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Mechanochemical synthesis method of 1,4-bis(4-nitrophenoxy)benzene

A nitrophenoxy and mechanochemical technology, applied in the field of mechanochemical synthesis of 1,4-bis(4-nitrophenoxy)benzene, can solve problems such as expensive catalysts, long reaction time, and long experiment cycle , to achieve the effect of short reaction time, good reaction selectivity and simple operation

Active Publication Date: 2019-09-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method of synthesizing 1,4-bis(4-nitrophenoxy)benzene and its derivatives is to use the sodium salt of substituted quinone ( Synth.Commun. ,2008,38,21-32) or potassium salt ( RSCAdv. ,2014,4,7959-7966) to carry out substitution reaction with halogenated nitrobenzene, the reaction requires a long reaction time, the conditions are harsh and difficult to control
At the same time, it is difficult to recycle using aprotic solvents DMF, DMSO, etc.
New synthetic methods such as phase transfer catalysis ( Ind. Eng. Chem. Res. , 2008,47,9081-9089), microwave method (CN105198713B), although it has the advantages of high product yield and fast reaction speed, but the former uses expensive catalysts and the cost is relatively high, while the latter is complicated to operate and has a long experimental period

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add hydroquinone (0.110g, 1.0mmol), p-nitrochlorobenzene (0.345g, 2.2mmol), ferric nitrate nonahydrate (0.323g, 0.8mmol), sodium acetate (0.164g, 2.0mmol), silica gel (100-200 mesh, 0.5g), put four stainless steel grinding balls with a diameter of 10mm, after feeding, seal the ball mill tank and put it in the ball mill, the ball milling speed is 500 rpm / minute, after 40 minutes of ball milling, the reaction is over, and the temperature of the tank is about 50 degrees (the temperature of the following examples is similar to this example). The reaction mixture was filtered to remove insoluble substances, and the filtrate was concentrated and then recrystallized with ethanol to obtain 0.327 g of a solid product, 1,4-bis(4-nitrophenoxy)benzene, with a yield of 92.8%.

Embodiment 2

[0026] Add hydroquinone (0.110g, 1.0mmol), p-nitrochlorobenzene (0.471g, 3.0mmol), cuprous iodide (0.190g, 1.0mmol), potassium carbonate (0.138g, 1.0mmol), silica gel (100-200 mesh, 0.5g), put four stainless steel grinding balls with a diameter of 10mm, after feeding, seal the ball mill tank and place it in the ball mill, the ball mill speed is 1000 rpm / minute, the reaction is over after 60 minutes of ball milling, and the temperature of the tank is about 50 degrees (the temperature of the following examples is similar to this example). The reaction mixture was filtered to remove insoluble matter, and the filtrate was concentrated and then recrystallized with ethanol to obtain 0.225 g of a solid product, 1,4-bis(4-nitrophenoxy)benzene, with a yield of 64.0%.

Embodiment 3

[0028] Add hydroquinone (0.110g, 1.0mmol), p-nitrochlorobenzene (0.628g, 4.0mmol), copper chloride dihydrate (0.170g, 1.0mmol), sodium hydroxide (0.080 g, 2.0mmol), silica gel (100-200 mesh, 0.5g), put four stainless steel grinding balls with a diameter of 10mm, after feeding, seal the ball mill tank and place it in the ball mill, and the ball milling speed is 800 rpm, ball milling for 50 minutes, the reaction is over, the temperature of the tank body is about 50 degrees (the temperature of the following example is similar to this example), after the ball mill stops operating, blow air to dissipate heat until the surface of the tank body drops to room temperature, use The reaction mixture was transferred with methanol, and the insoluble matter was filtered out. The filtrate was concentrated and then recrystallized with ethanol to obtain 0.322 g of a solid product, 1,4-bis(4-nitrophenoxy)benzene, with a yield of 91.4%.

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Abstract

The invention relates to a mechanochemical synthesis method of 1,4-bis(4-nitrophenoxy)benzene. The mechanochemical synthesis method is a natural synthesis method which includes that p-dihydroxybenzene and p-nitryl benzene halide are synthesized to form the 1,4-bis(4-nitrophenoxy)benzene by catalysis of metal salt and promotion of mechanical force. The mechanochemical synthesis method specifically includes: adding the p-dihydroxybenzene and the p-nitryl benzene halide into a ball-milling tank, adding a catalyst, alkali silica gel and a milling ball to perform mechanical and chemical reactions, after the reaction is over, transferring a reaction mixture by an organic solvent, filtering out undissolved matters, concentrating a filter liquid, and recrystallizing the concentrated filter liquid to obtain the yellow and green crystal product 1,4-bis(4-nitrophenoxy)benzene. The mechanochemical synthesis method of the 1,4-bis(4-nitrophenoxy)benzene has the advantages of simplicity in operation, short reaction time, high atom economy, high product yield, high product purity which is higher than 99% and applicability to industrial use.

Description

technical field [0001] The invention relates to a mechanochemical synthesis method of 1,4-bis(4-nitrophenoxy)benzene, specifically a method for synthesizing hydroquinone and p-nitrohalobenzene under the catalysis of metal salts and promoted by ball milling. Green synthesis of 1,4-bis(4-nitrophenoxy)benzene. Background technique [0002] As an important intermediate, 1,4-bis(4-nitrophenoxy)benzene and its derivatives are widely used in the fields of pesticides, medicines, pigments, dyes and rubbers. The aminophenylene ether obtained after its reduction is also an important class of compounds, which has good thermal stability, mechanical properties and electrical properties, and has wide applications in aerospace, electronic and electrical fields. [0003] The traditional method of synthesizing 1,4-bis(4-nitrophenoxy)benzene and its derivatives is to use the sodium salt of substituted quinone ( Synth.Commun. ,2008,38,21-32) or potassium salt ( RSCAdv. , 2014, 4, 7959-7966)...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/38
CPCC07C201/12C07C205/38
Inventor 李坚军蒋珺
Owner ZHEJIANG UNIV OF TECH
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