CN114507147B - Method for preparing 2, 6-dichloro-4-trifluoromethyl aniline - Google Patents
Method for preparing 2, 6-dichloro-4-trifluoromethyl aniline Download PDFInfo
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- CN114507147B CN114507147B CN202210260629.4A CN202210260629A CN114507147B CN 114507147 B CN114507147 B CN 114507147B CN 202210260629 A CN202210260629 A CN 202210260629A CN 114507147 B CN114507147 B CN 114507147B
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- trifluoromethylaniline
- dichloro
- trifluoromethyl aniline
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- ITNMAZSPBLRJLU-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ITNMAZSPBLRJLU-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 26
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims abstract description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 39
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims abstract description 19
- YECYUHRFXUFJRV-UHFFFAOYSA-N 2,4-dichloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=C(Cl)C=C1Cl YECYUHRFXUFJRV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000003513 alkali Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- MBBUTABXEITVNY-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1Cl MBBUTABXEITVNY-UHFFFAOYSA-N 0.000 claims description 6
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 230000001546 nitrifying effect Effects 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 238000002844 melting Methods 0.000 abstract description 4
- 230000008018 melting Effects 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 description 7
- 230000005526 G1 to G0 transition Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical class NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 2, 6-dichloro-4-trifluoromethyl aniline. The method for preparing 2, 6-dichloro-4-trifluoromethyl aniline comprises the following steps: the rectifying still residue of m-trifluoromethyl aniline is reacted with chlorine in a solvent until the content of 2, 4-dichloro-5-trifluoromethyl aniline in the reaction liquid is less than or equal to 0.3 percent, and the m-trifluoromethyl aniline is obtained; the rectification kettle residue of m-trifluoromethyl aniline comprises the following components: 69.6 to 72.5 percent of para-trifluoromethylaniline and 25.5 to 28.4 percent of meta-trifluoromethylaniline; the solvent is water or hydrochloric acid. The invention has simple process and no need of melting crystallization, and the purity of the prepared 2, 6-dichloro-4-trifluoromethyl aniline product is up to 99.5 percent, and the percentages are all mass percent.
Description
Technical Field
The invention relates to a method for preparing 2, 6-dichloro-4-trifluoromethyl aniline.
Background
Patent CN 101538206a discloses a process method for synthesizing 2, 6-dichloro-4-trifluoromethylaniline by dissolving the reaction kettle residue of benzotrifluoride in hydrochloric acid, and adding hydrogen peroxide for oxychlorination reaction. The kettle residue treated and utilized in the method is residual liquid obtained by batch kettle type nitration, hydrogenation reduction and redistillation of benzotrifluoride, and the residual liquid comprises the following components: 6-10% of m-trifluoromethylaniline, 30-60% of p-trifluoromethylaniline and the balance of N-alkyl-3-trifluoromethylaniline and a small amount of polymer.
The inventor finds that the residue components produced by different processes have larger difference, kettle residues produced by continuous nitration and hydrogenation reduction processes contain more m-trifluoromethyl aniline, if the same oxychlorination method is adopted to synthesize 2, 6-dichloro-4-trifluoromethyl aniline, the m-trifluoromethyl aniline is converted into 2, 4-dichloro-5-trifluoromethyl aniline which is an isomer of 2, 6-dichloro-4-trifluoromethyl aniline, the melting point and the boiling point of the isomer are close to those of the 2, 6-dichloro-4-trifluoromethyl aniline, the separation is difficult, the purity is only about 96% after conventional rectification and melt crystallization purification, and the product with the content more than or equal to 99% is difficult to obtain.
The method for preparing the 2, 6-dichloro-4-trifluoromethyl aniline by utilizing the rectifying still residue generated by continuously producing m-trifluoromethyl aniline is found, and the recycling of the still residue is realized, so that the method has important significance in changing waste into valuable.
Disclosure of Invention
In order to solve the problem that rectifying still residues generated in the continuous production of m-trifluoromethyl aniline are not easy to treat, the invention provides a method for preparing 2, 6-dichloro-4-trifluoromethyl aniline, the recycling of still residues is realized, waste is changed into valuable, the process is simple, the reaction time is short, melting crystallization is not needed, and the prepared 2, 6-dichloro-4-trifluoromethyl aniline has higher yield and purity.
The invention solves the technical problems by the following technical scheme:
the invention provides a method for preparing 2, 6-dichloro-4-trifluoromethyl aniline, which comprises the following steps:
the rectifying still residue of m-trifluoromethylaniline is reacted with chlorine in a solvent until the content of 2, 4-dichloro-5-trifluoromethylaniline in the reaction liquid is less than or equal to 0.3%, and the m-trifluoromethylaniline is obtained in percentage by mass;
the rectification kettle residue of m-trifluoromethyl aniline comprises the following components: 69.6 to 72.5 percent of para-trifluoromethylaniline, 25.5 to 28.4 percent of meta-trifluoromethylaniline, wherein the percentages are mass percentages;
the solvent is water or hydrochloric acid.
In the invention, the rectifying still residue of the m-trifluoromethylaniline is preferably still residue formed by continuously nitrifying, hydrogenation-reducing and rectifying m-trifluoromethylaniline from benzotrifluoride;
in the invention, the end point of the reaction preferably comprises the content of the intermediate trifluoromethylaniline in the reaction liquid is less than or equal to 0.1 percent, and the content of the 2-chloro-4-trifluoromethylaniline is less than or equal to 0.1 percent, wherein the percentages are in mass percent.
In the invention, the end point of the reaction preferably comprises the mass percent when the content of the trifluoromethyl aniline in the middle of the reaction solution is less than or equal to 0.23 percent.
In the invention, after the rectifying still residue of the m-trifluoromethyl aniline reacts with chlorine, the method preferably further comprises a post-treatment process, and the post-treatment preferably comprises the following steps: the reaction liquid is divided into an organic phase and an acid phase, and the organic phase is sequentially subjected to alkali washing, dehydration and rectification to obtain the 2, 6-dichloro-4-trifluoromethyl aniline.
Wherein the concentration of the alkali liquor used for alkali washing is preferably 2%, and the percentage is mass percent.
Wherein the acid phase is preferably diluted with water and recycled.
In the present invention, when the solvent is hydrochloric acid, the concentration of the hydrochloric acid is preferably not more than 20%, more preferably 8% to 12%, the percentage being by mass.
In the invention, when the solvent is hydrochloric acid, the mass ratio of the residue of the rectifying still of the m-trifluoromethyl aniline to the hydrogen chloride contained in the hydrochloric acid is preferably 1 (0-2), but not 0; more preferably 1 (1.0-1.3).
In the present invention, the temperature of the reaction is preferably 40 to 80 ℃, more preferably 50 to 60 ℃.
In the present invention, the reaction time is preferably 0.5 to 2.5 hours.
In the present invention, the end point of the reaction is preferably monitored by gas chromatography.
Under the chlorination reaction condition, the m-trifluoromethyl aniline in the rectifying still residue is chlorinated to sequentially generate a 1 chlorine substituent, a 2 chlorine substituent and a 3 chlorine substituent, and the p-trifluoromethyl aniline in the rectifying still residue is chlorinated to generate 2, 6-dichloro-4-trifluoromethyl aniline, so that the chlorination reaction is difficult to be carried out. The reaction principle is as follows:
the 3-chloro substituent is generated by deeply chlorinating the chlorination product 2, 4-dichloro-5-trifluoromethylaniline of m-trifluoromethylaniline, so that the separation of two isomers of 2, 4-dichloro-5-trifluoromethylaniline and 2, 6-dichloro-4-trifluoromethylaniline is avoided, and after alkaline washing and dehydration, the 2, 6-dichloro-4-trifluoromethylaniline product with the concentration of more than or equal to 99.5% can be obtained through conventional rectification.
On the basis of conforming to the common knowledge in the field, the above preferred conditions can be arbitrarily combined to obtain the preferred examples of the invention.
The reagents and materials used in the present invention are commercially available.
The invention has the positive progress effects that:
1) The process is simple, the reaction time is short, and the melting crystallization is not needed;
2) After the reaction is finished, the 2, 6-dichloro-4-trifluoromethyl aniline product with the purity more than or equal to 99.5 percent can be obtained through reduced pressure rectification; the percentages are mass percentages.
3) The three wastes are generated in small quantity.
Detailed Description
The invention is further illustrated by means of the following examples, which are not intended to limit the scope of the invention. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
In the following examples, the preparation process of the rectifying still residue of m-trifluoromethylaniline is as follows: benzotrifluoride is used as a starting material, and a mixture containing three isomers of o-, m-, and p-trifluoromethylaniline is obtained through continuous nitration and continuous hydrogenation reduction. And then rectifying and separating, and firstly extracting an o-trifluoromethyl aniline product and then extracting a m-trifluoromethyl aniline product. Because of the poor chemical stability of the para-trifluoromethylaniline, the para-trifluoromethylaniline is easy to explode, and the explosion-prone degree of the para-trifluoromethylaniline is positively correlated with the purity and the temperature of the para-trifluoromethylaniline. For production safety, after m-trifluoromethylaniline is extracted by rectification, p-trifluoromethylaniline and part of m-trifluoromethylaniline are left in the residue of the rectification kettle, so that the composition of the residue of the rectification kettle of m-trifluoromethylaniline is as follows: para-trifluoromethylaniline (about 69.6% -72.5%), meta-trifluoromethylaniline (about 25.5% -28.4%).
Example 1
1000g of hydrochloric acid (8%) and 80g of m-trifluoromethylaniline rectification residue (72.5% of p-trifluoromethylaniline and 25.5% of m-trifluoromethylaniline) were added to the reaction flask, and the residue was completely dissolved by stirring. After the temperature is raised to 40 ℃, chlorine is introduced, the reaction temperature is maintained to be 50-60 ℃, the GC monitors the reaction, the reaction is stopped when the content of 2, 4-dichloro-5-trifluoromethylaniline is equal to 0.18%, at the moment, neither the trifluoromethylaniline nor the 2-chloro-4-trifluoromethylaniline is detected, and the reaction time is 45min. The reaction solution is subjected to stationary phase separation, the lower organic phase is subjected to alkaline washing by 100mL of alkali liquor (2%), then the water is removed by reduced pressure distillation, and then 73.2g of 2, 6-dichloro-4-trifluoromethylaniline is obtained by reduced pressure rectification, the GC purity is 99.74%, and the yield is 88.4% based on the trifluoromethylaniline. The percentages are mass percentages.
Example 2
726g of hydrochloric acid (12%), 67g of m-trifluoromethylaniline rectification residual liquid (69.6% of p-trifluoromethylaniline and 28.4% of m-trifluoromethylaniline) are added into a reaction bottle, the residual liquid is completely dissolved by stirring, chlorine is introduced after the temperature is raised to 40 ℃, the reaction temperature is maintained to 50-60 ℃, the reaction is stopped when the GC detection reaction is carried out and the content of 2, 4-dichloro-5-trifluoromethylaniline is equal to 0.23%, and the reaction time is 38min at the moment that the p-trifluoromethylaniline and the 2-chloro-4-trifluoromethylaniline are not detected. The reaction solution is subjected to stationary phase separation, the lower organic phase is subjected to alkaline washing by 100mL of alkali liquor (2%), then the water is removed by reduced pressure distillation, and then 58.4g of 2, 6-dichloro-4-trifluoromethylaniline is obtained by reduced pressure rectification, the GC purity is 99.63%, and the yield is 87.6% based on the trifluoromethylaniline. The percentages are mass percentages.
Example 3
1600g of hydrochloric acid (20%), 160g of m-trifluoromethylaniline rectification residual liquid (71.2% of p-trifluoromethylaniline and 26.9% of m-trifluoromethylaniline) are added into a reaction bottle, the residual liquid is completely dissolved by stirring, chlorine is introduced after the temperature is raised to 40 ℃, the reaction temperature is maintained to 50-60 ℃, the GC detection reaction is stopped when the content of 2, 4-dichloro-5-trifluoromethylaniline is equal to 0.11%, and the reaction time is 55min at the moment that the p-trifluoromethylaniline and the 2-chloro-4-trifluoromethylaniline are not detected. The reaction solution is subjected to stationary phase separation, the lower organic phase is subjected to alkaline washing by 100mL of alkali liquor (2%), then the water is removed by reduced pressure distillation, and then 141.8g of 2, 6-dichloro-4-trifluoromethylaniline is obtained by reduced pressure rectification, the GC purity is 99.77%, and the yield is 86.9% based on the trifluoromethylaniline. The percentages are mass percentages.
Example 4
500mL of water, 300g of m-trifluoromethylaniline rectification residual liquid (70.4% of p-trifluoromethylaniline and 28.1% of m-trifluoromethylaniline) are added into a reaction bottle, chlorine is introduced after stirring and heating to 40 ℃, the reaction temperature is maintained between 50 ℃ and 60 ℃, the reaction is stopped when the GC detection reaction is carried out and the content of 2, 4-dichloro-5-trifluoromethylaniline is equal to 0.22%, and at the moment, the p-trifluoromethylaniline and the 2-chloro-4-trifluoromethylaniline are not detected, and the reaction time is 2.5h. The reaction solution is subjected to stationary phase separation, the lower organic phase is subjected to alkaline washing by 400mL of alkali liquor (2%), then the water is removed by reduced pressure distillation, and then 258.8g of 2, 6-dichloro-4-trifluoromethylaniline is obtained by reduced pressure rectification, the GC purity is 99.65%, and the yield is 85.8% based on the trifluoromethylaniline. The percentages are mass percentages.
Claims (9)
1. A process for the preparation of 2, 6-dichloro-4-trifluoromethylaniline, characterized in that it comprises the following steps:
the rectifying still residue of m-trifluoromethylaniline is reacted with chlorine in a solvent until the content of 2, 4-dichloro-5-trifluoromethylaniline in the reaction liquid is less than or equal to 0.3%, wherein the reaction temperature is 50-60 ℃, the reaction time is 0.5-2.5 h, and the percentages are mass percent;
the rectification kettle residue of m-trifluoromethyl aniline comprises the following components: 69.6 to 72.5 percent of para-trifluoromethylaniline and 25.5 to 28.4 percent of meta-trifluoromethylaniline, wherein the percentages are mass percentages;
the solvent is water or hydrochloric acid;
the rectifying still residue of m-trifluoromethylaniline is still residue formed by continuously nitrifying, hydrogenation reducing and rectifying m-trifluoromethylaniline from benzotrifluoride.
2. The method for preparing 2, 6-dichloro-4-trifluoromethylaniline according to claim 1, wherein the end point of the reaction further comprises a content of the intermediate trifluoromethylaniline in the reaction liquid of not more than 0.1% and a content of the 2-chloro-4-trifluoromethylaniline of not more than 0.1%, wherein the percentages are mass%.
3. A process for the preparation of 2, 6-dichloro-4-trifluoromethylaniline according to claim 1 wherein: the end point of the reaction also comprises the content of 2, 4-dichloro-5-trifluoromethyl aniline in the reaction liquid which is less than or equal to 0.23 percent, wherein the percentage is mass percent.
4. A process for the preparation of 2, 6-dichloro-4-trifluoromethylaniline according to claim 1 wherein: the rectification kettle residue of m-trifluoromethyl aniline reacts with chlorine and then further comprises a post-treatment process.
5. The method for producing 2, 6-dichloro-4-trifluoromethylaniline according to claim 4 wherein: the post-treatment comprises the following steps: dividing the reaction solution into an organic phase and an acid phase, and sequentially performing alkaline washing, dehydration and rectification on the organic phase to obtain 2, 6-dichloro-4-trifluoromethyl aniline;
wherein the concentration of the alkali liquor used for alkali washing is preferably 2%, and the percentage is mass percent.
6. The method for producing 2, 6-dichloro-4-trifluoromethylaniline according to claim 5 wherein: the acid phase is diluted by water and then recycled.
7. A process for the preparation of 2, 6-dichloro-4-trifluoromethylaniline according to claim 1 wherein:
when the solvent is hydrochloric acid, the concentration of the hydrochloric acid is not more than 20%, and the percentage is mass percent;
and/or when the solvent is hydrochloric acid, the mass ratio of the rectifying still residue of the m-trifluoromethyl aniline to the hydrogen chloride contained in the hydrochloric acid is 1 (0-2), but not 0.
8. The method for producing 2, 6-dichloro-4-trifluoromethylaniline according to claim 7, wherein when the solvent is hydrochloric acid, the concentration of the hydrochloric acid is 8% to 12%, the percentage being by mass;
and/or the mass ratio of the rectifying still residue of the m-trifluoromethyl aniline to the hydrogen chloride contained in the hydrochloric acid is 1 (1.0-1.3).
9. The method for preparing 2, 6-dichloro-4-trifluoromethylaniline according to claim 1 wherein the end point of the reaction is monitored by gas chromatography.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101143829A (en) * | 2007-10-16 | 2008-03-19 | 南通市东昌化工有限公司 | Method for producing 2,6-dichloro-4-trifluoromethylaniline |
| CN101538206A (en) * | 2009-04-27 | 2009-09-23 | 浙江工业大学 | Method for processing and utilizing trifluoromethyl aniline distillation still residue |
| CN103880686A (en) * | 2014-02-21 | 2014-06-25 | 江苏丰华化学工业有限公司 | Method for recycling wastes of trifluoromethyl phenylamine kettle residue |
| CN103910639A (en) * | 2014-03-13 | 2014-07-09 | 凯美泰克（天津）化工科技有限公司 | A method of preparing 2,6-dichloro-4-trifluoromethyl phenylamine |
| CN112624906A (en) * | 2020-12-11 | 2021-04-09 | 江苏优普生物化学科技股份有限公司 | P-trifluoromethylaniline rectification kettle residue treatment process |
-
2022
- 2022-03-16 CN CN202210260629.4A patent/CN114507147B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101143829A (en) * | 2007-10-16 | 2008-03-19 | 南通市东昌化工有限公司 | Method for producing 2,6-dichloro-4-trifluoromethylaniline |
| CN101538206A (en) * | 2009-04-27 | 2009-09-23 | 浙江工业大学 | Method for processing and utilizing trifluoromethyl aniline distillation still residue |
| CN103880686A (en) * | 2014-02-21 | 2014-06-25 | 江苏丰华化学工业有限公司 | Method for recycling wastes of trifluoromethyl phenylamine kettle residue |
| CN103910639A (en) * | 2014-03-13 | 2014-07-09 | 凯美泰克（天津）化工科技有限公司 | A method of preparing 2,6-dichloro-4-trifluoromethyl phenylamine |
| CN112624906A (en) * | 2020-12-11 | 2021-04-09 | 江苏优普生物化学科技股份有限公司 | P-trifluoromethylaniline rectification kettle residue treatment process |
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