Method for synthesizing 1,3-dinitrohalobenzene compound

A synthesis method and compound technology, applied in the preparation of nitro compounds, chemical instruments and methods, chemical/physical processes, etc., can solve the problems of severe exothermic heat of nitration reaction, large content of nitric acid, high cost of waste sulfuric acid treatment, etc.

Active Publication Date: 2019-07-05
SHANDONG HIMILE CHEM TECH
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  • Abstract
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  • Claims
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Problems solved by technology

However, the known large-scale nitration process for 1,3-dinitrohalobenzene compounds has the following disadvantages: the reaction time is long, the mixed acid addition time of concentrated nitric acid and concentrated sulfuric acid is as long as several hours, and the amount of nitric acid is much larger. Due to the theoretical consumption value, the content of nitric acid in the waste sulfuric acid produced is large, the cost of waste sulfuric acid treatment is high, the exothermic heat of the nitration reaction is violent, and the danger of explosion is prone to occur

Method used

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  • Method for synthesizing 1,3-dinitrohalobenzene compound
  • Method for synthesizing 1,3-dinitrohalobenzene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0097] 1000 g (5.93 mol) of 4-tert-butylchlorobenzene was dissolved in 250 g of 1,2-dichloroethane to prepare a 4-tert-butylchlorobenzene solution. 2000 grams (20 moles) of 95%-98% sulfuric acid are added dropwise to 643 grams (10 moles) of 95%-98% nitric acid dissolved in a 2 liter three-neck flask kept warm in an ice-water bath to prepare the mixed acid of nitric acid sulfuric acid .

[0098] The first nitration reaction: according to the molar ratio of 4-tert-butyl chlorobenzene and nitric acid 1:1.2, the flow rate of 4-tert-butyl chlorobenzene is 2.7ml / min, the flow rate of mixed acid is 2.8ml / min, and the residence time is preferred For 152s, the reaction temperature is 60-80°C, part of the 4-tert-butylchlorobenzene solution and the mixed acid of nitric acid and sulfuric acid are pumped through the continuous flow microreactor, which includes separate fluid modules connected in sequence, specifically the inlet mixed reaction module , 8 resident modules and one export mod...

Embodiment 2

[0113] 1000 g (5.93 mol) of 4-tert-butylchlorobenzene was dissolved in 250 g of 1,2-dichloroethane to prepare a 4-tert-butylchlorobenzene solution. 2000 grams (20 moles) of 95%-98% sulfuric acid are added dropwise to 643 grams (10 moles) of 95%-98% nitric acid dissolved in a 2 liter three-neck flask kept warm in an ice-water bath to prepare the mixed acid of nitric acid sulfuric acid .

[0114] The first nitration reaction: according to the molar ratio of 4-tert-butylchlorobenzene and nitric acid 1:1.2, the reaction temperature is 60-70°C, the flow rate of 4-tert-butylchlorobenzene is 2.6mL / min, and the flow rate of mixed acid is 2.7mL / min , part of the mixed acid of 4-tert-butylchlorobenzene solution and nitric acid sulfuric acid is pumped through a continuous flow microreactor, which includes separate fluid modules connected in sequence, specifically an inlet mixed reaction module, 8 resident modules and an outlet module , as above. Each individual fluidic module was maint...

Embodiment 3

[0122] 1000 g (5.93 mol) of 4-tert-butylchlorobenzene was dissolved in 250 g of 1,2-dichloroethane to prepare a 4-tert-butylchlorobenzene solution. 2000 grams (20 moles) of 95%-98% sulfuric acid are added dropwise to 643 grams (10 moles) of 95%-98% nitric acid dissolved in a 2 liter three-neck flask kept warm in an ice-water bath to prepare the mixed acid of nitric acid sulfuric acid .

[0123] The first nitration reaction: according to the molar ratio of 4-tert-butylchlorobenzene and nitric acid 1:1.2, the reaction temperature is 60-80°C, the flow rate of 4-tert-butylchlorobenzene is 2.5mL / min, and the flow rate of mixed acid is 2.6mL / min , part of the mixed acid of 4-tert-butylchlorobenzene solution and nitric acid sulfuric acid is pumped through a continuous flow microreactor, which includes separate fluid modules connected in sequence, specifically an inlet mixed reaction module, 8 resident modules and an outlet module , as above. Each individual fluidic module was maint...

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Abstract

The invention provides a method for synthesizing a 1,3-dinitrohalobenzene compound. The method comprises the following steps that A) a halogenated benzene compoundand mixed acid of nitric acid and sulfuric acid are subjected to a first nitrification reaction in a first-stage continuous flow microreactor, and oil-water separation is conducted to obtain a mononitrohalobenzene compound and first waste acid; B) the mononitrohalobenzene compound is drained into a second-stage continuous flow microreactor, a second nitrification reaction is conducted with the mixed acid of the nitric acid and the sulfuric acid, a generated nitration mixture is quenched at the outlet of the second-stage continuous flow microreactor, and filtering is conducted to obtain the 1,3-dinitrohalobenzene compound and second waste acid; C) the second waste acid is recycled to the first-stage continuous flow microreactor, a third nitration reaction with the halobenzene compound is carried out, the oil-water separation is conducted to obtain the mononitrohalobenzene compound and third waste acid, and steps B) and C) are repeated; the halobenzene compound has a structure shown in the formula I. The reaction time is short, the waste acid is less, and continuous production is achieved.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a method for synthesizing 1,3-dinitrohalobenzene compounds. Background technique [0002] 1,3-dinitrohalobenzene compound, its structural formula is as follows: [0003] [0004] R 1 is F, Cl, Br or I; R 2 For methyl, ethyl, methoxy and other electron-donating groups. [0005] 1,3-Dinitrohalobenzene compound is an important chemical intermediate and is a useful compound in the application of hair dyes, herbicides, insecticides and dye intermediates. A common route to the synthesis of 1,3-dinitrohalobenzenes involves the nitration of halobenzenes. However, the known large-scale nitration process for 1,3-dinitrohalobenzene compounds has the following disadvantages: the reaction time is long, the mixed acid addition time of concentrated nitric acid and concentrated sulfuric acid is as long as several hours, and the amount of nitric acid is much larger. Due to the t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/12C07C205/37B01J19/00
CPCC07C201/08B01J19/0093B01J19/0046B01J2219/00889C07C205/12C07C205/37
Inventor 王远超李日翔杨安明芦潇任苗苗张英杰
Owner SHANDONG HIMILE CHEM TECH
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