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Synthesis method of paranitrobenzoyl chloride

A technology of nitrobenzoyl chloride and a synthetic method, which is applied in the field of organic synthesis, can solve problems such as not occurring, and achieve the effects of saving equipment costs, high yield, and high selectivity

Inactive Publication Date: 2016-01-20
ANHUI GUANGXIN AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is a stable solid crystalline compound. It is safer to use, store and transport than phosgene, and can be accurately measured to reduce side reactions. There is no synthesis of p-nitrobenzoyl chloride using triphosgene in the current market and patent literature reports. precedent

Method used

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  • Synthesis method of paranitrobenzoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Take 3.0 moles of p-nitrobenzoic acid and 100 ml of dry toluene solution in a three-necked flask equipped with a reflux condenser, drop a small amount of dry pyridine as a catalyst, add 0.5 moles of triphosgene, and place the entire device in a 40-degree oil bath Magnetic stirring was carried out in the pot for 5 hours, the reaction by-product hydrogen chloride gas was drawn out with a reflux condenser, absorbed with lye, the crude product was distilled off under reduced pressure to remove the solvent, and the calculated yield was 95.89%;

Embodiment 2

[0018] Take 1.0 mole of p-nitrobenzoic acid and 100 ml of dry dichloromethane solution in a three-necked flask equipped with a reflux condenser, drop a small amount of dry N,N-dimethylformamide as a catalyst, and add 0.8 mole of Sanko Gas, the whole device was placed in a 50-degree oil bath and stirred magnetically for 5 hours. The reaction by-product hydrogen chloride gas was drawn out with a reflux condenser and absorbed with lye. The crude product was distilled under reduced pressure to remove the solvent, and the calculated yield was 97.65%;

Embodiment 3

[0020] Take 1.0 moles of p-nitrobenzoic acid and 100 milliliters of dry ethyl acetate solution and place it in a three-necked flask equipped with a reflux condenser, drop in trifluoroformic acid sulfonate with a mole fraction of 5% as a catalyst, and add 1.1 moles of Sanko The whole device was placed in a 60-degree oil bath with magnetic stirring for 12 hours. The reaction by-product hydrogen chloride gas was drawn out with a reflux condenser and absorbed with lye. The crude product was distilled under reduced pressure to remove the solvent. The calculated yield was 98.49%.

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Abstract

The invention discloses a synthesis method of paranitrobenzoyl chloride. The synthesis method comprises the steps that p-nitrobenzoic acid and triphosgene in a molar ratio of 1:(0.5-1.1) are placed in a three-mouth bottle provided with a reflux condensing tube, a dried catalyst is drop added, the mixture is subjected to magnetic stirring and oil-bath heating after dried methylbenzene is taken as a solvent for dissolving, and a crude product is obtained after 5-12 hours of reaction; a reaction by-product of hydrogen chloride is guided out by the reflux condensing tube, alkali liquor is used for absorption, and high-purity paranitrobenzoyl chloride is obtained after the solvent is removed from the crude product through reduced pressure distillation; compared with a traditional process, raw materials are stable, non-toxic and easy to preserve; the toxicity of the by-product is small, the by-product is easy to remove, and the equipment cost is saved; the reaction acyl chlorination effect is good, and the selectivity and the yield are high; the reaction is simple, the time is short, the use is convenient, the process energy consumption is low, and the synthesis method is an ideal preparation method of the paranitrobenzoyl chloride no matter from the angle of green chemistry or atom economy.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of p-nitrobenzoyl chloride. Background technique [0002] p-Nitrobenzoyl chloride is an important intermediate in organic synthesis, and has wide application value in the fields of medicine, textile industry and food industry. In medicine, it is often used to prepare procaine hydrochloride, p-aminobenzoyl glutamic acid and folic acid; in textile industry, it is often used to prepare acid dyes and direct dye brown 100, which can be used in leather and paper; in food industry, it can be used as food additives. [0003] The traditional synthesis techniques of p-nitrobenzoyl chloride include phosgene method, phosphorus trichloride method, phosphorus pentachloride method and thionyl chloride method. The raw material phosgene used in the phosgene method is a highly toxic gas, which is difficult to use, transport, and store, and it is difficult to measure accurately...

Claims

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Application Information

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IPC IPC(8): C07C205/57C07C201/12
Inventor 过学军胡安胜吴建平高焰兵戴玉婷张军刘长庆徐小兵黄显超朱张
Owner ANHUI GUANGXIN AGROCHEM
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