, and 3g of Pd / C catalyst in sequence, stir at room temperature for 5 minutes, replace with nitrogen 5 times, and observe whether the autoclave is leaking, heat up, and open Hydrogen inlet valve, the reaction temperature is 60°C, the pressure in the kettle is kept at 0.35MPa for 2h, adjust the hydrogen inlet valve to make the pressure inside the kettle reach 0.85MPa, keep the temperature for 0.5h, cool down to 40°C, replace with nitrogen 3 times, put The material was suction filtered, the Pd / C catalyst was recovered, and the filtrate was protected with nitrogen for use. Target product 61g, yield 90.52%, purity 98.4%

Embodiment 2

[0042] Step 1,2, the synthesis of 4-diaminophenol

[0043] In a 1000ml autoclave, put 100g of 2,4-dinitrophenol, 316ml of methanol, and 4.5g of Pd / C catalyst in turn, stir at room temperature for 5 minutes, replace with nitrogen 5 times, and observe whether the autoclave is leaking, and then heat up. Open the hydrogen inlet valve, keep the reaction temperature at 62°C, keep the pressure in the kettle at 0.40MPa for 1.5h, adjust the hydrogen inlet valve to make the pressure in the kettle reach 0.85MPa, keep the temperature for 0.5h, cool down to 40°C, and replace with nitrogen 3 times , discharging and suction filtration, recovering the Pd / C catalyst, and the filtrate is protected with nitrogen for use. Target product 63.4g, yield 94.1%, purity 98.7%

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Abstract

The invention discloses a synthesis method for a disperse dye intermediate. The synthesis method comprises the following steps: preparing 2,4-diaminophenol through reduction reaction of 2,4-dinitrophenol and hydrogen gas; enabling 2,4-diaminophenol and iodomethane to generate etherification reaction under action of a catalyst tributyl methyl ammonium carbonate to prepare 2,4-diaminoanisole; and enabling 2,4-diaminoanisole and acetic anhydride to generate acylation reaction to prepare a target product 3-amino-4-methoxya-cetanilide. Compared with a 2,4-diaminoanisole hydrogenation reduction process, the 2,4-dinitrophenol hydrogenation reduction process is adopted, so that the conversation rate is high and the side reactions are fewer.

Description

technical field [0001] The invention relates to a method for synthesizing a disperse dye intermediate, in particular to a method for synthesizing 3-amino-4-methoxyacetanilide, which belongs to the field of organic chemistry. Background technique [0002] 3-Amino-4-methoxyacetanilide is an important intermediate in the production of disperse dyes. It can be used to synthesize disperse dyes such as disperse blue 79, disperse blue 301, and disperse violet 58. It has a large market in China. Its molecular formula is C 9 h 12 N 2 o 2 , the relative molecular mass is 180.20, and the structural formula is: [0003] [0004] There are two synthetic routes for the preparation of 3-amino-4-methoxyacetanilide: ① 2,4-dinitrochlorobenzene route: 2,4-dinitrochlorobenzene is used as the starting material, The target product was synthesized through three steps of etherification, hydrogenation reduction and acylation. ② p-aminoanisole route: using p-aminoanisole as the starting mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/43C07C231/02C07C209/36C07C215/80C07C213/06C07C217/84
CPCC07C209/36C07C213/06C07C231/02C07C215/80C07C217/84C07C233/43
Inventor 刘学峰徐松郭维成陈路云朱止阳
Owner JIANGSU DAOBO CHEM
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