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Method for rapidly preparing 1-naphthylamine based on microchannel continuous flow technology

A technology of microchannel and microchannel reactor, which is applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of limited feasibility of industrial amplification, achieve the suppression of amplification effect and ensure product quality , the effect of improving production efficiency

Pending Publication Date: 2022-07-29
BIRDO (SHANGHAI) PHARM R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the synthesis method provided by this invention patent is limited to laboratory research and development, and the feasibility of industrial scale-up is not large.

Method used

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  • Method for rapidly preparing 1-naphthylamine based on microchannel continuous flow technology
  • Method for rapidly preparing 1-naphthylamine based on microchannel continuous flow technology

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: as figure 1As shown, the trifluoromethanesulfonic acid solution of 1-naphthoic acid with a concentration of 1.1 mol / L is loaded into the storage tank 1, and the chloroform solution of azidotrimethylsilane with a concentration of 0.6 mol / L is loaded into the storage tank In 2, the methanol is loaded into the storage tank 3, and the trifluoromethanesulfonic acid solution of 1-naphthoic acid and the chloroform solution of azidotrimethylsilane are pumped into the first metering pump 4 and the second metering pump 5 respectively. The Schmidt amination reaction is carried out in a microchannel reactor 7, the molar equivalent ratio of 1-naphthoic acid and azidotrimethylsilane is 1:1.2, and the reaction temperature of the first microchannel reactor is the first constant temperature bath 11 Controlled 100°C, the set pressure of the back pressure valve is 2.0MPa, the design residence time of the first microchannel reactor is 15min, and the actual residence time is 12mi...

Embodiment 2

[0036] Example 2: The specific reaction process was similar to that of Example 1, and post-processing processes such as column chromatography were not performed. The set pressure of the back pressure valve was changed to 2.3MPa; the design residence time of the first microchannel reactor was changed to 10min; the design residence time of the second microchannel reactor was changed to 3.3min, and the purity of the product in the reaction solution was 81.0 %.

Embodiment 3

[0037] Example 3: The specific reaction process was similar to that of Example 1, and post-processing processes such as column chromatography were not performed. Change the temperature of the first constant temperature bath for Schmidt amination reaction to 90°C; change the design residence time of the first microchannel reactor to 5min; change the design residence time of the second microchannel reactor to 3min to obtain the reaction The purity of the product in the liquid was 72.3%.

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Abstract

The invention discloses a method for rapidly preparing 1-naphthylamine based on a microchannel continuous flow technology. The method comprises the following steps: taking 1-naphthoic acid and azidotrimethylsilane as raw materials, and carrying out Schmidt amination reaction in a microreactor to generate the 1-naphthylamine. The method comprises the following steps: pumping a 1-naphthoic acid solution and an azidotrimethylsilane solution into a first micro-channel reactor, and reacting at a certain temperature for amination; and pumping a quenching agent into the reaction system, mixing the quenching agent with the reaction liquid from the first micro-channel reactor in the second micro-channel reactor, and carrying out reaction at a certain temperature to quench the reaction liquid so as to generate the stable product 1-naphthylamine. By coupling the micro-channel continuous flow technology with intrinsic safety, the safe and continuous operation of the amination process is realized, the danger level of Schmidt reaction in which azide compounds participate is greatly reduced, the production efficiency is remarkably improved, and the production cost is reduced. And a high-yield naphthylamine product is obtained under safe, controllable, environment-friendly, efficient and continuous conditions in the reaction.

Description

technical field [0001] The invention belongs to the field of organic synthesis of pharmaceutical intermediates, and relates to a method for synthesizing 1-naphthylamine, in particular to a method for rapidly preparing 1-naphthylamine by using a microchannel continuous flow technology. Background technique [0002] 1-Naphthylamine, CAS No. 134-32-7, as a naphthalene derivative, is an important organic intermediate. There are many kinds of downstream products, such as: 1,2-diaminonaphthalene, 1-phenylnaphthalene, 2-nitro-1-naphthylamine, 1-amino-4-nitronaphthalene and nitronaphthol compounds, all It is a basic organic compound with extremely high added value, and has a wide range of applications in molecular medicine, fine chemicals, functional materials and other fields. [0003] In [Journal of Molecular Catalysis A: Chemical, 2014, vol.383-384, p.17-22], Parisa Fakhri et al. introduced RGO / Cu NPs using 1-naphthaleneboronic acid as the substrate and ammonia water as the ammo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/58B01J8/00
CPCC07C209/00B01J19/0093C07C211/58
Inventor 王雷张鹏郑子圣张奇张宇超张龙
Owner BIRDO (SHANGHAI) PHARM R&D CO LTD
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