CN113582851A - Method for producing dinitrophenol based on mixed low oil - Google Patents
Method for producing dinitrophenol based on mixed low oil Download PDFInfo
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- CN113582851A CN113582851A CN202010366305.XA CN202010366305A CN113582851A CN 113582851 A CN113582851 A CN 113582851A CN 202010366305 A CN202010366305 A CN 202010366305A CN 113582851 A CN113582851 A CN 113582851A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
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Abstract
The invention relates to a method for producing dinitrophenol based on mixed low oil, comprising the first step of separating and purifying mixed mother liquor, and the step S1 of conveying the mixed mother liquor rich in 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, cooling to 15 +/-1 ℃; step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat; step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30 +/-1%; step S4: collecting mixed high oil, wherein the mixed high oil contains 2.6-dinitrochlorobenzene with the volume fraction of 10 +/-1%; step S5: finally obtaining 2, 4-dinitrochlorobenzene crystals with the purity of more than 99.5 percent; in the second step, dinitrophenol is produced by using the mixed low oil obtained in the step S3 in the first step as a reaction raw material. The derivatization of the 2, 4-dinitrochlorobenzene industrial chain is realized, the economic value of the derivative is improved, and the raw material cost for producing the dinitrophenol is reduced.
Description
Technical Field
The invention relates to a method for producing dinitrophenol based on mixed low oil, belonging to the technical field of chemical product purification methods.
Background
The 2, 4-dinitrochlorobenzene is a pale yellow or yellowish brown needle-shaped crystal with bitter almond taste, and the molecular formula is C6H3ClN2O4The molecular weight is 202.56, and the relative density is 1.69g/cm3Boiling point of 315 deg.C, melting point of 53.4 deg.C, flash point of 194 deg.C, water-insoluble, soluble in organic solvent such as ether, benzene, ethanol, etc., and can be used as dye, pesticide, and medicineRaw materials of medicines and the like can be used for producing sulfur black, dinitrophenol, dinitroaniline and m-phenylenediamine.
The production of 2, 4-dinitrochlorobenzene is carried out by three methods, namely chlorobenzene method, p-nitrochlorobenzene method and o-nitrochlorobenzene method. The chlorobenzene method is relatively high in cost, and the purity of a series of mixed mother liquor (the mixed mother liquor of 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene) produced by the p-nitrochlorobenzene method and the o-nitrochlorobenzene method cannot meet the requirement, namely the purity of the product (2, 4-dinitrochlorobenzene) cannot meet the requirement, because the isomers of a nitro mixture generated by mixed acid nitration are very close in chemical properties, particularly close in boiling point, in the prior art, the separation is difficult by using a rectification separation method, and a nitro compound is easy to decompose at high temperature and possibly explode, so that great potential safety hazards exist.
The applicant, as a 2, 4-dinitrochlorobenzene manufacturer, directly sells the produced mixed mother liquor as a product for many years, and further separation and purification are performed by downstream manufacturers, so that the product comprehensive value of the mixed mother liquor cannot be developed to the maximum, in addition, the raw material cost of dinitrophenol production is greatly increased, large-scale production is not facilitated to meet the market demand, and therefore, a method for producing dinitrophenol based on mixed low oil is urgently needed to be provided, the derivation of a 2, 4-dinitrochlorobenzene industrial chain is realized, the economic value of derivatives is improved, and the raw material cost of dinitrophenol production is reduced.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provides a method for producing dinitrophenol based on mixed low oil. The method is based on the mixed mother liquor of 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene, adopts a physical separation method to obtain the high-purity 2, 4-dinitrochlorobenzene, and has the advantages of low energy consumption, no pollution, high product quality, safety and reliability. The remaining residue (mixed low oil) is separated and further used as a raw material for the production of dinitrophenol.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
first, separation and purification of the mixed mother liquor
S1, conveying the mixed mother liquor rich in 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 +/-1 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30 +/-1%;
step S4: collecting mixed high oil, wherein the mixed high oil contains 2.6-dinitrochlorobenzene with the volume fraction of 10 +/-1%;
step S5: finally obtaining 2, 4-dinitrochlorobenzene crystals with the purity of more than 99.5 percent;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 55-65 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 90-95 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the pH at 8-9 and the temperature at 100-104 ℃ after the addition is finished, and stirring for 30-45min until the reaction is complete;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 1-2, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain a finished product.
Preferably, in step S1, the mixed mother liquor contains 89-93% of 2, 4-dinitrochlorobenzene, 7-11% of 2, 6-dinitrochlorobenzene, and the total content of the two is 100%.
Preferably, in step S1, the mixed mother liquor contains 90% of 2, 4-dinitrochlorobenzene and 10% of 2, 6-dinitrochlorobenzene.
Preferably, in step S1, the cooling rate of the mixed mother liquor in the crystallizer is 0.1-0.2 ℃/min, and the final temperature of cooling is controlled to be 15 ± 0.5 ℃.
More preferably, in step S1, the cooling rate of the mixed mother liquor in the crystallizer is 0.15 ℃/min.
Preferably, in step S2, the temperature-rising rate of temperature-rising sweating is 0.05-0.08 ℃/min, the final temperature of temperature-rising sweating is controlled at 50-64 ℃, and the total time of temperature-rising sweating is controlled at 10-12 hours.
More preferably, the heating rate for heating and sweating is 0.06 ℃/min.
Preferably, in step S7, the cooling rate is 0.3-0.5 ℃/min, and the final temperature of cooling is controlled to be 10 ± 0.5 ℃.
The invention has the beneficial effects that: the purification method disclosed by the invention is low in energy consumption and temperature, has no three wastes, is the cleanest separation method at present, avoids the risk of high-temperature separation, and also avoids the solvent recovery of a solvent crystallization method. In addition, the mixed high oil can be further purified and separated according to the steps of the invention repeatedly to obtain the 2, 4-dinitrochlorobenzene, and the mixed low oil is directly used as a raw material for producing the dinitrophenol, thereby improving the comprehensive utilization efficiency of the material, improving the additional value of the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene and reducing the production cost of the dinitrophenol.
Detailed Description
The technical solution of the present invention will be further specifically described below by way of specific examples.
In examples 1 to 5 of the present invention, all the crystallizers used were commercially available conventional crystallizers, and each of the raw materials was a commercially available conventional raw material.
Example 1:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
first, separation and purification of the mixed mother liquor
Step S1, conveying the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 14 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 29% volume fraction of 2.6-dinitrochlorobenzene;
step S4: collecting mixed high oil, wherein the mixed high oil contains 9% of 2.6-dinitrochlorobenzene by volume fraction;
step S5: finally obtaining the 2, 4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
Specifically, in step S1, the content of 2, 4-dinitrochlorobenzene in the mixed mother liquor is 89%, the content of 2, 6-dinitrochlorobenzene is 11%, and the sum of the contents is 100%, in step S1, the cooling rate of the mixed mother liquor in a crystallizer is 0.1 ℃/min, the final temperature of cooling is controlled at 14 ℃, in step S2, the heating rate of heating and sweating is 0.05 ℃/min, the final temperature of heating and sweating is controlled at 50 ℃, and the total time of heating and sweating is controlled at 12 hours;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 55 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 90 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the temperature at 100 ℃ and keeping the pH at 8 after the addition is finished, and stirring for 30min until the reaction is complete;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 1, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain the finished product. In step S7, the cooling rate is 0.3 ℃/min, and the final temperature of cooling is controlled at 10 ℃.
Example 2:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
first, separation and purification of the mixed mother liquor
Step S1, conveying the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 16 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 31% volume fraction of 2.6-dinitrochlorobenzene;
step S4: collecting mixed high oil, wherein the mixed high oil contains 11% of 2, 6-dinitrochlorobenzene by volume fraction;
step S5: finally obtaining the 2, 4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
Specifically, in step S1, the content of 2, 4-dinitrochlorobenzene in the mixed mother liquor is 93%, the content of 2, 6-dinitrochlorobenzene is 7%, and the sum of the contents of the two is 100%, in step S1, the cooling rate of the mixed mother liquor in a crystallizer is 0.2 ℃/min, the final temperature of cooling is controlled at 16 ℃, in step S2, the heating rate of heating and sweating is 0.08 ℃/min, the final temperature of heating and sweating is controlled at 64 ℃, and the total time of heating and sweating is controlled at 10 hours;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 65 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 95 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the temperature at 104 ℃ and stirring for 45min until the reaction is complete, wherein the pH value is 9 after the addition is finished;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 2, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain the finished product. In step S7, the cooling rate is 0.5 ℃/min, and the final temperature of cooling is controlled at 10.5 ℃.
Example 3:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
step S1, conveying the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30%;
step S4: collecting mixed high oil, wherein the mixed high oil contains 10% of 2.6-dinitrochlorobenzene by volume fraction;
step S5: finally obtaining the 2, 4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
Specifically, in the step S1, the content of the 2, 4-dinitrochlorobenzene in the mixed mother liquor is 90%, the content of the 2, 6-dinitrochlorobenzene is 10%, in the step S1, the cooling rate of the mixed mother liquor in a crystallizer is 0.15 ℃/min, the final temperature of the cooling is controlled at 15 ℃, in the step S2, the heating rate of the heating and sweating is 0.06 ℃/min, the final temperature of the heating and sweating is controlled at 51 ℃, and the total time of the heating and sweating is controlled at 10 hours;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 55 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 95 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the temperature at 104 ℃ and stirring for 45min until the reaction is complete, wherein the pH value is 9 after the addition is finished;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 1, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain the finished product. In step S7, the cooling rate is 0.3 ℃/min, and the final temperature of cooling is controlled at 10.5 ℃.
Example 4:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
first, separation and purification of the mixed mother liquor
Step S1, conveying the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 16 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 31% volume fraction of 2.6-dinitrochlorobenzene;
step S4: collecting mixed high oil, wherein the mixed high oil contains 11% of 2, 6-dinitrochlorobenzene by volume fraction;
step S5: finally obtaining the 2, 4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
Specifically, in step S1, the content of 2, 4-dinitrochlorobenzene in the mixed mother liquor is 92%, the content of 2, 6-dinitrochlorobenzene is 8%, and the sum of the contents of the two is 100%, in step S1, the cooling rate of the mixed mother liquor in a crystallizer is 0.2 ℃/min, the final temperature of cooling is controlled at 16 ℃, in step S2, the heating rate of heating and sweating is 0.06 ℃/min, the final temperature of heating and sweating is controlled at 59.2 ℃, and the total time of heating and sweating is controlled at 12 hours;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 65 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 95 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the temperature at 104 ℃ and stirring for 45min until the reaction is complete, wherein the pH value is 9 after the addition is finished;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 2, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain the finished product. In step S7, the cooling rate is 0.5 ℃/min, and the final temperature of cooling is controlled at 10 ℃.
Example 5:
a process for producing dinitrophenol based on mixed low oil, said process comprising the steps of:
first, separation and purification of the mixed mother liquor
Step S1, conveying the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30%;
step S4: collecting mixed high oil, wherein the mixed high oil contains 10% of 2.6-dinitrochlorobenzene by volume fraction;
step S5: finally obtaining the 2, 4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
Preferably, in step S1, the content of 2, 4-dinitrochlorobenzene in the mixed mother liquor is 91%, the content of 2, 6-dinitrochlorobenzene is 9%, and the sum of the contents is 100%, in step S1, the cooling rate of the mixed mother liquor in the crystallizer is 0.18 ℃/min, the final temperature of cooling is controlled at 15 ℃, in step S2, the heating rate of heating and sweating is 0.07 ℃/min, the final temperature of heating and sweating is controlled at 57 ℃, and the total time of heating and sweating is controlled at 10 hours;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 60 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 93 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the temperature at 102 ℃ and keeping the pH at 8.5 after the addition is finished, and stirring for 40min until the reaction is complete;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 1.5, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain the finished product. In step S7, the cooling rate is 0.4 ℃/min, and the final temperature of cooling is controlled at 10.5 ℃.
The purification method disclosed by the invention is low in energy consumption and temperature, has no three wastes, is the cleanest separation method at present, avoids the risk of high-temperature separation, and also avoids the solvent recovery of a solvent crystallization method. In addition, the mixed high oil can be further purified and separated according to the steps of the invention repeatedly to obtain the 2, 4-dinitrochlorobenzene, and the mixed low oil can be directly used as a raw material for producing the dinitrophenol, thereby improving the comprehensive utilization efficiency of the material and increasing the additional value of the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene.
The above-described embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention in any way, and other variations and modifications may be made without departing from the spirit of the invention as set forth in the claims.
Claims (8)
1. Process for the production of dinitrophenol based on mixed low oils, characterized in that it comprises the following steps:
first, separation and purification of the mixed mother liquor
S1, conveying the mixed mother liquor rich in 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 +/-1 ℃;
step S2: step S1, gradually heating the cooled mixed mother liquor to make the crystal sweat;
step S3, collecting mixed low oil in the process of heating and sweating, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30 +/-1%;
step S4: collecting mixed high oil, wherein the mixed high oil contains 2.6-dinitrochlorobenzene with the volume fraction of 10 +/-1%;
step S5: finally obtaining 2, 4-dinitrochlorobenzene crystals with the purity of more than 99.5 percent;
second step, production of dinitrophenol
Step S6: adding water into a reaction kettle, heating to 55-65 ℃, adding the mixed low oil obtained in the step S3 in the first step under stirring, heating to 90-95 ℃, slowly adding caustic soda for hydrolysis reaction, keeping the pH at 8-9 and the temperature at 100-104 ℃ after the addition is finished, and stirring for 30-45min until the reaction is complete;
step S7: and (4) cooling the material reacted in the step (S6), dissolving the crystal precipitated in the cooling process with water, adjusting the pH value to 1-2, precipitating dinitrophenol crystal, and recrystallizing the dinitrophenol crystal to obtain a finished product.
2. The method for producing dinitrophenol based on mixed low oil according to claim 1, wherein in step S1, the mixed mother liquor contains 89-93% of 2, 4-dinitrochlorobenzene, 7-11% of 2, 6-dinitrochlorobenzene, and the sum of the contents is 100%.
3. The method for producing dinitrophenol based on mixed low oil according to claim 2, wherein the mixed mother liquor contains 90% of 2.4-dinitrochlorobenzene and 10% of 2.6-dinitrochlorobenzene in step S1.
4. The method for producing dinitrophenol based on mixed low oil according to claim 1, wherein in step S1, the cooling rate of the mixed mother liquor in the crystallizer is 0.1-0.2 ℃/min, and the final temperature of the cooling is controlled to be 15 +/-0.5 ℃.
5. The method for producing dinitrophenol based on mixed low oil according to claim 4, wherein the cooling rate of the mixed mother liquor in the crystallizer is 0.15 ℃/min in step S1.
6. The method for producing dinitrophenol based on mixed low oil according to claim 1, wherein in step S2, the heating rate for heating and sweating is 0.05-0.08 ℃/min, the final temperature for heating and sweating is controlled at 50-64 ℃, and the total time for heating and sweating is controlled at 10-12 hours.
7. The method for producing dinitrophenol based on mixed low oil according to claim 6, wherein the heating rate for heating and sweating is 0.06 ℃/min.
8. The method for producing dinitrophenol based on mixed low oil according to claim 1, wherein in step S7, the cooling rate is 0.3-0.5 ℃/min, and the final temperature of cooling is controlled at 10 ± 0.5 ℃.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115160141A (en) * | 2021-04-01 | 2022-10-11 | 浙江省常山长盛化工有限公司 | Method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene |
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| US20050256343A1 (en) * | 2002-07-10 | 2005-11-17 | Eric Fache | Process for preparation of a nitrophenol |
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| SU783299A1 (en) * | 1978-05-22 | 1980-11-30 | Предприятие П/Я В-8611 | Method of purifying nitroaromatic compounds |
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| CN115160141A (en) * | 2021-04-01 | 2022-10-11 | 浙江省常山长盛化工有限公司 | Method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene |
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