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Method for preparing o-phenylenediamine and derivative of o-phenylenediamine

A technology of o-phenylenediamine and derivatives, which is applied in the field of synthesis of organic compounds, can solve the problems of difficult purification of by-products, harsh reaction conditions, complex process routes, etc., achieve simple routes, low equipment requirements, and avoid waste acid pollution Effect

Active Publication Date: 2015-01-07
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problems in the current method for synthesizing o-phenylenediamine and its derivatives such as complex process route, many by-products that are difficult to purify, harsh reaction conditions and serious environmental pollution, the present invention proposes a method for producing o-phenylenediamine and its derivatives The preparation method, the synthesis method of the present invention has the advantages of cheap and easy-to-obtain raw materials, simple and safe operation, short synthesis steps, simple purification, and no large amount of waste acid pollution.

Method used

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  • Method for preparing o-phenylenediamine and derivative of o-phenylenediamine
  • Method for preparing o-phenylenediamine and derivative of o-phenylenediamine
  • Method for preparing o-phenylenediamine and derivative of o-phenylenediamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 54.6 mg (0.3 mmol) azobenzene, 6.7 mg (0.03 mmol) palladium acetate, 92.3 mg (0.6 mmol) silver nitrite, 162.2 mg (0.6 mmol) potassium persulfate, 3.5 mL DCE into a closed reaction vessel , the reaction mixture was stirred and reacted at 110° C. for 72 hours. After the reaction stopped, cool to room temperature, add 10 mL of dichloromethane to the reaction solution, remove the solvent after suction filtration under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel (100-200 mesh); eluent was V (petroleum ether) / V(ethyl acetate)=6 / 1] separation and purification to obtain reddish-brown solid 2-nitroazobenzene with a yield of 95%. 2-Nitroazobenzene (0.3 mmol), zinc powder (0.36 mmol), and formic acid (2 mL) were mixed and reacted in methanol solvent under nitrogen atmosphere for 24 hours at room temperature to obtain o-benzene with a yield of 88%. diamine.

[0026]

[0027] mp 102-104 oC; IR (neat): n = 3352 (NH2) cm -1 ; 1H...

Embodiment 2

[0029] Add 54.6 mg (0.3 mmol) of azobenzene, 0.03 mmol of palladium chloride, 0.6 mmol of potassium nitrite, 0.6 mmol of ceric ammonium nitrate, 3.5 mL of DCE into a closed reaction vessel, and stir the reaction mixture at 110°C for 48 Hour. After the reaction stopped, cool to room temperature, add 10 mL of dichloromethane to the reaction solution, remove the solvent after suction filtration under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel (100-200 mesh); eluent was V (petroleum ether) / V(ethyl acetate)=6 / 1] separation and purification to obtain reddish-brown solid 2-nitroazobenzene with a yield of 70%. 2-Nitroazobenzene (0.3 mmol), zinc powder (0.45 mol), and formic acid (3 mL) were mixed and reacted in a methanol solvent under nitrogen at room temperature for 24 hours to obtain o-benzene with a yield of 80%. diamine.

[0030]

[0031] mp 102-104 oC; IR (neat): n = 3352 (NH2) cm -1 ; 1H NMR (CDCl3, 500 MHz): δ 6.76-6.72 (m,...

Embodiment 3

[0033] Add 0.3 mmol of azobenzene, 0.03 mmol of diacetonitrile palladium dichloride, 0.6 mmol of sodium nitrite, 0.6 mmol of potassium persulfate, 3.5 mL of DCE into a closed reaction vessel, and stir the reaction mixture at 110°C for 72 hours . After the reaction stopped, cool to room temperature, add 10 mL of dichloromethane to the reaction solution, remove the solvent after suction filtration under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel (100-200 mesh); eluent was V (petroleum ether) / V(ethyl acetate)=6 / 1] separation and purification to obtain reddish-brown solid 2-nitroazobenzene with a yield of 56%. 2-Nitroazobenzene (0.3 mmol), zinc powder (0.36 mol), and formic acid (2 mL) were mixed and reacted in methanol solvent under nitrogen at room temperature for 24 hours to obtain o-benzene with a yield of 88%. diamine.

[0034]

[0035] mp 102-104 oC; IR (neat): n = 3352 (NH2) cm -1 ; 1H NMR (CDCl3, 500 MHz): δ 6.76-6.72 (...

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Abstract

The invention relates to a method for synthesizing organic compounds, and provides a method for preparing o-phenylenediamine and a derivative of o-phenylenediamine, for solving the problems that the process route is complex, a great amount of byproducts can be generated and are hard to purify, the reaction condition is rigorous, the environment pollution is severe and the like in a conventional method for synthesizing o-phenylenediamine derivatives. The method disclosed by the invention comprises the following steps: by taking azobenzene and a derivative of the azobenzene as raw materials, synthesizing the o-nitro azobenzene and the derivative of the o-nitro azobenzene under the coactions of a catalyst, an oxidant and a nitrating agent, and further reducing by using a reducing agent, thereby obtaining the o-phenylenediamine and the derivative of the o-phenylenediamine. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, convenient and safe, the synthesis steps are short, the purification is simple, no great waste acid pollution is caused, and the like.

Description

technical field [0001] The invention specifically relates to a method for synthesizing organic compounds, in particular to a method for preparing o-phenylenediamine using azobenzene as a raw material, which is first nitrated and then reduced. Background technique [0002] O-phenylenediamine derivatives are an important class of organic synthesis and fine chemical intermediates, mainly used in the production of benzimidazole fungicides, such as the prevention and treatment of bacterial diseases of various crops, trees, fruits and vegetables, as well as the preservation and storage of fruits and vegetables Carbendazim and thiophanate-methyl, etc. In addition, o-phenylenediamine derivatives are used as dye intermediates for the preparation of vat dyes and cationic dyes, and the production of fur yellow brown M, cationic dyes, vat red GG, vat brilliant Orange Gr. It is also used in the manufacture of polyamide, polyurethane and leveling agent. [0003] At present, the domestic...

Claims

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Application Information

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IPC IPC(8): C07C209/42C07C211/51
Inventor 刘运奎张巍崔建海
Owner HUAWEI TEHCHNOLOGIES CO LTD
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