CN105418458A - Synthetic process of 2-cyano-4-nitroaniline - Google Patents
Synthetic process of 2-cyano-4-nitroaniline Download PDFInfo
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- CN105418458A CN105418458A CN201510963399.8A CN201510963399A CN105418458A CN 105418458 A CN105418458 A CN 105418458A CN 201510963399 A CN201510963399 A CN 201510963399A CN 105418458 A CN105418458 A CN 105418458A
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- cyano
- sulfuric acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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Abstract
The invention relates to a synthetic process of 2-cyano-4-nitroaniline, comprising the following steps: putting chlorobenzonitrile into a sulfuric acid medium, dropwise adding mixed acid for nitration, adding water for elutriation of a nitrated object, then filtering the nitrated object, dissolving a nitrated material in chlorobenzene, performing an ammonolysis reaction by nitre-chlorine mixed fluid and liquid ammonia, then distilling to recycle a solvent, performing suction filtration, and washing to be neutral, thus obtaining a wet product. The process is simple in step and easy to control, the obtained product is high in yield, high in purity and stable in quality, and has an environmental index capable of meeting the market need, the cost is low, sewage is little, energy consumption is reduced, and the synthetic process is a production process low in energy consumption and low in pollution.
Description
Technical field
The present invention relates to a kind of synthesis technique of dispersed dye intermediate, specifically relate to a kind of synthesis technique of 2 cyano 4 nitro aniline, belong to the technical field of fine chemistry industry.
Background technology
As everyone knows, 2 cyano 4 nitro aniline is a kind of very important dispersed dye intermediate, but, the synthesis technique step traditional due to 2 cyano 4 nitro aniline is complicated, by product is many, and yield is low, and purity is low, the requirement of this area to 2 cyano 4 nitro aniline annual production cannot be met, also cannot reach specification of quality and the environmental requirement of increasingly stringent.Therefore, seeking that a kind of technique is simple and product yield is high, the 2 cyano 4 nitro aniline production technique of constant product quality, is the technical problem that those skilled in the art are badly in need of solving.The present invention produces thus.
Summary of the invention
For the above-mentioned technical problem of prior art, the object of this invention is to provide a kind of synthesis technique of 2 cyano 4 nitro aniline, by the adjustment to 2 cyano 4 nitro aniline synthesis material and synthetic route, make the synthesis technique of 2 cyano 4 nitro aniline simple and constant product quality.
For achieving the above object, the present invention is achieved by the following technical solutions:
A synthesis technique for 2 cyano 4 nitro aniline, comprises the following steps:
(1) o-chloro benzonitrile is put into sulfuric acid medium, then drip nitration mixture, carry out nitrated at 5-10 DEG C, obtain itrated compound;
(2) itrated compound in step (1) through the elutriation that adding water, carry out filtration after elutriation and obtain nitrated material;
(3) the nitrated material in step (2) is dissolved in chlorobenzene, obtain nitre chlorine and mix liquid;
(4) the nitre chlorine in step (3) is mixed liquid and liquefied ammonia carries out ammonolysis reaction, to be reacted to after terminal distillating recovering solvent at 80 DEG C-100 DEG C; Described ammonolysis reaction temperature is 110 DEG C-150 DEG C, and ammonolysis reaction pressure is 2.6MPa-4.5MPa; The terminal of described reaction measures in liquid chromatograph;
(5) solvent in step (4) carried out suction filtration and is washed to neutrality, obtaining wet product product, be i.e. 2 cyano 4 nitro aniline wet product;
Nitration mixture in described step (1) is the mixture of nitric acid and sulfuric acid, by weight, and described nitric acid: sulfuric acid=0.5-1:1;
By weight percentage, the described o-chloro benzonitrile in described step (1): sulfuric acid medium: chlorobenzene=1.5-2.5:5-7:6-9;
Reaction equation in described step (1) is:
Beneficial effect of the present invention is as follows:
The synthesis technique of 2 cyano 4 nitro aniline of the present invention, processing step simply, easily controls, and obtained product yield is high, purity is high, steady quality, and environmental protection index can meet market demand, cost is low, and sewage is few, energy consumption reduces, and is an oligosaprobic production technique of less energy-consumption.
Embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated, but protection scope of the present invention is not limited to this.
The raw material used in the present invention, as nitric acid, sulfuric acid, o-chloro benzonitrile and chlorobenzene etc. all can adopt method well known in the art to synthesize, also can adopt commercially available prod.
Embodiment 1
The synthesis technique of 2 cyano 4 nitro aniline of the present invention, comprises the following steps:
(1) 100g o-chloro benzonitrile is put into 333g sulfuric acid medium, then drip nitration mixture, carry out nitrated at 5-10 DEG C, obtain itrated compound; Nitration mixture is HNO
3and H
2sO
4mix with the mass percent of 0.5:1;
(2) itrated compound in step (1) through the elutriation that adding water, carry out filtration after elutriation and obtain nitrated material;
(3) the nitrated material in step (2) is dissolved in 400g chlorobenzene, obtain nitre chlorine and mix liquid;
(4) the nitre chlorine in step (3) is mixed liquid and liquefied ammonia carries out ammonolysis reaction, to be reacted to after terminal distillating recovering solvent at 80 DEG C; Ammonolysis reaction temperature is 110 DEG C, and ammonolysis reaction pressure is 2.6MPa; The terminal of reaction measures in liquid chromatograph;
(5) solvent in step (4) carried out suction filtration and is washed to neutrality, obtaining wet product product, be i.e. 2 cyano 4 nitro aniline wet product;
Its reaction equation is:
it can thus be appreciated that the effect playing in fact solvent of sulfuric acid medium, for the carrying out of reaction provides acidic conditions, sulfuric acid does not participate in reaction.
Embodiment 2
The synthesis technique of 2 cyano 4 nitro aniline of the present invention, comprises the following steps:
(1) 100g o-chloro benzonitrile is put into 280g sulfuric acid medium, then drip nitration mixture, carry out nitrated at 5-10 DEG C, obtain itrated compound; Nitration mixture is HNO
3and H
2sO
4mix with the mass percent of 1:1;
(2) itrated compound in step (1) through the elutriation that adding water, carry out filtration after elutriation and obtain nitrated material;
(3) the nitrated material in step (2) is dissolved in 360g chlorobenzene, obtain nitre chlorine and mix liquid;
(4) the nitre chlorine in step (3) is mixed liquid and liquefied ammonia carries out ammonolysis reaction, to be reacted to after terminal distillating recovering solvent at 100 DEG C; Ammonolysis reaction temperature is 150 DEG C, and ammonolysis reaction pressure is 4.5MPa; The terminal of reaction measures in liquid chromatograph;
(5) solvent in step (4) carried out suction filtration and is washed to neutrality, obtaining wet product product, be i.e. 2 cyano 4 nitro aniline wet product;
Its reaction equation is:
it can thus be appreciated that the effect playing in fact solvent of sulfuric acid medium, for the carrying out of reaction provides acidic conditions, sulfuric acid does not participate in reaction.
Embodiment 3
The synthesis technique of 2 cyano 4 nitro aniline of the present invention, comprises the following steps:
(1) 100g o-chloro benzonitrile is put into 300g sulfuric acid medium, then drip nitration mixture, carry out nitrated at 5-10 DEG C, obtain itrated compound; Nitration mixture is HNO
3and H
2sO
4mix with the mass percent of 0.75:1;
(2) itrated compound in step (1) through the elutriation that adding water, carry out filtration after elutriation and obtain nitrated material;
(3) the nitrated material in step (2) is dissolved in 375g chlorobenzene, obtain nitre chlorine and mix liquid;
(4) the nitre chlorine in step (3) is mixed liquid and liquefied ammonia carries out ammonolysis reaction, to be reacted to after terminal distillating recovering solvent at 90 DEG C; Ammonolysis reaction temperature is 130 DEG C, and ammonolysis reaction pressure is 3.6MPa; The terminal of reaction measures in liquid chromatograph;
(5) solvent in step (4) carried out suction filtration and is washed to neutrality, obtaining wet product product, be i.e. 2 cyano 4 nitro aniline wet product;
Reaction equation in this step (1) is:
it can thus be appreciated that the effect playing in fact solvent of sulfuric acid medium, for the carrying out of reaction provides acidic conditions, sulfuric acid does not participate in reaction.
In the present invention, the control of reaction end all adopts hplc determination method, and concrete measuring method is the known property general knowledge of this area, does not repeat herein.
Comparative example 1
(1), 2 cyano 4 nitro aniline is prepared according to traditional technology well known in the art.
Performance test
Measure the property indices of the 2 cyano 4 nitro aniline that step (1) is obtained in embodiment 1-3 according to the national standard of HG/T2078-2012, test result is in table 1.
Table 1
From upper table 1, the 2 cyano 4 nitro aniline of production technique synthesis of the present invention is premium grads, and the 2 cyano 4 nitro aniline synthesized in traditional technology is salable product,
The synthesis technique of 2 cyano 4 nitro aniline of the present invention, processing step simply, easily controls, and obtained product yield is high, purity is high, steady quality, and environmental protection index can meet market demand, cost is low, and sewage is few, energy consumption reduces, and is an oligosaprobic production technique of less energy-consumption.
Above-described embodiment only illustrates inventive concept of the present invention for explaining, but not the restriction to rights protection of the present invention, all changes utilizing this design the present invention to be carried out to unsubstantiality, all should fall into protection scope of the present invention.
Claims (2)
1. a synthesis technique for 2 cyano 4 nitro aniline, is characterized in that comprising the following steps:
(1) o-chloro benzonitrile is put into sulfuric acid medium, then drip nitration mixture, carry out nitrated at 5-10 DEG C, obtain itrated compound;
(2) itrated compound in step (1) through the elutriation that adding water, carry out filtration after elutriation and obtain nitrated material;
(3) the nitrated material in step (2) is dissolved in chlorobenzene, obtain nitre chlorine and mix liquid;
(4) the nitre chlorine in step (3) is mixed liquid and liquefied ammonia carries out ammonolysis reaction, to be reacted to after terminal distillating recovering solvent at 80 DEG C-100 DEG C; Described ammonolysis reaction temperature is 110 DEG C-150 DEG C, and ammonolysis reaction pressure is 2.6MPa-4.5MPa; The terminal of described reaction measures in liquid chromatograph;
(5) solvent in step (4) carried out suction filtration and is washed to neutrality, obtaining wet product product, be i.e. 2 cyano 4 nitro aniline wet product;
Nitration mixture in described step (1) is the mixture of nitric acid and sulfuric acid, by weight, and described nitric acid: sulfuric acid=0.5-1:1;
By weight percentage, described o-chloro benzonitrile: sulfuric acid medium: chlorobenzene=1.5-2.5:5-7:6-9.
2. the synthesis technique of 2 cyano 4 nitro aniline as claimed in claim 1, is characterized in that: its reaction equation is:
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| CN201510963399.8A CN105418458A (en) | 2015-12-18 | 2015-12-18 | Synthetic process of 2-cyano-4-nitroaniline |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859581A (en) * | 2016-04-21 | 2016-08-17 | 河间瀛州化工有限责任公司 | New nitration technology used in production of 2-cyano-4-nitro chlorobenzene |
| CN109369453A (en) * | 2018-09-04 | 2019-02-22 | 浙江工业大学 | Pipelineization prepares the method and device of the chloro- 5- nitrobenzonitrile of 2- |
| CN110028424A (en) * | 2019-05-15 | 2019-07-19 | 浙江长华科技股份有限公司 | Synthesis technology based on 2- amino -5- nitrobenzonitrile |
| CN110028425A (en) * | 2019-05-16 | 2019-07-19 | 浙江长华科技股份有限公司 | A kind of micro- reaction preparation process of 2- amino -5- nitrobenzonitrile |
| CN110041228A (en) * | 2019-05-15 | 2019-07-23 | 浙江长华科技股份有限公司 | A kind of o-chloro benzonitrile nitration processes |
| CN110128294A (en) * | 2019-05-15 | 2019-08-16 | 浙江长华科技股份有限公司 | A kind of chloro- 5- nitrobenzonitrile ammonolysis technique of 2- |
| CN110683966A (en) * | 2019-08-11 | 2020-01-14 | 沈阳百傲化学有限公司 | Process for preparing 2-cyano-4-nitroaniline by using microchannel reaction |
| CN113480449A (en) * | 2021-07-05 | 2021-10-08 | 河北嘉泰化工科技有限公司 | Novel process for continuously nitrifying and synthesizing 2-cyano-4-nitrochlorobenzene by solvent method |
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| CN1088200A (en) * | 1992-12-12 | 1994-06-22 | 湘潭市染料化工总厂 | The preparation method of 2 cyano 4 nitro aniline |
| CN1105661A (en) * | 1994-01-21 | 1995-07-26 | 王旗 | 2-cyano-4-nitroaniline synthetic process |
| CN104341319A (en) * | 2014-10-08 | 2015-02-11 | 绍兴县江华化工有限公司 | Synthesis process of 2-cyano-4-nitro-6-bromaniline |
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2015
- 2015-12-18 CN CN201510963399.8A patent/CN105418458A/en active Pending
Patent Citations (3)
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| CN1088200A (en) * | 1992-12-12 | 1994-06-22 | 湘潭市染料化工总厂 | The preparation method of 2 cyano 4 nitro aniline |
| CN1105661A (en) * | 1994-01-21 | 1995-07-26 | 王旗 | 2-cyano-4-nitroaniline synthetic process |
| CN104341319A (en) * | 2014-10-08 | 2015-02-11 | 绍兴县江华化工有限公司 | Synthesis process of 2-cyano-4-nitro-6-bromaniline |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859581A (en) * | 2016-04-21 | 2016-08-17 | 河间瀛州化工有限责任公司 | New nitration technology used in production of 2-cyano-4-nitro chlorobenzene |
| CN109369453A (en) * | 2018-09-04 | 2019-02-22 | 浙江工业大学 | Pipelineization prepares the method and device of the chloro- 5- nitrobenzonitrile of 2- |
| CN109369453B (en) * | 2018-09-04 | 2021-06-25 | 浙江工业大学 | Method and device for preparing 2-chloro-5-nitrobenzonitrile through pipelining |
| CN110028424A (en) * | 2019-05-15 | 2019-07-19 | 浙江长华科技股份有限公司 | Synthesis technology based on 2- amino -5- nitrobenzonitrile |
| CN110041228A (en) * | 2019-05-15 | 2019-07-23 | 浙江长华科技股份有限公司 | A kind of o-chloro benzonitrile nitration processes |
| CN110128294A (en) * | 2019-05-15 | 2019-08-16 | 浙江长华科技股份有限公司 | A kind of chloro- 5- nitrobenzonitrile ammonolysis technique of 2- |
| CN110028425A (en) * | 2019-05-16 | 2019-07-19 | 浙江长华科技股份有限公司 | A kind of micro- reaction preparation process of 2- amino -5- nitrobenzonitrile |
| CN110683966A (en) * | 2019-08-11 | 2020-01-14 | 沈阳百傲化学有限公司 | Process for preparing 2-cyano-4-nitroaniline by using microchannel reaction |
| CN113480449A (en) * | 2021-07-05 | 2021-10-08 | 河北嘉泰化工科技有限公司 | Novel process for continuously nitrifying and synthesizing 2-cyano-4-nitrochlorobenzene by solvent method |
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Application publication date: 20160323 |