CN113582852A - Method for producing dinitroaniline - Google Patents
Method for producing dinitroaniline Download PDFInfo
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- CN113582852A CN113582852A CN202010366303.0A CN202010366303A CN113582852A CN 113582852 A CN113582852 A CN 113582852A CN 202010366303 A CN202010366303 A CN 202010366303A CN 113582852 A CN113582852 A CN 113582852A
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- dinitrochlorobenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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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
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Abstract
The invention relates to a production method of dinitroaniline, which comprises 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 into 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; and a second step, namely the production of dinitroaniline, wherein the mixed low oil obtained in the step S3 in the first step is used 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 dinitroaniline is reduced.
Description
Technical Field
The invention relates to a method for producing dinitroaniline, and belongs 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 ether, benzene, ethanol, etcThe organic solvent is mainly used as raw materials of dyes, pesticides, medicines and the like, and can be used for producing sulfur black, 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, has sold the produced mixed mother liquor directly as a product for many years, and further separated and purified by a downstream manufacturer, so that the comprehensive value of the product of the mixed mother liquor cannot be developed to the maximum, in addition, the raw material cost of dinitroaniline production is greatly increased, which is not beneficial to large-scale production to meet the market demand, therefore, a method for producing dinitroaniline is urgently needed to be provided, the derivation of a 2, 4-dinitrochlorobenzene industrial chain is realized, the economic value of a derivative is improved, and the raw material cost of dinitroaniline production is reduced.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provide a method for producing dinitroaniline. 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 dinitroaniline.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a process for producing dinitroaniline, 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 dinitroaniline
And (3) adding the mixed low-oil, 15-20% by mass of ammonia water and tap water obtained in the step (S3) into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of (3.5-4.0) and NH =13: the water mass ratio =1 (4-4.2); the reaction time is 35-50 minutes; the reaction temperature is 160-170 ℃, the reaction pressure is 0.8-1.5 MPa, the temperature of the reacted materials is reduced to 60-65 ℃, the pressure is reduced to normal pressure to form a solid-liquid mixed material, and the solid material is dinitroaniline after the solid-liquid mixed material is centrifugally washed.
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 the production of the dinitroaniline, the cooling rate is 0.2-0.4 ℃/min, and the final temperature of cooling is controlled at 60 +/-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 dinitroaniline, so that the comprehensive utilization efficiency of the material is improved, the additional value of the mixed mother liquor of the 2, 4-dinitrochlorobenzene and the 2, 6-dinitrochlorobenzene is improved, and the production cost of the dinitroaniline is reduced.
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 dinitroaniline, 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 dinitroaniline
And (4) adding the mixed low-oil, 15 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of =1:3.5, and NH3: water mass ratio =1: 4; the reaction time was 35 minutes; the reaction temperature is 160 ℃, the reaction pressure is 0.8MPa, the temperature of the reacted materials is reduced to 60 ℃ through temperature reduction and pressure reduction, the pressure is reduced to normal pressure, a solid-liquid mixed material is formed, and the solid material is the dinitroaniline after the solid-liquid mixed material is centrifugally washed. In the production of dinitroaniline, the cooling rate is 0.2 ℃/min.
Example 2:
a process for producing dinitroaniline, 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 dinitroaniline
And (4) adding the mixed low-oil, 20 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of =1:4.0, and NH3: water mass ratio =1: 4.2; the reaction time is 50 minutes; the reaction temperature is 170 ℃, the reaction pressure is 1.5Mpa, the temperature of the reacted materials is reduced to 65 ℃ and the pressure is reduced to normal pressure through temperature reduction and pressure discharge to form solid-liquid mixed materials, and the solid materials are the dinitroaniline after the solid-liquid mixed materials are centrifugally washed. In the production of dinitroaniline, the cooling rate is 0.4 ℃/min.
Example 3:
a process for producing dinitroaniline, 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 dinitroaniline
And (4) adding the mixed low-oil, 18 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of =1:4.0, and NH3: water mass ratio =1: 4; the reaction time was 35 minutes; the reaction temperature is 160 ℃, the reaction pressure is 0.8MPa, the temperature of the reacted materials is reduced to 60 ℃ through temperature reduction and pressure reduction, the pressure is reduced to normal pressure, a solid-liquid mixed material is formed, and the solid material is the dinitroaniline after the solid-liquid mixed material is centrifugally washed. In the production of dinitroaniline, the cooling rate is 0.25 ℃/min.
Example 4:
a process for producing dinitroaniline, 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 dinitroaniline
And (4) adding the mixed low-oil, 20 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of =1:4.0, and NH3: water mass ratio =1: 4.2; the reaction time is 50 minutes; the reaction temperature is 160 ℃, the reaction pressure is 1.5Mpa, the temperature of the material after the reaction is reduced to 60 ℃ and the pressure is reduced to normal pressure through temperature reduction and pressure discharge to form a solid-liquid mixed material, and the solid material is the dinitroaniline after the solid-liquid mixed material is centrifugally washed. In the production of dinitroaniline, the cooling rate is 0.3 ℃/min.
Example 5:
a process for producing dinitroaniline, 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 dinitroaniline
And (4) adding the mixed low-oil, 18 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2, 4-dinitrochlorobenzene: NH contained in aqueous ammonia3At a molar ratio of =1:3.8, and NH3: water mass ratio =1: 4.1; the reaction time is 40 minutes; the reaction temperature is 165 ℃, the reaction pressure is 1.0Mpa, the temperature of the reacted material is reduced to 60 ℃ and the pressure is reduced to normal pressure through temperature reduction and pressure discharge to form a solid-liquid mixed material, and the solid material is the dinitroaniline after the solid-liquid mixed material is centrifugally washed. In the production of dinitroaniline, the cooling rate is 0.35 ℃/min.
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 dinitroaniline, 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 (8)
1. A process for the production of dinitroaniline, 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 dinitroaniline
And (3) adding the mixed low-oil, 15-20 mass percent of ammonia water and tap water obtained in the step S3 into a reactor by using a metering pump for reaction, wherein the adding amount of the ammonia water and the tap water is that the ratio of 2,4 dinitrochlorobenzene: NH contained in aqueous ammonia31 (3.5-4.0), and NH3: the water mass ratio is 1 (4-4.2); reaction time 3550 minutes; the reaction temperature is 160-170 ℃, the reaction pressure is 0.8-1.5 Mpa, the temperature of the reacted materials is reduced to 60-65 ℃, the pressure is reduced to normal pressure to form solid-liquid mixed materials, and the solid materials are dinitroaniline after the solid-liquid mixed materials are centrifugally washed.
2. The process for producing dinitroaniline according to claim 1, wherein in step S1, the mixed mother liquor contains 2.4-dinitrochlorobenzene in an amount of 89 to 93% and 2.6-dinitrochlorobenzene in an amount of 7 to 11%, the sum of the amounts being 100%.
3. The process for producing dinitroaniline according to claim 2, wherein in step S1, the mixed mother liquor contains 90% of 2.4-dinitrochlorobenzene and 10% of 2.6-dinitrochlorobenzene.
4. The process for producing dinitroaniline 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 cooling temperature is controlled to 15 ± 0.5 ℃.
5. The process for producing dinitroaniline according to claim 4, wherein in step S1, the temperature of the mixed mother liquor in the crystallizer is lowered at a rate of 0.15 ℃/min.
6. The process for producing dinitroaniline according to claim 1, wherein in step S2, the temperature-raising and sweating rate is 0.05-0.08 ℃/min, the final temperature of the temperature-raising and sweating is controlled to 50-64 ℃, and the total time of the temperature-raising and sweating is controlled to 10-12 hours.
7. The process for producing dinitroaniline according to claim 6, wherein the rate of temperature rise for temperature rise and perspiration is 0.06 ℃/min.
8. The method for producing dinitroaniline according to claim 1, wherein in the production of dinitroaniline, the cooling rate is 0.2-0.4 ℃/min, and the final temperature of cooling is controlled to be 60 ± 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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| CN105859517A (en) * | 2016-05-03 | 2016-08-17 | 四川福思达生物技术开发有限责任公司 | Method for purifying 1,2,4-trichlorobenzene from trichlorobenzene mixture |
| CN108047054A (en) * | 2018-01-23 | 2018-05-18 | 贵州大学 | A kind of method of fusion-crystallization separating-purifying neighbour's Iodoaniline |
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| US5395995A (en) * | 1992-05-18 | 1995-03-07 | Bayer Aktiengesellschaft | Process for the preparation and purification of nitroaromatics |
| CN103086895A (en) * | 2011-10-31 | 2013-05-08 | 浙江龙盛化工研究有限公司 | Method for preparing aromatic amine from mixed nitrochlorobenzene |
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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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