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O-chlorotoluene catalytic nitration method by using microwaves for assisting zeolite

An o-chlorotoluene, microwave-assisted technology, applied in the field of microwave-assisted zeolite catalyzed nitration of o-chlorotoluene, can solve the problems of poor nitration selectivity and long time consumption, and achieve the goal of improving conversion rate and yield, high yield, and accelerating the reaction process Effect

Inactive Publication Date: 2018-10-23
LIHAI CHEM IND CO LTD OF JIANGSU JINQIAO SALT & CHEM GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention provides a method for microwave-assisted zeolite catalyzed nitration of o-chlorotoluene to overcome the problems of poor nitration selectivity and long time-consuming of the prior art o-chlorotoluene nitration method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Under magnetic stirring conditions, 10 mL of 1,2-dichloroethane, 3.0 mmol of o-chlorotoluene, 3.0 mmol of acetic anhydride, 12 mmol of fuming nitric acid, 0.20 g of Agβ zeolite molecular sieve catalyst and silica-supported Perfluorosulfonic acid resin 0.1g, microwave heating 8min (end point temperature is set to the boiling point temperature of 1,2-dichloroethane) heat preservation for 10min, add 5mL water to the reaction mixture to stop the reaction, filter to remove the catalyst, the organic phase is sequentially With 10mL of water, 10mL of NaHCO with a mass fraction of 5% 3 Wash with 10mL of water and let stand to separate the organic phase. Gas chromatographic analysis was performed using p-nitrotoluene as an internal standard. The results showed that the yield was 78.3%, and the selectivity of 2-chloro-4-nitrotoluene was 80.5%.

Embodiment 2

[0027] Add 10 mL of dichloromethane, 3.0 mmol of o-chlorotoluene, 6.0 mmol of acetic anhydride, 9 mmol of fuming nitric acid, 0.30 g of Hβ zeolite molecular sieve catalyst and silica-supported perfluorosulfonic acid into a 25 mL round bottom flask under magnetic stirring conditions Resin 0.1g, microwave heating 10min (end point temperature is set as the boiling point temperature of dichloromethane) heat preservation 10min, then add 5mL water to the reaction mixture to stop the reaction, after filtering to remove the catalyst, the organic phase is successively washed with 10mL water, 10mL mass fraction is 5 % NaHCO 3 Wash with 10mL of water and let stand to separate the organic phase. Gas chromatographic analysis was performed using p-nitrotoluene as an internal standard. The results showed that the yield was 75.4%, and the selectivity of 2-chloro-4-nitrotoluene was 80.2%.

Embodiment 3

[0029] Add 10 mL of ethyl acetate, 3.0 mmol of o-chlorotoluene, 9.0 mmol of acetic anhydride, 6 mmol of fuming nitric acid, 0.05 g of Biβ zeolite molecular sieve catalyst and silica-supported perfluorosulfonic acid into a 25 mL round bottom flask under magnetic stirring conditions. Resin 0.1g, microwave heating for 12min (the end point temperature is set as the boiling point of ethyl acetate) and heat preservation for 10min, then add 5mL water to the reaction mixture to stop the reaction. % NaHCO 3 Wash with 10mL of water and let stand to separate the organic phase. Gas chromatographic analysis was performed using p-nitrotoluene as an internal standard. The results showed that the yield was 74.6%, and the selectivity of 2-chloro-4-nitrotoluene was 83.7%.

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Abstract

The invention discloses an o-chlorotoluene catalytic nitration method by using microwaves for assisting zeolite. The method comprises the following steps of adding solvents into a container; sequentially adding o-chlorotoluene, acetic anhydride, nitrosonitric acid, modified zeolite molecular sieve catalysts and silicon dioxide loaded perfluorinated sulfonic acid resin; performing microwave temperature rise for 4 to 12min; performing heat insulation for 8 to 10min; terminating the reaction. The microwave technology is applied to the o-chlorotoluene nitration process; the reaction progress is greatly accelerated; meanwhile, silicon dioxide is used for loading perfluorinated sulfonic acid resin; the perfluorinated sulfonic acid resin is dispersed into SiO2 networks or pore passages; the effective surface area is greatly increased, so that the acid positions of the perfluorinated sulfonic acid resin are sufficiently exposed, so that the potential of the resin catalyst is achieved; the conversion rate and the yield are improved; in addition, the modified zeolite molecular sieve catalyst Bibeta provides acid centers and pore passage structures; the shape selection catalyst effect is provided; the reaction selectivity is improved; the yield is as high as 80.9 percent; the selectivity of the 2-chloro-4-nitrotoluene is as high as 84.1 percent. The method has the advantages that the operation is easy; the energy is saved; the efficiency is high; the control is easy; the method belongs to a green and environmental-friendly o-chlorotoluene nitration method.

Description

technical field [0001] The invention belongs to the field of organic matter nitration, and in particular relates to a microwave-assisted zeolite-catalyzed nitration method for o-chlorotoluene. Background technique [0002] Nitro-o-chlorotoluene is an important pesticide, dye, and pharmaceutical intermediate, which is mainly produced by nitration of o-chlorotoluene. The nitrating reagents used in the nitration method mainly include nitric acid, nitric acid sulfuric acid, nitric acid anhydride system and nitrates. The traditional industrial production adopts the nitric acid sulfuric acid mixed acid nitration method. However, this method has long time required for nitration, poor selectivity, and acid corrosion , waste acid pollution and other issues. [0003] At present, the commonly used heating method is to heat from the surface of the object first, and then the heat is transferred from the surface to the interior of the object. Microwave heating can directly heat the insi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/12B01J31/06B01J31/26B01J35/10
CPCC07C201/08B01J31/069B01J31/26B01J35/60C07C205/12
Inventor 董雄辎彭新华臧涵申卫卫姜红来吉凤成韩勇蒋校
Owner LIHAI CHEM IND CO LTD OF JIANGSU JINQIAO SALT & CHEM GRP
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