Method for preparing biphenyl derivative by using microchannel continuous flow reactor

A microchannel and reactor technology, applied in chemical instruments and methods, chemical/physical/physical chemical reactors, preparation of organic compounds, etc., can solve the problems of runaway reaction, slow reaction or even stop, low heat transfer efficiency, etc. , to achieve the effect of reducing the reaction time, shortening the diffusion distance, and increasing the reaction rate

Inactive Publication Date: 2019-09-10
SHANDONG GUANSEN POLYMER MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Low heat transfer efficiency will lead to high local temperature, and uneven mass transfer will lead to high local concentration of the material, which will easily lead to rapid temperature rise and lead to out-of-control reaction, eventually causing dangers such as overflow and explosion.
And as the reaction proceeds, the concentration of the reaction substrate will gradually decrease, and the reaction will gradually slow down or even stop. Even if the reaction ti...

Method used

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  • Method for preparing biphenyl derivative by using microchannel continuous flow reactor
  • Method for preparing biphenyl derivative by using microchannel continuous flow reactor

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0069] Experimental Example 1 Preparation of Grignard Reagent

[0070] Preparation of Grignard Reagent for 4-Chloro-o-xylene : According to the standard operation of Grignard reagent preparation, a small amount of 4-chloro-o-xylene and solvent are added dropwise to the activated magnesium chips under nitrogen gas, and a small amount of iodine is added as an initiator and heated to initiate. After initiation, the remaining 4-chloro-o-xylene and solvent were added dropwise and kept in a reflux state, and continued to reflux for 2 hours after the dropwise addition was completed. Calibrate format reagent, adjust the concentration to 2.5mol / L. record as 1 # format reagents.

[0071] Preparation of Grignard reagent for p-chlorotoluene : According to the standard operation of the Grignard reagent preparation, a small amount of p-chlorotoluene and solvent are added dropwise to the activated magnesium chips under nitrogen conditions, and a small amount of iodine is added as an ...

Embodiment 1

[0074] Example 1 Preparation of 3,3',4,4'-tetramethylbiphenyl

[0075] Typically, with figure 1 The process schematic diagram shown in is a route to prepare biphenyl compounds. The continuous flow reactor is a microchannel continuous flow reactor (Corning SiC-G1), and the internal structure of the microchannel continuous flow reactor is a heart-shaped channel. The diameter of the microchannel is 100 μm.

[0076] Preparation method 1

[0077] Take 10mol of calibrated 1 # The THF solution of Grignard reagent is used as material A solution, take 10mol of 4-chloro-o-xylene, 30mmol of NiCl 2 , PPh of 60mmol 3 Mix and heat to 80°C, and heat for 30 minutes, as material B solution;

[0078] Then through the metering pump, A and B are respectively entered into the preheating module of the continuous flow reactor according to the molar ratio of 1:1, and the temperature of the preheating module is controlled to 120°C;

[0079]After passing through the preheating module, solution...

Embodiment 2

[0083] Example 2 Preparation of 4,4'-dimethylbiphenyl

[0084] The preparation process is as figure 1 The process shown in Fig.

[0085] Take 10mol of calibrated 2 # The THF solution of Grignard reagent is used as material A solution, take 10mol of p-chlorotoluene, 20mmol of NiCl 2 , 40mmol of PPh 3 Mix and heat to 80°C, and heat for 30 minutes, as material B solution;

[0086] Then through the metering pump, A and B are respectively entered into the continuous flow reactor preheating module according to the molar ratio of 1:1, and the temperature of the preheating module is controlled to 140 °C; the continuous flow reactor is a microchannel continuous flow reactor (Corning SiC-G1) , the internal structure of the microchannel continuous flow reactor is a heart-shaped channel;

[0087] After passing through the preheating module, solutions A and B enter the mixed reaction module, the reaction temperature is set at 140°C (the first 80% module) + 175°C (the last 20% module),...

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Abstract

The invention belongs to the field of organic fine synthesis, and relates to a method for preparing a biphenyl derivative by using a microchannel continuous flow reactor. The method comprises the steps: adopting the microchannel continuous flow reactor, feeding a grignard reagent, halogenated benzene, a solvent and a catalyst in a slurry feeding mode, and performing a reaction at 50-200 DEG C anda pressure of 0.1-2.0 MPa so as to obtain the biphenyl derivative. The preparation process of the biphenyl derivative has the characteristic of continuous feeding, the reaction space is a channel witha depth of 100 [mu]m-10 mm, and the reaction temperature and pressure can be set flexibly when the reaction is compared with conventional batch reactions, the reaction time is shortened from severalhours to several tens of seconds, a high reaction yield, few side reactions and a good mass transfer effect are achieved, and the safety problem brought by fierce heat release of reactions and other problems are solved; and the method can be applied to large-scale production of biphenyl derivatives, and provides a green economical and environment-friendly industrial preparation route for the compounds.

Description

technical field [0001] The invention relates to the field of synthesis of fine organic compounds, in particular to a method for preparing biphenyl derivatives using a microchannel continuous flow reactor. Background technique [0002] Biphenyl compounds play an important role in modern materials and chemical industry. For example, they can be used as monomers to prepare high-performance polyimides and liquid crystal polymer materials. They can be used as important ligands for asymmetric catalysis, and as intermediates for drug molecules. Metal-catalyzed carbon-carbon bond coupling is the most important way to prepare biphenyl compounds. So far, many coupling methods have been developed for carbon-carbon bond structures: Suzuki coupling, Kumada coupling, Ullmann coupling, Nigishi coupling, Stille coupling, Hiyama coupling, etc. However, this type of reaction usually requires the preparation of expensive metal-organic compound precursors for coupling, the use of noble metal ...

Claims

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Application Information

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IPC IPC(8): C07C1/32C07C15/14C07C41/30C07C43/205B01J19/00B01J8/08
CPCB01J8/08B01J19/0006B01J19/0013B01J19/0093B01J2219/00074B01J2219/00162B01J2219/00862B01J2219/00873B01J2219/00889C07C1/326C07C41/30C07C15/14C07C43/2055
Inventor 李晓斐巴广芝刘顺一李有强魏来
Owner SHANDONG GUANSEN POLYMER MATERIAL TECH CO LTD
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