CN101613288A - A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline - Google Patents
A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline Download PDFInfo
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- CN101613288A CN101613288A CN200910117172A CN200910117172A CN101613288A CN 101613288 A CN101613288 A CN 101613288A CN 200910117172 A CN200910117172 A CN 200910117172A CN 200910117172 A CN200910117172 A CN 200910117172A CN 101613288 A CN101613288 A CN 101613288A
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Abstract
The present invention relates to a kind of preparation N, the method of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, add raw material 3,4-two chlorobenzotrifluorides and dimethylamine and N, the N-N,N-DIMETHYLACETAMIDE, stirring is warmed up to 120 ℃ of temperature and allows its reaction under pressure 2.0mpa, open cycle water is to the still processing of lowering the temperature during stirring, reaction finish the back layering wash product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline, product N, the yield of N-dimethyl-2-chloro-4-5-trifluoromethylaniline reaches more than 90%.The present invention can reduce the pressure and temperature in the production process widely, and improves the yield of product.
Description
Technical field
The present invention relates to a kind of synthetic method of compound, particularly a kind of fluoro-containing pesticide intermediate synthetic.
Background technology
Fluoro-containing pesticide is the novel agricultural chemicals of a class that recent two decades develops rapidly in the world, has characteristics efficient, low toxicity, especially low residue, thereby develops very fast.Fluorine worm nitrile (fipronil) be last century the nineties by one of representative of the fluorine-containing Insecticidal pyrazolines of French Luo Na-Rhone-Poulenc exploitation listing.This kind have insecticidal spectrum wide, active high, the longevity of residure is long, can stimulate plant growth, to characteristics such as beneficial organism safety and environmental pollution are little.Can be used for various crop such as paddy rice, corn, cotton, soybean, rape, tealeaves, potato, sugarcane, vegetables, fruit tree, forest and ornamental plant, various pests such as Hemiptera, lepidopteran, Thysanoptera, Coleoptera are had good prevention effect.Also can be used for the protection of public health, livestock industry, agricultural-food storage and some buildingss.Fluorine worm nitrile has special mechanism of action, and insecticidal spectrum is wide, and especially the insect that existing conventional pesticide is produced resistance has good prevention effect.According to popularization situation in recent years, the market outlook of this kind are boundless.Aspect non-agricultural purposes, because this kind has good prevention effect to locust, by the control medication of Food and Argriculture OrganizationFAO (FAO) recommendation as the desert area migratory locusts.From the experiment situation of some formulations, fluorine worm nitrile is also very high to the activity of sanitary insect pests such as cockroach, fly, mosquito, flea and termite, so also have bigger market potential aspect the health medication.
N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline are one of important intermediate of synthetic fluorine worm nitrile, and the synthetic of fluorine worm nitrile generally is with 3, and 4-two chlorobenzotrifluorides are starting raw material, finally generate by reactions such as amination, chlorination, pyrazoles rings.N, general conventional synthesizing of N-dimethyl-2-chloro-4-5-trifluoromethylaniline is with 3,4-two chlorobenzotrifluorides and N, and the dinethylformamide reaction generates, but there are great hidden danger factor in this reaction process pressure big (4.5Mpa), temperature height (205～215 ℃).And N, dinethylformamide is easily suction, easily the ignition hazard chemical, its consumption is also bigger, the reaction later stage will consume a large amount of steam unnecessary N, and dinethylformamide steams, and causes the wasting of resources, and the N that steams, dinethylformamide is being carried aminate secretly and is being spread in the air, and people's skin is had very big stimulation, causes a lot of personnel of this workshop section allergic serious, and the cycle of curing is very long, and employee's psychological burden is very heavy! Its target product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline yield is also lower, has only about 80%.
Summary of the invention
In order to solve a difficult problem of the prior art: pressure is big, temperature is high, have injury and yield low etc. to human body skin, and the present invention proposes a kind of new production method, reduces the pressure and temperature in the production process widely, and improves the yield of product.
The present invention is achieved by the following technical solutions:
A kind of preparation N, the method of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, add raw material 3,4-two chlorobenzotrifluorides and compd B, stirring is warmed up to and allows its reaction under the certain reaction temperature and pressure, reaction finish the back layering wash product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline, described compd B is dimethylamine and N,N-dimethylacetamide.
A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline, described temperature of reaction is 100 ℃-200 ℃, pressure is 1-2.5mpa.
A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline, described temperature of reaction is 120 ℃, pressure is 2.0mpa.
A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline, described product N, the yield of N-dimethyl 2 chloro-4-5-trifluoromethylanilines reaches more than 90%.
A kind of preparation N, the method for N-dimethyl-2-chloro-4-5-trifluoromethylaniline, described raw material 3,4-two chlorobenzotrifluorides mix when stirring open cycle water to the still processing of lowering the temperature with dimethylamine.
The dimethylamine molecular formula is C
2H
7N, molecular weight is less to have only 45.09, and is colourless inflammable gas or liquid, is mainly used in the production dimethyl formamide, and is used for agricultural chemicals, medicine, rubber ingredients, hydramine etc.
The N,N-dimethylacetamide molecular formula is C4H9NO, and structural formula is as follows:
Main as the raw material of synthon and the good polar solvent of organic synthesis
Catalyzer is solid sodium hydroxide commonly used, sodium-chlor and so on, and market is all on sale.
A kind of preparation N provided by the invention, the method of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, be with dimethylamine, N, the N-N,N-DIMETHYLACETAMIDE replaces N, dinethylformamide and 3,4-two chlorobenzotrifluoride after chemical reactions, pressure is less in this reaction process, temperature is not high yet, and the yield of important product has improved greatly.Through lab scale digital proof pressure of the present invention is about 1-2.5mpa, and optimum pressure is 2.0mpa, and temperature is 100 ℃-200 ℃, and optimum temps is 120 ± 3 ℃, and the ultimate yield of product reaches about 90%.
3,4-two chlorobenzotrifluorides and dimethylamine, N,N-dimethylacetamide add by 1: 4 mol ratio, and add appropriate amount of catalysts, want the ON cycle cooling water circulation before mixing, and lose magnetic with antimagnetic coupling apparatus because of temperature drift.Vacuumize and open steam and heat up, reaching pressure is about 2.0mpa, when temperature is 120 ± 3 ℃, keep reaction after 30-40 hour standing demix get product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline.
After the cooling of the waste water after the layering, add sheet alkali, be reduced into dimethylamine with the reaction of by product chloro dimethylamine,
Dimethylamine is recycled, complete because of the alkali reaction of chloro dimethylamine and adding, the injury that can not reproduce paired human body skin is to environment close friend relatively again.
(CH
3)
2NH+HCL→(CH
3)
2NH
2CL
(CH
3)
2NH
2CL+NaOH→(CH
3)
2NH+NaOH+H
2O
3,4-two chlorobenzotrifluorides and N,N-dimethylacetamide add by 1: 2 mol ratio, and add appropriate amount of catalysts, want the ON cycle cooling water circulation before mixing, and lose magnetic with antimagnetic coupling apparatus because of temperature drift.Vacuumize and open steam and heat up, reaching pressure is about 2.0mpa, when temperature is 120 ± 3 ℃, keep reaction after 30-40 hour standing demix get product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline.
3, the reaction process of 4-two chlorobenzotrifluorides and N,N-dimethylacetamide and front dimethylamine the same is this no longer auspicious stating.
Dimethylamine of the present invention and prior art N, dinethylformamide compares, and testing data sees the following form:
Table 1, N, dinethylformamide and 3,4-two chlorobenzotrifluorides generate N, the testing data of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, its product N, the yield of N-dimethyl-2-chloro-4-5-trifluoromethylaniline is 80.0-81.8%, average yield is 81.14%.
Table 2, dimethylamine and 3,4-two chlorobenzotrifluorides generate N, the testing data of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, product N, the yield of N-dimethyl-2-chloro-4-5-trifluoromethylaniline on average reaches 90.72%, is much higher than N, and dinethylformamide participates in the product yield of reaction.
Embodiment
Embodiment 1:
With 750KG3,4-two chlorobenzotrifluorides and catalyzer 13.5KG add in the autoclave, add the 840L dimethylamine again, vacuumize stirring, and the steam intensification, making the autoclave internal pressure is 2.0mpa, standing demix after being incubated 30 hours when temperature is 117 ℃, again through the washing, distill product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline 704KG, productive rate is 90.7%.
Embodiment 2
With 750KG3,4-two chlorobenzotrifluorides and catalyzer 13.5KG add in the autoclave, add 151LN again, the N-N,N-DIMETHYLACETAMIDE vacuumizes stirring, and steam heats up, making the autoclave internal pressure is 2.1mpa, when temperature is 123 ℃ the insulation 30 hours after standing demix, again through the washing, distill product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline 778KG, productive rate is 92.6%.
Claims (5)
1. one kind prepares N, the method of N-dimethyl-2-chloro-4-5-trifluoromethylaniline, add raw material 3,4-two chlorobenzotrifluorides and compd B, stirring is warmed up to and allows its reaction under the certain reaction temperature and pressure, reaction finish the back layering wash product N, N-dimethyl-2-chloro-4-5-trifluoromethylaniline, it is characterized in that described compd B is dimethylamine and N,N-dimethylacetamide.
2. preparation method according to claim 1 is characterized in that, described temperature of reaction is 100 ℃～200 ℃, and pressure is 1～2.5mpa.
3. preparation method according to claim 1 and 2 is characterized in that, temperature of reaction is 120 ℃, and pressure is 2.0mpa.
4. preparation method according to claim 1 is characterized in that described product N, and the yield of N-dimethyl-2-chloro-4-5-trifluoromethylaniline reaches more than 90%.
5, preparation method according to claim 1 is characterized in that described raw material 3, and 4-two chlorobenzotrifluorides mix when stirring open cycle water to the still processing of lowering the temperature with dimethylamine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108863810A (en) * | 2018-07-25 | 2018-11-23 | 安徽华星化工有限公司 | A kind of arylamine recovery process in Fipronil production waste liquid |
-
2009
- 2009-06-26 CN CN200910117172A patent/CN101613288A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108863810A (en) * | 2018-07-25 | 2018-11-23 | 安徽华星化工有限公司 | A kind of arylamine recovery process in Fipronil production waste liquid |
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