Method for catalytically synthesizing 2, 4-dichloronitrobenzene by adopting tetraphenylphosphine iodide

A technology of tetraphenylphosphine iodide and dichloronitrobenzene is applied in the field of preparation of 2,4-dichloronitrobenzene, and can solve the problem of low synthesis rate, low reaction activity, large consumption of ice water, etc. problem, to achieve the effect of improving selectivity and improving reactivity

Pending Publication Date: 2021-07-09

YUNNAN YUNTIANHUA +2

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Problems solved by technology

[0003] The purpose of the present invention is to provide a method for catalyzing the synthesis of 2,4-dichloronitrobenzene using tetraphenylphosphine iodide, which solves the problem that the e...

Abstract

The invention discloses a method for catalytically synthesizing 2, 4-dichloronitrobenzene by adopting tetraphenylphosphine iodide, and relates to the technical field of preparation of 2, 4-dichloronitrobenzene. The method specifically comprises the following steps: adding m-dichlorobenzene and tetraphenylphosphine iodide into a reaction container, uniformly mixing, heating the reaction container, and keeping the temperature of the reaction container at 70 DEG C; then dropwise adding mixed acid into the reaction container at a constant speed, continuously stirring for 2-2.5 hours after dropwise adding is completed within 1.5-2 hours, keeping the temperature at 70 DEG C, and standing for 1.5-2 hours after the reaction is completed; and after layered filtration, washing with cooling water, and drying to obtain the 2, 4-dichloronitrobenzene. Tetraphenylphosphine iodide is added in the nitration reaction process of m-dichlorobenzene, the selectivity of nitration reaction is greatly improved by using the tetraphenylphosphine iodide, the reaction activity is greatly improved, the nitration reaction efficiency is improved to 95% or above, the total reaction efficiency is improved to 92% from 63%, and the standard addition recovery rate of 2, 4-dichloronitrobenzene detected by gas chromatography is 98.9% on average.

Application Domain

Organic-compounds/hydrides/coordination-complexes catalystsNitro compound preparation

Technology Topic

IodideNitrobenzene +6

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Examples

Experimental program(4)

Example Embodiment

[0021] Example 1

[0022] HNO according to quality ratio 3 : H 2 SO 4 : H 2 O = 31: 62: 7, a mass fraction of 90.5% sulfuric acid, 92.3% of nitric acid were prepared in the reaction vessel for 2 hours at 22 to 25 ° C for 2 hours.

[0023] 600 g of dichlorobenzene was taken into a reaction vessel, and the reaction vessel was added to 70 ° C, and the reaction container was heated to 70 ° C, and the mixed acid was added dropwise over the stirring, and the mixed acid of 500 ml was dripped within 1.5 hours. The reaction vessel was allowed to continue to be stirred at 70 ° C for 2 hours. After the reaction was completed, it was allowed to stand for 2 h, and the tetraenzyl iodide nano particles were retained, and the filtrate was rinsed with ice water to obtain a white product. After drying 554g 2,4-dichlorobenzene.

[0024] The preparative 2,4-dichlorozene chlorobenzene was prepared by a 102G gas chromatograph and a CDMC-1 chromatographic data processor of the Shanghai Analytical Instrument Factory. The column specification is 2.2m × 2.9m stainless steel column, which is used as a fixing liquid, hydrogen gas carrier, and a thermal conductive detector, bridge stream using the silane 101 coated with 12% and 18% diphenne-18-crown-6. 180mA, the use of fixed liquid can be successfully separated from 6thrcoisomers and certain derivatives thereof; the fixed liquid starting temperature is 100 ° C, the pressure is 60 kPa, and the transfer temperature of the fixed liquid is higher than 145 ° C, temperature rise rate At 10 ° C / min, the pressure change amplitude is 10 kPa, the suitable analysis conditions are 280 ° C and 1 atmospheric pressure, take 20 mg of reaction product solution, and obtain a gas chromatogram of 2,4-dichloronitrobenzene products. figure 1 As shown, 2,4-dichloronitrobenzene content in 2,4-dichlorobenzene products is 12 mg, and the yield is 91%.

Example Embodiment

[0025] Example 2

[0026] HNO according to quality ratio 3 : H 2 SO 4 : H 2 O = 31: 62: 7, a mass fraction of 90.5% sulfuric acid, 92.3% of nitric acid were prepared in the reaction vessel for 2 hours at 22 to 25 ° C for 2 hours.

[0027] 400 g of dichlorobenzene, a particle size of 20 nm was added to the reaction vessel to the reaction vessel, and the reaction vessel was heated to 70 ° C, and the mixed acid was added dropwise on the stirring, and 300 ml of mixed acid was dripped within 2 hours. The reaction vessel was allowed to continue to stir at 70 ° C for 2.5 hours, and after the reaction was completed, it was allowed to stand for 1.5 h, and the tetraparaphenyl iodide nano particles were recovered, and the filtrate was rinsed with ice water to give 366 g. 2,4-dichlorobenzene.

[0028] The preparative 2,4-dichlorozene chlorobenzene was prepared by a 102G gas chromatograph and a CDMC-1 chromatographic data processor of the Shanghai Analytical Instrument Factory. The column specification is 2.2m × 2.9m stainless steel column, which is used as a fixing liquid, hydrogen gas carrier, and a thermal conductive detector, bridge stream using the silane 101 coated with 12% and 18% diphenne-18-crown-6. 180mA, the use of fixed liquid can be successfully separated from 6thrcoisomers and certain derivatives thereof; the fixed liquid starting temperature is 100 ° C, the pressure is 60 kPa, and the transfer temperature of the fixed liquid is higher than 145 ° C, temperature rise rate At 10 ° C / min, the pressure change amplitude is 10 kPa, the suitable analysis conditions are 280 ° C and 1 atmospheric pressure, take 20 mg of reaction product solution, and obtain a gas chromatogram of 2,4-dichloronitrobenzene products. figure 2 As shown, 2,4-dichloronitrobenzene content in 2,4-dichloronitrobenzene products is 11.5 mg, and the yield is 90%.

Example Embodiment

[0029] Example 3

[0030] HNO according to quality ratio 3 : H 2 SO 4 : H 2 O = 31: 62: 7, a mass fraction of 90.5% sulfuric acid, 92.3% of nitric acid were prepared in the reaction vessel for 2 hours at 22 to 25 ° C for 2 hours.

[0031] 800 g of dichlorobenzene was taken into a reaction vessel, and the reaction vessel was added to 70 ° C, and the mixed acid was added to 70 ° C, and the mixed acid was added dropwise over 2 hours. The reaction vessel was allowed to continue to stir at 70 ° C for 2.5 hours, and after the reaction was completed, it was stratified, and the tetraparaphenyl iodide nanophenyl, the filtrate was recovered, and the filtrate was rinsed to obtain a white product, 741 g 2,4-dichlorobenzene.

[0032] The preparative 2,4-dichlorozene chlorobenzene was prepared by a 102G gas chromatograph and a CDMC-1 chromatographic data processor of the Shanghai Analytical Instrument Factory. The column specification is 2.2m × 2.9m stainless steel column, which is used as a fixing liquid, hydrogen gas carrier, and a thermal conductive detector, bridge stream using the silane 101 coated with 12% and 18% diphenne-18-crown-6. 180mA, the use of fixed liquid can be successfully separated from 6thrcoisomers and certain derivatives thereof; the fixed liquid starting temperature is 100 ° C, the pressure is 60 kPa, and the transfer temperature of the fixed liquid is higher than 145 ° C, temperature rise rate At 10 ° C / min, the pressure change amplitude is 10 kPa, and the suitable analysis conditions are 280 ° C and 1 atmospheric pressure, take 20 mg of reaction products, and the solution to obtain a gas chromatogram of 2,4-dichloronitrobenzene products. image 3As shown, 2,4-dichloronitrobenzene content in 2,4-dichloronitrobenzene products is 12.6 mg, and the yield is 92%.

[0033] In the figure, 1 is tetramethyl iodide, 2 is between dichlorobenzene, 3 is 2,4-dichlorobenzene, 4 is 2,3-dichloronitrobenzene absorption peaks, as the product In the middle of the 2,4-dichlorobenzene content, a longer retention time is required, and a small amount of 2,3-dichlorozene is also contained in the reaction product. Under the action of tetramethyl iodide catalyst, the yield of 2,4-dichloroidylbenzene was significantly improved.

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Classification and recommendation of technical efficacy words

High reactivity
high selectivity

Method for catalytically synthesizing 2, 4-dichloronitrobenzene by adopting tetraphenylphosphine iodide

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

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Example Embodiment

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Description & Claims & Application Information

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