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Method for synthesizing chlorinated aromatic hydrocarbon with participation of trichloroisocyanuric acid

A technology of trichloroisocyanuric acid and chlorinated aromatic hydrocarbons, which is applied to the chlorination reaction of benzene ring and the synthesis field of chlorinated aromatic hydrocarbon compounds, can solve the problems of low reaction selectivity, high pollutant discharge, unsafe operation and the like, and achieves the The effect of improving economic efficiency, effectively utilizing resources, and being convenient to use

Inactive Publication Date: 2014-08-20
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Many traditional chlorinated reagents have some disadvantages such as high toxicity and inconvenient operation. Therefore, the existing synthetic methods of chlorinated aromatic compounds also have shortcomings such as unsafe operation, low reaction selectivity, and more pollutant emissions.

Method used

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  • Method for synthesizing chlorinated aromatic hydrocarbon with participation of trichloroisocyanuric acid
  • Method for synthesizing chlorinated aromatic hydrocarbon with participation of trichloroisocyanuric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] In a three-necked flask equipped with a magnetic stirring bar and a reflux condenser, add 1.08 g (10 mmol) of anisole (wherein the R group is CH 3 -), 2.79g (12mmol) trichloroisocyanuric acid, 0.032g (0.4mmol) ammonium nitrate, 30mL acetonitrile, heated up to 85°C, reacted for 1h, stopped the reaction, cooled to room temperature, filtered to remove the solid, and removed with a rotary evaporator After solvent acetonitrile, 1.35 g of colorless oily liquid 4-chloroanisole was obtained, yield: 95%. Boiling point: 199-201°C (101KPa) (literature value: 199-201°C (101KPa)). After testing, the physical property data of the product are all close to the literature values.

[0052] After NMR detection, proton spectrum data were obtained to characterize the structure of the product. The specific data are as follows:

[0053] 1 H NMR (CDCl 3 , 500 MHz) δ: 3.84 (s, 3H, OCH 3 ), 6.81 (d, J =7.6 Hz, 2H, ArH), 7.27 (d, J =7.6 Hz, 2H, ArH).

Embodiment 2

[0055] In a three-necked flask equipped with a magnetic stirring bar and a reflux condenser, add 1.70 g (10 mmol) of diphenyl ether (where the R group is C 6 h 5 O-), 2.79g (12 mmol) trichloroisocyanuric acid, 0.032g (0.4 mmol) ammonium nitrate, 30mL acetonitrile, heat up to 85°C, react for 1h, stop the reaction, cool to room temperature, filter to remove solids, and use rotary evaporation After removing the solvent acetonitrile, 1.96 g of colorless oily liquid 4-chlorodiphenyl ether was obtained. Yield: 96%. Boiling point: 283-285°C (101KPa) (literature value: 283-285°C (101KPa))

[0056] After NMR detection, proton spectrum data were obtained to characterize the structure of the product. The specific data are as follows:

[0057] 1 H NMR (CDCl 3 , 500 MHz) δ: 6.90 (d, J =8.0 Hz, 2H, ArH), 6.99-7.05 (m, 3H, ArH), 7.30-7.33 (m, 2H, ArH), 7.43 (d, J =8.0 Hz, 2H, ArH).

Embodiment 3

[0059] In a three-necked flask equipped with a magnetic stirring bar and a reflux condenser, add 1.23 g (10 mmol) of nitrobenzene (wherein the R group is NO 2 -), 2.79g (12mmol) trichloroisocyanuric acid, 0.81g (5mmol) ferric chloride, 30mL acetonitrile, heat up to 85°C, react for 24h, stop the reaction, and cool to room temperature. The solid was removed by filtration, and 1.42 g of solid 3-chloronitrobenzene was obtained after the solvent was spin-off acetonitrile. Yield: 90%. Melting point: 44-45°C (literature value: 46°C)

[0060] After NMR detection, proton spectrum data were obtained to characterize the structure of the product. The specific data are as follows:

[0061] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.53-7.55 (m, 1H, ArH), 7.68-7.70 (m, 1H, ArH), 8.12-8.14 (m, 1H, ArH), 8.23-8.25 (m, 1H, ArH).

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Abstract

The invention discloses a method for synthesizing chlorinated aromatic hydrocarbons with the participation of trichloroisocyanuric acid, that is, aromatic hydrocarbons are synthesized under the condition of acetonitrile as a solvent, inorganic salt as a catalyst, and trichloroisocyanuric acid as a chlorination reagent. Chlorination reaction, the temperature of the reaction is controlled at 70-90°C, and the time is 1-24 hours. After the reaction is completed, cool to room temperature, filter to remove the solid, and use a rotary evaporator to remove the solvent acetonitrile to obtain chlorinated aromatic compounds. For aromatic compounds with high reactivity, ammonium nitrate is used as catalyst; for aromatic compounds with low reactivity, ferric chloride is used as catalyst. The synthesis method of the chlorinated aromatic hydrocarbon compound participated by trichloroisocyanuric acid of the present invention uses safe and cheap compound as the chlorinated reagent, reduces the pollutant emission in the chlorination reaction process, and makes the aromatic hydrocarbon compound which is cheap and easy to obtain It reacts under relatively mild conditions and has the potential of industrial scale production.

Description

technical field [0001] The invention relates to a benzene ring chlorination reaction method, in particular to a synthesis method of chlorinated aromatic compounds using trichloroisocyanuric acid as a chlorination reagent, and belongs to the technical field of preparation and application of fine chemical products. Background technique [0002] Chlorinated aromatic compounds are important intermediates in organic synthesis and are widely used in the synthesis of functional chemicals such as medicines and pesticides. Chlorination reaction is one of the important basic reactions in organic synthesis. The most traditional chlorination reagent is chlorine gas, which is used to selectively monochlorinate aromatic compounds under alkaline conditions (H. Shimizu, K. Shimizu, N. Kubodera, T. Mikami, K. Tsuzaki, H. Suwa, K. Harada, A. Hiraide, M. Shimizu, K. Koyama, Y. Ichikawa, D. Hirasawa, Y. Kito, M. Kobayashi, M. Kigawa, M. Kato, T. Kozono, H. Tanaka, M. Tanabe, M. Iguchi and M. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B39/00C07C43/225C07C43/29C07C205/11C07C201/12
Inventor 吴范宏吴玉锋陈梓湛
Owner SHANGHAI INST OF TECH
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