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Method for converting benzene into benzotrifluoride through heterogeneous catalysis

A technology of trifluorotoluene and catalytic benzene, which is applied in chemical instruments and methods, organic chemistry, halogenated hydrocarbon preparation, etc., can solve problems such as high cost and high pollution, achieve cost reduction, simple reaction process, and is conducive to large-scale the effect of industrial production

Active Publication Date: 2016-05-18
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of organic synthesis method that heterogeneous catalytic benzene is converted into trifluorotoluene, and its system is simple, and reaction condition is gentle, and cost is low and can prepare trifluorotoluene in a large amount, has solved the present industrial preparation trifluorotoluene The problems of high pollution and high cost

Method used

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  • Method for converting benzene into benzotrifluoride through heterogeneous catalysis
  • Method for converting benzene into benzotrifluoride through heterogeneous catalysis
  • Method for converting benzene into benzotrifluoride through heterogeneous catalysis

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Effect test

Embodiment 1

[0024] (1) Weigh 0.2 mmol of manganese sulfate monohydrate as catalyst, 0.5 mmol of sodium trifluoromethyl sulfinate as trifluoromethyl source, mix in the reactor, add 1 mL of acetonitrile as solvent and 0.5 mL of reactant benzene;

[0025] (2) Put the reactor into an ultrasonic cleaning machine for 50KHz ultrasonic treatment for 30s, connect the reactor to an air balloon, and place it in a heat-collecting constant temperature magnetic stirrer at 50°C for 24 hours;

[0026] (3) Centrifuge after the reaction is complete, and detect the supernatant with a GC-MS5977A mass spectrometer. The chromatographic column used is HP-5MS (5% polymethylsilane fixed solution, the specification is 30m×0.32mm×0.25μm), and the quantitative analysis is performed by the FID detector of GCAgilent7890B chromatograph. The GC-MS spectrogram of the supernatant obtained by the reaction (see figure 1 -A), after matching ( figure 1 -B) After that, the peak with a retention time of 2.5min (a) is triflu...

Embodiment 2

[0028] (1) Weigh 0.2 mmol of manganese sulfate monohydrate as catalyst, 0.5 mmol of sodium trifluoromethyl sulfinate as trifluoromethyl source, mix in the reactor, add 1 mL of acetonitrile as solvent and 0.5 mL of reactant benzene;

[0029] (2) Put the reactor into an ultrasonic cleaning machine for 70KHz ultrasonic treatment for 30s, connect the reactor to an air balloon, and place it in a heat-collecting constant temperature magnetic stirrer at 50°C for 24 hours;

[0030] (3) Centrifuge after the reaction is complete, and detect the supernatant with a GC-MS5977A mass spectrometer;

[0031] (4) Take the precipitate after centrifugation in step (3), wash it with acetonitrile for 3 times, put it in a vacuum oven and dry it at 60°C, and then conduct a recycling experiment on the dried manganese sulfate monohydrate, that is, repeat the steps 7 times (1 )-(4) operation.

[0032] The results show that the mass spectrum and nuclear magnetic resonance spectra of the supernatant obta...

Embodiment 3

[0034] (1) Weigh 0.2 mmol of manganese sulfate monohydrate as catalyst, 0.5 mmol of sodium trifluoromethyl sulfinate as trifluoromethyl source, mix in the reactor, add 1 mL of acetonitrile as solvent and 0.5 mL of reactant benzene;

[0035] (2) Put the reactor into an ultrasonic cleaning machine for 60KHz ultrasonic treatment for 30s, connect the reactor to an air balloon, and place it in a heat-collecting constant temperature magnetic stirrer at 50°C for 6, 12, 18, and 24 hours respectively.

[0036] By the change relationship figure of different reaction times and trifluorotoluene productive rate (see Figure 4 ) It can be seen that with the prolongation of the reaction time, the yield of benzotrifluoride increases.

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Abstract

The invention discloses a method for converting benzene into benzotrifluoride through heterogeneous catalysis. Benzene is catalyzed to generate benzotrifluoride at lower temperature and normal pressure with manganese sulfate monohydrate as a catalyst, sodium trifluoromethanesulfinate as a trifluoromethyl source and acetonitrile as solvent. The raw materials are low in price and easy to obtain, conditions are mild, environment pollution is low, products are easy to separate, hydrogen fluoride, sulfur tetrafluoride and other highly-corrosive and highly-toxic fluorinated reagents used in current industrial trifluoromethylation reactions are avoided, large-scale industrial production is facilitated, and the method can be further used for trifluoromethyl modification of organic compounds with biological activity and medicine activity and has good application prospects and economic benefits.

Description

technical field [0001] The invention belongs to the technical field of thermocatalytic organic synthesis, and in particular relates to a method for converting benzene into trifluorotoluene through heterogeneous catalysis. Background technique [0002] Trifluoromethyl (·CF 3 ) has strong electric absorption and lipophilicity, and its C-F bond is very stable, and its introduction into organic compounds can significantly change the dipole moment, polarity, lipophilicity and chemical and metabolic stability of the compound. Aromatic compounds containing trifluoromethyl groups have been widely used in the fields of medicine, pesticides and organic materials, such as anticancer drug Sorafenib, antidepressant drug fluoxetine, new plant broad-spectrum fungicide trifloxystrobin, liquid crystal display Typical screen materials such as ZLI-2857 contain trifluoromethyl. Therefore, the development of novel and efficient organofluorine chemical reactions, especially the trifluoromethyla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C22/06C07C17/32
CPCC07C17/32C07C22/06
Inventor 员汝胜邵鸿鸽王乐乐邱文朝
Owner FUZHOU UNIV
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