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A kind of method utilizing the directional chlorination of benzene to synthesize m-dichlorobenzene and trichlorobenzene

A technology for m-dichlorobenzene and mestrichlorobenzene, which is applied in chemical instruments and methods, hydrocarbons, hydrocarbons, etc., can solve the problems of complicated separation process, difficulty in realizing large-scale production of mestrichlorobenzene, etc. Simple and convenient process, reducing the production of chemical pollutants, and having the effect of atom economy

Active Publication Date: 2020-06-09
JIANGSU YANGNONG CHEM GROUP +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method mainly uses the non-toxic body of HCH (hexachlorocyclohexane) as a raw material, and performs pyrolysis or alkaline hydrolysis to synthesize s-trichlorobenzene. Using these two methods, the obtained trichlorobenzene is 1,2,4- A mixture of three isomers of trichlorobenzene, 1,3,5-trichlorobenzene, and 1,2,3-trichlorobenzene, with 1,2,4-trichlorobenzene as the main component, 1,2, 3-Trichlorobenzene is only about 20%, and the separation process of the three components is complicated, and there is also the problem that it is difficult to achieve large-scale production of 3-Trichlorobenzene
[0008] Both m-dichlorobenzene and m-trichlorobenzene are products with higher added value in the series of polychlorobenzene products. However, the process route for the highly selective synthesis of m-dichlorobenzene and the by-product of high value-added m-trichlorobenzene has not yet been established. It has been reported that the ratio of m-dichlorobenzene and trichlorobenzene can be easily adjusted by controlling the depth of the chlorination reaction by using a highly selective chlorination process, which is of great significance

Method used

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  • A kind of method utilizing the directional chlorination of benzene to synthesize m-dichlorobenzene and trichlorobenzene
  • A kind of method utilizing the directional chlorination of benzene to synthesize m-dichlorobenzene and trichlorobenzene
  • A kind of method utilizing the directional chlorination of benzene to synthesize m-dichlorobenzene and trichlorobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Alkylation reaction: Add 100.0g of benzene and 948.1g of tert-butyl chloride into a 2000mL four-necked flask, stir thoroughly for 0.5h, cool down to -15°C, then add 17g of aluminum trichloride in batches within two hours, and At this temperature, the reaction was continued for 10 h. Subsequently, dilute hydrochloric acid was added to wash and remove the inorganic salts in the system. The resulting oil layer was distilled to recover 545.1 g of tert-butyl chloride to obtain 301.3 g of tri-tert-butylbenzene with a content of 98.6%.

[0027] Chlorination reaction: Add 301.3g of tri-tert-butylbenzene and 600g of chloroform into a 2000mL four-necked flask, then add 16.2g of aluminum trichloride and 22.7g of diphenyl sulfide, stir thoroughly for 0.5 hours, control the system temperature at 20°C, Chlorine gas 25g / h was introduced, and chlorine gas was continuously passed for 5.5h. Subsequently, dilute hydrochloric acid was added to wash and remove inorganic salts in the system,...

Embodiment 2-5

[0030] On the basis of Example 1, in the alkylation reaction part, different alkylating reagents were used (the number of moles was constant), and other conditions were constant. The obtained results are shown in Table 1.

[0031] Table 1 The influence of different alkylation reagents (alkylation reaction part) on the product yield

[0032]

[0033]

Embodiment 6-9

[0035] On the basis of Example 1, the chlorination reaction part adopts different catalyst systems, and other conditions remain unchanged. The obtained results are shown in Table 2.

[0036] Table 2 The influence of different catalyst systems (chlorination reaction part) on product yield

[0037]

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Abstract

The invention relates to a method for synthesizing m-dichlorobenzene and sym-trichlorobenzene by using directional chlorination of benzene; the method comprises the synthesis steps: with benzene as a raw material, carrying out alkylation, chlorination, dealkylation and other reactions, and directionally synthesizing m-dichlorobenzene and high-added-value sym-trichlorobenzene, wherein the product yield reaches 80% or more. The method solves the problem of poor selectivity of a conventional m-dichlorobenzene and sym-trichlorobenzene synthesis process, and the process has the advantages of convenient raw material sources, high product selectivity and simple and convenient process.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, in particular to a method for synthesizing m-dichlorobenzene and mes-trichlorobenzene by directional chlorination of benzene. Background technique [0002] m-Dichlorobenzene (CAS: 541-73-1) is an important raw material for organic synthesis. It is the raw material for the fungicides imazalil, propiconazole, and etoconazole, and is also the raw material for the insecticide dimeconazole. The currently disclosed preparation methods include the following: [0003] a. Using chlorobenzene as a raw material, after chlorination, p-dichlorobenzene, o-dichlorobenzene and m-dichlorobenzene are obtained, and after purification and separation, m-dichlorobenzene is obtained. The general separation method adopts continuous distillation of mixed dichlorobenzene, para- and meta-dichlorobenzene are distilled from the top of the tower, p-dichlorobenzene is precipitated by freezing crystallization...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/361C07C25/08C07C25/10
CPCC07C2/861C07C17/12C07C17/361C07C25/08C07C25/10C07C25/02C07C15/02
Inventor 王根林丁克鸿王刚陆林华崔竞方殷恒志顾咸建
Owner JIANGSU YANGNONG CHEM GROUP