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Process for preparing tetrafluorobenzene carbaldehyde alkyl acetal

A technology for tetrafluorobenzaldehyde alkyl acetal and tetrafluorobenzaldehyde, which is applied in the directions of hydrolysis to prepare carbonyl compounds, carbon-based compounds, chemical instruments and methods, etc. The catalyst cannot be reused, etc., to achieve the effect of reducing the burden on the equipment

Inactive Publication Date: 2008-06-18
SHOWA DENKO KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to these documents, the desired product can be obtained, but sponge nickel as a catalyst is added to sulfuric acid so that the catalyst is dissolved and the catalytic amount increases
In addition, the catalyst thus dissolved cannot be reused
In addition, there is a problem that the reaction yield is not so high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] In an Erlenmeyer flask, 20.6 g of 95% sulfuric acid was slowly added dropwise to 70 g (2.2 mol) of methanol with ice cooling. The resulting sulfuric acid / methanol solution and 0.25 g of 5% Rh / C catalyst on a dry weight basis (available from NE Chemcat Corporation as an aqueous product) were then charged into a 300-ml glass autoclave. The system was purged with hydrogen to generate a hydrogen pressure of 0.1 MPa at room temperature. The heating of the autoclave was started and the contents of the autoclave were stirred, the temperature was raised to 40°C and held constant for 1 hour. After cooling the autoclave, 10 g (50 mmol) of tetrafluoroterephthalonitrile (available from Tokyo Kasei Kogyo Co., Ltd.) was fed into the autoclave, and the temperature was raised to 70°C in a nitrogen atmosphere . At 70°C, the introduction of hydrogen was started. The reaction pressure was controlled so that the hydrogen adsorption rate should become no more than 10 ml / min. After 6 hou...

Embodiment 2

[0075] The same operation as in Example 1 was carried out, except that 0.25 g of 5% Pd / C catalyst (available from NE Chemcat Corporation, aqueous product) was charged as catalyst on a dry weight basis. After 3.3 hours, the adsorption of hydrogen was stopped. The adsorption amount of hydrogen was 117% of the theoretical adsorption amount of hydrogen. The treatment of the reaction solution was carried out in the same manner as in Example 1.

[0076] A small sample was taken from the toluene extract and subjected to GC analysis. As a result of the analysis, the peak value of tetrafluoroterephthalonitrile as a raw material was below the detection limit, and the amount of tetrafluoroterephthalaldehyde was 68.9 mol %. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of analysis, it was confirmed that 14.8 mol% of 2,3,5,6-tetrafluorobenzylamine was present. The results are described in Table 1.

Embodiment 3

[0078] The same operation as in Example 1 was carried out, except that the temperature of the catalyst pretreated with hydrogen was changed from 40°C to 50°C. After 5.5 hours, the adsorption of hydrogen was stopped. The adsorption amount of hydrogen was 106% of the theoretical adsorption amount of hydrogen. The treatment of the reaction solution was carried out in the same manner as in Example 1.

[0079] A small sample was taken from the toluene extract and subjected to GC analysis. As a result of the analysis, the peak value of tetrafluoroterephthalonitrile as a raw material was below the detection limit, the amount of tetrafluoroterephthalaldehyde was 89.4 mol %, and the amount of 2,3,5,6-tetrafluorobenzene was 1.31 mol %, and the amount of 2,3,5,6-tetrafluorobenzonitrile was 1.03 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of analysis, it was confirmed that 2.35 mol% of 2,3,5,6-tetrafluorobenzylamine was pre...

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PUM

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Abstract

A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R-OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This application claims priority under 35 USC.sctn.119 to US Provisional Application No. 60 / 695,428, filed July 1, 2005. technical field [0003] The present invention relates to a method for producing a tetrafluorobenzenecarbaldehyde alkyl acetal represented by the following formula (II) and useful as a raw material, an intermediate, etc. for producing agrochemicals, pharmaceuticals, etc., [0004] (Formula II) [0005] wherein m is 1 or 2, n is 0 or 1, m+n is 2, and R is an alkyl group of 1 to 4 carbon atoms, and a method for preparing tetrafluorobenzaldehyde, comprising: hydrolyzing the condensation aldehyde to convert it into a tetrafluorobenzaldehyde represented by the following formula (III), and then purify the tetrafluorobenzaldehyde by extraction with a solvent for two-phase separation between an aqueous phase and a solvent phase, [0006] (Formula III) [0007] wherein m and n are the same as those in for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/50C07C43/313C07C45/42
CPCC07C43/313C07C41/50C07C45/44C07C45/515C07C47/55C07C2523/40
Inventor 池田晴彦宫田英雄大野胜俊浦川克朗
Owner SHOWA DENKO KK
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