CN101343232B - Preparation method for 2-chloro-4-nitroaniline - Google Patents
Preparation method for 2-chloro-4-nitroaniline Download PDFInfo
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- CN101343232B CN101343232B CN2008101962126A CN200810196212A CN101343232B CN 101343232 B CN101343232 B CN 101343232B CN 2008101962126 A CN2008101962126 A CN 2008101962126A CN 200810196212 A CN200810196212 A CN 200810196212A CN 101343232 B CN101343232 B CN 101343232B
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Abstract
The invention relates to a preparation method of o-chloro-p-nitroaniline, which takes p-nitroaniline as a raw material, and prepares the o-chloro-p-nitroaniline by directly inputting chlorine gas for implementing the chlorination reaction in a diluted hydrochloric acid medium with a temperature of between -20 and 10 DEG C, wherein, the p-nitroaniline and the input chlorine gas are present in a molar ratio of 1:1-1.1. The preparation method can prepare the o-chloro-p-nitroaniline with best quality, and has advantages of simple process, high yield, low production cost and non wastewater discharge.
Description
Technical field
The present invention relates to a kind of preparation method of ortho-chlor-para nitraniline.
Background technology
Ortho-chlor-para nitraniline is the important dyestuff and the intermediate of pigment, and it can also be used to synthetic fourth spiral shell agricultural chemicals.At present, the preparation method of ortho-chlor-para nitraniline mainly contains two kinds, and a kind of is by 3, and the 4-dichloronitrobenzene carries out the high pressure ammonolysis reaction and forms in the strong aqua medium; Another kind be p-Nitroaniline in diluted hydrochloric acid medium, under cold condition, prepare by slowly dripping the chlorine bleach liquor.Adopt the preparation method of high pressure ammonolysis reaction, though the quality of the ortho-chlor-para nitraniline of preparation is better, facility investment is huge, and operational hazards, and because it generates by product NH
4Cl can produce a large amount of waste water, pollutes to environment.And preparing in the method for ortho-chlor-para nitraniline to drip the chlorine bleach liquor, at first to make the chlorine bleach liquor, be about to chlorine feed in the sodium hydroxide solution, not only need investment goods, also can cause a large amount of spent acid mother liquors.In addition, in the clorox production process, control the quality of production of clorox well, i.e. available chlorine and free alkali, technology is very loaded down with trivial details; And during owing to chlorine bleach liquor and p-Nitroaniline reaction, can produce sodium-chlor, thereby make the mother liquor in the reaction process can't recycled and all exert an influence for the quality and the outward appearance of ortho-chlor-para nitraniline, cause the ortho-chlor-para nitraniline appearance poor for preparing, content be low.
Summary of the invention
Technical problem to be solved by this invention provides a kind of preparation method of ortho-chlor-para nitraniline, the ortho-chlor-para nitraniline purity height of this method preparation, and this method is simple, the yield height, and production cost is low, non-wastewater discharge.
For solving above technical problem, the technical scheme that the present invention takes is:
A kind of preparation method of ortho-chlor-para nitraniline, with the p-Nitroaniline is raw material, and in-20～10 ℃ diluted hydrochloric acid medium, directly logical chlorine carries out chlorination reaction and makes ortho-chlor-para nitraniline, wherein, p-Nitroaniline is 1: 1～1.1 with the mol ratio that feeds chlorine.
Preferably, described chlorination reaction is carried out under-10～0 ℃.
The speed that feeds chlorine can not be too fast, is preferably 0.35～0.5L/h.
It is to carry out in 8～11% the diluted hydrochloric acid medium that chlorination reaction is preferably in mass percent concentration.
This preparation method's concrete steps are after feeding chlorine reaches the terminal point of chlorination reaction, to stop logical chlorine, continue insulation reaction 1～1.5h down at-20～10 ℃, carry out suction filtration then under 0～10 ℃, filter cake washes neutrality with water, and drying promptly gets described ortho-chlor-para nitraniline; Filtrate is then directly overlapped and is used for batch reaction down.
Because the technique scheme utilization, the present invention compared with prior art has following advantage:
With the p-Nitroaniline is raw material, in diluted hydrochloric acid medium, directly feed chlorine down in low temperature and make ortho-chlor-para nitraniline, save the clorox dripping method of original process using, promptly save clorox production unit and operation, reduced equipment cost and running cost; Sodium chloride-containing not in the mother liquor behind the direct chlorination can be overlapped and is used for batch reaction down, without sewage discharge and reduce raw materials cost; In addition, adopt this preparation method, the molar yield of product ortho-chlor-para nitraniline is greater than 98%, and purity is greater than 95%, and is best in quality.
Embodiment
The present invention will be described in detail below in conjunction with specific embodiment, but be not limited to this.
Example 1
Preparation method according to the ortho-chlor-para nitraniline of present embodiment is specific as follows:
At first the 20g p-Nitroaniline is added among the 200g 10%HCl, heating makes whole dissolvings, then solution is cooled to-10～0 ℃, feeds chlorine with 0.49L/h, the logical chlorine time was controlled at about 7 hours, after logical chlorine finishes, continuation is-10～0 ℃ of following insulated and stirred 1 hour, carries out suction filtration in 0 ℃ then, and mother liquor is waited until next batch and applied mechanically, filter cake wash with water neutral and drain dry product 24.7g, be described ortho-chlor-para nitraniline.Ortho-chlor-para nitraniline chromatogram content 96.3%, calculating its molar yield is 98.2%.
Example 2
At first the 20g p-Nitroaniline is added among the 200g 8%HCl, heating makes whole dissolvings, then solution is cooled to-10～0 ℃, feeds chlorine with 0.49L/h, the logical chlorine time was controlled at about 7 hours, after logical chlorine finishes, continuation is-10～0 ℃ of following insulated and stirred 1 hour, carries out suction filtration in 0 ℃ then, and mother liquor is waited until next batch and applied mechanically, filter cake wash with water neutral and drain dry product 24.7g, be described ortho-chlor-para nitraniline.Ortho-chlor-para nitraniline chromatogram content 95.8%, calculating its molar yield is 98.2%.
Example 3
Except that dilute hydrochloric acid concentration with 11%, all the other are all identical with example 1, make ortho-chlor-para nitraniline 24.5g, chromatogram content 94.8%, calculating molar yield is 97.4%.
Example 4
Demineralizing acid concentration is with outside 7%, and all the other are all identical with example 1, make ortho-chlor-para nitraniline quality 24.4g, chromatogram content 94.6%, and calculating molar yield is 97.0%.
Comparative example 1: industrial conventional production methods
Getting p-Nitroaniline 20g joins among the 200g 10%HCl, heating makes dissolving, cooling solution-5～0 ℃ then, slowly drip 45 cold chlorine bleach liquores' (available chlorine 10%), time is 3 hours, after dropwising, suction filtration after this temperature-5～0 ℃ stirs 1 hour down again, the mother liquor treatment plant of anhydrating is handled; Filter cake is drained and is promptly got the 24g ortho-chlor-para nitraniline for after washing neutrality with water, chlorine p-Nitroaniline chromatogram content 92%.
Compare ratio, the embodiment of the invention 1 to 4 has been saved clorox production unit and operation, reduces equipment cost and running cost; Sodium chloride-containing not in the mother liquor behind the direct chlorination can be overlapped and is used for batch reaction down, without sewage discharge and reduce raw materials cost; In addition, adopt the preparation method, the molar yield of product ortho-chlor-para nitraniline is greater than 98%, and purity is greater than 95%, and is best in quality.
Claims (6)
1. the preparation method of an ortho-chlor-para nitraniline, it is characterized in that: be raw material with the p-Nitroaniline, in-20～10 ℃ diluted hydrochloric acid medium, directly logical chlorine carries out chlorination reaction and makes ortho-chlor-para nitraniline, wherein, p-Nitroaniline is 1: 1～1.1 with the mol ratio that feeds chlorine, and sodium chloride-containing not in the mother liquor behind the direct chlorination can be overlapped and is used for following batch chlorination reaction.
2. the preparation method of a kind of ortho-chlor-para nitraniline according to claim 1, it is characterized in that: the temperature of described chlorination reaction is-10～0 ℃.
3. the preparation method of a kind of ortho-chlor-para nitraniline according to claim 1 and 2 is characterized in that: the speed that feeds chlorine is 0.35～0.5L/h.
4. the preparation method of a kind of ortho-chlor-para nitraniline according to claim 1, it is characterized in that: the mass percent concentration of described dilute hydrochloric acid is 8～11%.
5. the preparation method of a kind of ortho-chlor-para nitraniline according to claim 1, it is characterized in that: after the chlorine feeding finishes, continue insulation reaction 1～1.5h down at-20～10 ℃, under 0～10 ℃, carry out suction filtration then, filter cake washes neutrality with water, and drying promptly gets described ortho-chlor-para nitraniline.
6. the preparation method of a kind of ortho-chlor-para nitraniline according to claim 5 is characterized in that: the filtrate of carrying out gained behind the suction filtration directly cover is used for chlorination reaction.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2008101962126A CN101343232B (en) | 2008-08-21 | 2008-08-21 | Preparation method for 2-chloro-4-nitroaniline |
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| CN2008101962126A CN101343232B (en) | 2008-08-21 | 2008-08-21 | Preparation method for 2-chloro-4-nitroaniline |
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| CN101343232A CN101343232A (en) | 2009-01-14 |
| CN101343232B true CN101343232B (en) | 2011-05-04 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104592042A (en) * | 2014-12-29 | 2015-05-06 | 浙江龙盛集团股份有限公司 | Clean technology for continuously synthesizing 2,4-binitro-6-chloroaniline |
| CN111704806B (en) * | 2020-06-22 | 2021-05-11 | 清华大学 | Continuous preparation method of disperse dye |
| CN111620785B (en) * | 2020-06-22 | 2023-03-28 | 浙江迪邦化工有限公司 | Continuous chlorination method of nitroaniline |
| CN111704553B (en) * | 2020-06-22 | 2021-05-14 | 清华大学 | Cyclic synthesis method of nitroaniline chloride |
| CN115385798A (en) * | 2022-09-19 | 2022-11-25 | 苏州市罗森助剂有限公司 | Method for directly preparing o-chloro-p-nitroaniline through chlorination reaction |
| CN115490598A (en) * | 2022-09-19 | 2022-12-20 | 苏州市罗森助剂有限公司 | Production process of o-chloro-p-nitroaniline |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL110698B1 (en) * | 1977-08-29 | 1980-07-31 | Zachem Zaklady Chem Organika | Method of producing 2-chloro-4-nitroaniline |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL110698B1 (en) * | 1977-08-29 | 1980-07-31 | Zachem Zaklady Chem Organika | Method of producing 2-chloro-4-nitroaniline |
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