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Clean nitration reaction of p-chlorobenzotrifluoride under catalysis of degradable functional ionic liquid

A technology of p-chlorotrifluorotoluene and ionic liquid, applied in physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, organic chemistry, etc., can solve the difficulty of increasing post-processing, product separation, imidazole ionic liquids are expensive, cannot meet environmental and economic problems, and achieve the effects of good industrial application prospects, environmental friendliness, and convenient preparation.

Active Publication Date: 2014-02-12
内蒙古大中实业化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high cost of imidazole-type ionic liquids, it is not conducive to large-scale application
In addition, a series of studies have shown (Garcia M TGathergood N, Scammells P J. Biodegradable ionic liquids Part II. Effect of theanion and toxicity. Green Chem. 2005, 7: 9-14), conventional ions such as imidazole and pyridine The liquid has poor degradability and is not easily degraded by the most widely used biological treatment process or biological self-purification, which has potential harm to the environment, and the use of acetic anhydride and trifluoroacetic anhydride increases the difficulty of post-processing and product separation. Can not meet the dual benefits of environment and economy

Method used

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  • Clean nitration reaction of p-chlorobenzotrifluoride under catalysis of degradable functional ionic liquid
  • Clean nitration reaction of p-chlorobenzotrifluoride under catalysis of degradable functional ionic liquid
  • Clean nitration reaction of p-chlorobenzotrifluoride under catalysis of degradable functional ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 25mL round bottom flask, add 10mmol (1.81g) of p-chlorobenzotrifluoride, 30mmol (2.8g) of 68% nitric acid, and 1.5mmol (0.65g) of catalyst in sequence, mix and stir for 10 hours at 100°C, cool, and statically The phases were separated, the crude product in the upper layer was washed with water, neutralized and dried in vacuum to obtain the pure product 4-chloro-3-nitrobenzotrifluoride with a yield of 80%.

Embodiment 2

[0024] In a 25mL round bottom flask, add 10mmol (1.81g) of p-chlorobenzotrifluoride, 10mmol (0.63g) of 100% nitric acid, and 1mmol (0.43g) of catalyst in turn, mix and stir at 30°C for 8 hours, cool and stand The phases were separated, the crude product in the upper layer was washed with water, neutralized and dried in vacuum to obtain the pure product 4-chloro-3-nitrobenzotrifluoride with a yield of 81%.

Embodiment 3

[0026] In a 25mL round bottom flask, add 10mmol (1.81g) of p-chlorobenzotrifluoride, 20mmol (1.4g) of 90% nitric acid, and 0.5mmol (0.22g) of catalyst in turn, mix and stir for 5 hours at 80°C, cool and statically The phases were separated, the crude product in the upper layer was washed with water, neutralized and dried in vacuum to obtain the pure product 4-chloro-3-nitrobenzotrifluoride with a yield of 85%.

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Abstract

The invention discloses a new method of clean nitration reaction of p-chlorobenzotrifluoride under catalysis of degradable functional ionic liquid. Biodegradable ionic liquid of quaternary ammonium cation structure is used as a catalyst, p-chlorobenzotrifluoride and nitric acid are used as raw materials, and 4-chloro-3-nitrobenzotrifluoride is obtained by nitration reaction under the action of the catalyst. Compared with the prior art, the method has the advantages that: (1) because the degradable ionic liquid of quaternary ammonium cation structure is adopted, the raw material source is extensive, and the preparation is convenient; the catalyst has high activity, low consumption and water stability, is not inactivated and can be recycled; (2) the ionic liquid is biodegradable and environment-friendly; and (3) because the ionic liquid is used for substituting concentrated sulfuric acid, the method is an environment-friendly chemical process, and has good industrialized application prospect.

Description

a technical field [0001] The invention relates to a new method for catalyzing the clean nitration reaction of p-chlorobenzotrifluoride by a degradable functionalized ionic liquid, which belongs to the technical field of chemical material preparation. The method is applicable to the occasion of synthesizing 4-chloro-3-nitrobenzotrifluoride with p-chlorobenzotrifluoride and nitric acid as raw materials by heating and stirring under normal pressure. Two background technology [0002] Aromatic nitration compounds are a very important class of chemical products. For a long time, both academia and industry have conducted in-depth and meticulous research on the methods and processes of nitration reactions of aromatic compounds. At present, the clean nitrification of aromatic compounds has become one of the research hotspots. [0003] The nitrated product of p-chlorobenzotrifluoride, 4-chloro-3-nitrobenzotrifluoride, is widely used in industrial fields such as pharmaceuticals, pest...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/12C07C201/08B01J31/02
Inventor 方东郑龙洲谢毅
Owner 内蒙古大中实业化工有限公司
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