CN110734386A - Preparation method of kinds of p-aminoacetanilides - Google Patents
Preparation method of kinds of p-aminoacetanilides Download PDFInfo
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- CN110734386A CN110734386A CN201911036470.2A CN201911036470A CN110734386A CN 110734386 A CN110734386 A CN 110734386A CN 201911036470 A CN201911036470 A CN 201911036470A CN 110734386 A CN110734386 A CN 110734386A
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- Prior art keywords
- aminoacetanilide
- filtering
- cooling
- solution
- heating
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- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical class CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000001914 filtration Methods 0.000 claims abstract description 30
- 238000001816 cooling Methods 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- NQRLPDFELNCFHW-UHFFFAOYSA-N nitroacetanilide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 NQRLPDFELNCFHW-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000004321 preservation Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PXOZAFXVEWKXED-UHFFFAOYSA-N chembl1590721 Chemical compound C1=CC(NC(=O)C)=CC=C1N=NC1=CC(C)=CC=C1O PXOZAFXVEWKXED-UHFFFAOYSA-N 0.000 description 1
- NLMHXPDMNXMQBY-UHFFFAOYSA-L chembl260999 Chemical compound [Na+].[Na+].C1=CC(NC(=O)C)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C(O)C1=CC=C2NC(=O)NC1=CC=C(C(O)=C(N=NC=2C=CC=CC=2)C(=C2)S([O-])(=O)=O)C2=C1 NLMHXPDMNXMQBY-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of kinds of p-aminoacetanilide, which comprises the following preparation steps of ① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, uniformly mixing, heating and preserving heat, ② cooling, crystallizing and filtering the solution obtained in the step ① 0, ③ completely dissolving and cooling the solution obtained in the step ②, recrystallizing and filtering the solution with ethanol to obtain a p-aminoacetanilide solution, ④ filtering the p-aminoacetanilide solution obtained in the step ③ at 65-75 ℃, distilling, cooling and filtering to obtain a p-aminoacetanilide crude product, ⑥ heating and dissolving the p-aminoacetanilide crude product, cooling, filtering and drying in vacuum to obtain a p-aminoacetanilide product, wherein the temperature of the p-nitroacetanilide, the zinc powder, the ammonium chloride and the water added into the reaction kettle is 95-100 ℃, the heating and preserving heat time of the step ① is 0.5-1.5h, the yield of the step ① is 95%, the zinc powder and the ammonium chloride are used as reducing agents, and the water is used as solvents to reduce the p-nitroaetanilide to synthesize the.
Description
Technical Field
The invention belongs to the technical field of industrial dyes, and particularly relates to a preparation method of kinds of p-aminoacetanilide.
Background
The p-aminoacetanilide is also called N-acetyl-p-phenylenediamine, is an important dye intermediate, is mainly used for preparing disperse dyes, direct dyes, acid dyes and active dyes, such as disperse yellow G, direct acid-resistant scarlet 4BS, acid-resistant fuchsin 6B, active blue AG and the like, and the like.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of paracetamol, which has the advantages of simple preparation method, small pollution and convenient preparation.
The invention aims to realize the preparation method of kinds of p-aminoacetanilides, which comprises the following steps:
① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, mixing uniformly, heating and preserving heat;
② cooling and crystallizing the solution ①, and filtering;
③ completely dissolving in ② solution, cooling, recrystallizing with ethanol, and filtering to obtain p-aminoacetanilide solution;
④ filtering the solution of p-aminoacetanilide from step ③ at 65-75 deg.C, distilling, cooling, and filtering to obtain crude p-aminoacetanilide;
⑤ heating and dissolving the crude product of p-aminoacetanilide, cooling, filtering, and vacuum drying to obtain p-aminoacetanilide product.
Adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle at the temperature of 95-100 ℃.
The heating and heat preservation time in the step ① is 0.5-1.5 h.
The yield in step ① was 95%.
Zinc powder and ammonium chloride are used as reducing agents, water is used as a solvent to reduce p-nitroacetanilide, and p-aminoacetanilide is synthesized.
The method has the advantages that the pollution is extremely low, the reduction yield is high, the complex post-treatment caused by the use of organic solvent is avoided due to the fact that only solvent water is used in the reaction process, the cost is reduced, the method has broad development prospect, and other beneficial effects are detailed in specific embodiments.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described, and it is obvious that the described embodiments are only some embodiments of the present invention , but not all embodiments, and all other embodiments obtained by those skilled in the art without any inventive work based on the embodiments of the present invention belong to the protection scope of the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and the terms used herein are for the purpose of describing particular embodiments only and are not intended to be limiting, and terms such as "and/or" include any and all combinations of or more of the associated listed items, and furthermore, the features of various embodiments of the invention described below may be combined with each other as long as they do not conflict with each other.
Example 1
A process for preparing p-aminoacetanilide, which comprises the following steps:
① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, mixing uniformly, heating and preserving heat;
② cooling and crystallizing the solution ①, and filtering;
③ completely dissolving in ② solution, cooling, recrystallizing with ethanol, and filtering to obtain p-aminoacetanilide solution;
④ filtering the solution of p-aminoacetanilide from step ③ at 65 deg.C, distilling, cooling, and filtering to obtain crude p-aminoacetanilide;
⑤ heating and dissolving the crude product of p-aminoacetanilide, cooling, filtering, and vacuum drying to obtain p-aminoacetanilide product.
The temperature of adding p-nitroacetanilide, zinc powder, ammonium chloride and water into the reaction kettle is 95 ℃.
The heating and heat preservation time in the step ① is 0.5 h.
The yield in step ① was 95%.
Zinc powder and ammonium chloride are used as reducing agents, water is used as a solvent to reduce p-nitroacetanilide, and p-aminoacetanilide is synthesized.
The method has the advantages of little pollution, high reduction yield, no complicated post-treatment caused by the use of organic solvent due to the use of only solvent water in the reaction process, low cost and wide development prospect of .
Example 2
A process for preparing p-aminoacetanilide, which comprises the following steps:
① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, mixing uniformly, heating and preserving heat;
② cooling and crystallizing the solution ①, and filtering;
③ completely dissolving in ② solution, cooling, recrystallizing with ethanol, and filtering to obtain p-aminoacetanilide solution;
④ filtering the solution of p-aminoacetanilide from step ③ at 70 deg.C, distilling, cooling, and filtering to obtain crude p-aminoacetanilide;
⑤ heating and dissolving the crude product of p-aminoacetanilide, cooling, filtering, and vacuum drying to obtain p-aminoacetanilide product.
The temperature of adding the paranitroacetanilide, the zinc powder, the ammonium chloride and the water into the reaction kettle is 98 ℃.
The heating and heat preservation time in the step ① is 1 h.
The yield in step ① was 95%.
Zinc powder and ammonium chloride are used as reducing agents, water is used as a solvent to reduce p-nitroacetanilide, and p-aminoacetanilide is synthesized.
The preparation method has the advantages that in order to avoid the yield reduction caused by hydrolysis, the temperature adopted in the preparation method is 98, and the temperature can not only ensure that the reduction speed is , but also effectively avoid the hydrolysis of acetanilide.
Example 3
A process for preparing p-aminoacetanilide, which comprises the following steps:
① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, mixing uniformly, heating and preserving heat;
② cooling and crystallizing the solution ①, and filtering;
③ completely dissolving in ② solution, cooling, recrystallizing with ethanol, and filtering to obtain p-aminoacetanilide solution;
④ filtering the solution of p-aminoacetanilide from step ③ at 75 deg.C, distilling, cooling, and filtering to obtain crude p-aminoacetanilide;
⑤ heating and dissolving the crude product of p-aminoacetanilide, cooling, filtering, and vacuum drying to obtain p-aminoacetanilide product.
The temperature of adding the paranitroacetanilide, the zinc powder, the ammonium chloride and the water into the reaction kettle is 99 ℃.
The heating and heat preservation time in the step ① is 1.5 h.
The yield in step ① was 95%.
Zinc powder and ammonium chloride are used as reducing agents, water is used as a solvent to reduce p-nitroacetanilide, and p-aminoacetanilide is synthesized.
The method has the advantages of little pollution, high reduction yield, no complicated post-treatment caused by the use of organic solvent due to the use of only solvent water in the reaction process, low cost and wide development prospect of .
The present invention is further illustrated by , and not by way of limitation, and it will be apparent to those of ordinary skill in the art that modifications can be made in the structure without departing from the spirit of the invention and all such modifications are intended to fall within the scope of the appended claims.
Claims (5)
- The preparation method of kinds of p-aminoacetanilide is characterized by comprising the following steps:① adding p-nitroacetanilide, zinc powder, ammonium chloride and water into a reaction kettle, mixing uniformly, heating and preserving heat;② cooling and crystallizing the solution ①, and filtering;③ completely dissolving in ② solution, cooling, recrystallizing with ethanol, and filtering to obtain p-aminoacetanilide solution;④ filtering the solution of p-aminoacetanilide from step ③ at 65-75 deg.C, distilling, cooling, and filtering to obtain crude p-aminoacetanilide;⑤ heating and dissolving the crude product of p-aminoacetanilide, cooling, filtering, and vacuum drying to obtain p-aminoacetanilide product.
- 2. The process for preparing kinds of p-aminoacetanilide according to claim 1, wherein the temperature of p-nitroacetanilide, zinc powder, ammonium chloride and water in the reaction vessel is 95-100 ℃.
- 3. The method for preparing kinds of p-aminoacetanilides according to claim 1, wherein the heating and holding time in step ① is 0.5-1.5 h.
- 4. The method of Paracetanilide production according to claim 1, wherein the yield in step ① is 95%.
- 5. The method for preparing kinds of p-aminoacetanilides as claimed in claim 1, wherein zinc powder and ammonium chloride are used as reducing agents, and water is used as a solvent to reduce p-nitroacetanilides, thereby synthesizing p-aminoacetanilides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911036470.2A CN110734386A (en) | 2019-10-28 | 2019-10-28 | Preparation method of kinds of p-aminoacetanilides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911036470.2A CN110734386A (en) | 2019-10-28 | 2019-10-28 | Preparation method of kinds of p-aminoacetanilides |
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| Publication Number | Publication Date |
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| CN110734386A true CN110734386A (en) | 2020-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201911036470.2A Pending CN110734386A (en) | 2019-10-28 | 2019-10-28 | Preparation method of kinds of p-aminoacetanilides |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101730688A (en) * | 2007-03-09 | 2010-06-09 | 先正达参股股份有限公司 | 2-aryl-5-heterocyclyl-cyclohexane-1,3-dione compounds and their use as herbicides |
-
2019
- 2019-10-28 CN CN201911036470.2A patent/CN110734386A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101730688A (en) * | 2007-03-09 | 2010-06-09 | 先正达参股股份有限公司 | 2-aryl-5-heterocyclyl-cyclohexane-1,3-dione compounds and their use as herbicides |
Non-Patent Citations (2)
| Title |
|---|
| TAKEHITO TSUKINOKI等: "Organic reaction in water. Part 5.1 Novel synthesis of anilines by zinc metal-mediated chemoselective reduction of nitroarenes", 《GREEN CHEMISTRY》 * |
| 曹玮等: "对氨基乙酰苯胺合成绿色工艺的研究", 《化工时刊》 * |
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Application publication date: 20200131 |
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