Method for synthesizing 4-fluoro-2-nitroaniline by micro-channel reactor

A technology of microchannel reactor and channel reactor, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds, etc., can solve strong irritation and corrosion, yield is only 54%, increase production cost, etc. problem, achieve the effect of promoting the reaction yield, shortening the reaction cycle, and keeping a small amount

Pending Publication Date: 2020-04-17
成都艾必克医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN109553534A has reported a method utilizing 1,4-difluorobenzene to first nitrate and then ammonolyze to synthesize the target product, wherein ammonia gas is highly irritating and corrosive, and can easily cause damage to the mucous membranes of the skin, eyes, and respiratory organs. Burns, excessive inhalation, can cause lung swelling, and 1,4-difluorobenzene is a relatively expensive reagent, industrial production will significantly increase production costs
Literature 2 (Leyva S, Castanedo V, Leyva E. Synthesis of novel fluorobenzofuroxans by oxidation ofanilines and thermal cycling of arylazides[J]. Journal of fluorinechemistry, 2003, 121(2): 171-175.) (Sokoro Ley Watt, Victor Castanedo, Eliza Leiva. Synthesis of novel fluorobenzofuran compounds by oxidation of anilines and thermal cyclization of azides[J]. J FLUORINECHEM, 2003, 121( 2): 171-175.) Using p-fluoroaniline to prepare 4-fluoro-2-nitroaniline through nitration and hydrolysis, but the synthesis method is complicated in operation, consumes a lot of solvent, and the yield is only 54%

Method used

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  • Method for synthesizing 4-fluoro-2-nitroaniline by micro-channel reactor

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Embodiment 1

[0031] A method for synthesizing 4-fluoro-2-nitroaniline in a microchannel reactor, the steps are:

[0032] a. Equipped with reactor and raw materials:

[0033] Equipped with Corning high-throughput continuous flow microchannel reactor (direct-flow microchannel preheating module + T-type microchannel enhanced mass transfer mixing module) as the reactor, the number of mixed reaction modules is determined according to the flow rate and reaction residence time, and the heat exchange medium For heat transfer oil;

[0034] The Corning high-throughput continuous flow microchannel reactor contains a direct-flow preheating module (that is, a direct-flow microchannel preheating module), a mass transfer-enhanced mixing module (that is, a T-shaped microchannel enhanced mass-transfer mixing module), an outlet ;

[0035] Be that the acetic acid-acetic anhydride solution of p-fluoroacetanilide of 20% by mass percentage concentration, sherwood oil and the nitric acid aqueous solution of 68...

Embodiment 2

[0041] A method for synthesizing 4-fluoro-2-nitroaniline in a microchannel reactor, the steps are:

[0042] a. Equipped with reactor and raw materials:

[0043] Equipped with Corning high-throughput continuous flow microchannel reactor (direct-flow microchannel preheating module + spherical microchannel enhanced mass transfer mixing module) as the reactor, the number of mixed reaction modules is determined according to the flow rate and reaction residence time, and the heat exchange medium For heat transfer oil;

[0044] The Corning high-throughput continuous flow microchannel reactor contains a direct-flow preheating module (ie, a direct-flow microchannel preheating module), a mass transfer-enhanced mixing module (ie, a spherical microchannel-enhanced mass-transfer mixing module), an outlet ;

[0045] Be that the acetic acid-acetic anhydride solution of p-fluoroacetanilide of 30% by mass percentage concentration, sherwood oil and the nitric acid aqueous solution of 68% by m...

Embodiment 3

[0051] A method for synthesizing 4-fluoro-2-nitroaniline in a microchannel reactor, the steps are:

[0052] a. Equipped with reactor and raw materials:

[0053] Equipped with Corning high-throughput continuous flow microchannel reactor (direct-flow microchannel preheating module + heart-shaped microchannel enhanced mass transfer mixing module) as the reactor, the number of mixed reaction modules is determined according to the flow rate and reaction residence time, and the heat exchange medium For heat transfer oil;

[0054] The Corning high-throughput continuous flow microchannel reactor contains a direct-flow preheating module (ie, a direct-flow microchannel preheating module), a mass transfer-enhanced mixing module (ie, a heart-shaped microchannel-enhanced mass-transfer mixing module), an outlet ;

[0055] Be that the acetic acid-acetic anhydride solution of p-fluoroacetanilide of 35% by mass percentage concentration, sherwood oil and the nitric acid aqueous solution of 68...

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Abstract

The invention discloses a method for synthesizing 4-fluoro-2-nitroaniline through a micro-channel reactor. The method is characterized by comprising the steps; adopting a Corning high-flux continuousflow micro-channel reactor, with the molar ratio of p-fluoroacetanilide to nitric acid being 1:(1.0-1.5) as a benchmark, respectively setting the flow rates of an acetic acid-acetic anhydride solutionof 20%-40% of p-fluoroacetanilide and 68% of nitric acid to be 40.0-100.0 mL/min and 4.0-30.0 mL/min, and preheating; carrying out a reaction for 50-200 s at a temperature of 30 DEG C-70 DEG C; and dissolving the product in water, carrying out hydrolysis reaction at the temperature of 90 DEG C-100 DEG C for 2-4 h, stirring in ice water at the temperature of 0 DEG C-5 DEG C for 0.5 h, filtering, washing a filter cake until the filter cake is weakly acidic or neutral, adding petroleum ether, mixing, and drying to obtain the orange solid 4-fluoro-2-nitroaniline with the yield of 83-94%. The method has the advantages of short time, high efficiency, few byproducts and safe, stable and controllable reaction process.

Description

technical field [0001] The invention belongs to the preparation of organic compounds, and relates to a method for synthesizing 4-fluoro-2-nitroaniline with a microchannel reactor. The 4-fluoro-2-nitroaniline prepared by the invention is suitable for use as a pharmaceutical and chemical intermediate. Background technique [0002] 4-Fluoro-2-nitroaniline is an important pharmaceutical and chemical intermediate, and the market demand is also increasing every year. And its synthesis method is also divided into different types due to the different raw materials used. At present, the synthesis method of 4-fluoro-2-nitroaniline is mainly based on nitration. But present 4-fluoro-2-nitroaniline synthetic technology basically all exists process operation complexity, and reaction time is long, and yield is low etc. problem, and carry out nitration reaction in conventional tank reactor and all exists process is difficult to control, and reaction heat Concentration can easily lead to a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/62C07C211/52
CPCC07C209/62C07C211/52
Inventor 白林奎李杰王新龙
Owner 成都艾必克医药科技有限公司
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