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The preparation method of 2-nitro-4-trifluoromethylbenzonitrile

A technology of trifluoromethylbenzonitrile and trifluoromethylbenzaldehyde, which is applied in the field of preparation of 2-nitro-4-trifluoromethylbenzonitrile, can solve problems such as high cost and inappropriate mass production, Achieve the effect of reducing manufacturing cost, low price and high activity

Active Publication Date: 2021-09-07
DALIAN QIKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although potassium ferrocyanide is non-toxic, the disadvantage is that it uses noble metal catalysts such as palladium, which has high cost and is not suitable for mass production.

Method used

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  • The preparation method of 2-nitro-4-trifluoromethylbenzonitrile
  • The preparation method of 2-nitro-4-trifluoromethylbenzonitrile
  • The preparation method of 2-nitro-4-trifluoromethylbenzonitrile

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Experimental program
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Effect test

Embodiment 1

[0036] Step 1: Add 219g of 2-nitro-4-trifluoromethylbenzaldehyde and 657g of water to the reactor, then add 69g of hydroxylamine hydrochloride, start stirring, and add 160g of 50% sodium hydroxide dropwise at 10-20°C , after the reaction was completed, it was neutralized to pH=7 with hydrochloric acid, extracted three times with ether, and the extract was concentrated to obtain 215 g of 2-nitro-4-trifluoromethylbenzaldoxime as a solid, yield: 92%.

[0037] The second step: take 235g of dry product of 2-nitro-4-trifluoromethylbenzaldehyde oxime and dissolve in 700g of acetonitrile, add 235g of acetic anhydride under stirring, then add 47g of compounded catalyst, heat up to 85°C and reflux, After reacting for 2 hours, cool down to room temperature, filter, and reclaim 63g of the catalyst, then raise the temperature of the mother liquor and concentrate, reclaim the solvent, and rectify the still liquid on the upper tower to obtain 178g of 2-nitro-4-trifluoromethylbenzonitrile. It...

Embodiment 2

[0039] Step 1: Add 220g of 2-nitro-4-trifluoromethylbenzaldehyde and 650g of water to the reactor, then add 70g of hydroxylamine hydrochloride, start stirring, and add 224g of 50% potassium hydroxide dropwise at 12-20°C , after the reaction was completed, neutralized with hydrochloric acid to pH=7, extracted three times with ether, concentrated the extract to obtain 2-nitro-4-trifluoromethylbenzaldehyde oxime, and obtained 208 g of solid after drying, yield: 89% .

[0040] The second step: take 260g of dry product of 2-nitro-4-trifluoromethylbenzaldehyde oxime and dissolve in 780g of acetonitrile, add 260g of acetic anhydride under stirring, then add 52g of compounded catalyst, heat up to 84°C and reflux, After reacting for 2 hours, cool down to room temperature, filter, and reclaim 70 g of the catalyst, then raise the temperature of the mother liquor and concentrate, reclaim the solvent, and rectify the still liquid on the upper tower to obtain 200 g of 2-nitro-4-trifluoromet...

Embodiment 3

[0042] The first step: add 4.4kg of 2-nitro-4-trifluoromethylbenzaldehyde and 13kg of water to the reaction kettle, then add 1.4kg of hydroxylamine hydrochloride, start stirring, and add 50% of hydroxide dropwise at 8-20°C Sodium 3.2kg, after the completion of the reaction, neutralize to pH=7 with hydrochloric acid, extract three times with ether, concentrate the extract to obtain 2-nitro-4-trifluoromethylbenzaldehyde oxime, obtain 4.1kg of solid after drying, and collect Rate: 88%.

[0043] Step 2: Take 4kg of dry 2-nitro-4-trifluoromethylbenzaldehyde oxime and dissolve it in 12kg of acetonitrile, add 4kg of acetic anhydride under stirring, then add 0.8kg of compounded catalyst, heat up to 83°C and reflux , after reacting for 2 hours, cool down to room temperature, filter, reclaim catalyst 1.1kg, then mother liquor is warmed up and concentrated, solvent is reclaimed, and still liquid is rectified on the tower to obtain 3.1kg of 2-nitro-4-trifluoromethylbenzonitrile , solidif...

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Abstract

The invention discloses a preparation method of 2-nitro-4-trifluoromethylbenzonitrile, which belongs to the technical field of synthesis of fine chemical intermediates. Take 2-nitro-4-trifluoromethylbenzaldehyde as raw material, react with hydroxylamine hydrochloride and inorganic base in water, obtain 2-nitro-4-trifluoromethylbenzaldehyde oxime, then in the presence of nickel composite catalyst 2-nitro-4-trifluoromethylbenzaldehyde oxime is dehydrated to obtain 2-nitro-4-trifluoromethylbenzonitrile. The dehydration reaction catalyst of the present invention is compounded of nickel acetate and Raney nickel, has high activity, can improve reaction selectivity and product yield, and because of low price, simultaneously reduces manufacturing cost and increases economic benefits.

Description

technical field [0001] The invention relates to a preparation method of 2-nitro-4-trifluoromethylbenzonitrile, which belongs to the technical field of synthesis of pharmaceutical and chemical intermediates. Background technique [0002] 2-Nitro-4-trifluoromethylbenzonitrile, CAS: 778-94-9, is an important chemical raw material and intermediate of pharmaceuticals and pesticides, and has a wide range of applications in drug synthesis, for example, it can be used to synthesize isoxane Herbicides such as fentrazone, pyrazole sulfonyl, etc. [0003] The synthesis of 2-nitro-4-trifluoromethylbenzonitrile is basically prepared by nucleophilic substitution reaction of 2-nitro-4-trifluoromethyl halobenzene and nitrile in the presence of a catalyst. Specifically include the following: [0004] Method 1. Nucleophilic substitution method using 2-nitro-4-trifluoromethyl chlorobenzene and potassium cyanide as raw materials [0005] [0006] Using 2-nitro-4-trifluoromethyl chlorobenz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/00C07C255/50
CPCC07C249/08C07C253/00C07C255/50C07C251/48
Inventor 张忠姜殿宝张洪学
Owner DALIAN QIKAI MEDICAL TECH
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