CN117229150A - Synthesis method of m-chloroaniline - Google Patents
Synthesis method of m-chloroaniline Download PDFInfo
- Publication number
- CN117229150A CN117229150A CN202311144986.5A CN202311144986A CN117229150A CN 117229150 A CN117229150 A CN 117229150A CN 202311144986 A CN202311144986 A CN 202311144986A CN 117229150 A CN117229150 A CN 117229150A
- Authority
- CN
- China
- Prior art keywords
- washing
- chlorobenzene
- chloroaniline
- chlorine
- solution
- 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
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000001308 synthesis method Methods 0.000 title claims description 3
- 238000005406 washing Methods 0.000 claims abstract description 75
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000000460 chlorine Substances 0.000 claims abstract description 37
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 16
- 230000001546 nitrifying effect Effects 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 13
- 238000010189 synthetic method Methods 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 9
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 4
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 37
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000008235 industrial water Substances 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- -1 and after washing Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 238000005868 electrolysis reaction Methods 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 239000003595 mist Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- 239000011973 solid acid Substances 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 239000008346 aqueous phase Substances 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 238000006298 dechlorination reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of m-chloroaniline, and discloses a synthetic method of m-chloroaniline, which comprises the following steps: 1) Firstly, benzene is synthesized into chlorobenzene, benzene and chlorine are continuously chlorinated under the catalysis of ferric chloride to obtain a chlorinated solution, and after washing, alkali washing, neutralization and salt drying, the chlorinated solution enters into a primary distillation benzene removal tower for removing tar, the crude chlorobenzene enters into a rectifying tower, and a chlorobenzene finished product is distilled from the top of the tower; 2) Nitrifying the obtained chlorobenzene, and nitrifying the chlorobenzene mixed acid to obtain o-nitrochlorobenzene; 3) The o-nitrochlorobenzene is reduced to nitro, that is, hydrochloric acid and iron powder are added to produce m-chloroaniline, crude product is produced when the temperature of the material reaches 150-160 ℃, and the product is collected when the temperature of the material reaches 180-190 ℃. According to the synthetic method of the m-chloroaniline, the purity of chlorobenzene under the reaction is improved through the fine operations of fully washing chlorine, alkaline washing and tar removal during the chlorination reaction, so that the purity of chlorobenzene in the reaction is effectively improved, and the purity of the m-chloroaniline is improved in the later processing.
Description
Technical Field
The invention relates to the technical field of m-chloroaniline, in particular to a synthetic method of m-chloroaniline.
Background
The m-chloroaniline, also called 3-chloroaniline, is an organic compound with a chemical formula of C6H6Cl N and is mainly used as an intermediate of dyes, pesticides and medicines.
The existing technology for synthesizing the m-chloroaniline is not fine enough in chlorine treatment, so that the dechlorination effect and purity are not high enough, and the purity of the synthesized m-chloroaniline is not high enough, so that a synthetic method of the m-chloroaniline is provided.
Disclosure of Invention
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides a synthetic method of m-chloroaniline, which has the advantages of improving the purity of a finished product and the like, and solves the problems that the dechlorination effect and the purity are not high enough, so that the purity of the synthesized m-chloroaniline is influenced to be not high enough.
(II) technical scheme
In order to achieve the purpose of improving the purity of the finished product, the invention provides the following technical scheme: a synthetic method of m-chloroaniline comprises the following steps:
1) Firstly, benzene is synthesized into chlorobenzene, benzene and chlorine are continuously chlorinated under the catalysis of ferric chloride to obtain a chlorinated solution, and after washing, alkali washing, neutralization and salt drying, the chlorinated solution enters into a primary distillation benzene removal tower for removing tar, the crude chlorobenzene enters into a rectifying tower, and a chlorobenzene finished product is distilled from the top of the tower;
2) Nitrifying the obtained chlorobenzene, and nitrifying the chlorobenzene mixed acid to obtain o-nitrochlorobenzene;
3) The o-nitrochlorobenzene is reduced to nitro, that is, hydrochloric acid and iron powder are added to produce m-chloroaniline, water is removed first, crude product is produced when the material temperature reaches 150-160 ℃, and the product is collected when the material temperature reaches 180-190 ℃.
Preferably, the catalyst for nitrifying the chlorobenzene is zeolite, solid acid or the like.
Preferably, phosphoric acid is added into nitric acid or mixed nitric acid and sulfuric acid during the nitration reaction, so that the comparison of products can be obviously reduced, and in a 98% nitric acid-98% phosphoric acid nitration system, the comparison is reduced to 0.9; in the case of a reaction mass ratio of chlorobenzene to nitric acid to phosphoric acid=1.0:1.06:2.0, the para-ortho ratio can be reduced to 1.63 with a yield of 71%.
Preferably, the chloridizing solution water washing comprises three water washing steps of first water washing, second water washing and third water washing which are sequentially carried out on the chloridizing solution, when the weight percentage concentration of hydrogen chloride and ferric trichloride in the first water washing reaches 1%, the first water washing is sent into the second water washing step, and purified water is synchronously supplemented to the first water washing step; when the weight percentage concentration of hydrogen chloride and ferric trichloride in the secondary washing water in the secondary washing step reaches 5%, sending the secondary washing water into the third washing step; when the weight percentage concentration of the hydrogen chloride and the ferric trichloride in the three-stage washing water in the third-stage washing step reaches 10%, the three-stage washing water is sent into a crystallization kettle to be concentrated and crystallized, the solid-phase ferric trichloride is obtained after the hydrogen chloride is removed, and a pipeline static mixer for mixing the chlorine chloride and the corresponding-stage washing water is arranged in each stage washing step.
Preferably, alkaline washing in the chloridizing solution comprises the steps of producing 70-85 ℃ wet chlorine through electrolysis, washing the wet chlorine by using industrial water in a chlorine washing tower, cooling the wet chlorine by using industrial water in a section of titanium cooler, cooling the wet chlorine to 12-15 ℃ by using +5C saline water in a second section of titanium cooler, drying the wet chlorine in a foam drying tower and a bubble cap tower by using sulfuric acid, and compressing the dried chlorine by using a chlorine compressor after passing through an acid mist catcher and conveying the chlorine to various chlorine stations.
Preferably, the neutralization of the chloridizing solution comprises the steps of cooling the chloridizing reaction solution, adding weak base saline solution to neutralize to a pH value of 5.5-7.5, adding strong alkaline aqueous solution to neutralize to a pH value of 8.5-9.5, adding concentrated hydrochloric acid aqueous solution to the reaction solution, adjusting the pH value of the reaction solution to 6.5-7.5, and cooling the chloridizing reaction solution to 15-35 ℃.
Preferably, the tar removal of the chloridizing solution comprises continuous water vapor distillation of the chloridizing benzene rectifying still solution under normal pressure, separating out water phase and oil phase in a water separator after gas phase condensation, and refluxing the water phase into the distilling still, wherein a certain volume of oil phase is reserved in the water separator.
(III) beneficial effects
Compared with the prior art, the invention provides a synthetic method of m-chloroaniline, which has the following beneficial effects:
according to the synthetic method of the m-chloroaniline, during the chlorination reaction, the fine operations of washing chlorine, alkaline washing and tar removal are fully performed on the chlorine, so that the purity of chlorobenzene under the reaction is improved, the purity of chlorobenzene in the reaction is effectively improved, the purity of the m-chloroaniline is improved in the later processing, the synthetic efficiency of the m-chloroaniline is improved, and the problems that the dechlorination effect and the purity are not high enough, and the purity of the synthesized m-chloroaniline is influenced are solved.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Embodiment one: a synthetic method of m-chloroaniline comprises the following steps:
1) Firstly, benzene is synthesized into chlorobenzene, benzene and chlorine are continuously chlorinated under the catalysis of ferric chloride to obtain a chlorinated solution, and after washing, alkali washing, neutralization and salt drying, the chlorinated solution enters into a primary distillation benzene removal tower for removing tar, the crude chlorobenzene enters into a rectifying tower, and a chlorobenzene finished product is distilled from the top of the tower; the chloridizing liquid washing comprises a first-stage washing step, a second-stage washing step and a third-stage washing step which are sequentially carried out on the chloridizing liquid, when the weight percentage concentration of hydrogen chloride and ferric trichloride in the first washing reaches 1%, the first washing step is sent into the second-stage washing step, and purified water is synchronously supplemented to the first-stage washing step; when the weight percentage concentration of hydrogen chloride and ferric trichloride in the secondary washing water in the secondary washing step reaches 5%, sending the secondary washing water into the third washing step; when the weight percentage concentration of hydrogen chloride and ferric trichloride in the tertiary washing water in the tertiary washing step reaches 10%, the tertiary washing water is sent into a crystallization kettle to be concentrated and crystallized, the solid-phase ferric trichloride is obtained after the hydrogen chloride is removed, a pipeline static mixer for mixing the chloridizing solution and the corresponding washing water is arranged in each stage of washing step, alkaline washing in the chloridizing solution comprises electrolysis to produce wet chlorine with the temperature of 70-85 ℃, after the wet chlorine is washed by industrial water in a chlorine washing tower, the wet chlorine enters a section titanium cooler to be cooled by industrial water, then enters a two section titanium cooler to be further cooled to the temperature of 12-15 ℃ by +5C brine, and then enters a foam drying tower and a bubble cap tower to be dried by sulfuric acid, the dried chlorine is compressed and conveyed to various chlorine stations by a chlorine compressor after passing through an acid mist catcher, the chloridizing solution is neutralized, namely, after cooling the chloridizing reaction solution, weak alkali saline solution is added to neutralize until the pH value is 5.5-7.5, strong alkaline aqueous solution is added to neutralize until the pH value of the reaction solution is 8.5-9.5, finally, concentrated hydrochloric acid aqueous solution is added to the reaction solution, the pH value of the reaction solution is regulated to be 6.5-7.5, the chloridizing reaction solution is cooled to 15-35 ℃, the tar removal of the chloridizing solution comprises continuous water vapor distillation under normal pressure of a chloridizing benzene rectifying still solution, water phase and oil phase are separated in a water separator after vapor phase condensation, the water phase flows back to a distillation still, and a certain volume of oil phase is reserved in the water separator;
2) Nitrifying the obtained chlorobenzene, and nitrifying the chlorobenzene mixed acid to obtain o-nitrochlorobenzene; the catalyst for nitrifying the chlorobenzene is zeolite, solid acid and the like, and phosphoric acid is added into nitric acid or mixed nitric-sulfuric acid during the nitrifying reaction to obviously reduce the contrast ratio of the product, and the contrast ratio is reduced to 0.9 in a 98% nitric acid-98% phosphoric acid nitrifying system; in the case of a reaction mass ratio of chlorobenzene to nitric acid to phosphoric acid=1.0:1.06:2.0, the para-ortho ratio can be reduced to 1.63, and the yield is 71%;
3) The o-nitrochlorobenzene is reduced to nitro, that is, hydrochloric acid and iron powder are added to produce m-chloroaniline, water is removed first, crude product is produced when the material temperature reaches 150-160 ℃, and the product is collected when the material temperature reaches 180-190 ℃.
The beneficial effects of the invention are as follows: according to the synthetic method of the m-chloroaniline, during the chlorination reaction, the fine operations of washing chlorine, alkaline washing and tar removal are fully performed on the chlorine, so that the purity of chlorobenzene under the reaction is improved, the purity of chlorobenzene in the reaction is effectively improved, the purity of the m-chloroaniline is improved in the later processing, the synthetic efficiency of the m-chloroaniline is improved, and the problems that the dechlorination effect and the purity are not high enough, and the purity of the synthesized m-chloroaniline is influenced are solved.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. The synthesis method of m-chloroaniline is characterized by comprising the following steps of:
1) Firstly, benzene is synthesized into chlorobenzene, benzene and chlorine are continuously chlorinated under the catalysis of ferric chloride to obtain a chlorinated solution, and after washing, alkali washing, neutralization and salt drying, the chlorinated solution enters into a primary distillation benzene removal tower for removing tar, the crude chlorobenzene enters into a rectifying tower, and a chlorobenzene finished product is distilled from the top of the tower;
2) Nitrifying the obtained chlorobenzene, and nitrifying the chlorobenzene mixed acid to obtain o-nitrochlorobenzene;
3) The o-nitrochlorobenzene is reduced to nitro, that is, hydrochloric acid and iron powder are added to produce m-chloroaniline, water is removed first, crude product is produced when the material temperature reaches 150-160 ℃, and the product is collected when the material temperature reaches 180-190 ℃.
2. The method for synthesizing meta-chloroaniline according to claim 1, wherein the catalyst for nitrifying chlorobenzene is zeolite, solid acid or the like.
3. The method for synthesizing m-chloroaniline according to claim 1, wherein the addition of phosphoric acid to nitric acid or mixed nitric acid and sulfur during the nitration reaction can obviously reduce the product to ortho ratio, and in a 98% nitric acid-98% phosphoric acid nitration system, the ortho ratio is reduced to 0.9; in the case of a reaction mass ratio of chlorobenzene to nitric acid to phosphoric acid=1.0:1.06:2.0, the para-ortho ratio can be reduced to 1.63 with a yield of 71%.
4. The method for synthesizing m-chloroaniline according to claim 1, wherein the chloridizing solution washing comprises a three-stage washing step of sequentially performing first-stage washing, second-stage washing and third-stage washing on the chloridizing solution, and when the weight percentage concentration of hydrogen chloride and ferric trichloride in the first washing reaches 1%, the first washing is sent to the second-stage washing step, and purified water is synchronously supplemented to the first-stage washing step; when the weight percentage concentration of hydrogen chloride and ferric trichloride in the secondary washing water in the secondary washing step reaches 5%, sending the secondary washing water into the third washing step; when the weight percentage concentration of the hydrogen chloride and the ferric trichloride in the three-stage washing water in the third-stage washing step reaches 10%, the three-stage washing water is sent into a crystallization kettle to be concentrated and crystallized, the solid-phase ferric trichloride is obtained after the hydrogen chloride is removed, and a pipeline static mixer for mixing the chlorine chloride and the corresponding-stage washing water is arranged in each stage washing step.
5. A synthetic method of m-chloroaniline is characterized in that alkaline washing in chloridizing solution comprises the steps of producing 70-85 ℃ wet chlorine through electrolysis, washing the wet chlorine with industrial water in a chlorine washing tower, cooling the wet chlorine with industrial water in a section of titanium cooler, cooling the wet chlorine with +5C saline water in a second section of titanium cooler to 12-15 ℃ further, drying the wet chlorine in a foam drying tower and a bubble cap tower with sulfuric acid, compressing the dried chlorine with a chlorine compressor after passing through an acid mist catcher, and conveying the chlorine to various chlorine stations.
6. The method for synthesizing m-chloroaniline according to claim 1, wherein the neutralization of the chloridizing solution comprises the steps of cooling the chloridizing reaction solution, adding weak base saline solution to neutralize to a pH value of 5.5-7.5, adding strong alkaline aqueous solution to neutralize to a pH value of 8.5-9.5, adding concentrated hydrochloric acid aqueous solution to the reaction solution, adjusting the pH value of the reaction solution to 6.5-7.5, and cooling the chloridizing reaction solution to 15-35 ℃.
7. The method for synthesizing m-chloroaniline according to claim 1, wherein the step of removing tar from the chlorinated solution comprises continuous steam distillation of the chlorinated benzene rectifying still solution under normal pressure, separating an aqueous phase and an oil phase in a water separator after gas phase condensation, and refluxing the aqueous phase to the distilling still, wherein a certain volume of the oil phase is reserved in the water separator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311144986.5A CN117229150A (en) | 2023-09-06 | 2023-09-06 | Synthesis method of m-chloroaniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311144986.5A CN117229150A (en) | 2023-09-06 | 2023-09-06 | Synthesis method of m-chloroaniline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117229150A true CN117229150A (en) | 2023-12-15 |
Family
ID=89095949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311144986.5A Pending CN117229150A (en) | 2023-09-06 | 2023-09-06 | Synthesis method of m-chloroaniline |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117229150A (en) |
-
2023
- 2023-09-06 CN CN202311144986.5A patent/CN117229150A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109503312B (en) | Process for continuously producing chloroethane by using byproduct hydrogen chloride produced in chlorobenzene production | |
| CN104311383B (en) | A kind of method of the hydrogen chloride production monochloro methane that utilizes by-product in tetrachloro-ethylene production process | |
| CN108084033B (en) | Preparation method of N, N-diethyl ethylenediamine | |
| CN106831315B (en) | Continuous production method of chloroethane | |
| CN103130197A (en) | Continuous-pressure-changing rectification method and device for preparing medicine-level sulfoxide chloride | |
| CN108558607B (en) | Efficient synthesis method of o-fluorophenol | |
| WO2014104894A1 (en) | Urea synthesis process and plant | |
| CN114907234B (en) | Preparation method of 2-fluoro-5-formylbenzonitrile | |
| CN117229150A (en) | Synthesis method of m-chloroaniline | |
| CN112724047A (en) | Device and method for preparing trifluoromethanesulfonyl fluoride | |
| CN106008183B (en) | The preparation method of ephedrine or pseudoephedrine and ephedrine or pseudoephedrine intermediate | |
| CN111646878A (en) | Method for recovering byproduct chloromethane in maltol production | |
| CN106831702A (en) | A kind of preparation method of the thiophenic acid of 5 substitution 2 | |
| CN113248446B (en) | 4, 6-dichloropyrimidine purification and phosphorus recycling treatment process | |
| CN109721496A (en) | A kind of synthetic method of 3- nitro ortho-xylene | |
| CN110590576A (en) | Preparation method of 4-polyfluoro methoxy o-phenylenediamine | |
| CN112221312A (en) | Method and device for separating and recovering tail gas in thionyl chloride production process | |
| CN110655442A (en) | Novel chlorination process of o-chlorotrifluoromethylene | |
| CN115521232B (en) | Preparation method of high-purity perfluoroalkyl sulfonyl bromide | |
| CN111303045A (en) | Production process of 2-ethoxy-4, 6-difluoropyrimidine | |
| CN112851518B (en) | Synthesis method of N-methyl o-fluoroaniline | |
| CN115010694B (en) | Fluoroethylene carbonate and preparation method thereof | |
| EP2941416A1 (en) | Urea plant revamping method | |
| CN116023257B (en) | Continuous production method of high-purity propionyl chloride | |
| CN114835589B (en) | Preparation method of 2,4-difluoro-3,5-dichloroaniline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |