CN108358806B - Continuous synthesis method of m-acetamidophenol - Google Patents
Continuous synthesis method of m-acetamidophenol Download PDFInfo
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- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000001308 synthesis method Methods 0.000 title claims abstract description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 46
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 38
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 15
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 14
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 25
- 239000007864 aqueous solution Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000012295 chemical reaction liquid Substances 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 238000005086 pumping Methods 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 239000002699 waste material Substances 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000012954 diazonium Substances 0.000 description 8
- 150000001989 diazonium salts Chemical class 0.000 description 8
- 229940018563 3-aminophenol Drugs 0.000 description 7
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- DGMUOPTYPWAHII-UHFFFAOYSA-N (3-aminophenyl) benzenesulfonate Chemical compound NC1=CC=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 DGMUOPTYPWAHII-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NALDFXSDXQXFPL-UHFFFAOYSA-N (3-acetamidophenyl)azanium;chloride Chemical compound [Cl-].CC(=O)NC1=CC=CC([NH3+])=C1 NALDFXSDXQXFPL-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 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
- 238000010606 normalization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000007039 two-step 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
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Abstract
The invention discloses a continuous synthesis method of m-acetamido phenol, which takes m-acetamido aniline, sulfuric acid, sodium nitrite and the like as raw materials to prepare two solutions respectively, the two solutions are pumped into a tubular reactor respectively through a metering pump continuously according to set flow rate to carry out diazotization and hydrolysis reaction, and then products are obtained through cooling, extraction, drying and desolventizing, wherein the diazotization reaction and the hydrolysis reaction are completed in the same tubular reactor. The method has the characteristics of sufficient raw material sources, low price, high safety of the synthesis process, high product yield, less three-waste pollution and the like, and has higher industrial value.
Description
Technical Field
The invention relates to a continuous synthesis method of m-acetamidophenol, belonging to the field of fine chemical engineering.
Background
M-acetamidophenol is a key intermediate of pyridone heterocyclic disperse dye disperse yellow 114, and the disperse yellow 114 has the characteristics of good fastness performances such as sunlight resistance, sublimation resistance, washing resistance, friction resistance and the like, high level-dyeing property, high lifting force and the like, can be used independently or in color matching, and is one of yellow disperse dyes with the widest application at present.
The diazo component m-benzenesulfonyloxyaniline of disperse yellow 114 is synthesized at home and abroad by using m-aminophenol as a raw material through three-step reactions of amino acetylation protection, hydroxyl benzenesulfonic acid esterification and deacetylation deprotection, but the m-aminophenol used as the raw material in the method is high in price, and the synthesis process of the m-aminophenol is serious in three wastes and high in risk, so that the use of disperse yellow 114 is restricted.
Zhang et al (Zhejiang university Master's academic thesis 2010) reported a method for synthesizing m-acetamido aniline hydrochloride from m-phenylenediamine through single amino salt formation and acetic anhydride monoacetylation, and then synthesizing m-aminophenol through diazotization and diazonium salt hydrolysis reaction, but the method has the disadvantages of intermittent reaction during diazotization and diazonium salt hydrolysis, poor process safety, more three wastes and low yield. In addition, the diazo group and acetyl group are simultaneously hydrolyzed in the reaction of diazonium salt hydrolysis, and the obtained product is m-aminophenol. For synthesizing the m-phenylsulfonyloxyaniline which is the intermediate of disperse yellow 114, m-aminophenol needs to be acetylated again, so the cost is still high, and the defects of poor process safety, more three wastes and the like exist. Therefore, the method has important practical significance for searching the m-aminophenol or m-acetamidophenol synthesis process with low cost, less three wastes and good safety.
Disclosure of Invention
In order to overcome the defects of high preparation technology cost, serious three wastes, poor safety and the like of the m-acetaminophenol as the intermediate of disperse yellow 114, the invention provides a continuous synthesis method of the m-acetaminophenol.
In order to achieve the purpose, the invention adopts the technical scheme that: a continuous synthesis method of m-acetamidophenol is characterized in that a sulfuric acid aqueous solution A and a sodium nitrite aqueous solution B of m-acetamidophenol are respectively and continuously pumped into a tubular reactor to be mixed to form a reaction solution, the tubular reactor is provided with a pipeline type reaction section for providing a chemical reaction site, and the flow rate ratio of the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B pumped into the m-acetamidophenol is 1: 1-15; in the pipeline type reaction section, diazotization reaction and hydrolysis reaction are successively carried out at the temperature of 50-130 ℃, and the residence time of reaction liquid in the pipeline type reaction section is controlled to be 10-500 s; after the reaction is finished, cooling, extracting, drying and desolventizing the reaction solution to obtain a product, wherein the reaction formula is as follows:
the relevant content in the above technical solution is explained as follows:
1. in the scheme, the sulfuric acid aqueous solution A of the m-acetamino aniline comprises m-acetamino aniline, sulfuric acid and water, wherein the mass ratio of the m-acetamino aniline to the sulfuric acid to the water is 1: 1-5: 4-15.
2. In the scheme, the mass concentration of the sodium nitrite water solution B is 10-35%.
3. In the scheme, the molar ratio of the m-acetamino aniline to the sodium nitrite is 1: 1.01-1.08, wherein the molar ratio is adjusted and controlled by the concentration and flow rate ratio of the sulfuric acid aqueous solution A of the m-acetamino aniline and the sodium nitrite aqueous solution B.
4. In the scheme, the reaction temperature of the tubular reactor is controlled to be 60-120 ℃.
5. In the scheme, the inner diameter of the pipeline type reaction section of the tubular reactor is 2-25 mm, and the length of the pipeline type reaction section is 2-50 m.
6. In the scheme, after the diazotization reaction and the hydrolysis reaction are completed, the solvent for extraction is one of ethyl acetate, butyl acetate, toluene, cyclohexane, methylcyclohexane, methyl isopropyl ketone and methyl isobutyl ketone, and the extraction temperature is 20-60 ℃.
7. In the scheme, after the diazotization reaction and the hydrolysis reaction are finished, the reaction liquid is cooled by adopting a tubular reactor or a reaction kettle, and then is extracted by an organic solvent, dried and removed to obtain a product.
8. In the scheme, the specific flow rates of the two metering pumps for pumping the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B of the m-acetamino aniline are determined according to the inner diameter and the length of the tubular reactor and the residence time of the reaction liquid in the tubular reactor.
The invention has the beneficial effects that:
(1) the continuous synthesis method of the invention combines the two steps of reaction of traditional low-temperature diazotization reaction and high-temperature diazonium salt hydrolysis in a one-section pipeline reactor, the reaction is rapid, and compared with a kettle type reactor, the amount of materials in the pipeline reactor at any time is small, so the safety of the process is greatly improved.
(2) The diazotization of amino and the hydrolysis of diazonium salt are continuously completed in the same pipeline reactor, separation or low-temperature placement of unstable diazonium salt intermediates is not needed, the reaction time is short, byproducts generated by decomposition are few, and the product yield and content are high.
(3) Because the diazotization reaction of amino and the hydrolysis reaction of diazonium salt are both completed under the condition of strong acidity, a large amount of sulfuric acid is needed in the two-step reaction of the batch method, the two steps are combined into one tube to be completed by the pipelining method, and the excessive sulfuric acid is directly used for the hydrolysis of the diazonium salt in the diazotization reaction, so the needed sulfuric acid is greatly reduced, and the generated waste acid amount is obviously reduced.
(4) The flow rate ratio of the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B of the m-acetamino aniline and the retention time in the pipeline type reaction section are controlled, the flow rate ratio is adjusted in a proper range to control the molar ratio of the m-acetamino aniline and the sodium nitrite, so that the reaction is in a mild and controllable state, the reaction can be fully carried out, and the yield can be improved. The specific flow rates of the two metering pumps for pumping the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B of m-acetamidoaniline are determined according to the inner diameter and the length of the tubular reactor and the residence time of the reaction liquid in the tubular reactor.
In conclusion, the continuous synthesis method of m-acetamidophenol provided by the invention has the characteristics of high product yield, sufficient raw material source, low price, high synthesis process safety, less three-waste pollution and the like, and the yield of the product is over 85 percent, the content of the product is over 96 percent, and the method has high industrial value.
Detailed Description
The invention is further described below with reference to the following examples:
the starting materials and the like used in the following examples are all technical grade products and were not further purified. The content determination is performed by High Performance Liquid Chromatography (HPLC) normalization and Thin Layer Chromatography (TLC) with G254A silica gel plate.
EXAMPLE 1 Synthesis of m-acetamidophenol
91.5g (0.61 mol) of m-acetaminophenylamine, 270 g (2.70 mol) of 98% sulfuric acid and 1200 mL of water were stirred uniformly to prepare solution A, and 42.8 g (0.62 mol) of sodium nitrite and 180 mL of water were stirred uniformly to prepare solution B. Feeding the solution A and the solution B by a metering pump A and a metering pump B respectively, and controlling the flow rate ratio of the metering pump A to the metering pump B to be 1: 7.1, controlling the residence time of the reaction liquid in the tubular reactor to be 25 s. The tubular reactor is integrally a copper tube with an inner diameter of 16 mm and a length of 2 m, and the tube is immersed in an oil bath at a constant temperature of 120 ℃. And (3) allowing the reaction solution to flow out into a four-mouth bottle with stirring and cooling, extracting by using 3x200 mL of methyl isobutyl ketone at the extraction temperature of 20-35 ℃, washing with water, and drying with anhydrous sodium sulfate. Filtering and desolventizing to obtain 79.3 g of crude product m-acetaminophenol, the yield is 87.2 percent, the content is 96.4 percent, and the TLC and HPLC retention time is consistent with that of the m-acetaminophenol standard product.
EXAMPLE 2 Synthesis of m-acetamidophenol
91.5g (0.61 mol) of m-acetaminophenylamine, 180 g (1.80 mol) of 98% sulfuric acid and 1000 mL of water were stirred uniformly to prepare solution A, and 44.2 g (0.64 mol) of sodium nitrite and 160 mL of water were stirred uniformly to prepare solution B. Feeding the solution A and the solution B by a metering pump A and a metering pump B respectively, and controlling the flow rate ratio of the metering pump A to the metering pump B to be 1: 6.3, controlling the residence time of the reaction liquid in the tubular reactor to be 80 s. The tubular reactor consists of two parts, wherein the first part reaction section is a copper tube, the inner diameter is 4mm, the length is 10 m, and the pipeline is immersed in an oil bath with constant temperature of 100 ℃; the second part cooling section is a stainless steel pipe with the inner diameter of 4mm and the length of 10 m, and the pipe is immersed in an ice water bath. And collecting reaction liquid, extracting with 4x150 mL of toluene at the extraction temperature of 50-60 ℃, washing with water, and drying with anhydrous sodium sulfate. Filtering and desolventizing to obtain 77.7 g of crude product m-acetaminophenol, the yield is 85.5 percent, the content is 96.2 percent, and the TLC and HPLC retention time is consistent with that of the m-acetaminophenol standard product.
EXAMPLE 3 Synthesis of m-acetamidophenol
91.5g (0.61 mol) of m-acetaminoaniline, 360 g (3.60 mol) of 98% sulfuric acid and 800 mL of water were stirred uniformly to prepare solution A, and 45.0 g (0.65 mol) of sodium nitrite and 110 mL of water were stirred uniformly to prepare solution B. Feeding the solution A and the solution B by a metering pump A and a metering pump B respectively, and controlling the flow rate ratio of the metering pump A to the metering pump B to be 1: 8.1, controlling the residence time of the reaction liquid in the tubular reactor to be 220 s. The whole tubular reactor is a copper tube, the inner diameter is 6 mm, the length is 40 m, and the tube is immersed in an oil bath with the constant temperature of 70 ℃. And (3) allowing the reaction solution to flow out into a four-mouth bottle with stirring and cooling, extracting with 4x180 mL of cyclohexane at the extraction temperature of 45-55 ℃, washing with water, and drying with anhydrous magnesium sulfate. Filtering and desolventizing to obtain 80.1 g of crude product m-acetaminophenol, wherein the yield is 88.1 percent, the content is 96.6 percent, and the TLC and HPLC retention time is consistent with the m-acetaminophenol standard product.
EXAMPLE 4 Synthesis of m-acetamidophenol
91.5g (0.61 mol) of m-acetaminophenylamine, 140 g (1.40 mol) of 98% sulfuric acid and 550 mL of water were stirred uniformly to prepare solution A, and 43.8 g (0.635 mol) of sodium nitrite and 320 mL of water were stirred uniformly to prepare solution B. Feeding the solution A and the solution B by a metering pump A and a metering pump B respectively, and controlling the flow rate ratio of the metering pump A to the metering pump B to be 1: 2.2, controlling the residence time of the reaction liquid in the tubular reactor to be 25 s. The tubular reactor consists of two parts: the first part of the reaction section is a copper pipe, the inner diameter of the first part of the reaction section is 10 mm, the length of the first part of the reaction section is 18 m, and the first part of the reaction section is immersed in an oil bath with the constant temperature of 90 ℃; the second part cooling section is also a copper pipe with the inner diameter of 10 mm and the length of 10 m, and the pipe is immersed in the ice-water bath. And collecting reaction liquid, extracting with 3x200 mL of ethyl acetate at the extraction temperature of 25-40 ℃, washing with water, and drying with anhydrous magnesium sulfate. Filtering and desolventizing to obtain 78.3 g of crude product m-acetaminophenol, wherein the yield is 86.1 percent, the content is 97.1 percent, and the TLC and HPLC retention time is consistent with the m-acetaminophenol standard product.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. A continuous synthesis method of m-acetamidophenol is characterized in that: continuously pumping the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B of the m-acetamido aniline into a tubular reactor respectively to mix to form a reaction solution, wherein the tubular reactor is provided with a pipeline type reaction section which provides a chemical reaction site, and the flow rate ratio of the sulfuric acid aqueous solution A and the sodium nitrite aqueous solution B of the m-acetamido aniline pumped into the tubular reactor is 1: 1-15; in the pipeline type reaction section, diazotization reaction and hydrolysis reaction are successively carried out at the temperature of 50-130 ℃, and the residence time of reaction liquid in the pipeline type reaction section is controlled to be 10-500 s; after the reaction is finished, cooling, extracting, drying and desolventizing the reaction solution to obtain a product, wherein the reaction formula is as follows:
2. a continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: the composition of the sulfuric acid aqueous solution A of the m-acetamino aniline is m-acetamino aniline, sulfuric acid and water, and the mass ratio of the m-acetamino aniline to the sulfuric acid to the water is 1: 1-5: 4-15.
3. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: the mass concentration of the sodium nitrite water solution B is 10-35%.
4. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: the molar ratio of the m-acetamino aniline to the sodium nitrite is 1: 1.01-1.08, wherein the molar ratio is adjusted and controlled by the concentration and flow rate ratio of the sulfuric acid aqueous solution A of the m-acetamino aniline and the sodium nitrite aqueous solution B.
5. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: the reaction temperature of the tubular reactor is controlled to be 60-120 ℃.
6. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: the inner diameter of the pipeline type reaction section of the tubular reactor is 2-25 mm, and the length of the pipeline type reaction section is 2-50 m.
7. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: after the diazotization reaction and the hydrolysis reaction are finished, the solvent for extraction is one of ethyl acetate, butyl acetate, toluene, cyclohexane, methylcyclohexane, methyl isopropyl ketone and methyl isobutyl ketone, and the extraction temperature is 20-60 ℃.
8. A continuous synthesis method of m-acetamidophenol as claimed in claim 1, wherein: after the diazotization reaction and the hydrolysis reaction are finished, the reaction liquid is cooled by adopting a tubular reactor or a reaction kettle, and then is extracted by an organic solvent, dried and removed to obtain a product.
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| CN109134297A (en) * | 2018-08-27 | 2019-01-04 | 江苏迪安化工有限公司 | One inter-species di alkylamino group phenol is continuously synthesizing to method |
| CN112538030A (en) * | 2020-11-05 | 2021-03-23 | 乐威医药（江苏）股份有限公司 | Low-temperature continuous reactor and working method for producing diazo compound |
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