CN110963925A - Method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine dioxide solution method - Google Patents
Method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine dioxide solution method Download PDFInfo
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Abstract
The invention introduces a method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine hydrogen peroxide method, wherein 2, 4-dinitroaniline is added into a kettle after being ground; adding chlorine and hydrogen peroxide combined chlorination mother liquor into the kettle, raising the temperature to 25-65 ℃, and stirring for 1-2 hours; introducing chlorine at the temperature of 25-65 ℃, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1: 0.51-0.53; then preserving the heat for 1-2 hours at the temperature of 30-70 ℃; raising the temperature to 45-80 ℃, and adding hydrogen peroxide according to the molar ratio of the 2, 4-dinitroaniline to the hydrogen peroxide of 1: 0.52-0.8; and (3) keeping the temperature of 80 +/-5 ℃ for reaction for 1-2 hours, and finishing solid-liquid separation to obtain a filter cake and a chlorine-hydrogen peroxide combined chlorination mother liquor respectively. The method has the advantages of high product purity and high production efficiency, and the mother liquor can be continuously recycled, so that zero-emission clean production is realized.
Description
Technical Field
The invention relates to a technology for synthesizing 6-chloro-2, 4-dinitroaniline and utilizing waste water, in particular to a method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine hydrogen peroxide method.
Background
The 6-chloro-2, 4-dinitroaniline is an important intermediate of disperse dyes, the using amount is large at home and abroad, and the method generally takes 2, 4-dinitroaniline, hydrochloric acid and water as raw materials and adds an oxidant dropwise to prepare the dye. The oxidant mainly comprises sodium chlorate, sodium hypochlorite and chlorine.
1) Sodium chlorate is used as oxidant.
The method has mature process, high product purity up to 98%, short reaction time and high unit yield. However, the salt-containing low-acidity acidic wastewater generated in the reaction process cannot be continuously recycled, and chlorine dioxide is generated in the reaction process, so that the workshop production environment is influenced.
2) Sodium hypochlorite is used as oxidant.
The method has the advantages of complex production process, byproduct generation, poor product quality, deep color, long reaction time and low equipment utilization rate, generates the salty low-acidity acidic wastewater, and cannot be continuously recycled.
3) Chlorine chlorination process.
The method can be used for chlorination by introducing chlorine gas in a hydrochloric acid medium in the presence of a catalyst, or chlorination by introducing chlorine gas in an acetic acid medium. The method has the advantages that the method is low in production raw material cost, high in product impurity content, low in melting point and low in product content, and the 2, 4-dinitroaniline needs to be ground very finely, the reaction time is long, and the equipment productivity is not high; chlorine is introduced into an acetic acid medium for chlorination reaction, the process is simple, the crystal form of the product is good, the color is good, the purity of the product is high, the yield is also good, but the acetic acid needs to be regenerated, and the production cost is relatively increased.
In order to solve the problems, a process which can recycle mother liquor, is economical and environment-friendly, reduces the discharge of acid wastewater and realizes clean production is needed.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine hydrogen peroxide method, which improves the product purity and economic benefit, can completely and continuously recycle mother liquor, reduces the subsequent treatment cost and realizes clean production.
In order to solve the technical problems, the invention adopts the following technical scheme:
the method for synthesizing 6-chloro-2, 4-dinitroaniline by using chlorine dioxide solution method comprises the following steps:
step A1: grinding 100 parts by mass of 2, 4-dinitroaniline with the purity of more than 99.85 percent by a colloid mill, and adding the ground 2, 4-dinitroaniline into a reaction kettle;
step A2: a hydrochloric acid adding procedure: hydrochloric acid with the mass concentration of 31% and water are added into the reaction kettle, and the concentration of the hydrochloric acid is controlled to be 16% -20%; raising the temperature to 25-55 ℃, and stirring for 1-2 hours under the condition of heat preservation; and controlling the amount ratio of the 2, 4-dinitroaniline to the HCl substance to be 2, 4-dinitroaniline: HCl = 1: (4-9);
specifically, the concentration of the hydrochloric acid is the mass concentration of HCl in the total amount of water and HCl;
step A3: introducing chlorine into the reaction kettle at the temperature of 25-55 ℃, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1 (0.51-0.53); in the time range of 4-5 hours, the chlorine is added completely;
specifically, the temperature of the materials in the reaction kettle is firstly increased to 25-55 ℃ before chlorine gas is introduced in the step A3, then the chlorine gas is introduced into the reaction kettle, the chlorine gas and the 2, 4-dinitroaniline release heat, the temperature in the reaction kettle is increased, and the temperature in the reaction kettle is controlled to be 35-60 ℃ in the chlorine gas introduction process;
step A4: after chlorine gas is introduced, controlling the temperature of the reaction kettle to be 50-70 ℃, preserving heat for 1-2 hours, and supplementing high-concentration hydrochloric acid as required during or after the heat preservation process to keep the concentration of the hydrochloric acid higher than 20%;
step A5: after heat preservation, raising the temperature of the reaction kettle to 50-70 ℃, continuously adding 22-27.5% hydrogen peroxide into the reaction kettle according to the molar ratio of 2, 4-dinitroaniline to hydrogen peroxide being 1 (0.51-0.8), controlling the temperature to 50-70 ℃ in the adding process, and finishing the adding of the hydrogen peroxide within the time range of 3-6 hours;
step A6: after the hydrogen peroxide is added, carrying out heat preservation reaction for 1-2 hours, and finishing the heat preservation reaction; or the reaction end point is the content of the 6-chloro-2, 4-dinitroaniline in the solid after the separation and drying of the reaction mixture is higher than 98 percent, and the heat preservation process is finished; keeping the stirring state in the heat preservation process; controlling the temperature to be 60 +/-10 ℃;
the content of superior products in the 6-chloro-2, 4-dinitroaniline industrial standard is 96 percent, the content of qualified products in the 6-chloro-2, 4-dinitroaniline industrial standard is 94.5 percent, and the content of the 6-chloro-2, 4-dinitroaniline is higher than 96 percent and can reach the superior products;
step A7: a separation process: after the heat preservation is finished, separating the reaction mixture to obtain a filter cake and a chlorine and hydrogen peroxide combined chlorination mother liquor;
more specifically, after the heat preservation process of the step A7 is finished, the separation process is directly carried out; the temperature does not need to be reduced;
the effective content of the chlorination mother liquor by the chlorine and hydrogen peroxide combined method is as follows: the concentration of the hydrochloric acid is 16-20%, and the content of the hydrogen peroxide is 0.01-0.03%;
step A8: after separation, the filter cake is dried to obtain the product 6-chloro-2, 4-dinitroaniline, and the chlorination mother liquor is completely recycled by a chlorine and hydrogen peroxide combination method.
Preferably, the purity of the 2, 4-dinitroaniline in step A1 is more than 99.85%.
Preferably, the temperature of the chlorine introduction process in the step A3 is controlled to be 35-60 ℃.
Preferably, the temperature of the hydrogen peroxide solution in the step A5 is controlled below 30 ℃.
Preferably, the reaction time in step A6 is the reaction end point when the content of 6-chloro-2, 4-dinitroaniline after sampling and centrifugal separation is higher than 98%.
After the hydrogen peroxide is dripped, the concentration of hydrochloric acid in a reaction system is reduced, the concentration of residual hydrogen peroxide after reaction is only 0.01-0.03%, the mother solution can be reused, and the reaction conditions are not changed.
A method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine hydrogen peroxide method is characterized by comprising the following steps: with cyclically generated H-containing2O2The chlorine and hydrogen peroxide combined chlorination mother liquor with HCl is used as a raw material, and comprises the following steps:
step B1: mother liquor concentration blending process: adding chlorine and hydrogen peroxide combined chlorination mother liquor containing hydrochloric acid with the concentration of 16% -20%, hydrogen peroxide with the concentration of 0.01% -0.03% and 2, 4-dinitroaniline dissolved in the hydrochloric acid into a reaction kettle; when the amount of the chlorination mother liquor is insufficient by using a chlorine and hydrogen peroxide combined method, high-concentration hydrochloric acid and water are supplemented, and after the high-concentration hydrochloric acid and the water are supplemented, the concentration of the hydrochloric acid is ensured to be 16-20%;
more specifically, the mother liquor obtained in the step B1 is chlorine mother liquor obtained in the step B7 or obtained in the following step A7 by a chlorine and hydrogen peroxide combined method;
step B2: grinding and feeding: grinding 2, 4-dinitroaniline by a colloid mill, and adding the ground 2, 4-dinitroaniline into a reaction kettle; and controlling the amount ratio of the 2, 4-dinitroaniline to the HCl substance to be 2, 4-dinitroaniline: HCl = 1: (4-9);
step B3: introducing chlorine into the reaction kettle at the temperature of 25-55 ℃, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1 (0.51-0.53); in the time range of 4-5 hours, the chlorine is added completely;
specifically, before chlorine is introduced, the temperature of materials in a reaction kettle is raised to 25-55 ℃, then the chlorine is introduced into the reaction kettle, the chlorine and 2, 4-dinitroaniline release heat, the temperature in the reaction kettle is raised, and the temperature in the reaction kettle is controlled to be 35-60 ℃ in the chlorine introducing process;
step B4: after chlorine gas is introduced, controlling the temperature of the reaction kettle to be 50-70 ℃, preserving heat for 1-2 hours, and supplementing high-concentration hydrochloric acid as required during or after the heat preservation process to keep the concentration of the hydrochloric acid higher than 20%;
step B5: after heat preservation, raising the temperature of the reaction kettle to 50-70 ℃, continuously adding hydrogen peroxide into the reaction kettle according to the molar ratio of the 2, 4-dinitroaniline to the hydrogen peroxide being 1 (0.51-0.8), wherein the temperature is controlled to be 50-70 ℃ in the adding process, and the adding of the hydrogen peroxide is finished within the time range of 3-6 hours;
specifically, the concentration of the added hydrogen peroxide is 22-27.5%;
step B6: after the hydrogen peroxide is added, carrying out heat preservation reaction for 1-2 hours, and finishing the heat preservation reaction; or the reaction end point is the content of the 6-chloro-2, 4-dinitroaniline in the separated and dried solid is higher than 96 percent, and the heat preservation process is finished; keeping the stirring state in the heat preservation process; controlling the temperature to be 60 +/-10 ℃;
the content of superior products in the 6-chloro-2, 4-dinitroaniline industrial standard is 96 percent, the content of qualified products in the 6-chloro-2, 4-dinitroaniline industrial standard is 94.5 percent, and the content of the 6-chloro-2, 4-dinitroaniline is higher than 96 percent and can reach the superior products;
step B7: a separation process: after the heat preservation is finished, separating the reaction mixture to obtain a filter cake and a mother liquor of chlorination mother liquor by a chlorine and hydrogen peroxide combination method;
more specifically, the separation process is directly carried out after the heat preservation process is finished; the temperature does not need to be reduced;
the effective content of the chlorination mother liquor by the chlorine and hydrogen peroxide combined method is as follows: the concentration of the hydrochloric acid is 16-20%, the content of the hydrogen peroxide is 0.01-0.03%, and the balance is dissolved 2, 4-dinitroaniline and inevitable impurities.
Step B8: after separation, the filter cake is dried to obtain the product 6-chloro-2, 4-dinitroaniline. The separated chlorine and hydrogen peroxide combined chlorination mother liquor can be completely recycled.
Preferably, the purity of the 2, 4-dinitroaniline in step B1 is more than 99.85%.
Preferably, the temperature of the chlorine introducing process in the step B3 is controlled to be 35-60 ℃.
Preferably, the temperature of the hydrogen peroxide in the step B5 is controlled below 30 ℃.
Concentrations not mentioned in this document are all mass concentrations.
After the hydrogen peroxide is dripped, the concentration of hydrochloric acid in a reaction system is reduced, the concentration of residual hydrogen peroxide after reaction is only 0.01-0.03%, the mother solution can be reused, and the reaction conditions are not changed.
The reaction principle is as follows:
the reaction principle of the method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine dioxide hydrogen peroxide method is as follows: under an acid medium with hydrochloric acid concentration of 16-27%, reacting 2, 4-dinitroaniline with chlorine to generate 6-chloro-2, 4-dinitroaniline and hydrogen chloride, after chlorine introduction is finished, performing heat preservation reaction, increasing the hydrochloric acid concentration in a reaction system at the moment, wherein the hydrochloric acid concentration is 20-30%, increasing the temperature of a reaction kettle, dropwise adding hydrogen peroxide, oxidizing the hydrogen chloride into chlorine by utilizing the oxidability of the hydrogen peroxide, and performing chlorination reaction on the chlorine and unreacted 2, 4-dinitroaniline. Because hydrogen peroxide oxidizes part of hydrogen chloride into chlorine, the amount of hydrogen chloride in the reaction system can be reduced, the concentration of hydrochloric acid can be reduced, and the concentration of hydrochloric acid in the reaction system after the reaction is 16% -27%. The mother liquor of the product after reaction after centrifugation has no salt, the recycling of the mother liquor is not influenced, the concentration of hydrogen peroxide in the mother liquor is only 0.01-0.03 percent through detection, the content is very low, and the reutilization of the mother liquor has no influence on the reaction temperature.
By adopting the technical scheme, the invention has the following beneficial effects: improves the product purity and economic benefit, can completely and continuously recycle the mother liquor, reduces the subsequent treatment cost and realizes clean production.
Detailed Description
The patent is further illustrated below with reference to examples. The scope of protection of the patent is not limited to the specific embodiments.
Example 1
The method for synthesizing 6-chloro-2, 4-dinitroaniline by using chlorine dioxide solution method comprises the following steps:
350 g, 700 g of 2, 4-dinitroaniline with 99.86 percent of content after being ground by a colloid millAt a mass concentration of 31%Hydrochloric acidAnd 500 g of water are added into the reaction kettle, the temperature is raised to 35 plus or minus 5 ℃, and the mixture is stirred for 2 hours.
Adding 83 grams of chlorine into the reaction kettle, and controlling the temperature to be 45 +/-5 ℃; in the time range of 4-5 hours, the chlorine is added completely; then keeping the temperature at 45 +/-5 ℃ for 2 hours.
After the reaction is carried out for 2 hours under the condition of heat preservation, the temperature of the reaction kettle is raised to 60 +/-5 ℃, 96 grams of hydrogen peroxide with the concentration of 27.5 percent is dripped, the temperature is controlled to 65 +/-5 ℃, and the hydrogen peroxide is added within 4 hours; after the dropwise addition, the reaction is carried out for 2 hours at 65 +/-5 ℃, 513 g of wet product is obtained after suction filtration, 409 g of product with HPLC content of 98.3% is obtained after drying, the product yield is 98.4%, 1210 g of mother liquor containing 17.78% of hydrogen chloride and 0.022% of hydrogen peroxide is obtained, and 1210 g of the mother liquor is completely recycled.
Example 2
The invention relates to a method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine hydrogen peroxide method, which comprises the following steps:
350 g of 2, 4-dinitroaniline with the content of 99.86 percent after being ground by a colloid mill and 1210 g of mother liquor of the embodiment 1 are added into a reaction kettle, the temperature is raised to 40 ℃, and the mixture is stirred for 1 hour.
Adding 84 g of chlorine gas into the reaction kettle, and controlling the temperature at 40 ℃; in the time range of 4-5 hours, the chlorine is added completely; then incubated at 45 ℃ for 2 hours.
After the reaction is carried out for 2 hours under the condition of heat preservation, the temperature of the reaction kettle is raised to 60 +/-5 ℃, 95 grams of hydrogen peroxide with the concentration of 27.5 percent is dripped, the temperature is controlled to 65 +/-5 ℃, and the addition of the hydrogen peroxide is finished within 4 hours; after the dropwise addition, the reaction is carried out for 2 hours at 65 +/-5 ℃, 515 g of wet product is obtained after suction filtration, 409 g of product with HPLC content of 98.3% is obtained after drying, 98.4% of product yield is obtained, 1209 g of mother liquor with hydrogen chloride concentration of 17.62% and hydrogen peroxide concentration of 0.024% is obtained, and 1209 g of mother liquor can be completely recycled.
Claims (8)
1. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine dioxide hydrogen peroxide is characterized by comprising the following steps: with cyclically generated H-containing2O2Chlorine and hydrogen peroxide combined method chlorine of HClThe method takes the chemical mother liquor as the raw material and comprises the following steps:
step B1: mother liquor concentration blending process: adding chlorine and hydrogen peroxide combined chlorination mother liquor containing hydrochloric acid with the concentration of 16% -20%, hydrogen peroxide with the concentration of 0.01% -0.03% and 2, 4-dinitroaniline dissolved in the hydrochloric acid into a reaction kettle; when the amount of the chlorination mother liquor is insufficient by using a chlorine and hydrogen peroxide combined method, high-concentration hydrochloric acid and water are supplemented, and after the high-concentration hydrochloric acid and the water are supplemented, the concentration of the hydrochloric acid is ensured to be 16-20%;
step B2: grinding and feeding: grinding 2, 4-dinitroaniline by a colloid mill, and adding the ground 2, 4-dinitroaniline into a reaction kettle; and controlling the amount ratio of the 2, 4-dinitroaniline to the HCl substance to be 2, 4-dinitroaniline: HCl = 1: (4-9); step B3: introducing chlorine into the reaction kettle at the temperature of 25-55 ℃, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1 (0.51-0.53); in the time range of 4-5 hours, the chlorine is added completely;
step B4: after chlorine gas is introduced, controlling the temperature of the reaction kettle to be 50-70 ℃, preserving heat for 1-2 hours, and supplementing high-concentration hydrochloric acid as required during or after the heat preservation process to keep the concentration of the hydrochloric acid higher than 20%;
step B5: after heat preservation, raising the temperature of the reaction kettle to 50-70 ℃, continuously adding hydrogen peroxide into the reaction kettle according to the molar ratio of the 2, 4-dinitroaniline to the hydrogen peroxide being 1 (0.51-0.8), wherein the temperature is controlled to be 50-70 ℃ in the adding process, and the adding of the hydrogen peroxide is finished within the time range of 3-6 hours;
step B6: after the hydrogen peroxide is added, carrying out heat preservation reaction for 1-2 hours, and finishing the heat preservation reaction; or the reaction end point is the content of the 6-chloro-2, 4-dinitroaniline in the solid after the separation and drying of the reaction mixture is higher than 98 percent, and the heat preservation process is finished; keeping the stirring state in the heat preservation process; controlling the temperature to be 60 +/-10 ℃;
step B7: a separation process: after the heat preservation is finished, separating the reaction mixture to obtain a filter cake and a mother liquor of chlorination mother liquor by a chlorine and hydrogen peroxide combination method;
step B8: after separation, the filter cake is dried to obtain the product 6-chloro-2, 4-dinitroaniline.
2. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 1, which is characterized in that: the step B3: before chlorine gas is introduced, the temperature of materials in the reaction kettle is firstly raised to 25-55 ℃, then the chlorine gas is introduced into the reaction kettle, the chlorine gas and the 2, 4-dinitroaniline release heat, the temperature in the reaction kettle is raised, and the temperature in the reaction kettle is controlled to 35-60 ℃ in the chlorine gas introduction process.
3. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 1, which is characterized in that: and B5, adding hydrogen peroxide with the concentration of 22-27.5%.
4. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 1, which is characterized in that: step B6, directly entering a separation process after heat preservation is finished; no cooling is required.
5. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 1, which is characterized in that: and in the step B5, the temperature of the hydrogen peroxide is controlled to be below 30 ℃.
6. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 1, which is characterized in that: the mother liquor obtained in the step B1 is chlorine mother liquor obtained in the step B7 or obtained in the following step A7 by a chlorine and hydrogen peroxide combined method;
step A1: grinding 100 parts by mass of 2, 4-dinitroaniline with the purity of more than 99.85 percent by a colloid mill, and adding the ground 2, 4-dinitroaniline into a reaction kettle;
step A2: a hydrochloric acid adding procedure: hydrochloric acid with the mass concentration of 31% and water are added into the reaction kettle, and the concentration of the hydrochloric acid is controlled to be 16% -20%; raising the temperature to 25-55 ℃, and stirring for 1-2 hours under the condition of heat preservation; and controlling the amount ratio of the 2, 4-dinitroaniline to the HCl substance to be 2, 4-dinitroaniline: HCl = 1: (4-9);
step A3: introducing chlorine into the reaction kettle at the temperature of 25-55 ℃, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1 (0.51-0.53); in the time range of 4-5 hours, the chlorine is added completely;
step A4: after chlorine gas is introduced, controlling the temperature of the reaction kettle to be 50-70 ℃, preserving heat for 1-2 hours, and supplementing high-concentration hydrochloric acid as required during or after the heat preservation process to keep the concentration of the hydrochloric acid higher than 20%;
step A5: after heat preservation, raising the temperature of the reaction kettle to 50-70 ℃, continuously adding 22-27.5% hydrogen peroxide into the reaction kettle according to the molar ratio of 2, 4-dinitroaniline to hydrogen peroxide being 1 (0.51-0.8), controlling the temperature to 50-70 ℃ in the adding process, and finishing the adding of the hydrogen peroxide within the time range of 3-6 hours;
step A6: after the hydrogen peroxide is added, carrying out heat preservation reaction for 1-2 hours, and finishing the heat preservation reaction; or the reaction end point is the content of the 6-chloro-2, 4-dinitroaniline in the solid after the separation and drying of the reaction mixture is higher than 98 percent, and the heat preservation process is finished; keeping the stirring state in the heat preservation process; controlling the temperature to be 60 +/-10 ℃;
step A7: a separation process: after the heat preservation is finished, separating the reaction mixture to obtain a filter cake and a chlorine and hydrogen peroxide combined chlorination mother liquor;
step A8: after separation, the filter cake is dried to obtain the product 6-chloro-2, 4-dinitroaniline, and the chlorination mother liquor is recycled by a chlorine and hydrogen peroxide combination method.
7. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 6, which is characterized in that: the temperature of the materials in the reaction kettle is firstly increased to 25-55 ℃ before chlorine is introduced in the step A3, then the chlorine is introduced into the reaction kettle, the chlorine and the 2, 4-dinitroaniline release heat, the temperature in the reaction kettle is increased, and the temperature in the reaction kettle is controlled to 35-60 ℃ in the chlorine introducing process.
8. The method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine-hydrogen peroxide method according to claim 6, which is characterized in that: the step A7 is directly carried out in the separation process after the heat preservation process is finished; no cooling is required.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0154239A2 (en) * | 1984-03-01 | 1985-09-11 | Hoechst Aktiengesellschaft | Process for the preparation of 6-chloro-2,4-nitroaniline |
| KR0152585B1 (en) * | 1995-07-15 | 1998-10-15 | 배종순 | Process for the preparation of 6-chloro-2,4-dinitroaniline |
| CN108191672A (en) * | 2017-12-19 | 2018-06-22 | 浙江龙盛集团股份有限公司 | A kind of synthetic method of 2,4- dinitros -6- chloroanilines |
-
2019
- 2019-12-30 CN CN201911393058.6A patent/CN110963925A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0154239A2 (en) * | 1984-03-01 | 1985-09-11 | Hoechst Aktiengesellschaft | Process for the preparation of 6-chloro-2,4-nitroaniline |
| KR0152585B1 (en) * | 1995-07-15 | 1998-10-15 | 배종순 | Process for the preparation of 6-chloro-2,4-dinitroaniline |
| CN108191672A (en) * | 2017-12-19 | 2018-06-22 | 浙江龙盛集团股份有限公司 | A kind of synthetic method of 2,4- dinitros -6- chloroanilines |
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Application publication date: 20200407 |