Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile

A technology of nitrophenylacetonitrile and chlorophenylacetonitrile, which is applied in the field of preparation of anticoccidial intermediate 2,6-dichloro-α--4-nitrophenylacetonitrile, which can solve the problem of 4-position chlorine being substituted Low cost, difficult to complete condensation, high cost, etc., to achieve high industrial production value, avoid isomers, and low cost

Active Publication Date: 2013-02-06
江苏中丽新材料有限公司
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AI-Extracted Technical Summary

Problems solved by technology

[0011] In order to overcome the disadvantages of high preparation cost of raw material 3,4,5-trichloronitrobenzene, serious three wastes, low activity of substituted chlorine at the 4-position and d...
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Abstract

The invention discloses a method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile by condensation of 3,5-dichloro-4-fluronitrobenzene and p-chloro-phenylacetonitrile, wherein the used raw material 3,5-dichloro-4-fluronitrobenzene is derived from distillation residue of a production process for preparing 2,4-dichloro-3-fluronitrobenzene by nitrifying 2,6-dichlor fluorbenzene; and the residue contains 83.5-88.2% of 3,5-dichloro-4-fluronitrobenzene and 9.0-13.3% of 2,4-dichloro-3-fluronitrobenzene, and 3,5-dichloro-4-fluronitrobenzene with content more than 98% can be obtained by selective solvent extraction and once or twice recrystallization and is subjected to condensation with p-chloro-phenylacetonitrile to obtain 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile with yield above 98%. Compared with the existing method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile, the method has the characteristics of inexpensive and easily available raw materials, sufficient utilization of resources, mild conditions, high yield, low wastewater discharge and the like, and is more suitable for industrial production.

Application Domain

Carboxylic acid nitrile preparationOrganic compound preparation

Technology Topic

NitrobenzeneDistillation +6

Image

  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile
  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile
  • Method for preparing 2,6-dichloro-alpha-(4-chlorphenyl)-4-nitro phenylacetonitrile

Examples

  • Experimental program(3)

Example Embodiment

[0023] Example 1
[0024] Get 50g of distillation residue of 2,4-dichloro-3-fluoronitrobenzene production process (3,5-dichloro-4-fluoronitrobenzene content 87.7%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 9.6%, and the content of other impurities is 2.3%. It comes from a dark brown distillation residue with batch number LH20111223 of an enterprise in Linhai, Zhejiang Province in 2011) and is heated and dissolved in 200mL of petroleum ether. Remove the solvent, recrystallize with methanol, filter, wash with cold methanol, and dry in vacuo to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.3% and a yield of 77%.
[0025] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained above, 70g of sodium hydroxide dissolved in 70mL of water to make 50% liquid caustic soda, 3g of benzyltriethylammonium chloride and 140mL In tetrahydrofuran, add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL THF at 30°C, heat up to 50°C for 6 hours after dropping, pour the mixture into crushed ice, acidify with concentrated hydrochloric acid, extract 3 times with dichloroethane, and then After drying, filtering, and precipitation to obtain a residue, washing with isopropyl ether, and drying to obtain 33.8 g of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile, the content is 97.8%, and the yield is 99.8%.

Example Embodiment

[0026] Example 2
[0027]Take 2,4-dichloro-3-fluoronitrobenzene distillation residue 50g (3,5-dichloro-4-fluoronitrobenzene content 86.5%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 10.1%, and the content of other impurities is 1.2%. It comes from the beige distillation residue with the batch number KH20120211 of a company in Kaihua, Zhejiang Province in 2012). The solvent was distilled off, then recrystallized with absolute ethanol, filtered, washed with cold ethanol, and vacuum dried to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.4% and a yield of 75%.
[0028] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained above, 60g of sodium hydroxide dissolved in 60mL of water to form 50% liquid caustic soda, 3g of tetrabutylammonium bromide and 120mL of tetrahydrofuran, Add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL tetrahydrofuran at 40°C, heat up to 60°C and react for 4h after dropping, pour the mixture into crushed ice, acidify with concentrated hydrochloric acid, extract 3 times with chloroform, then dry, filter, The residue obtained was precipitated, washed with tetrahydrofuran, and dried to obtain 33.6 g of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile with a content of 97.6% and a yield of 98.3%.

Example Embodiment

[0029] Example 3
[0030] Get 50g of distillation residue of 2,4-dichloro-3-fluoronitrobenzene production process (3,5-dichloro-4-fluoronitrobenzene content 84.3%, 2,4-dichloro-3-fluoronitrobenzene The content of benzene is 12.4%, and the content of other impurities is 2.7%. It comes from the dark brown distillation residue with batch number QZ20120324 of a certain enterprise in Quzhou, Zhejiang Province in 2012) and is heated and dissolved in 260mL of toluene. The solvent was recrystallized once with isopropanol and methanol respectively, and vacuum-dried to obtain 3,5-dichloro-4-fluoronitrobenzene with a content of 98.5% and a yield of 72%.
[0031] Take 21.0g (0.1mol) of 3,5-dichloro-4-fluoronitrobenzene obtained above, 70g of sodium hydroxide dissolved in 70mL of water to make 50% liquid caustic soda, 3g of benzyltriethylammonium chloride and 140mL Add dropwise a solution of 17.0g p-chlorophenylacetonitrile in 50mL tetrahydrofuran to THF at 30°C, heat up to 50°C for 6 hours after dropping, pour the mixture into crushed ice, acidify with concentrated hydrochloric acid, extract 3 times with chloroform, then dry and filter , concentrated to about 120mL, cooled and crystallized, filtered, and dried to obtain 33.6g of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile, with a content of 98.3% and a yield of 98.3%.
[0032] The raw materials used in the above example reactions are all industrial grade products without further purification. The contents of raw materials, impurities and products were all measured by high performance liquid chromatography normalization method.
[0033]

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