Method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene

A technology for o-dichlorobenzene and o-phenylenediamine, which is applied in the field of synthesizing o-phenylenediamine, can solve the problems of increased equipment investment, potential safety hazards, long reaction time, etc., so as to improve reaction efficiency and reaction yield, and reduce reaction time. Difficulty, the effect of promoting the reaction process

Active Publication Date: 2015-11-11
江阴市华亚化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The process route is relatively mature, but the disadvantages are: the reaction time of the kettle-type ammonium solution is long, the high temperatur...

Method used

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  • Method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene
  • Method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene
  • Method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In a 1L autoclave, add 100g of o-dichlorobenzene, 2g of cuprous iodide, 0.5g of triphenylphosphine and 200g of liquid ammonia, control the reaction temperature at 85-100°C, and the reaction pressure at 5-7MPa. After 6 hours of reaction, Then, the oil phase was separated at 100° C., and 66.9 g of white o-phenylenediamine was obtained by vacuum distillation, with a yield of 90.5% and a purity of 99.3% (GC). The combination of cuprous iodide and triphenylphosphine forms copper diamine (I) and copper triamine (I) complexes with higher activity, lower reaction enthalpy, mild reaction conditions, and increased yield. The product is less, and the purity of the product is high.

Embodiment 2

[0024] In a 1L autoclave, add 100g of o-dichlorobenzene, 5g of cuprous iodide, 4g of triphenylphosphine and 200g of liquid ammonia, control the reaction temperature at 85-100°C, and the reaction pressure at 5-6MPa. After reacting for 10 hours, The oil phase was separated at 90° C., and 68.0 g of white o-phenylenediamine was obtained by vacuum distillation, with a yield of 92% and a purity of 99.0% (GC).

Embodiment 3

[0026] In a 1L autoclave, add 100g of o-dichlorobenzene, 3g of cuprous iodide, 1g of triphenylphosphine and 200g of liquid ammonia, control the reaction temperature at 85-100°C, and the reaction pressure at 5-6MPa. After reacting for 10 hours, then The oil phase was separated at 90° C., and 68.0 g of white o-phenylenediamine was obtained by vacuum distillation, with a yield of 92% and a purity of 99.1% (GC).

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Abstract

The invention relates to a method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene. The method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene comprises the following steps: putting orthodichlorobenzene, a copper catalyst and a ligand into an autoclave according to a molar ratio of 1:(0.25-5%):(0.25-5%), and then adding liquid ammonia or ammonia water into the autoclave, wherein the molar ratio of the added liquid ammonia or ammonia water to orthodichlorobenzene is (2-20):1; reacting for 2-36 hours while the reaction temperature is controlled to be 20-300 DEG C and the reaction pressure is controlled to be 1-10MPa; and finally, discharging while the inner temperature is controlled to be 90-100 DEG C, transferring into a distillation still, and carrying out vacuum distillation, so that white o-phenylenediamine is obtained. The method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene has the advantages that orthodichlorobenzene is taken as a raw material, direct amination is carried out to obtain o-phenylenediamine, a high power-supply ligand is adopted for improving the activity of the copper catalyst, the reaction difficulty is reduced, reaction conditions are mild, the reaction efficiency and reaction yield are obviously improved, and thus the method is applicable to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing o-phenylenediamine with o-dichlorobenzene as the main raw material. Background technique [0002] O-phenylenediamine is an important organic chemical intermediate. In addition to being used in the production of dyes, it is also the main raw material for systemic fungicides such as pesticides carbendazim, benomyl, and (methyl) thiophanate. It is also a developer , Leveling agent and surfactant, etc. are important raw materials. [0003] At present, there are several routes for the synthesis of o-phenylenediamine, and two of the more important routes are as follows: [0004] First, patent CN102633653 reports a method for producing o-phenylenediamine by catalytic hydrogenation of o-nitroaniline, using o-nitroaniline as a raw material, alcohol as a solvent, and nickel as a catalyst. Under a hydrogen pressure of 1 to 6 MPa, 40 At a temperature of ~80°C, the reduction reaction is carried out for 2 to 10 ho...

Claims

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Application Information

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IPC IPC(8): C07C211/51C07C209/10
Inventor 谭建新马牧
Owner 江阴市华亚化工有限公司
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