CN105753730A - Method for preparing 2-amino-4-chloro-5-nitrophenol - Google Patents
Method for preparing 2-amino-4-chloro-5-nitrophenol Download PDFInfo
- Publication number
- CN105753730A CN105753730A CN201610206756.0A CN201610206756A CN105753730A CN 105753730 A CN105753730 A CN 105753730A CN 201610206756 A CN201610206756 A CN 201610206756A CN 105753730 A CN105753730 A CN 105753730A
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- Prior art keywords
- chloro
- amino
- nitrophenol
- chlorophenol
- methyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cosmetics (AREA)
Abstract
The invention relates to the field of dyeing industry, and in particular relates to a method for preparing 2-amino-4-chloro-5-nitrophenol. The method for preparing 2-amino-4-chloro-5-nitrophenol comprises the following steps: (1) by taking 2-amino-4-chlorophenol as a raw material, performing acetic anhydride acylation so as to obtain 2-acetamido-4-chlorophenol; (2) performing loop closure on the 2-acetamido-4-chlorophenol in the presence of a dehydrant so as to generate 5-chloro-2-methylbenzoxazole; (3) performing mixed acid nitration on the 5-chloro-2-methylbenzoxazole so as to generate 5-chloro-2-methyl-6-nitrobenzoxazole; (4) performing alkaline hydrolysis and acidification on the 5-chloro-2-methyl-6-nitrobenzoxazole, thereby obtaining the product 2-amino-4-chloro-5-nitrophenol, wherein the concentration of concentrated nitric acid used in the step (3) is 80-90%, and an acidifier used in the step (4) is concentrated hydrochloric acid. The method has the beneficial effects that as hair dye or a color former, the 2-amino-4-chloro-5-nitrophenol prepared by using the method is good in tinting strength, good in color fixation property and small in irritability to skin, and hair can be natural, soft and moist and glossy.
Description
Technical field
The present invention relates to dyeing field, be specifically related to the preparation method of a kind of 2-amino-4-chloro-5-nitrophenol.
Background technology
Chloro-5 nitrophenols of 2-amino-4-are a kind of important organic synthesis raw materials, for synthetic herbicide, dyestuff, photosensitive material colour coupler and medicine.The most several producers once carried out industrialization trial production, but because product yield priority low, of poor quality stops producing, the Wei Weimude company of the external mainly India producing this product at present, but the special process of this product they use sulfuric acid as dehydrating agent, the longer needs of dewatering time 24 hours, coloured product after dehydration is relatively deep, causes final finished color the deepest.This product with its distinctive high safety, colouring is fast, chemical characteristic is stable, the excellent characteristic such as natural beauty after hair dyeing, is widely used in domestic and international cosmetics, fur dyeing.
Summary of the invention
Problem to be solved by this invention is to overcome the deficiencies in the prior art, a kind of new preparation method is provided, 2-amino-4-chloro-5-nitrophenol prepared by this kind of preparation method is good, little to the excitant of skin as hair dye or colour coupler strong coloring force, solid color, and hair is natural, soft and moist, glossy.
For solving the problems referred to above, the technical solution used in the present invention is: the preparation method of a kind of 2-amino-4-chloro-5-nitrophenol, comprises the following steps:
The preparation method of a kind of 2-amino-4-chloro-5-nitrophenol, comprises the following steps:
(1) with 2-amino-4-chlorophenol as raw material, 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol it is acylated to obtain through aceticanhydride；
(2) 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol closed loop in the presence of a dehydrating agent is made to generate 5-chloro-2-methyl benzothiazole；
(3) 5-chloro-2-methyl benzothiazole generates 5-chloro-2-methyl-6-nitro benzothiazole through mixed acid nitrification；
(4) 5-chloro-2-methyl-6-nitro benzothiazole obtains product 2-amino-4-chloro-5-nitrophenol through alkaline hydrolysis and acidifying.
Preferably, the concentration of the red fuming nitric acid (RFNA) used in step (3) is 80-90%.
Preferably, the acidulant employed in step (4) is concentrated hydrochloric acid.
The beneficial effects of the present invention is: 2-amino-4-chloro-5-nitrophenol prepared by this kind of preparation method is good, little to the excitant of skin as hair dye or colour coupler strong coloring force, solid color, and hair is natural, soft and moist, glossy.
Detailed description of the invention
Below the present invention is described further:
The preparation method of a kind of 2-amino-4-chloro-5-nitrophenol, comprises the following steps:
(1) with 2-amino-4-chlorophenol as raw material, 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol it is acylated to obtain through aceticanhydride；
(2) 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol closed loop in the presence of a dehydrating agent is made to generate 5-chloro-2-methyl benzothiazole；
(3) 5-chloro-2-methyl benzothiazole generates 5-chloro-2-methyl-6-nitro benzothiazole through mixed acid nitrification；
(4) 5-chloro-2-methyl-6-nitro benzothiazole obtains product 2-amino-4-chloro-5-nitrophenol through alkaline hydrolysis and acidifying.
The concentration of the red fuming nitric acid (RFNA) used in step (3) is 80-90%, and the acidulant employed in step (4) is concentrated hydrochloric acid.
The beneficial effects of the present invention is: 2-amino-4-chloro-5-nitrophenol prepared by this kind of preparation method is good, little to the excitant of skin as hair dye or colour coupler strong coloring force, solid color, and hair is natural, soft and moist, glossy.
The above, be only presently preferred embodiments of the present invention, is not the restriction that the present invention makees other form.Any those skilled in the art are changed possibly also with the technology contents of the disclosure above or are modified as the Equivalent embodiments of equivalent variations.But every without departing from technical solution of the present invention content, any simple modification, equivalent variations and remodeling above example made according to structure and the operation principle of the present invention, still fall within the protection domain of technical solution of the present invention.
Claims (3)
1. the preparation method of a 2-amino-4-chloro-5-nitrophenol, it is characterised in that:
Comprise the following steps:
(1) with 2-amino-4-chlorophenol as raw material, 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol it is acylated to obtain through aceticanhydride；
(2) 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol closed loop in the presence of a dehydrating agent is made to generate 5-chloro-2-methyl benzothiazole；
(3) 5-chloro-2-methyl benzothiazole generates 5-chloro-2-methyl-6-nitro benzothiazole through mixed acid nitrification；
(4) 5-chloro-2-methyl-6-nitro benzothiazole obtains product 2-amino-4-chloro-5-nitrophenol through alkaline hydrolysis and acidifying.
The preparation method of a kind of 2-amino-4-the most according to claim 1 chloro-5-nitrophenol, it is characterised in that: the concentration of the red fuming nitric acid (RFNA) used in step (3) is 80-90%.
The preparation method of a kind of 2-amino-4-the most according to claim 1 chloro-5-nitrophenol, it is characterised in that: the acidulant employed in step (4) is concentrated hydrochloric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610206756.0A CN105753730A (en) | 2016-04-06 | 2016-04-06 | Method for preparing 2-amino-4-chloro-5-nitrophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610206756.0A CN105753730A (en) | 2016-04-06 | 2016-04-06 | Method for preparing 2-amino-4-chloro-5-nitrophenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105753730A true CN105753730A (en) | 2016-07-13 |
Family
ID=56333465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610206756.0A Pending CN105753730A (en) | 2016-04-06 | 2016-04-06 | Method for preparing 2-amino-4-chloro-5-nitrophenol |
Country Status (1)
| Country | Link |
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| CN (1) | CN105753730A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950764A (en) * | 2019-12-12 | 2020-04-03 | 沈阳感光化工研究院有限公司 | Method for synthesizing 2-amino-4-chloro-5 nitrophenol in microchannel reactor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108241A (en) * | 1993-04-30 | 1995-09-13 | 赫希斯特人造丝公司 | Improved process for preparing acyl aminophenols |
| CN101066929A (en) * | 2007-06-08 | 2007-11-07 | 江苏工业学院 | Process of preparing 4-amino-3-nitro phenol |
-
2016
- 2016-04-06 CN CN201610206756.0A patent/CN105753730A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108241A (en) * | 1993-04-30 | 1995-09-13 | 赫希斯特人造丝公司 | Improved process for preparing acyl aminophenols |
| CN101066929A (en) * | 2007-06-08 | 2007-11-07 | 江苏工业学院 | Process of preparing 4-amino-3-nitro phenol |
Non-Patent Citations (1)
| Title |
|---|
| 吴振刚等: "2-氨基-4-氯-5-硝基苯酚的生产工艺", 《山东化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950764A (en) * | 2019-12-12 | 2020-04-03 | 沈阳感光化工研究院有限公司 | Method for synthesizing 2-amino-4-chloro-5 nitrophenol in microchannel reactor |
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Application publication date: 20160713 |
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