CN115850085A - Method for preparing fluoronitrobenzene from chloronitrobenzene - Google Patents
Method for preparing fluoronitrobenzene from chloronitrobenzene Download PDFInfo
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- CN115850085A CN115850085A CN202211709460.2A CN202211709460A CN115850085A CN 115850085 A CN115850085 A CN 115850085A CN 202211709460 A CN202211709460 A CN 202211709460A CN 115850085 A CN115850085 A CN 115850085A
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- Prior art keywords
- chloronitrobenzene
- fluoro
- fluoronitrobenzene
- catalyst
- reaction
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- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 29
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000011698 potassium fluoride Substances 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 235000003270 potassium fluoride Nutrition 0.000 claims description 9
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 4
- 235000013024 sodium fluoride Nutrition 0.000 claims description 4
- 239000011775 sodium fluoride Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- -1 phenyl aromatic hydrocarbon Chemical class 0.000 claims description 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 229910001510 metal chloride Inorganic materials 0.000 abstract description 3
- 150000001491 aromatic compounds Chemical class 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 1
- WWJBDSBGLBEFSH-UHFFFAOYSA-N 2-(4-methoxyphenyl)azepane Chemical compound C1=CC(OC)=CC=C1C1NCCCCC1 WWJBDSBGLBEFSH-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229960003814 lomefloxacin hydrochloride Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940072132 quinolone antibacterials Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing fluoronitrobenzene from chloronitrobenzene. Through the mode, the method for preparing the fluoronitrobenzene from the chloronitrobenzene generates metal chloride without environmental pollution, reduces the production cost, reduces the pollution to the environment, greatly improves the operation environment, reduces harmful substances, and ensures that the prepared fluoronitrobenzene contains more than 98 percent of purity, thereby being suitable for the preparation and synthesis of monofluoro compounds and the production of polyfluoro aromatic compounds.
Description
Technical Field
The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for preparing fluoronitrobenzene from chloronitrobenzene.
Background
Organic fluoro-compounds have been widely used in many fields such as pesticides, medicines, dye industry, liquid crystal materials, etc. due to their unique physicochemical properties. Among them, fluorine atoms have the characteristics of small atomic radius, strong electronegativity, low polarizability and the like, so that the fluorine-containing compounds generally have good physiological activity. One or more fluorine atoms are introduced into the nitroaromatic compound, so that the electronic effect of the compound molecules can be obviously changed, and the physiological activity of the compound is improved. Such as intermediate 2,3, 4-trifluoronitrobenzene, which can be used for synthesizing the third generation quinolone antibacterial drugs ofloxacin, lomefloxacin hydrochloride and the like. The intermediate 2, 4-difluoronitrobenzene can be used for preparing diflunisal for treating partial arthritis and the like. The traditional method for synthesizing fluoronitrobenzene mainly comprises the following steps: (1) The chlorobenzene is taken as a raw material, and is subjected to nitration and fluorination to obtain the corresponding fluoronitrobenzene; (2) Chloroaniline is used as a raw material, and corresponding fluoronitrobenzene is obtained through diazotization, thermal decomposition, nitration and fluorination.
As reported in patent CN 107325001: chlorobenzene is used as a raw material, and products are obtained through nitration, fluorination and ultrasonic reaction. On one hand, the production is dangerous, on the other hand, the reaction is not suitable for industrial production, the production and maintenance cost is high, meanwhile, the pollution in the nitration process is large, the green production is not facilitated, and the environmental protection cost is increased.
For example, in chemical production and technology 2005 (04), 1-5-43-51: chloroaniline was used as the starting material, HCl, H 2 SO 4 、HNO 3 As an auxiliary agent for the reaction, the environment is polluted, and the strong acid corrodes pipelines and reaction kettles, so that the equipment cost and the maintenance cost are increased.
The commonly used method for synthesizing the fluoronitrobenzene uses raw materials which are polluted greatly, are harmful greatly, are not friendly to the environment, have high requirements on production equipment, are dangerous and not environment-friendly in the production process, have severe production environment and do not accord with the modern industrialized green environment-friendly concept.
Disclosure of Invention
The invention mainly solves the technical problem of providing the method for preparing the fluoronitrobenzene from the chloronitrobenzene, and the preparation process is mild and environment-friendly.
In order to solve the technical problems, the invention adopts a technical scheme that: provided is a method for preparing fluoronitrobenzene from chloronitrobenzene, comprising the steps of: mixing chloronitrobenzene, fluoro-metal salt, a catalyst and a solvent for reaction to obtain the fluoro-nitrobenzene.
In a preferred embodiment of the invention, the chloronitrobenzene is ArCl x NO 2 Wherein x is 1, 2 or 3.
In a preferred embodiment of the present invention, the fluoro-metal salt is one or more of sodium fluoride, lithium fluoride, potassium fluoride and ammonium fluoride.
In a preferred embodiment of the present invention, the fluoro-metal salt is one or a mixture of two of sodium fluoride and potassium fluoride.
In a preferred embodiment of the present invention, the fluorinated metal salt is industrially recycled fluorinated metal salt or fluorinated metal salt having a mass content of 98% or more; the fluoro-metal salt is present as a solid.
In a preferred embodiment of the invention, the catalyst is a two-phase catalyst.
In a preferred embodiment of the invention, the catalyst is a quaternary phosphonium salt R 4 PX or R 2 P(CH 2 ) n R 2 PX 2 Wherein R is straight chain, branched chain or cyclic alkane and phenyl arene containing C-H bonds, and X is F, cl, br, I, HSO 4 。
In a preferred embodiment of the present invention, the mass ratio of the chloronitrobenzene to the fluoro-metal salt is 1:1 to 10.
In a preferred embodiment of the invention, the catalyst is added in an amount of 1 to 30% of the amount of the chloronitrobenzene substance.
In a preferred embodiment of the present invention, the temperature of the mixing reaction is 80-300 deg.C, and the pressure is 0.1-10 MPa.
The invention has the beneficial effects that: the method for preparing fluoronitrobenzene from chloronitrobenzene generates metal chloride without environmental pollution, reduces the production cost, reduces the environmental pollution, greatly improves the operating environment, reduces harmful substances, and ensures that the prepared fluoronitrobenzene contains more than 98 percent of purity, thereby not only being suitable for preparing and synthesizing monofluoro compounds, but also being suitable for producing polyfluoro aromatic compounds.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
provided is a method for preparing fluoronitrobenzene from chloronitrobenzene, comprising the steps of: 740g of potassium fluoride KF, 1000g of o-chloronitrobenzene and a catalyst Ph are sequentially added into an anhydrous reaction bottle 2 P(CH 2 ) 3 PPh 2 Br30g and DMSO6000g as solvent, heating to 70-80 ℃ under reduced pressure, stirring for 1-3h until no water drops exist in the distillation head, and removing water in the raw material, the catalyst and the solvent by the step, so that the reaction effect of the subsequent mixing reaction is good. And then heating to 165 ℃ to start reaction, tracking the reaction process by HPLC, and stopping the reaction after reacting for 16 hours until the content of the o-fluoronitrobenzene product is more than or equal to 85 percent, wherein no product is converted even if the reaction is continued. Cooling, filtering, and rectifying the filtrate to separate DMSO and the product.
Example two:
provided is a method for preparing fluoronitrobenzene from chloronitrobenzene, comprising the steps of: 740g of potassium fluoride KF, 1000g of o-chloronitrobenzene and a catalyst Ph are sequentially added into an anhydrous reaction bottle 4 PBr 30g and solvent DMSO6000g, and the temperature is increased to 70-80 ℃ under reduced pressure and stirred for 1-3h until no water drops exist in the distillation head. Heating to 120 ℃ to start reaction, tracking the reaction process through HPLC, and stopping the reaction after the reaction is carried out for 16 hours until the content of the product o-fluoronitrobenzene is more than or equal to 80%. And (3) cooling, filtering, and rectifying the filtrate to separate DMSO and a product.
Example three:
a method for preparing fluoronitrobenzene from chloronitrobenzene is provided, which comprises the following steps: 740g of potassium fluoride KF, 1000g of o-chloronitrobenzene and a catalyst Ph are sequentially added into an anhydrous reaction bottle 4 PBr 30g and solvent DMSO6000g, and the temperature is increased to 70-80 ℃ under reduced pressure and stirred for 1-3h until no water drops exist in the distillation head. And (3) heating to 140 ℃ to start reaction, tracking the reaction process by HPLC, and stopping the reaction after reacting for 16 hours until the content of the o-fluoronitrobenzene product is more than or equal to 86%. Cooling, filtering, and rectifying the filtrate to separate DMSO and the product.
Example four:
provides a method for preparing fluoronitrobenzene from chloronitrobenzene, comprising the following stepsThe method comprises the following steps: sequentially adding 1100g of potassium fluoride KF, 1000g of p-chloronitrobenzene and catalyst Ph into an anhydrous reaction bottle 2 P(CH 2 ) 3 PPh 2 Br30g and DMSO6000g, heating to 70-80 ℃ under reduced pressure, and stirring for 1-3h until no water drops exist in the distillation head. And (3) heating to 165 ℃ to start reaction, tracking the reaction process by HPLC, and stopping the reaction after reacting for 16 hours until the content of the o-fluoronitrobenzene product is more than or equal to 85%. Cooling, filtering, and rectifying the filtrate to separate DMSO and the product.
Example five:
a method for preparing fluoronitrobenzene from chloronitrobenzene is provided, which comprises the following steps: sequentially adding 410g of potassium fluoride KF, 1000g of m-chloronitrobenzene and catalyst Ph into an anhydrous reaction bottle 4 PBr 30g and solvent DMSO5000g, and the temperature is increased to 70-80 ℃ under reduced pressure and stirred for 1-3h until no water drops are left on the distillation head. And (3) heating to 165 ℃ to start reaction, tracking the reaction process by HPLC, and stopping the reaction after reacting for 16 hours until the content of the o-fluoronitrobenzene product is more than or equal to 80%. Cooling, filtering, and rectifying the filtrate to separate DMSO and the product.
The invention takes chloronitrobenzene and fluoro metal salt as raw materials to synthesize fluoro nitrobenzene under the condition of catalyst catalysis, then the reaction solution is filtered and rectified to prepare the fluoro nitrobenzene, filter residue is washed by DMSO, the phase transfer catalyst can be washed out and can be directly used, namely, the phase transfer catalyst can be recycled, and insoluble components are the chloro metal salt and excessive fluoro metal salt. The invention synthesizes the fluoronitrobenzene, and simultaneously, the byproduct is the metal chloride salt, and the raw materials are simple and easy to obtain and have little pollution. Acid is not used in the reaction process, the diffusion of harmful substances in the air is reduced, the production environment is better, the pollution is small, the harm and the pollution to the environment are reduced, the idea of modern green production can be met, the environment-friendly pollution discharge cost is reduced, the operation environment is greatly improved, the profit is improved, the method is more economic, and the clean production is realized.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (10)
1. A method for preparing fluoronitrobenzene from chloronitrobenzene is characterized by comprising the following steps: mixing chloronitrobenzene, fluoro metal salt, catalyst and solvent for reaction to obtain the fluoro nitrobenzene.
2. The process according to claim 1, characterized in that the chloronitrobenzene is ArCl x NO 2 Wherein x is 1, 2 or 3.
3. The method of claim 1, wherein the fluoro-metal salt is a mixture of one or more of sodium fluoride, lithium fluoride, potassium fluoride, and ammonium fluoride.
4. The method of claim 3, wherein the fluoro-metal salt is one or a mixture of sodium fluoride and potassium fluoride.
5. The method according to claim 1, wherein the metal fluoro salt is industrially recycled metal fluoro salt or metal fluoro salt having a mass content of 98% or more; the fluoro metal salt is present as a solid.
6. The process of claim 1, wherein the catalyst is a two-phase catalyst.
7. The process of claim 6 wherein the catalyst is a quaternary phosphonium salt R 4 PX or R 2 P(CH 2 ) n R 2 PX 2 Wherein R is straight chain, branched chain or cyclic alkane containing C-H bond, or phenyl aromatic hydrocarbon, and X is F, cl, br, I, HSO 4 。
8. The process according to claim 1, characterized in that the mass ratio of chloronitrobenzene to fluoro-metal salt is 1:1 to 10.
9. The process according to claim 1, characterized in that the catalyst is added in an amount of 1 to 30% of the mass of chloronitrobenzene.
10. The method according to claim 1, wherein the temperature of the mixing reaction is 80 to 300 ℃ and the pressure is 0.1 to 10MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211709460.2A CN115850085A (en) | 2022-12-29 | 2022-12-29 | Method for preparing fluoronitrobenzene from chloronitrobenzene |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211709460.2A CN115850085A (en) | 2022-12-29 | 2022-12-29 | Method for preparing fluoronitrobenzene from chloronitrobenzene |
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| CN202211709460.2A Pending CN115850085A (en) | 2022-12-29 | 2022-12-29 | Method for preparing fluoronitrobenzene from chloronitrobenzene |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2791670A1 (en) * | 1999-03-31 | 2000-10-06 | Rhodia Chimie Sa | METHOD FOR ACTIVATION OF AROMATIC SUBSTRATES BY MICROWAVE |
| US20050228201A1 (en) * | 2001-06-15 | 2005-10-13 | Marielouise Henrich | Process for preparing nuclear-fluorinated aromatics |
| CN101134712A (en) * | 2007-10-08 | 2008-03-05 | 浙江省常山长盛化工有限公司 | Preparation method of 2,4-dichloro fluorobenzene |
| CN101585771A (en) * | 2009-07-07 | 2009-11-25 | 浙江富盛控股集团有限公司 | Method of comprehensively use of chloronitrobenzene mixture by fluoro-reaction |
| CN101613286A (en) * | 2009-07-17 | 2009-12-30 | 淮安嘉诚高新化工股份有限公司 | The separation of nitrobenzene chlorides and method of comprehensive utilization |
| CN103420842A (en) * | 2013-08-01 | 2013-12-04 | 上虞市临江化工有限公司 | Preparation method for 2,3,4-trifluoronitrobenzene |
| CN113943222A (en) * | 2021-10-25 | 2022-01-18 | 顺毅宜昌化工有限公司 | Preparation method of fluoronitrobenzene |
-
2022
- 2022-12-29 CN CN202211709460.2A patent/CN115850085A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2791670A1 (en) * | 1999-03-31 | 2000-10-06 | Rhodia Chimie Sa | METHOD FOR ACTIVATION OF AROMATIC SUBSTRATES BY MICROWAVE |
| US20050228201A1 (en) * | 2001-06-15 | 2005-10-13 | Marielouise Henrich | Process for preparing nuclear-fluorinated aromatics |
| CN101134712A (en) * | 2007-10-08 | 2008-03-05 | 浙江省常山长盛化工有限公司 | Preparation method of 2,4-dichloro fluorobenzene |
| CN101585771A (en) * | 2009-07-07 | 2009-11-25 | 浙江富盛控股集团有限公司 | Method of comprehensively use of chloronitrobenzene mixture by fluoro-reaction |
| CN101613286A (en) * | 2009-07-17 | 2009-12-30 | 淮安嘉诚高新化工股份有限公司 | The separation of nitrobenzene chlorides and method of comprehensive utilization |
| CN103420842A (en) * | 2013-08-01 | 2013-12-04 | 上虞市临江化工有限公司 | Preparation method for 2,3,4-trifluoronitrobenzene |
| CN113943222A (en) * | 2021-10-25 | 2022-01-18 | 顺毅宜昌化工有限公司 | Preparation method of fluoronitrobenzene |
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