CN115160141A - Method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene - Google Patents
Method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- 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
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by 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
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention relates to a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, which comprises the following steps: heating chlorobenzene in a first step to 50-70 ℃, dropwise adding mixed acid, heating to 80-90 ℃ after dropwise adding, carrying out heat preservation reaction for 30-40 minutes, taking samples to analyze that the content of chlorobenzene is less than 0.2%, the total content of mononitrochlorobenzene is less than 0.2%, the content of 2.4 dinitrochlorobenzene is more than or equal to 95.5%, the content of 2.6 dinitrochlorobenzene is less than or equal to 4%, standing for 30-40 minutes to carry out acid separation, and washing the mixed mother liquor of the upper layer of 2.4-dinitrochlorobenzene and 2.6-dinitrochlorobenzene to pH6.5-7.5; the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 1.8-2.0; and a second step of crystallization and purification. The method is based on chlorobenzene as a raw material, and the 2,4-dinitrochlorobenzene is produced by one-step nitration, so that the method is good in safety, low in energy consumption, free of pollution, high in product quality, safe and reliable, and greatly reduced in production cost.
Description
Technical Field
The invention relates to a production method of 2,4-dinitrochlorobenzene, in particular to a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, and belongs to the technical field of chemical product purification methods.
Background
2, 4-dinitrochlorobenzene is a pale yellow or yellowish brown needle-like crystal with bitter almond taste, and its molecular formula is C 6 H 3 ClN 2 O 4 The molecular weight is 202.56, and the relative density is 1.69g/cm 3 Boiling point 315 deg.C, melting point 53.4 deg.CThe product has a flash point of 194 ℃, is insoluble in water, is soluble in organic solvents such as ether, benzene, ethanol and the like, is mainly used as a raw material of dyes, pesticides, medicines and the like, and can be used for producing sulfur black, dinitrophenol, dinitroaniline and m-phenylenediamine.
Three methods are available for producing 2, 4-dinitrochlorobenzene, namely chlorobenzene method, p-nitrochlorobenzene method and o-nitrochlorobenzene method. The chlorobenzene method has higher cost, and the purity of products produced by the p-nitrochlorobenzene method and the o-nitrochlorobenzene method cannot meet the requirement, because the isomers of the nitro mixture generated by the nitration reaction of mixed acid have very close chemical properties, especially close boiling points. Therefore, the problem of high cost needs to be solved aiming at the chlorobenzene method with high safety, and the invention aims to solve the technical problem.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provides a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene. The method is based on chlorobenzene as a raw material, and is used for producing 2,4-dinitrochlorobenzene by one-step nitration, so that the method is good in safety, low in energy consumption, free of pollution, high in product quality, safe and reliable, and greatly reduced in production cost.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, which is characterized by comprising the following steps:
first nitration reaction
Heating benzene chloride to 50-70 ℃ in a reaction kettle, dropwise adding mixed acid, heating to 80-90 ℃ after dropwise adding, carrying out heat preservation reaction for 30-40 minutes, taking samples to analyze that the content of the benzene chloride is less than 0.2%, the total content of the mononitro chlorobenzene is less than 0.2%, the content of the 2.4 dinitrochlorobenzene is more than or equal to 95.5%, when the content of the 2.6 dinitro chlorobenzene is less than or equal to 4%, finishing the reaction, standing for 30-40 minutes for acid separation, and washing the mixed mother liquor of the upper layer of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene to the pH value of 6.5-7.5;
the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 1.8-2.0;
second step of crystallization purification
1): firstly, conveying mixed mother liquor of 2.4-dinitrochlorobenzene and 2.6-dinitrochlorobenzene into a crystallizer, and cooling to 15 +/-1 ℃;
2): the temperature of the cooled mixed mother liquor in the step S1 is gradually increased to make the crystal sweat;
21): in the process of heating and sweating, firstly collecting mixed low oil, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30 +/-1%;
22): collecting mixed high oil, wherein the mixed high oil contains 2.6-dinitrochlorobenzene with the volume fraction of 10 +/-1%;
23): finally obtaining the 2.4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
The method comprises the following steps: the chlorobenzene is nitrified in one step, the generation of m-nitrochlorobenzene is very little, the m-nitrochlorobenzene is 0.02 percent, and the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent. If the chlorobenzene is first mononitrated to produce the mixture of mononitrochlorobenzene, and then the p-nitrochlorobenzene, the o-nitrochlorobenzene and the m-nitrochlorobenzene are separated by crystallization and rectification, a large amount of common oil, namely meta-position oil, is generated, and the meta-position oil treatment is a worldwide problem. And the mononitrated separated material o-nitrochlorobenzene is used for re-nitration, wherein the content of 2.4 dinitrochlorobenzene is about 90 percent, and the content of 2.6 dinitrochlorobenzene is about 10 percent, so that the required amount of 2.4 dinitrochlorobenzene is reduced. In addition, the chlorobenzene one-step dinitration mixture can be directly used for producing sulfur black without separation. The nitration product of o-nitrochlorobenzene cannot be directly marketed because of the high content of 2.6 dinitrochlorobenzene.
The purification method of the invention has low energy consumption, low temperature and no three wastes, is the cleanest separation method at present, avoids the danger of high-temperature separation and 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 2,4-dinitrochlorobenzene, and the mixed low oil can be directly used as a raw material for producing the sulfur black, so that the comprehensive utilization efficiency of the material is improved, and the additional value of the mixed mother liquor of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene is improved.
Preferably, the mass ratio of the chlorobenzene to the mixed acid is 1:3-3.5, and the total dropping time of the mixed acid is controlled within 1 hour.
Preferably, in the second step 1), 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 ℃. More preferably, in the second step 1), the cooling rate of the mixed mother liquor in the crystallizer is 0.15 ℃/min.
Preferably, in the second step 2), the temperature-rising and sweating rate is 0.05-0.08 ℃/min, the final temperature of temperature-rising and sweating is controlled to be 50-64 ℃, and the total time of temperature-rising and sweating is controlled to be 10-12 hours.
More preferably, the heating rate for heating and sweating is 0.06 ℃/min.
The invention has the beneficial effects that:
the method comprises the following steps: the chlorobenzene is nitrified in one step, the generation of m-nitrochlorobenzene is very little, the m-nitrochlorobenzene is 0.02 percent, and the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent. If the chlorobenzene is first mononitrated to produce the mixture of mononitrochlorobenzene, and then the p-nitrochlorobenzene, the o-nitrochlorobenzene and the m-nitrochlorobenzene are separated by crystallization and rectification, a large amount of common oil, namely meta-position oil, is generated, and the meta-position oil treatment is a worldwide problem. And the mononitrated separated material o-nitrochlorobenzene is used for re-nitration, wherein the content of 2.4 dinitrochlorobenzene is about 90 percent, and the content of 2.6 dinitrochlorobenzene is about 10 percent, so that the required amount of 2.4 dinitrochlorobenzene is reduced. In addition, the chlorobenzene one-step dinitration mixture can be directly used for producing sulfur black without separation. The nitration product of o-nitrochlorobenzene cannot be directly marketed because of the high content of 2.6 dinitrochlorobenzene.
The purification method has the advantages of low energy consumption, low temperature and no three wastes, is the cleanest separation method at present, avoids the danger 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 2,4-dinitrochlorobenzene, and the mixed low oil can be directly used as a raw material for producing the sulfur black, so that the comprehensive utilization efficiency of the material is improved, and the additional value of the mixed mother liquor of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene is improved.
Detailed Description
The technical solution of the present invention will be further specifically described below by way of specific examples.
In examples 1 to 3 of the present invention, all the crystallizers used were commercially available conventional crystallizers, and each raw material was a commercially available conventional raw material.
Example 1:
a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorinated benzene, comprising the steps of:
first nitration reaction
Heating chlorobenzene in a reaction kettle to 50 ℃, dropwise adding mixed acid, heating to 80 ℃ after dropwise adding, carrying out heat preservation reaction for 40 minutes, taking samples to analyze that the content of the chlorobenzene is less than 0.2 percent, the total content of the mononitrochlorobenzene is less than 0.2 percent, the content of 2.4 dinitrochlorobenzene is more than or equal to 95.5 percent, the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent, standing for 30-40 minutes for acid separation, and washing the mixed mother liquor of the upper layer of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene to pH6.5;
the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 1.8;
second step of crystallization purification
1): firstly, conveying mixed mother liquor of 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 ℃;
2): the temperature of the cooled mixed mother liquor in the step S1 is gradually increased to make the crystal sweat;
21): in the process of heating and sweating, firstly collecting mixed low oil, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30%;
22): collecting mixed high oil, wherein the mixed high oil contains 10% of 2.6-dinitrochlorobenzene by volume fraction;
23): finally obtaining the 2.4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
In the embodiment 1, the mass ratio of the chlorobenzene to the mixed acid is 1:3, and the total dropping time of the mixed acid is controlled within 1 hour; in the second step 1), the cooling rate of the mixed mother liquor in the crystallizer is 0.1 ℃/min, and the final temperature of cooling is controlled at 15 ℃; the heating rate of the heating and sweating is 0.05 ℃/min, and the final temperature of the heating and sweating is controlled at 50 ℃.
Example 2:
a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, which comprises the following steps:
first nitration reaction
Heating chlorobenzene in a reaction kettle to 70 ℃, dropwise adding mixed acid, heating to 90 ℃ after dropwise adding, carrying out heat preservation reaction for 30 minutes, taking samples to analyze that the content of the chlorobenzene is less than 0.2 percent, the total content of the mononitrochlorobenzene is less than 0.2 percent, the content of 2.4 dinitrochlorobenzene is more than or equal to 95.5 percent, the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent, standing for 40 minutes to carry out acid separation, and washing the mixed mother liquor of the upper layer of 2.4-dinitrochlorobenzene and 2.6-dinitrochlorobenzene to the pH value of 7.5;
the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 2.0;
second step of crystallization purification
1): firstly, conveying mixed mother liquor of 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 16 ℃;
2): the temperature of the cooled mixed mother liquor in the step S1 is gradually increased to make the crystal sweat;
21): in the process of heating and sweating, firstly collecting mixed low oil, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30%;
22): collecting mixed high oil, wherein the mixed high oil contains 10% of 2.6-dinitrochlorobenzene by volume fraction;
23): finally obtaining the 2.4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
In example 2, the mass ratio of the chlorobenzene to the mixed acid is 1.5, the total dropping time of the mixed acid is controlled within 1 hour, in the second step 1), the cooling rate of the mixed mother liquor in the crystallizer is 0.2 ℃/min, the final temperature of the cooling is controlled at 15.5 ℃, the heating rate of the heating and sweating is 0.08 ℃/min, and the final temperature of the heating and sweating is controlled at 64 ℃.
Example 3:
a method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, which is characterized by comprising the following steps:
first nitration reaction
Heating chlorobenzene in a reaction kettle to 60 ℃, dropwise adding mixed acid, heating to 85 ℃ after dropwise adding, keeping the temperature for 35 minutes, finishing the reaction when the content of the chlorobenzene is less than 0.2 percent, the total content of the mononitrochlorobenzene is less than 0.2 percent, the content of 2.4 dinitrochlorobenzene is more than or equal to 95.5 percent, and the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent by sampling analysis, standing for 35 minutes for acid separation, and washing the mixed mother liquor of the upper layer of 2.4-dinitrochlorobenzene and 2.6-dinitrochlorobenzene to pH7.0 by water;
the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 1.8;
second step of crystallization purification
1): firstly, conveying mixed mother liquor of 2, 4-dinitrochlorobenzene and 2, 6-dinitrochlorobenzene to a crystallizer, and cooling to 15 ℃;
2): the temperature of the cooled mixed mother liquor in the step S1 is gradually increased to make the crystal sweat;
21): in the process of heating and sweating, firstly collecting mixed low oil, wherein the mixed low oil contains 30 volume percent of 2.6-dinitrochlorobenzene;
22): collecting mixed high oil, wherein the mixed high oil contains 10% of 2.6-dinitrochlorobenzene by volume fraction;
23): finally obtaining the 2.4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
In the embodiment 3, the mass ratio of the chlorobenzene to the mixed acid is 1:3, the total dropping time of the mixed acid is controlled within 1 hour, in the step 1) of the second step, the cooling rate of the mixed mother liquor in the crystallizer is 0.15 ℃/min, the final temperature of cooling is controlled at 15 ℃, the heating rate of heating and sweating is 0.06 ℃/min, and the final temperature of heating and sweating is controlled at 60 ℃.
The purity and the crystallization yield of 2,4-dinitrochlorobenzene obtained by purification in examples 1-3 were as follows:
the method comprises the following steps: the chlorobenzene is nitrified in one step, the generation of m-nitrochlorobenzene is very little, the m-nitrochlorobenzene is 0.02 percent, and the content of 2.6 dinitrochlorobenzene is less than or equal to 4 percent. If the chlorobenzene is first mononitrated to produce the mixture of mononitrochlorobenzene, which is then crystallized and rectified to separate p-nitrochlorobenzene, o-nitrochlorobenzene and m-nitrochlorobenzene, a great amount of common oil, i.e. meta-position oil, is produced, and the meta-position oil treatment is a worldwide problem. And the mononitrated separated material o-nitrochlorobenzene is used for re-nitration, wherein the content of 2.4 dinitrochlorobenzene is about 90 percent, and the content of 2.6 dinitrochlorobenzene is about 10 percent, so that the required amount of 2.4 dinitrochlorobenzene is reduced. In addition, the chlorobenzene one-step dinitration mixture can be directly used for producing sulfur black without separation. The nitration product of o-nitrochlorobenzene cannot be directly marketed because of the high content of 2.6 dinitrochlorobenzene.
The purification method of the invention has low energy consumption, low temperature and no three wastes, is the cleanest separation method at present, avoids the danger of high-temperature separation and 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 2,4-dinitrochlorobenzene, and the mixed low oil can be directly used as a raw material for producing the sulfur black, so that the comprehensive utilization efficiency of the material is improved, and the additional value of the mixed mother liquor of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene is improved.
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 (6)
1. A method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene, which is characterized by comprising the following steps:
first nitration reaction
Heating benzene chloride to 50-70 ℃ in a reaction kettle, dropwise adding mixed acid, heating to 80-90 ℃ after dropwise adding, carrying out heat preservation reaction for 30-40 minutes, taking samples to analyze that the content of the benzene chloride is less than 0.2%, the total content of the mononitro chlorobenzene is less than 0.2%, the content of the 2.4 dinitrochlorobenzene is more than or equal to 95.5%, when the content of the 2.6 dinitro chlorobenzene is less than or equal to 4%, finishing the reaction, standing for 30-40 minutes for acid separation, and washing the mixed mother liquor of the upper layer of the 2.4-dinitrochlorobenzene and the 2.6-dinitrochlorobenzene to the pH value of 6.5-7.5;
the mixed acid is formed by mixing concentrated sulfuric acid and concentrated nitric acid according to the mass ratio of 1.8-2.0;
second step of crystallization purification
1): firstly, conveying mixed mother liquor of 2.4-dinitrochlorobenzene and 2.6-dinitrochlorobenzene into a crystallizer, and cooling to 15 +/-1 ℃;
2): the temperature of the mixed mother liquor cooled in the step S1 is gradually increased to enable crystals to sweat;
21): in the process of heating and sweating, firstly collecting mixed low oil, wherein the mixed low oil contains 2.6-dinitrochlorobenzene with the volume fraction of 30 +/-1%;
22): collecting mixed high oil, wherein the mixed high oil contains 2.6-dinitrochlorobenzene with the volume fraction of 10 +/-1%;
23): finally obtaining the 2.4-dinitrochlorobenzene crystal with the purity of more than 99.5 percent.
2. The method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene according to claim 1, wherein the mass ratio of the chlorobenzene to the mixed acid is 1:3-3.5, and the total dropping time of the mixed acid is controlled within 1 hour.
3. The method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene according to claim 1, wherein in the second step 1), the cooling rate of the mixed mother liquor in the crystallizer is 0.1-0.2 ℃/min, and the final cooling temperature is controlled to be 15 ± 0.5 ℃.
4. The method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene according to claim 5, wherein in the second step 1), the cooling rate of the mixed mother liquor in the crystallizer is 0.15 ℃/min.
5. The method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene according to claim 1, wherein in the second step 2), the temperature rise rate of temperature rise and sweating is 0.05-0.08 ℃/min, the final temperature of temperature rise and sweating is controlled to be 50-64 ℃, and the total time of temperature rise and sweating is controlled to be 10-12 hours.
6. The method for producing 2,4-dinitrochlorobenzene by one-step nitration of chlorobenzene according to claim 5, wherein the rate of temperature rise for temperature rise and sweating is 0.06 ℃/min.
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