CN103497111B - A kind of synthetic method of 2,3,4-trifluoromethyl aniline - Google Patents
A kind of synthetic method of 2,3,4-trifluoromethyl aniline Download PDFInfo
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- CN103497111B CN103497111B CN201310404056.9A CN201310404056A CN103497111B CN 103497111 B CN103497111 B CN 103497111B CN 201310404056 A CN201310404056 A CN 201310404056A CN 103497111 B CN103497111 B CN 103497111B
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Abstract
The invention discloses a kind of synthetic method of 2,3,4-trifluoromethyl aniline, with benzene lead to fluorine gas fluoridize prepare penta fluoro benzene tankage tetra fluoro benzene for starting raw material, under solvent and liquefied ammonia existence condition, high-pressure synthesis 2,3,4-trifluoromethyl aniline, reaction treatment obtains target product.Present invention process is simple, and easy to operate, product yield reaches 91%.
Description
Technical field
The present invention relates to a kind of synthetic method of 2,3,4-trifluoromethyl aniline.
Background technology
2,3,4-trifluoromethyl aniline belongs to aromatic series fluorochemicals, is a kind of important chemical industry, medicine intermediate.At chemical industry, Material Field, with 2,3,4-trifluoromethyl aniline for raw material, can synthesize multiple 2,3,4-trifluoro diphenylacetylene liquid crystal compounds, therefore 2,3,4-trifluoromethyl aniline becomes the basic material of development of new liquid crystal material.At pesticide field; 2; the intermediate 2,3 of 3,4-trifluoromethyl aniline; 4-trifluoronitrobenzene is well applied; by the N-acyl group-N-(2 of its derivative synthesis, 3,4-trifluoro-benzene amido) propionic acid ester compound; wheat hypochnus and melon gray mold are reached to the prevention effect of more than 70%, have the drug effect of individual compound suitable with derosal.On medicine industry, 2,3,4-trifluoromethyl aniline can be used for synthesis Comprecin as lomefloxacin, norfloxicin, levofloxacin, Ofloxacine USP 23 etc.Due to this kind of medicine there is hypotoxicity, duration of efficacy is long, side effect is little, make its application widely.
2,3,4-trifluoromethyl aniline is the one of aromatic series fluoride-containing PMMA, and it uses wide market.The main physico-chemical property of product and quality standard: molecular formula: C
6h
4f
3n; Molecular weight: 147.10; Quality standard: proterties: this product is light yellow transparent liquid; Boiling point 92 DEG C (6.4KPa); Content:>=99.5%.
The existing production technique scheme of 2,3,4-trifluoromethyl aniline adopts orthodichlorobenzene to be the operational path of starting raw material, by nitrated, fluoridize, chlorination etc. is repeatedly obtained by reacting 2,3,4-trifluoromethyl anilines.Product main raw material: orthodichlorobenzene, nitric acid, sulfuric acid, 2,3-dichloronitrobenzenes, Potassium monofluoride, tetramethyl ammonium chloride, chlorine, liquid caustic soda, ethanol, platinum carbon, hydrogen etc.Main production flow process: the operation such as nitration reaction, fluoridation, rectifying, chlorination reaction, nitration reaction, fluoridation, hydrogenating reduction.Principal reaction equation is as follows:
。
Summary of the invention
The object of the invention is to solve defect of the prior art, provide a kind of technique simple, easy to operate, be applicable to the synthesis production method of one 2,3, the 4-trifluoromethyl aniline of suitability for industrialized production.
For solving the problems of the technologies described above, the present invention adopts following technical scheme route to realize:
1 is added, 2,3 in autoclave, 4-tetra fluoro benzene and solvent and catalyzer, according to 1,2,3,4-tetra fluoro benzene: solvent: catalyzer is that the mol ratio of 1:2-20:0.8-20:0.001-1 adds, and is cooled to less than 15 DEG C, be filled with nitrogen replacement and go out air, be filled with the liquefied ammonia of metering after emptying again, being raised to temperature is 180-250 DEG C, and reaction in reaction times 36-72 hour terminates rear stirring borehole cooling to 20 DEG C, add liquid caustic soda after emptying and stir layering, aftertreatment obtains target product.
Reaction formula is:
Beneficial effect of the present invention: present invention process is simple, safety is easy to operate, and product yield is high.
Embodiment
Below in conjunction with specific embodiment, the present invention is elaborated.
embodiment 1
1500 grams 1 is added in autoclave, 2,3,4-tetra fluoro benzene and 3800 grams of propylene glycol, 20 grams of copper powders, be cooled to less than 15 DEG C, be filled with nitrogen replacement and go out air, be filled with the liquefied ammonia of the metering of liquid ammonia of 180 grams after emptying again, being raised to temperature is 220 DEG C, and the reaction of 48 hours reaction times terminates rear stirring borehole cooling to 20 DEG C, add liquid caustic soda after emptying and stir layering, oil reservoir underpressure distillation obtains target product.
Above-described embodiment is only in order to illustrate technical scheme of the present invention but not to limit design of the present invention and protection domain; those of ordinary skill of the present invention is modified to technical scheme of the present invention or equivalent replacement; and not departing from aim and the scope of technical scheme, it all should be encompassed in right of the present invention.
Claims (3)
1. one kind 2, the synthetic method of 3,4 trifluoromethyl anilines, it is characterized in that: in autoclave, add 1,2,3,4 tetra fluoro benzenes and solvent and catalyzer, be cooled to less than 15 DEG C, be filled with nitrogen replacement and go out air, after emptying, be filled with the liquid nitrogen of metering again, reaction terminates rear stirring borehole cooling to 20 DEG C, add liquid caustic soda after emptying and stir layering, aftertreatment obtains target product, and reaction formula is:
，
Above-mentioned solvent is propylene glycol; Above-mentioned catalyzer is copper powder.
2. the synthetic method of a kind of 2,3,4-trifluoromethyl anilines according to claim 1, it is characterized in that: described temperature of reaction is 180-250 DEG C, the reaction times is 36-72 hour.
3. the synthetic method of a kind of 2,3,4-trifluoromethyl anilines according to claim 1, is characterized in that: the mol ratio of described 1,2,3,4-tetra fluoro benzene, solvent, liquefied ammonia and catalyzer is 1 ︰ 2-20 ︰ 0.8-20 ︰ 0.001-1.
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| CN201310404056.9A CN103497111B (en) | 2013-09-09 | 2013-09-09 | A kind of synthetic method of 2,3,4-trifluoromethyl aniline |
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| CN201310404056.9A CN103497111B (en) | 2013-09-09 | 2013-09-09 | A kind of synthetic method of 2,3,4-trifluoromethyl aniline |
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| Publication Number | Publication Date |
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| CN103497111A CN103497111A (en) | 2014-01-08 |
| CN103497111B true CN103497111B (en) | 2015-10-21 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05255206A (en) * | 1992-03-12 | 1993-10-05 | Toray Ind Inc | Production of fluoroaniline |
| CN1861554A (en) * | 2005-05-09 | 2006-11-15 | 临海市永太化工有限公司 | Production tech, of 3,4,5 trifluorophenol |
| CN101245020A (en) * | 2008-03-11 | 2008-08-20 | 浙江永太科技股份有限公司 | Process for synthesizing 2,3-difluoroaniline |
| CN101811973A (en) * | 2010-04-23 | 2010-08-25 | 浙江工业大学 | Method for synthesizing halogen aromatic amines by high-selectivity liquid phase hydrogenation under the condition of no solvent |
-
2013
- 2013-09-09 CN CN201310404056.9A patent/CN103497111B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05255206A (en) * | 1992-03-12 | 1993-10-05 | Toray Ind Inc | Production of fluoroaniline |
| CN1861554A (en) * | 2005-05-09 | 2006-11-15 | 临海市永太化工有限公司 | Production tech, of 3,4,5 trifluorophenol |
| CN101245020A (en) * | 2008-03-11 | 2008-08-20 | 浙江永太科技股份有限公司 | Process for synthesizing 2,3-difluoroaniline |
| CN101811973A (en) * | 2010-04-23 | 2010-08-25 | 浙江工业大学 | Method for synthesizing halogen aromatic amines by high-selectivity liquid phase hydrogenation under the condition of no solvent |
Non-Patent Citations (1)
| Title |
|---|
| 2,3,4-三氟苯胺的合成研究;曾台彪等;《精细与专用化学品》;20070206;第15卷;第18页倒数第1-2行，第19页第1-10行 * |
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Effective date of registration: 20171227 Address after: 065402 Langfang city of Hebei province Xianghe County ZTE Backstreet No. 11 Tin Yuet District Building 3 room 2201 unit 2 Patentee after: Jiang Shulin Address before: The Yangtze River town of Rugao city of Jiangsu province in 226500 in Nantong city (Rugao port) Yuejiang Road No. 28 Patentee before: Jiangsu Defeng Pharmaceutical Co., Ltd. |
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