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A kind of synthetic method of 1,3-dinitrohalobenzene compound

A synthesis method and compound technology, applied to the preparation of nitro compounds, chemical instruments and methods, chemical/physical processes, etc., can solve the problems of high cost of waste sulfuric acid treatment, severe heat release of nitration reaction, long reaction time, etc., and achieve nitric acid Effects of reduced dosage, efficient synthesis, and shortened reaction time

Active Publication Date: 2022-01-04
SHANDONG HIMILE CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of synthetic method of 1,3-dinitrohalobenzene compound
  • A kind of synthetic method of 1,3-dinitrohalobenzene compound
  • A kind of synthetic method of 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 present invention provides the synthetic method of 1,3-dinitrohalobenzene compound, comprises the following steps: A) halobenzene compound, and the mixed acid of nitric acid, sulfuric acid, carry out the first nitration reaction in one-stage continuous flow microreactor , through oil-water separation, to obtain a nitrohalobenzene compound and the first waste acid; B) diverting the mononitrohalobenzene compound into the secondary continuous flow microreactor, and carrying out the second nitration reaction with the mixed acid of nitric acid and sulfuric acid , the nitration mixture generated is quenched and filtered at the outlet of the secondary continuous flow microreactor to obtain 1,3-dinitrohalobenzene compound and the second waste acid; C) the second waste acid is recycled to the first-level continuous flow In the microreactor, carry out the third nitration reaction with the halobenzene compound, and separate the oil and water to obtain the mononitrohalobenzene compound and the third waste acid; repeat steps B), C); the halobenzene compound has the formula I structure. Short reaction time and less waste acid realize continuous production.

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 Patents(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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