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
- Authority
- CN
- China
- Prior art keywords
- chloro
- amino
- nitrophenol
- chlorophenol
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 12
- -1 2-acetylaminohydroxyphenylarsonic acid 4-chlorophenol Chemical compound 0.000 claims description 6
- XCALAYIRFYALSX-UHFFFAOYSA-N 5-chloro-2-methyl-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(C)=NC2=C1 XCALAYIRFYALSX-UHFFFAOYSA-N 0.000 claims description 6
- HCIFTTCECGSAPA-UHFFFAOYSA-N 5-chloro-2-methyl-6-nitro-1,3-benzothiazole Chemical compound ClC1=C([N+]([O-])=O)C=C2SC(C)=NC2=C1 HCIFTTCECGSAPA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- BUMGQSCPTLELLS-UHFFFAOYSA-N 2-chloro-5-nitrophenol Chemical compound OC1=CC([N+]([O-])=O)=CC=C1Cl BUMGQSCPTLELLS-UHFFFAOYSA-N 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 abstract description 4
- 239000000118 hair dye Substances 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- HJCIGAUHTJBHBQ-UHFFFAOYSA-N 5-chloro-2-methyl-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(C)=NC2=C1 HJCIGAUHTJBHBQ-UHFFFAOYSA-N 0.000 abstract 2
- HLNUPKJPTAHIEV-UHFFFAOYSA-N 5-chloro-2-methyl-6-nitro-1,3-benzoxazole Chemical compound ClC1=C([N+]([O-])=O)C=C2OC(C)=NC2=C1 HLNUPKJPTAHIEV-UHFFFAOYSA-N 0.000 abstract 2
- HGDAFIJKXCFHPG-UHFFFAOYSA-N n-(5-chloro-2-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1O HGDAFIJKXCFHPG-UHFFFAOYSA-N 0.000 abstract 2
- 206010022998 Irritability Diseases 0.000 abstract 1
- 239000002535 acidifier Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 238000004040 coloring Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003796 beauty Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 |
|---|---|
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160713 |
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| WD01 | Invention patent application deemed withdrawn after publication |