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Preparation method of perfluorinated nitrile compound

A compound, the technology of fluoronitrile, which is applied in the field of synthesis of perfluoronitrile compounds, can solve the problems of complicated steps, complicated operation and high production cost

Inactive Publication Date: 2020-10-30
ELECTRIC POWER RES INST OF GUANGDONG POWER GRID
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process requires cyanogen chloride as a cyanide reagent, which is highly toxic and complicated to operate.
[0005] The traditional method of synthesizing perfluoronitriles not only has complicated steps, low yield, but also high production cost

Method used

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  • Preparation method of perfluorinated nitrile compound
  • Preparation method of perfluorinated nitrile compound
  • Preparation method of perfluorinated nitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Please refer to figure 1 with figure 2 , the embodiment of this application will follow figure 1 The synthetic route shown prepares perfluoronitrile compound wherein, Ar is phenyl, R 1 For methyl, n is equal to 3. figure 2 Prepare the synthetic route figure of heptafluoroisobutyronitrile for the embodiment of the present application, the specific steps are as follows:

[0041] (1) At -78°C, add 1 molar equivalent of methyl heptafluoroisobutyrate (2.28g, 10mmol) and 25mL of the first solvent, anhydrous dichloromethane, into a round bottom flask, drop by drop 1.01mol / L reducing agent diisobutylaluminum hydride (DIBAL-H) ​​cyclohexane solution (19.8mL, 20mmol), carry out the reduction reaction for 2h, then slowly add anhydrous methanol dropwise until no bubbles are generated, heat up to room temperature, and The reaction solution in the round bottom flask was added into 20mL dilute hydrochloric acid solution to quench the reaction, then extracted three times in batch...

Embodiment 2

[0047] According to the preparation method described in Example 1, the difference is only in the amount of reducing agent used in step (1) and the reduction reaction time. Table 1 shows the amount of reducing agent used, the reduction reaction time and the yield of heptafluoroisobutyraldehyde in the examples of the present application.

[0048] Table 1

[0049]

[0050] It can be seen from Table 1 that the amount of reducing agent diisobutylaluminum hydride is 1.2-3mol%, the reduction reaction time is 2-4h, and heptafluoroisobutylene can be prepared in excellent yield under the condition of -78°C. aldehyde.

Embodiment 3

[0052] According to the preparation method described in Example 1, the difference is only in the amount of phenylsulfinamide used in step (2), the selection and amount of catalyst, the temperature and time of the amination reaction. Table 2 shows the amount of phenylsulfinamide used in the examples of the application, the selection and amount of catalyst, the temperature and time of the amination reaction and the preparation of N-(2,3,3,3-tetrafluoro-2-(tri The yield of fluoromethyl) propylene) benzene sulfonamide.

[0053] Table 2

[0054]

[0055]

[0056] It can be seen from Table 2 that the addition equivalent of phenylsulfinamide is 1-1.5 molar equivalents, the addition equivalent of catalyst tetrahydropyrrole is 5-15 molar equivalents, the amination reaction time is 1-7h, and the reaction temperature is 40-70°C Both can produce 2-hexafluorobutyne N-(2,3,3,3-tetrafluoro-2-(trifluoromethyl)propylene)benzenesulfonamide.

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Abstract

The invention belongs to the technical field of synthesis of perfluorinated nitrile compounds. The invention provides a preparation method of a perfluorinated nitrile compound. The perfluorinated nitrile compound is prepared by carrying out decomposition reaction on a perfluorinated imine compound with sulfinamide groups. Highly toxic reagents and expensive metal catalysts do not need to participate in the reaction process, violent high-temperature conditions are also avoided, and the prepared target product is high in chemical yield and good in stability. The synthetic route provided by the invention is a green and economic preparation route, has the advantages of simple operation, short synthetic route, cheap and easily available raw materials, safe and practical preparation conditions and wide applicability, and can meet the needs of industrial production of perfluorinated nitrile compounds.

Description

technical field [0001] The application belongs to the technical field of synthesis of perfluoronitrile compounds, and in particular relates to a preparation method of perfluoronitrile compounds. Background technique [0002] Sulfur hexafluoride (SF 6 ) gas is widely used in medium and high voltage power equipment with excellent insulation and arc extinguishing properties. However, SF 6 It is a gas with a serious greenhouse effect, and its greenhouse effect potential (GWP) is about CO 2 23,900 times that of , and the survival time in the atmosphere is about 3,200 years, SF 6 It has been listed as one of the six greenhouse gases whose emissions are restricted, and it is also the gas with the largest global warming potential (GWP) among the six gases. Therefore, looking for an alternative to SF 6 The environment-friendly gas of gas has become one of the hot issues of research at home and abroad. Perfluoronitrile compounds, such as heptafluoroisobutyronitrile (C 4 f 7 N)...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C255/10
CPCC07C45/41C07C253/00C07C313/06C07C255/10C07C47/14
Inventor 孙东伟李丽唐念周永言
Owner ELECTRIC POWER RES INST OF GUANGDONG POWER GRID
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