CN116143649A - Synthesis method of 2-amino-4-acetamido anisole - Google Patents
Synthesis method of 2-amino-4-acetamido anisole Download PDFInfo
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- CN116143649A CN116143649A CN202310221753.4A CN202310221753A CN116143649A CN 116143649 A CN116143649 A CN 116143649A CN 202310221753 A CN202310221753 A CN 202310221753A CN 116143649 A CN116143649 A CN 116143649A
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- acetamido
- anisole
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- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 17
- MYIUWCZXTNZSMN-UHFFFAOYSA-N n-(4-methoxy-3-nitrophenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1[N+]([O-])=O MYIUWCZXTNZSMN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000012044 organic layer Substances 0.000 claims abstract description 9
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 7
- 238000006722 reduction reaction Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 16
- 239000006228 supernatant Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 229960005489 paracetamol Drugs 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012065 filter cake Substances 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 238000004537 pulping Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 4
- 238000004821 distillation Methods 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000004062 sedimentation Methods 0.000 abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a synthesis method of 2-amino-4-acetamido anisole, which comprises a reaction step of generating 2-amino-4-acetamido anisole from 2-nitro-4-acetamido anisole, wherein in the reaction step, catalytic hydrogenation reduction reaction is carried out in the presence of a catalyst, and a reaction solvent is an organic solvent which is insoluble with water. The synthesis method uses the organic solvent which is not mutually soluble with water as the hydrogenation reaction solvent, after the reaction is finished, the catalyst and the reaction liquid are separated by sedimentation, water generated in the reaction process can be separated by standing and layering, the organic layer is cooled and crystallized to separate out the product, the reaction solvent can be used mechanically without high-temperature distillation and rectification processes, and the problems of high energy consumption, complex post-treatment procedures and the like of the traditional synthesis process are solved.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a method for synthesizing 2-amino-4-acetamido anisole.
Background
2-amino-4-acetamidoanisole is an important intermediate for dye and medicine production, is mainly used as a disperse dye intermediate, and is also used for synthesizing acid dye, reactive dye and pigment, and plays an important role in industry.
The current synthetic route of 2-amino-4-acetamido anisole mainly comprises the following two steps:
route one:
route two:
the intermediate 2, 4-diaminoanisole in the second route is listed by European Union as 24 harmful aromatic amines, which are forbidden to be used in textile industry, and the final step has low selective acylation yield, and the process has not been industrially produced. Therefore, the first route is used by both domestic and foreign manufacturers at present.
The last catalytic hydrogenation reduction of the first route is as follows:
in this step, methanol is currently used as a solvent (for example, chinese patent document publication No. CN107903182 a), and dealcoholization is required after the reaction is completed, and methanol is required to be reused after rectification and dehydration, so that energy consumption is high. Water and 2-amino-4-acetaminophen as a product are also reported to be used as solvents for reaction (for example, chinese patent document with publication number of CN 106242990A), the reaction conditions of the solvents are harsh, the temperature and the pressure are high, and under the conditions, the acetamido of the product can be hydrolyzed, tar is generated at high temperature, so that the subsequent dye application is not facilitated.
Disclosure of Invention
The invention provides a synthesis method of 2-amino-4-acetamido anisole, which avoids high-temperature distillation and rectification processes in the reaction process, and has mild reaction conditions, high product yield and high purity.
The technical scheme of the invention is as follows:
a synthetic method of 2-amino-4-acetamido anisole comprises a reaction step of generating 2-amino-4-acetamido anisole from 2-nitro-4-acetamido anisole; in the reaction step, catalytic hydrogenation reduction reaction is carried out in the presence of a catalyst, and the reaction solvent is an organic solvent which is not mutually soluble with water.
Preferably, the reaction solvent is at least one of dichloromethane, dichloroethane, carbon tetrachloride, toluene and chlorobenzene.
Most preferably, the reaction solvent is dichloroethane.
Preferably, the catalyst is Raney nickel, and the addition amount of the catalyst is 8% -10% of the mass of the raw material; the catalytic hydrogenation reduction reaction temperature is 70-90 ℃, and the reaction pressure is 0.5-1Mpa.
Preferably, in the reaction step, catalytic hydrogenation reduction reaction is performed in the presence of a catalyst and a cocatalyst; the promoter is sodium acetate.
Preferably, the synthesis method of the 2-amino-4-acetamido anisole comprises the following steps:
(1) Pulping the wet 2-nitro-4-acetamido anisole and the reaction solvent, and adding the wet 2-nitro-4-acetamido anisole and the reaction solvent into an autoclave;
(2) Adding a catalyst into the autoclave, sealing, heating to 70-90 ℃ after nitrogen replacement, and starting to introduce hydrogen to 0.5-1Mpa for reaction;
(3) After the reaction is carried out until the pressure in the autoclave is no longer reduced, standing, extracting supernatant, and reserving a catalyst for reuse;
(4) And standing the supernatant, layering, cooling the organic layer, separating out a product, and filtering and separating to obtain a filter cake, namely the product 2-amino-4-acetaminophen.
In the synthesis method, after the reaction is finished, the catalyst and the reaction liquid are separated through sedimentation, the reaction liquid is stood for separation to obtain a water layer, and the organic layer is cooled for crystallization to obtain a product.
Preferably, in the step (1), the solid content of the wet 2-nitro-4-acetaminophen product is 85% or more.
Preferably, in the step (4), the filtrate is used for the next batch reaction after being supplemented with the reaction solvent and being used with the catalyst remained in the autoclave.
Preferably, in the step (4), the water layer is sleeved with water for crystal washing in the nitration process of the synthesis process of the 2-amino-4-acetamido anisole.
Compared with the prior art, the invention has the beneficial effects that:
the synthesis method uses the organic solvent which is not mutually soluble with water as the hydrogenation reaction solvent, after the reaction is finished, the catalyst and the reaction liquid are separated by sedimentation, water generated in the reaction process can be separated by standing and layering, the organic layer is cooled and crystallized to separate out the product, the reaction solvent can be used mechanically without high-temperature distillation and rectification processes, and the problems of high energy consumption, complex post-treatment procedures and the like of the traditional synthesis process are solved.
The synthetic method has high product yield and high purity.
Detailed Description
Example 1
200g of 2-nitro-4-acetamido anisole (containing 85% of solid) is put into a 2L autoclave, 850g of dichloroethane, 20g of Raney nickel catalyst, 0.2g of cocatalyst (sodium acetate), sealing, replacing nitrogen for three times, replacing hydrogen for three times, pressurizing to 0.8MPa, slowly heating to 70 ℃ under stirring, obviously starting reaction, releasing heat of the system, controlling the temperature of circulating water to be 70-90 ℃ for reaction, continuously introducing hydrogen until the pressure of the reaction system is not reduced, detecting the content of 2-nitro-4-acetamido anisole by sampling liquid chromatography to be 0.06%, after the reaction is finished, standing for 30min, decompressing, extracting supernatant, and leaving the catalyst at the bottom. The supernatant is layered while hot, 59g of water is separated, the organic layer is slowly stirred and cooled to 10 ℃, solid is separated out, 143.2g of 2-amino-4-acetamido anisole wet product is obtained through suction filtration, the purity is 99.3%, the amino value is 90.1%, the yield is 88.53%, and the filtrate is 850.2g.
Example 2 of the embodiment
200g of 2-nitro-4-acetamido anisole (containing 85% of solid) is put into an autoclave containing the catalyst of example 1, mother liquor is added in the batch, 14g of dichloroethane, 2g of Raney nickel catalyst and 0.2g of cocatalyst are added, sealing and nitrogen replacement are carried out for three times, hydrogen replacement is carried out for three times, pressurizing is carried out to 0.8MPa, slowly heating to 70 ℃, obviously starting reaction, heating the system, controlling the temperature to 70-90 ℃ for reaction, continuously introducing hydrogen until the pressure of the reaction system is not reduced any more, sampling liquid chromatography detects that the content of 2-nitro-4-acetamido anisole is 0.05%, after the reaction is finished, standing for 30min, pressure is released, supernatant is extracted, and the catalyst is reserved. Separating the supernatant into layers while the supernatant is hot, separating 59g of water, slowly stirring the organic layer, cooling to 10 ℃, precipitating solid, and suction-filtering to obtain 159.3g of 2-amino-4-acetaminophen wet product with purity of 99.2%, amino value of 90.6% and yield of 98.8%.
Example 3
200g of 2-nitro-4-acetamido anisole (containing 85% of solid), 850g of toluene, 20g of Raney nickel catalyst, 0.2g of cocatalyst (sodium acetate), sealing, replacing nitrogen for three times, replacing hydrogen for three times, pressurizing to 0.8MPa, slowly heating to 75 ℃ under stirring to obviously start reaction, releasing heat of the system, controlling the temperature of circulating water to 70-90 ℃ for reaction, continuously introducing hydrogen until the pressure of the reaction system is not reduced, detecting the content of 2-nitro-4-acetamido anisole by sampling liquid chromatography to be 0.08%, ending the reaction, standing for 30min, decompressing, extracting supernatant, and reserving the catalyst. Separating the supernatant, separating 58g of water, slowly stirring the organic layer, cooling to 5 ℃ to precipitate solid, and carrying out suction filtration to obtain 150g of wet 2-amino-4-acetamidoanisole product with purity of 99.1%, amino value of 89.3%, yield of 91.91% and filtrate of 840g.
Example 4
200g of 2-nitro-4-acetamido anisole (containing 85% of solid) is put into a 2L autoclave, 840g of example 4 mother liquor, 20g of toluene, 20g of Raney nickel catalyst, 0.2g of promoter (sodium acetate), sealing, replacing nitrogen for three times, replacing hydrogen for three times, pressurizing to 0.8MPa, slowly heating to 78 ℃ while stirring, obviously starting reaction, releasing heat of the system, controlling the temperature of circulating water to react at 70-90 ℃, continuously introducing hydrogen until the pressure of the reaction system is not reduced any more, detecting the content of 2-nitro-4-acetamido anisole by sampling liquid chromatography to be 0.06%, after the reaction is finished and standing for 30min, decompressing, extracting supernatant, and reserving the catalyst. Separating the supernatant, separating 58g of water, slowly stirring the organic layer, cooling to 0-3 ℃, precipitating solid, and suction-filtering to obtain 160g of 2-amino-4-acetaminophen dimethyl ether wet product with purity of 99.0%, amino value of 90.2%, yield of 99.03%, and filtrate 838g.
The foregoing embodiments have described the technical solutions and advantages of the present invention in detail, and it should be understood that the foregoing embodiments are merely illustrative of the present invention and are not intended to limit the invention, and any modifications, additions, substitutions and the like that fall within the principles of the present invention should be included in the scope of the invention.
Claims (8)
1. The synthesis method of 2-amino-4-acetamido anisole comprises a reaction step of generating 2-amino-4-acetamido anisole from 2-nitro-4-acetamido anisole, and is characterized in that in the reaction step, catalytic hydrogenation reduction reaction is carried out in the presence of a catalyst, and a reaction solvent is an organic solvent which is not mutually soluble with water.
2. The method for synthesizing 2-amino-4-acetamido anisole according to claim 1, wherein the reaction solvent is at least one of dichloromethane, dichloroethane, carbon tetrachloride, toluene and chlorobenzene.
3. The method for synthesizing 2-amino-4-acetamido anisole as in claim 2, wherein the reaction solvent is dichloroethane.
4. The method for synthesizing 2-amino-4-acetamido anisole according to claim 1, wherein the catalyst is Raney nickel, and the addition amount of the catalyst is 8% -10% of the mass of the raw material; the catalytic hydrogenation reduction reaction temperature is 70-90 ℃ and the reaction pressure is 0.5-1MPa.
5. The method for synthesizing 2-amino-4-acetamido anisole as claimed in claim 1, comprising:
(1) Pulping the wet 2-nitro-4-acetamido anisole and the reaction solvent, and adding the wet 2-nitro-4-acetamido anisole and the reaction solvent into an autoclave;
(2) Adding a catalyst into the autoclave, sealing, heating to 70-90 ℃ after nitrogen replacement, and starting to introduce hydrogen to 0.5-1Mpa for reaction;
(3) After the reaction is carried out until the pressure in the autoclave is no longer reduced, standing, extracting supernatant, and reserving a catalyst for reuse;
(4) And standing the supernatant, layering, cooling the organic layer, separating out a product, and filtering and separating to obtain a filter cake, namely the product 2-amino-4-acetaminophen.
6. The method for synthesizing 2-amino-4-acetaminophen ether according to claim 5, wherein in step (1), the solid content of the wet 2-nitro-4-acetaminophen ether product is 85% or more.
7. The method for synthesizing 2-amino-4-acetaminophen according to claim 5, wherein in step (4), the filtrate is used in the next reaction after being supplemented with the reaction solvent and with the catalyst remaining in the autoclave.
8. The method for synthesizing 2-amino-4-acetaminophen according to claim 5, wherein in step (4), the water layer is used as water for crystal washing in the nitration step of the 2-amino-4-acetaminophen synthesis process.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO54814A2 (en) * | 1969-12-29 | 1973-06-11 | ||
| CN1775353A (en) * | 2005-07-28 | 2006-05-24 | 大连理工大学 | Preparation of high activity hydrogenation catalyst backbone ruthenium and use method |
| CN104844461A (en) * | 2015-03-24 | 2015-08-19 | 安徽生源化工有限公司 | Synthetic process for amino aromatic hydrocarbon compound |
| CN106242990A (en) * | 2016-07-28 | 2016-12-21 | 浙江闰土研究院有限公司 | A kind of preparation method of 2 amino 4 acetyl-anisidines |
| CN106866449A (en) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | A kind of method that the acetyl-anisidine of 2 amino 4 is prepared using 2,4 dinitrophenol hydrogenating reduction by-product recoveries |
| CN107286043A (en) * | 2016-04-01 | 2017-10-24 | 上海安诺其集团股份有限公司 | The preparation method of 2- methoxyl group -5- acetylaminoanilines |
| CN107746380A (en) * | 2017-11-06 | 2018-03-02 | 宁夏中盛新科技有限公司 | A kind of industrialized preparing process of the acetyl-anisidine of 2 amino 4 |
| CN108373424A (en) * | 2018-03-21 | 2018-08-07 | 浙江闰土研究院有限公司 | A kind of preparation method of 2- amino -4- acetyl-anisidines |
-
2023
- 2023-03-09 CN CN202310221753.4A patent/CN116143649A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO54814A2 (en) * | 1969-12-29 | 1973-06-11 | ||
| CN1775353A (en) * | 2005-07-28 | 2006-05-24 | 大连理工大学 | Preparation of high activity hydrogenation catalyst backbone ruthenium and use method |
| CN104844461A (en) * | 2015-03-24 | 2015-08-19 | 安徽生源化工有限公司 | Synthetic process for amino aromatic hydrocarbon compound |
| CN107286043A (en) * | 2016-04-01 | 2017-10-24 | 上海安诺其集团股份有限公司 | The preparation method of 2- methoxyl group -5- acetylaminoanilines |
| CN106242990A (en) * | 2016-07-28 | 2016-12-21 | 浙江闰土研究院有限公司 | A kind of preparation method of 2 amino 4 acetyl-anisidines |
| CN106866449A (en) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | A kind of method that the acetyl-anisidine of 2 amino 4 is prepared using 2,4 dinitrophenol hydrogenating reduction by-product recoveries |
| CN107746380A (en) * | 2017-11-06 | 2018-03-02 | 宁夏中盛新科技有限公司 | A kind of industrialized preparing process of the acetyl-anisidine of 2 amino 4 |
| CN108373424A (en) * | 2018-03-21 | 2018-08-07 | 浙江闰土研究院有限公司 | A kind of preparation method of 2- amino -4- acetyl-anisidines |
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