A kind of production technology of p-aminobenzamide

A technology of aminobenzamide and production process, which is applied in the field of production technology of p-aminobenzamide, can solve the problems of unfavorable green industrial production of aminobenzamide, high price of acyl chloride reagents, equipment corrosion, etc. Industrialized production, low cost and high total yield

Active Publication Date: 2021-09-28
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The price of the acyl chloride reagent used in the above method is relatively high, the acyl chloride reaction releases a large amount of acid gas, the equipment is severely corroded, the amidation reaction of ammonia water produces a large amount of waste water, and the reduction of iron powder produces a large amount of iron sludge. Green industrial production of benzamide

Method used

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  • A kind of production technology of p-aminobenzamide
  • A kind of production technology of p-aminobenzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Preparation of ethyl p-nitrobenzoate

[0036] In a 1000 ml four-neck flask connected with stirring, thermometer, water separator, and reflux condenser, 83.5 grams (0.5 moles) of p-nitrobenzoic acid, 250 grams of ethanol, 1.5 grams of p-toluenesulfonic acid, and 120 grams of toluene , 74.4 ° C (toluene-ethanol-water azeotropic) reflux with water for 7 hours, then cooled to 50-60 ° C, low vacuum and reduced pressure recovery ethanol and toluene (for the next batch of reactions), then high vacuum vacuum distillation ( 5-10mmHg) distilled 94.2 grams of ethyl p-nitrobenzoate, yield 96.5%, GC purity 99.9%.

[0037] (2) Preparation of p-aminobenzamide

[0038] In 500 milliliters of stainless steel autoclaves, add 39.0 grams (0.2 moles) ethyl p-nitrobenzoate prepared by step (1), 200 grams of 10% ammonia methanol solution, 0.3 grams of 5% palladium carbon catalyst, after nitrogen replacement three times, Pass in hydrogen, keep the hydrogen pressure at 0.2-0.3 MPa, and rea...

Embodiment 2

[0041] (1) Preparation of ethyl p-nitrobenzoate

[0042] In the 1000 milliliter four-neck flask that is connected with stirring, thermometer, water separator, reflux condenser, 83.5 grams (0.5 moles) p-nitrobenzoic acid, 230 grams of ethanol, 1.5 grams of solid super acid, 120 grams of normal hexane, 56 ℃ (n-hexane-ethanol-water azeotrope) was refluxed with water for 9 hours, then cooled to 40-50°C, low-vacuum and decompressed to recover n-hexane and ethanol (for the next batch of reactions), and then high-vacuum and reduced-pressure distillation ( 5-10mmHg) distilled 95.7 grams of ethyl p-nitrobenzoate, yield 98.2%, GC purity 99.8%.

[0043] (2) Preparation of p-aminobenzamide

[0044]Get 39.0 grams (0.2 moles) of ethyl p-nitrobenzoate prepared in step (1) and join in 500 milliliters of stainless steel autoclave, and add 200 grams of 10% ammonia ethanol solution, 3.5 grams of 50% Raney nickel catalyst, nitrogen displacement After three times, hydrogen gas was introduced to ...

Embodiment 3

[0046] (1) Preparation of ethyl p-nitrobenzoate

[0047] In a 1000 ml four-necked flask connected with stirring, thermometer, water separator, and reflux condenser, 75.0 grams (0.45 moles) of p-nitrobenzoic acid, 250 grams of ethanol, 1.5 grams of p-toluenesulfonic acid, and 150 grams of petroleum Ether, reflux at 65.5°C (petroleum ether-ethanol-water azeotrope) with water to react for 8 hours, then cool to 50-60°C, recover petroleum ether and ethanol (for the next batch reaction) under low vacuum and decompression, and then reduce Pressure distillation (5-10mmHg) distilled 86.5 grams of ethyl p-nitrobenzoate, yield 98.5%, GC purity 99.9%.

[0048] (2) Preparation of p-aminobenzamide

[0049] In 500 milliliters of stainless steel autoclaves, add 39.0 grams (0.2 moles) ethyl p-nitrobenzoate prepared by step (1), 200 grams of 10% ammonia methanol solution, 0.3 grams of 5% palladium carbon catalyst, after nitrogen replacement three times, Pass in hydrogen, keep the hydrogen pre...

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Abstract

The invention relates to a production process of p-aminobenzamide. The process utilizes p-nitrobenzoic acid and alcohol to generate p-nitrobenzoic acid ester through catalytic esterification reaction, and then in the presence of hydrogenation catalyst and hydrogen, ammonia Preparation of p-aminobenzamide by amidation reaction in alcohol solution. The raw materials used in the invention are cheap and easy to obtain, easy to operate, less waste water, high in operation safety, high in reaction selectivity, high in product yield and purity, and low in cost.

Description

technical field [0001] The invention relates to a production process of p-aminobenzamide, belonging to the technical field of chemistry and chemical engineering. Background technique [0002] P-aminobenzamide is an important intermediate used in the preparation of medicines, dyes, and pigments, in the dyeing of cotton, rayon, and hemp fibers, and in the preparation of inks. It has a wide range of uses. [0003] At present, the preparation of p-aminobenzamide is to prepare p-nitrobenzoyl chloride through acyl chloride reaction (acyl chloride reagent is thionyl chloride or triphosgene) with p-nitrobenzoic acid, and then react with ammonia to generate p-nitrobenzene Formamide, then prepare p-aminobenzamide through iron powder reduction or catalytic hydrogenation reduction (catalyst-hydrazine hydrate method), the total yield is 82.8%, such as CN104193646 and CN106946726, the reaction is described as synthetic route 1 as follows: [0004] [0005] The price of the acid chlori...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/57C07C231/02C07C233/65C07C231/12C07C237/30
Inventor 戚聿新鞠立柱王涛
Owner XINFA PHARMA
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